Sample records for carbazoles

  1. Photolumincscent Properties of Polyacetylenes Carbazole

    Institute of Scientific and Technical Information of China (English)

    XUE Qing; HUANG Yuan-ming


    The optical properties of one mono-substituted polyacetylene and two di-substituted polyacetylenes have been investigated. Each of the substituted polyacetylenes bears a carbazole unit in the side chain. In spite of the differences in their molecular structures, the dilute solutions(about 1×10-6 M) of these substituted polyacetylenes exhibit the same absorptions and deep-blue emissions(about 360 nm). Interestingly, the absorption and emission spectra of these substituted polyacetylenes are similar to those of the small molecule carbazole. As the concentration of the substituted polyacetylenes increases to about 1×10-6 M, we have detected intense blue emissions at about 475 nm. Our results indicate that the absorption, the deep-blue emission(about 360 nm) and the intense blue emission(about 475 nm) originate from the carbazole chromophores in the side chain.

  2. 21 CFR 73.3107 - Carbazole violet. (United States)


    ... 21 Food and Drugs 1 2010-04-01 2010-04-01 false Carbazole violet. 73.3107 Section 73.3107 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF COLOR... additive is carbazole violet (Pigment Violet 23) (CAS Reg. No. 6358-30-1, Colour Index No. 51319). (b)...

  3. 75 FR 62765 - Carbazole Violet Pigment 23 From India: Final Results of Antidumping Duty Changed-Circumstances... (United States)


    ... International Trade Administration Carbazole Violet Pigment 23 From India: Final Results of Antidumping Duty.... See Carbazole Violet Pigment 23 From India: Preliminary Results of Antidumping Duty Changed... most recently completed review. See Carbazole Violet Pigment 23 From India: Final Results...

  4. A convenient preparation of 9 H -carbazole-3,6-dicarbonitrile and 9 H -carbazole-3,6-dicarboxylic acid

    KAUST Repository

    Weselinski, Lukasz Jan


    A catalytic, high yielding and scalable procedure for the synthesis of 9H-carbazole-3,6-dicarbonitrile has been developed. Subsequent hydrolysis of the dinitrile in the presence of a catalytic copper species (i.e., CuI) yields 9H-carbazole-3,6-dicarboxylic acid. Both compounds are versatile and fine-tunable organic building blocks and therefore offer potential in material science, medicinal and supramolecular chemistry. © Georg Thieme Verlag Stuttgart New York.

  5. Carbazole degradation in the soil microcosm by tropical bacterial strains

    Directory of Open Access Journals (Sweden)

    Lateef B. Salam


    Full Text Available In a previous study, three bacterial strains isolated from tropical hydrocarbon-contaminated soils and phylogenetically identified as Achromobacter sp. strain SL1, Pseudomonassp. strain SL4 and Microbacterium esteraromaticum strain SL6 displayed angular dioxygenation and mineralization of carbazole in batch cultures. In this study, the ability of these isolates to survive and enhance carbazole degradation in soil were tested in field-moist microcosms. Strain SL4 had the highest survival rate (1.8 x 107 cfu/g after 30 days of incubation in sterilized soil, while there was a decrease in population density in native (unsterilized soil when compared with the initial population. Gas chromatographic analysis after 30 days of incubation showed that in sterilized soil amended with carbazole (100 mg/kg, 66.96, 82.15 and 68.54% were degraded by strains SL1, SL4 and SL6, respectively, with rates of degradation of 0.093, 0.114 and 0.095 mg kg−1 h−1. The combination of the three isolates as inoculum in sterilized soil degraded 87.13% carbazole at a rate of 0.121 mg kg−1 h−1. In native soil amended with carbazole (100 mg/kg, 91.64, 87.29 and 89.13% were degraded by strains SL1, SL4 and SL6 after 30 days of incubation, with rates of degradation of 0.127, 0.121 and 0.124 mg kg−1h−1, respectively. This study successfully established the survivability (> 106 cfu/g detected after 30 days and carbazole-degrading ability of these bacterial strains in soil, and highlights the potential of these isolates as seed for the bioremediation of carbazole-impacted environments.

  6. 75 FR 27815 - Carbazole Violet Pigment 23 From China and India; Determinations (United States)


    ... (Review) Carbazole Violet Pigment 23 From China and India; Determinations On the basis of the record \\1... countervailing duty order on carbazole violet pigment 23 from India would be likely to lead to continuation or... that revocation of the antidumping duty orders on carbazole violet pigment 23 from China and...

  7. Synthesis of new heteroaryldi(diindolyl)methanes: Colorimetric detection of DNA by di(diindolylmethyl)carbazoles

    Indian Academy of Sciences (India)

    Ramu Meesala; Rajagopal Nagarajan


    We have synthesized di(diindolylmethyl)carbazoles and di(diindolylmethyl)pyrroles by the reaction of substituted indoles with the corresponding carbazole and pyrroledicarboxaldehydes by employing a new catalyst PPh3.CF3SO3H. We have also demonstrated the utility of di(diindolylmethyl) carbazole derivatives for the colourimetric and fluorometric detection of DNA.

  8. 75 FR 14468 - Carbazole Violet Pigment 23 From China and India (United States)


    ... COMMISSION Carbazole Violet Pigment 23 From China and India AGENCY: United States International Trade... carbazole violet pigment 23 from India and the antidumping duty orders on carbazole violet pigment 23 from China and India. SUMMARY: The Commission hereby gives notice of the scheduling of expedited...

  9. Novel Complex Polymers with Carbazole Functionality by Controlled Radical Polymerization

    Directory of Open Access Journals (Sweden)

    Kazuhiro Nakabayashi


    Full Text Available This review summarizes recent advances in the design and synthesis of novel complex polymers with carbazole moieties using controlled radical polymerization techniques. We focus on the polymeric architectures of block copolymers, star polymers, including star block copolymers and miktoarm star copolymers, comb-shaped copolymers, and hybrids. Controlled radical polymerization of N-vinylcarbazole (NVC and styrene and (methacrylate derivatives having carbazole moieties is well advanced, leading to the well-controlled synthesis of complex macromolecules. Characteristic optoelectronic properties, assembled structures, and three-dimensional architectures are briefly introduced.

  10. Synthesis of Carbazoles and Carbazole-Containing Heterocycles via Rhodium-Catalyzed Tandem Carbonylative Benzannulations. (United States)

    Song, Wangze; Li, Xiaoxun; Yang, Ka; Zhao, Xian-liang; Glazier, Daniel A; Xi, Bao-min; Tang, Weiping


    Polycyclic aromatic compounds are important constituents of pharmaceuticals and other materials. We have developed a series of Rh-catalyzed tandem carbonylative benzannulations for the synthesis of tri-, tetra-, and pentacyclic heterocycles from different types of aryl propargylic alcohols. These tandem reactions provide efficient access to highly substituted carbazoles, furocarbazoles, pyrrolocarbazoles, thiophenocarbazoles, and indolocarbazoles. While tricyclic heterocycles could be derived from vinyl aryl propargylic alcohols, tetra- and pentacyclic heterocycles were synthesized from diaryl propargylic alcohols. The tandem carbonylative benzannulation is initiated by a π-acidic rhodium(I) catalyst-mediated nucleophilic addition to alkyne to generate a key metal-carbene intermediate, which is then trapped by carbon monoxide to form a ketene species for 6π electrocyclization. Overall, three bonds and two rings are formed in all of these tandem carbonylative benzannulation reactions.

  11. 7H-1-Benzofuro[2,3-b]carbazole

    Directory of Open Access Journals (Sweden)

    V. Manivannan


    Full Text Available In the title compound, C18H11NO, the carbazole and benzofuran rings are almost co-planar, making a dihedral angle of 3.31 (3°. The crystal structure is stabilized by weak C—H...π interactions.

  12. Carbazole functionalized isocyanide brushes in heterojunction photovoltaic devices

    NARCIS (Netherlands)

    Lim, E.; Gao, F.; Schwartz, E.; Cornelissen, J.J.L.M.; Nolte, R.J.M.; Rowan, A.E.; Greenham, N.C.; Do, L.M.


    In this work, carbazole-containing polyisocyanide (PIACz) brushes were used for photovoltaic devices. A photovoltaic device was fabricated on top of the brushes by spin-coating a suitable acceptor and evaporating an Al cathode. Devices with a poly(N-vinylcarbazole) (PVK) bulk polymer were also prepa

  13. Synthesis and Photophysical Properties of C60-carbazole Adducts

    Institute of Scientific and Technical Information of China (English)

    YIN ,Gui(尹桂); YIN,Gui; MAO,Xin-Ping(毛新平); MAO,Xin-Ping; SUO,Zhi-Yong(锁志勇); SUO,Zhi-Yong; XU,Zheng(徐正); XU,Zheng


    Three C60-cartazole adducts have been synthesized by 1,3-dipolar cycloaddition reaction.Intramolecular energy/electron transfer from carbazole to C60 was observed by steady-state absorption and fluorescence spectra.The fluorescence spectra of these adducts were similau to each other and dependent on the excitation wavelength and solvent.

  14. Synthesis, Characterization, and Surface Initiated Polymerization of Carbazole Functionalized Isocyanides

    NARCIS (Netherlands)

    Schwartz, Erik; Lim, Eunhee; Gowda, Chandrakala M.; Liscio, Andrea; Fenwick, Oliver; Tu, Guoli; Palermo, Vincenzo; Gelder, de Rene; Cornelissen, Jeroen J.L.M.; Eck, van Ernst R.H.; Kentgens, Arno P.M.; Cacialli, Franco; Nolte, Roeland J.M.; Samori, Paolo; Huck, Wilhelm T.S.; Rowan, Alan E.


    We describe the design and synthesis of carbazole functionalized isocyanides and the detailed investigation of their properties. Characterization by solid state NMR, CD, and IR spectroscopic techniques reveals that the polymer has a well-defined helical architecture. Surface-initiated polymerization

  15. Quantitative analysis of bioactive carbazole alkaloids in Murraya koenigii. (United States)

    Joshi, Trapti; Mahar, Rohit; Singh, Sumit K; Srivastava, Piush; Shukla, Sanjeev K; Mishra, Dipak K; Bhatta, R S; Kanojiya, Sanjeev


    Carbazole alkaloids induce apoptosis in HL-60 cells through activation of the caspase-9/caspase-3 pathway and they are targeted as potential anticancer agents. Thus, the naturally occurring carbazole alkaloids become important as precursors for lead optimization in drug development. A method based on ultra performance liquid chromatography coupled with photodiode-array detection was developed using reverse phase isocratic elution with 85:15 acetonitrile and ammonium acetate buffer (5 mM). Seven samples of Murrya koenigii (L.) Spreng. from north-central India (Uttar Pradesh) were analyzed. All three targeted analytes, koenimbidine (mk1), koenimbine (mk2) and mahanimbine (mk3), were well separated within 4.0 min with linearity of the calibration curves (r2 > 0.999). The limits of detection and quantification of mk1, mk2 and mk3 were 0.7, 0.4, 0.04 μg/mL and 2.14, 1.21, 0.12 μg/mL, respectively. The natural abundance of mk1, mk2 and mk3 was 0.06-0.20, 0.04-0.69 and 0.13-0.42%, w/w, respectively, in the dried powdered leaves, whereas, the tissue specific distribution of carbazole alkaloids was observed in the order of predominance, mk1 leaf>root>fruit>stem, mk2 fruit>leaf >stem>root, and mk3 fruit>leaf>root>stem. The developed method was validated for limits of detection and quantification, repeatability, accuracy, precision and stability. This is the first report on the natural abundance of the major carbazole alkaloids in M. koenigii and the method developed can be used in HPLC/UPLC systems.

  16. 9-Ethyl-3,6-diformyl-9H-carbazole

    Directory of Open Access Journals (Sweden)

    Jun Jie Wang


    Full Text Available The structure of the title compound, C16H13NO2, was determined as a part of a project on the synthesis of new compounds which can make two-photon absorptions. In the crystal structure, both aldehyde groups are located within the carbazole plane. One of these groups is disordered and was refined using a split model with site-occupation factors for each position of 0.5.

  17. 9-(4-Bromophenyl-9H-carbazole

    Directory of Open Access Journals (Sweden)

    Paul Kautny


    Full Text Available In the title molecule, C18H12BrN, the 4-bromophenyl ring is inclined to the mean plane of the carbazole moiety (r.m.s. devation = 0.027 Å by 49.87 (5°. In the crystal, molecules stack along [001] and are linked by C—H...π interactions forming a corrugated two-dimensional network lying parallel to (100.

  18. (4,9-Dimethyl-9H-carbazol-3-ylmethanol

    Directory of Open Access Journals (Sweden)

    Serkan Öncüoğlu


    Full Text Available In the title compound, C15H15NO, the carbazole skeleton includes a methanol group at the 3-position. The indole ring system is almost planar [maximum deviation = 0.045 (2 Å]. In the crystal, O—H...O hydrogen bonds link the molecules into zigzag chains along the b-axis direction. There are weak C—H...π interactions within the chains and linking neighbouring chains forming sheets lying parallel to (001.

  19. Alternative products to carbazoles in the oxidation of diphenylamines with palladium (II) acetate


    Raposo, M. Manuela M.; Campos, Ana M. F. Oliveira; Shannon, Patrick V. R.


    Although simple diphenylamines are conveniently oxidised with Palladium (II) acetate to give carbazoles, for more complex examples, carbazoles are minor products amongst many. CRUP (Portugal). British Council - Treaty of Windsor Programme. Junta Nacional de Investigação Científica e Tecnológica.

  20. A complete gear system in N-benzoyl-carbazole derivatives. (United States)

    Tabata, Hidetsugu; Kayama, Susumu; Takahashi, Yuka; Tani, Norihiko; Wakamatsu, Shintaro; Tasaka, Tomohiko; Oshitari, Tetsuta; Natsugari, Hideaki; Takahashi, Hideyo


    2',6'-Disubstituted N-benzoylated carbazole derivatives were found to exhibit atropisomerism. The bulky substituents restricted rotation about the N-C7' and C7'-C1' bonds to separate four atropisomers, in which rotation about the C7'-C1' bond was in perfect concert with rotation about the N-C7' bond. Complete geared rotation without slippage at 37 °C for 7 days was observed for the first time. Conformational analysis clarified the preference for the gear system over other internal conversion pathways.

  1. Electronic transitions of fluorene, dibenzofuran, carbazole, and dibenzothiophene

    DEFF Research Database (Denmark)

    Nguyen, Duy Duc; Trunk, John; Nakhimovsky, Lina;


    A comparative study of the electronic transitions of fluorene and its hetero-analogues dibenzofuran, carbazole, and dibenzothiophene was performed in a wide energy range. Gas phase, crystal phase, and linear dichroism electronic transmittance spectra were measured with synchrotron radiation....... Prediction of electronic transitions to excited singlet states was performed by using time-dependent density functional theory TD-B3LYP/6-31+G(d,p). Based on the experimental and theoretical results, symmetry assignments of electronic transitions in the vacuum and near-UV region are suggested...

  2. Synthesis and photoluminescence of a dendritic europium complex with carbazole moieties

    Institute of Scientific and Technical Information of China (English)

    ZHENG Youxuan; ZHOU Yonghui; Gianluca Accorsi; Nicola Armaroli


    A novel dendritic europium complex containing grafted carbazole units as functional peripheries was synthesized and characterized. The Forster energy transfer from the peripheries of carbazole units to β-diketonate as well as from the ligands to the central Eu(III) ions in the complex was demonstrated. Under the excitation of carbazole units and β-diketonate, characteristic red emission peaks at 612 nm with four shoulders due to the Eu(III) ion transition of 5D0→7FJ (J=0-4) were observed for the complex.

  3. Modulation of π-spacer of carbazole-carbazole based organic dyes toward high efficient dye-sensitized solar cells (United States)

    Chitpakdee, Chirawat; Jungsuttiwong, Siriporn; Sudyoadsuk, Taweesak; Promarak, Vinich; Kungwan, Nawee; Namuangruk, Supawadee


    The effects of type and position of π-linker in carbazole-carbazole based dyes on their performance in dye-sensitized solar cells (DSSCs) were investigated by DFT and TDDFT methods. The calculated electronic energy level, electron density composition, charge injection and charge recombination properties were compared with those of the high performance CCT3A dye synthesized recently. It is found that that mixing a benzothiadizole (B) unit with two thiophene (T) units in the π-spacer can greatly shift absorption wavelength to near infrared region and enhance the light harvesting efficiency (LHE) resulting in increasing of short-circuit current density (Jsc), whereas a thienothiophene unit does not affect those properties. However, a B should be not directly connected to the anchoring group of the dye because it brings electrolyte to the TiO2 surface which may increase charge recombination rate and consequently decrease open circuit voltage (Voc). This work shows how type and position of the π-linker affect the performance of DSSCs, and how to modulate those properties. We predicted that the designed dye derived from insertion of the B unit in between the two T units would have higher performance than CCT3A dye. The insight understanding from this study is useful for further design of higher performance dyes by molecular engineering.

  4. Novel Blue Light-emitting PPV-based Copolymer Containing Triazole and Carbazole Units

    Institute of Scientific and Technical Information of China (English)


    A novel alternating conjugated copolymer containing triazole and carbazole units was synthesized by the Wittig reaction. The resulting bipolar conjugated polymer emits a pure light with good thermal stability, which is a promising candidate for polymer light emitting display.

  5. Novel Blue Light—emitting PPV—based Copolymer Containing Trazole and Carbazole Units

    Institute of Scientific and Technical Information of China (English)

    ZeLIU; LiXiangWANG; 等


    A novel alternating conjugated copolymer containing triazole and carbazole units was synthesized by the Witting reaction. The resulting bipolar conjugated polymer emits a pure light with good thermal stability, which is a promising candidate for polymer light emitting display.

  6. Copper catalyzed synthesis of quinolinopyrano[2,3-]carbazole derivatives via Povarov reaction

    Indian Academy of Sciences (India)

    Subburethinam Ramesh; Rajagopal Nagarajan


    An efficient procedure for the synthesis of pyranocarbazole derivatives using copper catalysed Povarov reaction between aromatic amines and -propargyl carbazole carboxaldehyde has been developed. Ionic liquid is found to be a good solvent medium.

  7. Synthesis of Novel Derivatives of Carbazole-Thiophene, Their Electronic Properties, and Computational Studies

    Directory of Open Access Journals (Sweden)

    E. F. Damit


    Full Text Available A series of carbazole-thiophene dimers, P1–P9, were synthesized using Suzuki-Miyaura and Ullmann coupling reactions. In P1–P9, carbazole-thiophenes were linked at the N-9 position for different core groups via biphenyl, dimethylbiphenyl, and phenyl. Electronic properties were evaluated by UV-Vis, cyclic voltammogram, and theoretical calculations. Particularly, the effects of conjugation connectivity on photophysical and electrochemical properties, as well as the correlation between carbazole-thiophene and the core, were studied. Carbazole connecting with thiophenes at the 3,6-positions and the phenyl group as a core group leads to increased stabilization of HOMO and LUMO energy levels where the bandgap (ΔE is significantly reduced.

  8. Research on polyfluorene derivatives end-capped by N-hexyl-carbazole and benzene

    Institute of Scientific and Technical Information of China (English)


    Copolymers of 9,9-dioctylfluorene (DOF) and 2-thienyl-benzothiadiazole (DBT) were synthesized by Suzuki reaction and end-capped by N-hexyl-carbazole and benzene, which were abbreviated as PDOF-DBT-Cz and PDOF-DBT-B, respectively. The photophysical, electrochemical and thermal properties of the copolymers were studied. The results indicated that replacement of N-hexyl-carbazole as end-capping group of PDOF-DBT can vary light color and improve luminescence efficiency.

  9. Carbazole is a naturally occurring inhibitor of angiogenesis and inflammation isolated from antipsoriatic coal tar

    Energy Technology Data Exchange (ETDEWEB)

    Jack L. Arbiser; Baskaran Govindarajan; Traci E. Battle; Rebecca Lynch; David A. Frank; Masuko Ushio-Fukai; Betsy N. Perry; David F. Stern; G. Tim Bowden; Anquan Liu; Eva Klein; Pawel J. Kolodziejski; N. Tony Eissa; Chowdhury F. Hossain; Dale G. Nagle [Emory University School of Medicine, Atlanta, GA (United States). Department of Dermatology


    Coal tar is one of the oldest and an effective treatment for psoriasis. Coal tar has been directly applied to the skin, or used in combination with UV light as part of the Goeckerman treatment. The use of coal tar has caused long-term remissions in psoriasis, but has fallen out of favor because the treatment requires hospitalization and coal tar is poorly acceptable aesthetically to patients. Thus, determining the active antipsoriatic component of coal tar is of considerable therapeutic interest. We fractionated coal tar into its components, and tested them using the SVR angiogenesis inhibitor assay. Treatment of SVR endothelial cells with coal tar fractions resulted in the isolation of a single fraction with antiangiogenic activity. The active antiangiogenic compound in coal tar is carbazole. In addition to antiangiogenic activity, carbazole inhibited the production of inflammatory IL-15 by human mononuclear cells. IL-15 is elevated in psoriasis and is thought to contribute to psoriatic inflammation. Carbazole treatment also reduced activity of inducible nitric oxide synthase (iNOS), which is proinflammatory and elevated in psoriasis. The effect of carbazole on upstream pathways in human psoriasis was determined, and carbazole was shown to inhibit signal transducer and activator of transcription (stat)3-mediated transcription, which has been shown to be relevant in human psoriasis. IL-15, iNOS, and stat3 activation require the activation of the small GTPase rac for optimal activity. Carbazole was found to inhibit rac activation as a mechanism for its inhibition of downstream inflammatory and angiogenic pathways. Given its antiangiogenic and anti-inflammatory activities, carbazole is likely a major component of the antipsoriatic activity of coal tar. Carbazole and derivatives may be useful in the therapy of human psoriasis.

  10. N-[(9-Ethyl-9H-carbazol-3-ylmethylene]-3,4-dimethylisoxazol-5-amine

    Directory of Open Access Journals (Sweden)

    Abdullah Mohamed Asiri


    Full Text Available The title compound, N-[(9-ethyl-9H-carbazol-3-ylmethylene]-3,4-dimethylisoxazol-5-amine has been synthesized by reaction of 9-ethyl-9H-carbazole-3-carbaldehyde with 5-amino-3,4-dimethylisoxazole in the presence of acetic acid in ethanol. The structure of this new compound was confirmed by elemental analysis, IR, 1H-NMR, 13C-NMR and EI-MS spectral analysis.

  11. Ethyl 2-(1,2,3,4-tetrahydrospiro[carbazole-3,2′-[1,3]dioxolan]-9-ylacetate

    Directory of Open Access Journals (Sweden)

    Philipp M. G. Löffler


    Full Text Available In the title compound, C18H21NO4, the hydrogenated six-membered ring of the carbazole unit adopts a half-chair conformation. The dioxolane ring and ethylacetate substituent point to opposite sides of the carbazole plane. The ethylacetate substituent adopts an essentially fully extended conformation, and its mean plane forms a dihedral angle of 83.8 (1° with respect to the carbazole mean plane. The molecules are arranged into stacks in which the carbazole planes form a dihedral angle of 4.4 (1° and have an approximate interplanar separation of 3.6 Å.

  12. [Environmental Behaviors and Ecotoxicology of the Emerging Contaminants Polyhalogenated Carbazoles]. (United States)

    Lin, Kun-de; Chen, Yan-qiu; Yuan, Dong-xing


    Polyhalogenated carbazoles (PHCs), with a complex chemical structure similar to polychlorinated dibenzofurans, are a class of emerging environmental organic contaminants. There are 135 congeners for PHCs with a pure halogenation. Most of PHCs are not man-made products. Although PHCs in the environment were firstly discovered in the 1980s, these emerging halogenated compounds were not seriously considered until recent years. Recently, more than 20 PHCs have been detected in sediment and soil samples. In addition, studies have shown that PHCs exhibited dioxin-like toxicity and were persistent and bioaccumulative. Therefore, it is very important to understand the distribution, origins and ecotoxicology of PHCs for a better assessment of their environmental risks. To date, research on the environmental behaviors of PHCs is relatively limited and warrants further investigations. In this review, the environmental distribution, source, analytical methods and toxicity of PHCs were summarized and future research needs were outlined.

  13. Oegylated and cross-linking carbazole dendrons and dendrimers: Synthesis, characterization, assembly and thin film fabrication (United States)

    Felipe, Mary Jane Legaspi


    Dendrimers and dendrons (fractional dendrimers) are macromolecular structures that have well-defined molecular weights and precise number of functional groups. Tailoring these structures has provided designer molecules that can be used for various applications including drug delivery, sensors, and anti-biofouling surfaces. Overall, this dissertation provides novel protocols for the understanding of molecular design, synthesis, and structure-property relationship of OEGylated and conjugated carbazole dendrons and dendrimers. In this design, the use of oligo(ethylene glycol) (OEG) allows for the fabrication of biocompatible materials and imparts hydrophilicity on the structure while the carbazole functionality allows the cross-linking of these designer molecules. Such fine-tuning of macromolecular structures leading to the fabrication of anti-biofouling thin films, nanostructuring at the air-water interface, and assembly into supramolecular superstructures are considered in this dissertation. Chapter 2 details the synthesis, characterization, and electrochemical cross-linking of OEGylated linear dendrons and "Janus-type" dendrimers. Cross-linking the carbazole moieties enables the deposition of these films on Au, indium tin oxide-coated glass, and doped silicon through cyclic voltammetry and provides films with secondary level of organization imparted by the inter- and intra-molecular interaction among the carbazole units. Chapter 3 describes the fabrication of nonspecific protein adsorption resistant surfaces through electrochemical grafting of three different dendrons on SAM carbazole-coated gold substrates. The predictable shape of each dendron and the ability to cross-link the carbazole units have enabled parametrization of OEG conformation and density on these interfaces. Chapter 4 demonstrates the fundamental architectural requirements for obtaining stable films with OEGylated linear dendron molecules providing a new architectural design of nanostructuring

  14. Carbazole-containing light- emitting polymers: Properties of excited states

    Institute of Scientific and Technical Information of China (English)


    A series of light-emitting conjugated polymers alternatively involving carbazole and bivinylene arylene moieties in the main chain were synthesized via Wittig-Horner type copolymerization. The photoinduced charge transfer process relating to these polymers was investigated by using the technique of fluorescence spectroscopy. The interaction between excited copolymers and C60 in benzene solution was studied. The fluorescence quenching can be well described by the "sphere-of-action" mechanism. It is believed that two basic steps are involved in the quenching process, i.e. the diffusion of excitation within the conjugated polymers and the dissociation of the exctions trapped by fullerene. The radius of the sphere-of-action can be related to the excitation diffusion length, which depends on the lifetime of the exciton. The dynamic fluorescence quenching of the copolymers by another quencher, 1,4-dicyanobenzene (DCB) was also surveyed. Copolymers with different chain conformations show different temperature effects in the dynamic quenching. A planar conformation is beneficial for the quenching via bimolecular collision.

  15. 2,7-Bis(2-nitrophenyl-9-octyl-9H-carbazole

    Directory of Open Access Journals (Sweden)

    Norma Wrobel


    Full Text Available The title compound, C32H31N3O4, was obtained in a Suzuki coupling of carbazole diboronic acid and bromonitrobenzene. In the crystal, the molecule adopts a non-symmetric conformation. The carbazole ring system is approximately planar [maximum deviation from the least-squares plane = 0.039 (2 Å]. The planes of the carbazole unit and the benzene rings subtend dihedral angles of 48.42 (7 and 41.81 (6°. The dihedral angles between the planes of the nitrophenyl rings and the nitro groups are 44.34 (19 and 61.64 (15°. The crystal is built from two strands of parallel molecules with interdigitated octyl chains. These strands are symmetry related by a twofold screw axis.

  16. Charge photogeneration and transport in side-chain carbazole polymers and co-polymers

    KAUST Repository

    Li, Huawei


    The photoconductivity, hole mobility and charge photogeneration efficiency of a series of side-chain carbazole homopolymers and copolymers (with azo side-chains) have been investigated. Cyclic voltammetry measurement of frontier orbitals energies show that the HOMO energy is determined by the nature and the position of attachment of the linker between the main chain and the carbazole, the azo-moiety being not relevant in this respect. Hole mobility is not influenced by the HOMO energy but seems to depend on the degree of conformational mobility of the side-chains, reaching values of the order of 10-3cm2V-1s-1 in the best cases. The HOMO energy is instead extremely important when considering photogeneration efficiency, that can change by 10 orders of magnitude depending on the density of the carbazole side-chains in co-polymers and on the linker nature and attachment position. © 2011 Elsevier B.V. All rights reserved.

  17. A New Maleamide Bridged Carbazole Chromogenic-sensor Based on Proton Transfer Signaling Mode

    Institute of Scientific and Technical Information of China (English)

    WANG Yue-hong; LIN Hai; SHAO Jie; LIN Hua-kuan


    A Maleamide bridged carbazole receptor was designed and synthesized, the interactions between the receptor and anions, such as Ac-, H2PO4-, OH-, F-, Cl-, Br- and I- in DMSO were investigated by UV-Vis spectroscopy and 1H NMR titration. The results of UV-Vis spectral studies indicate that interactions existed between receptor and anions, which induced remarkable color changes. The 1H NMR titration indicated amide moiety of the receptor was deprontonated first when a small quantity of anions such as Ac-, H2PO4-, F- were added; however, the carbazole N-H was gradually deprontonated upon the addition of anions.

  18. Effect of air annealing on the optical electrical and structural properties of carbazole thin films

    Energy Technology Data Exchange (ETDEWEB)

    Pisharady, Sreejith K. [School of Pure and Applied Physics, Mahatma Gandhi University, Kottayam, Kerala 656560 (India)]. E-mail:; Menon, C.S. [School of Pure and Applied Physics, Mahatma Gandhi University, Kottayam, Kerala 656560 (India); Sudarshana Kumar, C. [School of Pure and Applied Physics, Mahatma Gandhi University, Kottayam, Kerala 656560 (India); Gopinathan, T.G. [School of Pure and Applied Physics, Mahatma Gandhi University, Kottayam, Kerala 656560 (India)


    Thin films of carbazole films have been prepared using vacuum sublimation technique. Post-evaporation annealing is done for various periods of time. The optical absorption spectrum is recorded and the band gap is calculated from the observed spectrum. The current-voltage characteristics are studied for the sandwiched structure of carbazole thin films with silver electrodes. From the J-V characteristics trap density and number of thermally generated charge carriers are determined. Their structure and grain size have been determined from the X-ray diffraction studies.

  19. 75 FR 34699 - Carbazole Violet Pigment 23 from India: Rescission of Countervailing Duty Administrative Review (United States)


    ... International Trade Administration Carbazole Violet Pigment 23 from India: Rescission of Countervailing Duty... 23(CVP-23) from India. See Antidumping or Countervailing Duty Order, Finding, or Suspended... countervailing duty order on CVP-23 from India for the period January 1, 2008 through December 31, 2008. In...

  20. Controlled electropolymerisation of a carbazole-functionalised iron porphyrin electrocatalyst for CO2 reduction

    DEFF Research Database (Denmark)

    Hu, Xinming; Salmi, Zakaria; Lillethorup, Mie;


    Using a one-step electropolymerisation procedure, CO2 absorbing microporous carbazole-functionalised films of iron porphyrins are prepared in a controlled manner. The electrocatalytic reduction of CO2 for these films is investigated to elucidate their efficiency and the origin of their ultimate...

  1. A novel synthesis of 4-toluene 9H-carbazole-9-carbodithioate, electropolymerization and impedance study

    Directory of Open Access Journals (Sweden)

    M. Ates


    Full Text Available A novel synthesis of 4-toluene 9H-carbazole-9-carbodithioate (TCzC was chemically synthesized and characterized by Fourier Transform Infrared (FTIR, proton nuclear magnetic resonance (1H-NMR, and carbon nuclear magnetic resonance (13C-NMR spectroscopies. Specific (Csp and double layer capacitances (Cdl of the electro-coated poly(carbazole and poly(TCzC films were obtained on glassy carbon electrode (GCE by impedimetric method with DC potential from –0.1 to +1.0 V by increasing potential of 0.2 V. The polymers were characterized by Cyclic voltammetry (CV, Fourier transform infrared reflectance-attenuated total reflection spectroscopy (FTIR-ATR, Atomic force microscopy (AFM, and Electrochemical impedance spectroscopy (EIS. The use of additional variable (DC potential helped to disambiguate the equivalent circuit model of R(C(R(Q(RW(CR. Simulation results were compared with experimental data. In this study, substituted group effects of CS2 and tosyl on carbazole polymer were investigated by EIS technique. CS2 group together with tosyl group in the structure of carbazole decreased the specific capacitance value (Csp = 0.43 mF•cm–2 compared to PCz (Csp = 1.44 mF•cm–2. Electropolymerization formation was seriously affected by substituted groups of CS2 and tosyl on conjugation system because of the electron donor and acceptor ability.

  2. The binding modes of carbazole derivatives with telomere G-quadruplex (United States)

    Zhang, Xiu-feng; Zhang, Hui-juan; Xiang, Jun-feng; Li, Qian; Yang, Qian-fan; Shang, Qian; Zhang, Yan-xia; Tang, Ya-lin


    It is reported that carbazole derivatives can stabilize G-quadruplex DNA structure formed by human telomeric sequence, and therefore, they have the potential to serve as anti-cancer agents. In this present study, in order to further explore the binding mode between carbazole derivatives and G-quadruplex formed by human telomeric sequence, two carbazole iodides (BMVEC, MVEC) molecules were synthesized and used to investigate the interaction with the human telomeric parallel and antiparallel G-quadruplex structures by NMR, CD and molecular modeling study. Interestingly, it is the pivotal the cationic charge pendant groups of pyridinium rings of carbazole that plays an essential role in the stabilizing and binding mode of the human telomeric sequences G-quadruplex structure. It was found that BMVEC with two cationic charge pendant groups of pyridinium rings of 9-ethylcarbazole cannot only stabilize parallel G-quadruple of Hum6 by groove binding and G-tetrad stacking modes and antiparallel G-quadruplex of Hum22 by groove binding, but also induce the formation of mixed G-quadruplex of Hum22. While MVEC with one cationic charge pendant groups of pyridinium ring only can bind with the parallel G-quadruplex of Hum6 by the stacking onto the G4 G-tetrad and could not interact with the G-quadruplex of Hum22.

  3. 75 FR 29718 - Carbazole Violet Pigment 23 From India and the People's Republic of China: Continuation of... (United States)


    ... of Sales at Less Than Fair Value and Antidumping Duty Order: Carbazole Violet Pigment 23 From India...-proprietary information. In this case, the brackets are simply part of the chemical nomenclature....

  4. Cu-catalyzed arylation of the amino group in the indazole ring: regioselective synthesis of pyrazolo-carbazoles. (United States)

    Anil Kumar, K; Kannaboina, Prakash; Dhaked, Devendra K; Vishwakarma, Ram A; Bharatam, Prasad V; Das, Parthasarathi


    Cu(II)-catalyzed cross-coupling of various aryl boronic acids with 5 and 6-amino indazoles has resulted in (arylamino)-indazoles. These (arylamino)-indazoles have been utilized in synthesizing medicinally important pyrazole-fused carbazoles via Pd(II)-catalyzed cross-dehydrogenative coupling (CDC). This combined N-arylation/C-H arylation strategy has been successfully applied to the regioselective synthesis of polyheterocycles 3,6-dihydropyrazolo[3,4-c]carbazoles and 1,6-dihydro pyrazolo[4,3-c]carbazoles. Quantum chemical analysis has been carried out to understand the regioselectivity and to trace the potential energy surface of the entire reaction upon 5-N-aryl-indazole conversion to the corresponding carbazole.

  5. Synthesis of Dendrimer Containing Carbazole Unit as a Core Chromophore

    Energy Technology Data Exchange (ETDEWEB)

    Han, Seung Choul; Lee, Jae Wook [Dong-A Univ., Busan (Korea, Republic of); Jin, Sungho [Pusan National Univ., Busan (Korea, Republic of)


    for the synthesis of Frechet-type dendrimers having a carbazole unit at core, which will be soluble in common organic solvents and easily spin-coated with high quality optical thin films.

  6. 3-Bromomethyl-4-methoxy-2-(2-nitrophenyl-9-phenylsulfonyl-9H-carbazole

    Directory of Open Access Journals (Sweden)

    S. Gopinath


    Full Text Available In the title compound, C26H19BrN2O5S, the carbazole tricycle is essentially planar, with the largest deviation being 0.126 (3 Å for the C atom connected to the nitrophenyl group. The carbazole moiety is almost orthogonal to the benzene rings of the adjacent phenylsulfonyl and nitrophenyl groups, making dihedral angles of 85.43 (15 and 88.62 (12°, respectively. The molecular conformation is stabilized by two C—H...O hydrogen bonds involving the sulfone group, which form similar six-membered rings. In the crystal, molecules symmetrically related by a glide plane are linked in C(6 chains parallel to [001] by C—H...O hydrogen bonds formed with the participation of the nitro group. The chains are reinforced by additional C—H...π interactions.

  7. Carbazole Scaffold in Medicinal Chemistry and Natural Products: A Review from 2010-2015. (United States)

    Tsutsumi, Lissa S; Gündisch, Daniela; Sun, Dianqing


    9H-carbazole is an aromatic molecule that is tricyclic in nature, with two benzene rings fused onto a 5-membered pyrrole ring. Obtained from natural sources or by synthetic routes, this scaffold has gained much interest due to its wide range of biological activity upon modifications, including antibacterial, antimalarial, anticancer, and anti-Alzheimer properties. This review reports a survey of the literature on carbazole-containing molecules and their medicinal activities from 2010 through 2015. In particular, we focus on their in vitro and in vivo activities and summarize structure-activity relationships (SAR), mechanisms of action, and/or cytotoxicity/selectivity findings when available to provide future guidance for the development of clinically useful agents from this template.

  8. Nanoscale characterization of carbazole-indole copolymers modified carbon fiber surfaces. (United States)

    Sarac, A Sezai; Serantoni, Marina; Tofail, Syed A M; Cunnane, Vincent J


    Polycarbazole, carbazole and indole containing copolymers were electrochemically coated onto carbon fiber. The resulting polymers and copolymers were characterized by scanning electron microscopy, atomic force microscopy, X-ray photoelectron spectroscopy, and Raman spectroscopy. Characterization of the thin polymer films were performed on the polymer-coated surface of the carbon fiber. Therefore, the results obtained could elucidate the relationship between the initial feed monomer ratio, the resulting polymer/copolymer film morphology and the surface structure formed. The thickness increase (in diameter) was 0.3 and 0.9 microm, for two different composition of carbazole/indole on the carbon fiber. The carbon fibers coated with copolymer thin films were from 6.5 to 8.2 microm in diameter (from AFM measurement).

  9. 1H and 15N Dynamic Nuclear Polarization Studies of Carbazole

    Energy Technology Data Exchange (ETDEWEB)

    Hu, Jian Zhi; Solum, Mark S.; Wind, Robert A.; Nilsson, Brad L.; Peterson, Matt A.; Pugmire, Ronald J.; Grant, David M.


    15N NMR experiments, combined with dynamic nuclear polarization (DNP), are reported on carbazole doped with the stable free radical 1,3 bisdiphenylene-2 phenylally1 (BDPA). Doping shortens the nuclear relaxation times and provides paramagnetic centers that can be used to enhance the nuclear signal by means of DNP so that 15 N NMR experiments can be done in minutes. The factors were measured in a 1.4 T external field, using both unlabeled and 98% 15N labeled carbazole with doping levels varying between 0.65 and 5.0 wt % BDPA. A doping level of approximately 1 wt % produced optimal results. DNP enhancement factors of 35 and 930 were obtained for 1H and 15N, respectively making it possible to perform 15N DNP NMR experiments at the natural abundance level.

  10. Calix[3]carbazole: A C3-symmetrical receptor for barium ion (United States)

    Yang, Zhaozheng; Tian, Zhangmin; Yang, Peng; Deng, Tuo; Li, Gang; Zhou, Xue; Chen, Yan; Zhao, Liang; Shen, Hongyan


    The binding ability of calix[3]carbazole (1) to metal ions has been investigated. It is found that 1 could serve as a non crown ether based, C3-symmetrical receptor for Ba2 + via the marriage of cation-π and cation-dipole interactions. FID assay further illustrates that 1 could selectively interact with Ba2 + over Pd2 +. A possible binding mechanism for [1-Ba2 +] complex is proposed.

  11. Highly Selective Fluoride Recognition by a Simple Carbazole-based Hydrozone Derivative

    Institute of Scientific and Technical Information of China (English)

    TANG Li-jun; ZHAO Guo-you; HUANG Zhen-long; WANG Nan-nan; GUO Jiao-jiao


    A simple carbazole hydrozone derivative(1) was synthesized and used as an optical probe for fluoride recognition in CH3CN.Receptor 1 exhibited colorimetric and fluorescent dual-channel response to fluoride anions.Addition of fluoride to a receptor 1 solution in CH3CN induced a distinct color change from yellow to magenta,the solution also displayed significant fluorescence blue shift.Thus receptor 1 exhibited dual-channel responses to fluoride with a high selectivity and sensitivity.

  12. Electrochemical impedance of poly(9-tosyl-9H-carbazole-co-pyrrole) electrocoated carbon fiber

    Energy Technology Data Exchange (ETDEWEB)

    Ates, Murat; Uludag, Nesimi [Department of Chemistry, Faculty of Arts and Sciences, Namik Kemal University, Degirmenalti Campus, 59030, Tekirdag (Turkey); Sarac, A. Sezai, E-mail: [Department of Chemistry, Polymer Science and Technology, Istanbul Technical University, Maslak, 34469, Istanbul (Turkey)


    Research highlights: {yields} Impedance study of poly(9-tosyl-9H-carbazole-co-pyrrole) electrocoated carbon fiber. {yields} Copolymer of 9-tosyl-9H-carbazole and pyrrole were electrocoated on carbon fiber. {yields} Impedance spectroscopy and circuit models of poly(9-tosyl-9H-carbazole-co-pyrrole). - Abstract: In this paper, copolymer of 9-tosyl-9H-carbazole (TCz) and pyrrole (Py) comonomers were electrochemically deposited onto carbon fiber micro electrode (CFME) as an active electrode material. An electrochemical impedance study on the prepared electrodes is reported. Poly(TCz-co-Py)/CFME is characterized by cyclic voltammetry (CV), Fourier transform infrared reflectance-attenuated total reflection spectroscopy (FTIR-ATR), scanning electron microscopy-energy dispersive X-ray analysis (SEM-EDX), and electrochemical impedance spectroscopy (EIS). Capacitive behaviors of modified CFMEs were defined via Nyquist, Bode-magnitude and Bode-phase plots. An examination is made of which equivalent circuits of R(C(R(Q(RW)))) and R(C(R(Q(RW))))(CR) used for modeling the system. The effect of monomer ratio (mole fraction, X{sub TCz} = n{sub TCz}/n{sub TCz} + n{sub Py}) on the formation of copolymer is reported in 0.1 M sodium perchlorate (NaClO{sub 4})/acetonitrile (ACN) solution. The inclusion of TCz in the copolymer structure was also confirmed by FTIR-ATR, SEM, and CV measurements. The highest low frequency capacitance (C{sub LF} = 22.7 for R(C(R(Q(RW)))) and C{sub LF} = 22.6 mF cm{sup -2} for R(C(R(Q(RW))))(CR)) were obtained for X{sub TCz} = 0.91.

  13. Carbazole alkaloids from Murraya koenigii trigger apoptosis and autophagic flux inhibition in human oral squamous cell carcinoma cells. (United States)

    Utaipan, Tanyarath; Athipornchai, Anan; Suksamrarn, Apichart; Jirachotikoon, Canussanun; Yuan, Xiaohong; Lertcanawanichakul, Monthon; Chunglok, Warangkana


    Carbazole alkaloids, a major constituent of Murraya koenigii (L.) Sprengel (Rutaceae), exhibit biological effects such as anticancer activity via the induction of apoptosis, and they represent candidate chemotherapeutic agents. Oral squamous cell carcinoma (OSCC) is the most prevalent cancer of the oral cavity and a growing and serious health problem worldwide. In this study, we investigated the anticancer properties and mechanisms of action of two carbazole alkaloids derived from M. koenigii leaves, mahanine and isomahanine, in the OSCC cell line CLS-354. At 15 μM, mahanine and isomahanine were cytotoxic to CLS-354 cells, triggering apoptosis via caspase-dependent and -independent mechanisms. Autophagosomes, visualised using monodansylcadaverine (MDC) labelling, were numerous in carbazole alkaloid-treated cells. Mahanine and isomahanine markedly induced the expression of the autophagosome marker microtubule-associated protein 1 light chain 3, type II (LC3B-II). Genetic and chemical inhibition of autophagy via silencing of the Autophagy protein 5 gene and exposure to bafilomycin A1 (BafA1), respectively, did not arrest carbazole alkaloid-induced apoptosis, indicating that it occurs independently of autophagic activation. Surprisingly, both carbazole alkaloids caused increased accumulation of p62/sequestosome1 (p62/SQSTM1), with coordinated expression of LC3B-II and cleaved caspase-3, suggesting inhibition of autophagic flux. Our results suggest that inhibition of autophagic flux is associated with carbazole alkaloid-induced apoptosis. Our findings provide evidence of a novel cytotoxic action of natural carbazole alkaloids and support their use as candidate chemotherapeutic agents for the treatment of OSCC.

  14. N-Alkyl Carbazole Derivatives as New Tools for Alzheimer’s Disease: Preliminary Studies

    Directory of Open Access Journals (Sweden)

    Carmela Saturnino


    Full Text Available Alzheimer’s disease (AD is a progressive and age-related neurodegenerative disorder affecting brain cells and is the most common form of “dementia”, because of the cognitive detriment which takes place. Neuronal disruption represents its major feature, due to the cytosolic accumulation of amyloid β-peptide (Aβ which leads to senile plaques formation and intracellular neurofibrillary tangles. Many studies have focused on the design and therapeutic use of new molecules able to inhibit Aβ aggregation. In this context, we evaluated the ability of two recently synthesized series of N-alkyl carbazole derivatives to increase the Aβ soluble forms, through molecular docking simulations and in vitro experiments. Our data evidenced that two carbazole derivatives, the most active, adopt distinct binding modes involving key residues for Aβ fibrillization. They exhibit a good interfering activity on Aβ aggregation in mouse (N2a cells, stably expressing wild-type human amyloid precursor protein (APP 695. These preliminary results are promising and we are confident that the N-alkyl carbazole derivatives may encourage next future studies needed for enlarging the knowledge about the AD disease approach.

  15. Synthesis and Properties of 1,8-Carbazole-Based Conjugated Copolymers

    Directory of Open Access Journals (Sweden)

    Tsuyoshi Michinobu


    Full Text Available A new series of conjugated carbazole polymers based on the 1,8-carbazolylene unit was synthesized by the Pd-catalyzed polycondensation between the 1,8-diiodocarbazole derivative and various bifunctional counter comonomers. An alkyne spacer was found to be a key to increasing the molecular weight of the resulting polymers. All the obtained polymers showed good solubilities in the common organic solvents, and they were fully characterized by Gel permeation chromatography (GPC, and 1H NMR and infrared (IR spectroscopies. The UV-vis absorption and fluorescence spectra revealed the relationship between the chemical structure and effective conjugation length. The efficiency order of the carbazole connectivity was 2,7-carbazolylene > 1,8-carbazolylene > 3,6-carbazolylene. The electrochemical properties of these polymers suggested the relatively facile oxidation at ca. +0.5–0.7 V vs. Fc/Fc+ or a high potential as p-type semiconductors. The combination of the electrochemical oxidation potentials and the optical band gaps allowed us to estimate the HOMO and LUMO levels of the polymers. It was shown that the energy levels of the 1,8-carbazole-based conjugated polymers can be tunable by selecting the appropriate comonomer structures.

  16. Vascular barrier protective effects of 3-N- or 3-O-cinnamoyl carbazole derivatives. (United States)

    Ku, Sae-Kwang; Lee, Jee-Hyun; O, Yuseok; Lee, Wonhwa; Song, Gyu-Yong; Bae, Jong-Sup


    In this Letter, we investigated the barrier protective effects of 3-N-(MeO)n-cinnamoyl carbazoles (BS 1; n=1, BS 2; n=2, BS 3; n=3) and 3-O-(MeO)3-cinnamoyl carbazole (BS 4) against high-mobility group box 1 (HMGB1)-mediated vascular disruptive responses in human umbilical vein endothelial cells (HUVECs) and in mice for the first time. Data showed that BS 2, BS 3, and BS 4, but not BS 1, inhibited HMGB1-mediated vascular disruptive responses and transendothelial migration of human neutrophils to HUVECs. BS 2, BS3, and BS 4 also suppressed HMGB1-induced hyperpermeability and leukocyte migration in mice. Interestingly, the barrier protective effects of BS 3 and BS 4 were better than those of BS 2. These results suggest that the number of methoxy groups substituted on the cinnamamide or cinnamate moiety of the 9H-3-carbazole derivative is an important pharmacophore for the barrier protective effects of these compounds.

  17. Electrochemical Polymerization of Carbazole in Acetic Acid Containing Boron Trifluoride Diethyl Etherate

    Institute of Scientific and Technical Information of China (English)

    MIAO,Hua-Ming; ZHANG,Hong-Lin; XU,Jing-Kun; FAN,Chang-Li; DONG,Bin; ZENG,Li-Qiang; ZHAO,Feng


    High-quality polycarbazole (PCz) films with an electrical conductivity of 10-2 S·cm-1 were synthesized elec-trochemically by direct anodic oxidation of carbazole in a novel mixed electrolyte of acetic acid containing 26% boron trifluoride diethyl etherate (BTDE) and 5% poly(ethylene glycol) with molar mass of 400 (by volume). The oxidation potential of carbazole in this medium was measured to be only 0.89 V vs. a saturated calomel electrode (SCE), which was much lower than that determined in acetonitrile containing 0.1mol·L-1 Bu4NBF4 (1.36 V vs. SCE). PCz films obtained from this medium showed good electrochemical behavior, good thermal stability, and were partly soluble in strong polar organic solvents such as dimethyl sulfoxide and tetrahydrofuran. The fluorescence spectra implied that PCz obtained from this medium was a good blue-light emitter. FT-IR, 1H NMR and theoretical studies showed that the polymerization of carbazole mainly occurred at the 3,6-positions. To the best of our knowledge, this is the first report on the electrosyntheses of conducting polymers in mixed electrolyte of acetic acid and BTDE.

  18. Star-shaped carbazole derivative based efficient solid-state dye sensitized solar cell (United States)

    Michaleviciute, Asta; Degbia, Martial; Tomkeviciene, Ausra; Schmaltz, Bruno; Gurskyte, Egle; Grazulevicius, Juozas Vidas; Bouclé, Johan; Tran-Van, François


    Two new star-shaped carbazole molecules, including tri(9-(methoxyphenyl)carbazol-3-yl)amine named TMPCA having molecular glasses properties and hole transport properties were synthesized. Their thermal, optical, photophysical and electrochemical properties were studied. The carbazole based molecules exhibit high thermal stability with 5% weight loss temperatures over 480 °C with higher glass temperature transitions 164-175 °C than the classical spiro-OMeTAD reference molecule. Their optical band gaps (2.76 eV) are low enough not to hinder neither the absorption of the indoline sensitizer (D102) nor its photoexcitation and charge transfer. Solid state ionization potential (IPs) of TMPCA is well adapted to that of D102 and ensure a driving force ΔrG >0.2 eV for an efficient transfer and regeneration of the photo-oxidized dye. Solid-state dye sensitized solar cells ITO/TiO2/D102/T4MPCA/Au showed a power conversion efficiency of 2.23% with Jsc of 8.85 mA cm-2 under standard AM 1.5 simulated solar irradiation.

  19. Color-Tunable Solid-State Fluorescence Emission from Carbazole-Based BODIPYs. (United States)

    Maeda, Chihiro; Todaka, Takumi; Ueda, Tomomi; Ema, Tadashi


    Several carbazole-based boron dipyrromethene (BODIPY) dyes were synthesized by organometallic approaches. Thiazole, benzothiazole, imidazole, benzimidazole, triazole, and indolone substituents were introduced at the 1-position of the carbazole moiety, and boron complexation of each dipyrrin generated the corresponding compounds 1, 2 a, and 3-6. The properties of these products were investigated by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, X-ray crystallography, and DFT calculations. These compounds exhibited large Stokes shifts, and compounds 1, 2 a, and 3-5 fluoresced both in solution and in the solid state. Complex 2 a showed the highest fluorescence quantum yield (ΦF ) in the solid state, therefore boron complexes of the carbazole-benzothiazole hybrids 2 b-f, which had several different substituents, were prepared and the effects of the substituents on the photophysical properties of the compounds were examined. The fluorescence properties showed good correlation with the results of crystal-packing analyses, and the dyes exhibited color-tunable solid-state fluorescence.

  20. Carbazole-based sensitizers for potential application to dye sensitized solar cells

    Indian Academy of Sciences (India)

    Naresh Duvva; Ravi Kumar Kanaparthi; Jaipal Kandhadi; Gabriele Marotta; Paolo Salvatori; Filippo De Angelis; Lingamallu Giribabu


    Two push-pull molecules employing carbazole and alkyl thiophene (CAR-THIOHX) or carbazole and triphenylamine (CAR-TPA) as donor moieties, with the cyanoacrylic group as the acceptor, have been designed and synthesized by simple organic transformations. Photophysical and electrochemical studies revealed the potential of these two systems in dye sensitized solar cells (DSSC). Under standard irradiation conditions, CAR-TPA and CAR-THIOHX exhibited 2.12 and 1.83% of overall power conversion efficiencies respectively. The moderate photovoltaic efficiency of the sensitizers has been attributed to the poor light absorption of the sensitizers in the visible region. Density functional theory (DFT) calculations have shown a strong intramolecular charge transfer character, with the HOMOs of both the sensitizers exclusively localized on the corresponding donor moieties and LUMOs on the cyanoacrylic acid acceptor. On the other hand, the calculated high dihedral angle between the carbazole donor and the phenyl bridge for these sensitizers impedes the conjugation along the dyes backbone, and thus leads to less extended and intense absorption spectra in the visible region.

  1. Carbazole-degradative IncP-7 plasmid pCAR1.2 is structurally unstable in Pseudomonas fluorescens Pf0-1, which accumulates catechol, the intermediate of the carbazole degradation pathway. (United States)

    Takahashi, Yurika; Shintani, Masaki; Li, Li; Yamane, Hisakazu; Nojiri, Hideaki


    We determined the effect of the host on the function and structure of the nearly identical IncP-7 carbazole-degradative plasmids pCAR1.1 and pCAR1.2. We constructed Pseudomonas aeruginosa PAO1(pCAR1.2) and P. fluorescens Pf0-1Km(pCAR1.2) and compared their growth on carbazole- and succinate-containing media with that of P. putida KT2440(pCAR1.1). We also assessed the stability of the genetic structures of the plasmids in each of the three hosts. Pf0-1Km(pCAR1.2) showed dramatically delayed growth when carbazole was supplied as the sole carbon source, while the three strains grew at nearly the same rate on succinate. Among the carbazole-grown Pf0-1Km(pCAR1.2) cells, two types of deficient strains appeared and dominated the population; such dominance was not observed in the other two strains or for succinate-grown Pf0-1Km(pCAR1.2). Genetic analysis showed that the two deficient strains possessed pCAR1.2 derivatives in which the carbazole-degradative car operon was deleted or its regulatory gene, antR, was deleted by homologous recombination between insertion sequences. From genomic information and quantitative reverse transcription-PCR analyses of the genes involved in carbazole mineralization by Pf0-1Km(pCAR1.2), we found that the cat genes on the chromosome of Pf0-1Km, which are necessary for the degradation of catechol (a toxic intermediate in the carbazole catabolic pathway), were not induced in the presence of carbazole. The resulting accumulation of catechol may have enabled the strain that lost its carbazole-degrading ability to have overall higher fitness than the wild-type strain. These results suggest that the functions of the chromosomal genes contributed to the selection of plasmid derivatives with altered structures.

  2. 3,6-Carbazole vs 2,7-carbazole: A comparative study of hole-transporting polymeric materials for inorganic–organic hybrid perovskite solar cells (United States)

    Li, Wei; Otsuka, Munechika; Wang, Yang; Mori, Takehiko


    Summary The ever increasing demand for clean energy has encouraged researchers to intensively investigate environmentally friendly photovoltaic devices. Inorganic–organic hybrid perovskite solar cells (PSCs) are very promising due to their potentials of easy fabrication processes and high power conversion efficiencies (PCEs). Designing hole-transporting materials (HTMs) is one of the key factors in achieving the high PCEs of PSCs. We now report the synthesis of two types of carbazole-based polymers, namely 3,6-Cbz-EDOT and 2,7-Cbz-EDOT, by Stille polycondensation. Despite the same chemical composition, 3,6-Cbz-EDOT and 2,7-Cbz-EDOT displayed different optical and electrochemical properties due to the different connectivity mode of the carbazole unit. Therefore, their performances as hole-transporting polymeric materials in the PSCs were also different. The device based on 2,7-Cbz-EDOT showed better photovoltaic properties with the PCE of 4.47% than that based on 3,6-Cbz-EDOT. This could be due to its more suitable highest occupied molecular orbital (HOMO) level and higher hole mobility. PMID:27559390

  3. Effect of Substituents on the Electronic Structure and Degradation Process in Carbazole Derivatives for Blue OLED Host Materials

    KAUST Repository

    Hong, Minki


    We investigate the dissociation mechanism of the C-N bond between carbazole and dibenzothiophene in carbazole-dibenzothiophene (Cz-DBT) positional isomers, selected as representative systems for blue host materials in organic light-emitting diodes (OLEDs). The C-N bond dissociation energies, calculated at the density functional theory level, are found to depend strongly on the charge states of the parental molecules. In particular, the anionic C-N bond dissociations resulting in a carbazole anion can have low dissociation energies (∼1.6 eV) with respect to blue emission energy. These low values are attributed to the large electron affinity of the carbazole radical, a feature that importantly can be modulated via substitution. Substitution also impacts the energies of the first excited electronic states of the Cz-DBT molecules since these states have an intramolecular charge-transfer nature due to the spatially localized character of the frontier molecular orbitals within the carbazole moiety (for the HOMO) and the dibenzothiophene moiety (for the LUMO). The implications of these results must be considered when designing blue OLED hosts since these materials must combine chemical stability and high triplet energy. © 2016 American Chemical Society.

  4. Photochemical Synthesis of Complex Carbazoles: Evaluation of Electronic Effects in Both UV- and Visible-Light Methods in Continuous Flow. (United States)

    Hernandez-Perez, Augusto C; Caron, Antoine; Collins, Shawn K


    An evaluation of both a visible-light- and UV-light-mediated synthesis of carbazoles from various triarylamines with differing electronic properties under continuous-flow conditions has been conducted. In general, triarylamines bearing electron-rich groups tend to produce higher yields than triarylamines possessing electron-withdrawing groups. The incorporation of nitrogen-based heterocycles, as well as halogen-containing arenes in carbazole skeletons, was well tolerated, and often synthetically useful complementarity was observed between the UV-light and visible-light (photoredox) methods.

  5. Synthesis and characterization of novel star-shaped pyridine cored compounds with alternating carbazole and triphenylamine moieties

    Institute of Scientific and Technical Information of China (English)

    Ji Bing Yuan; Zhi Guo Zhang; Louis Man Leung; Ke Li Zhang


    Amorphous 2,4,6-trissubstituted pyridines containing three peripheral carbazole or two triphenylamine and one carbazole moieties, respectively, have been synthesized and characterized. The properties of the compounds are investigated by UV-visabsorption, photoluminescence spectroscopy, thermal analysis as well as cyclic voltammetry. The results show that the compounds have high thermal stability, emit blue light. Also, the compounds possess the HOMO and LUMO energy levels comparable to those of NPB. The effects of different substituents on the electronic properties of the materials have been discussed.

  6. Carbazoles, benzocarbazoles et dibenzocarbazoles des pétroles et de produits pétroliers Carbazoles, Benzocarbazoles and Dibenzocarbazoles from Oil and Petroleum Products

    Directory of Open Access Journals (Sweden)

    Arpino P.


    Full Text Available On décrit dans cet article les principales techniques d'analyse des dérivés du pyrrole dans les pétroles et les produits pétroliers et on présente les principaux résultats obtenus. La méthode la plus efficace consiste en une concentration de ces composés par chromatographie liquide; l'identification des principaux composés individuels se fait par chromatographie gazeuse et son couplage avec la spectrométrie de masse. On a essentiellement identifié ou caractérisé : le carbazole et certains de ses dérivés alkylés, les dibenzo(a-, -(b- et -(ccarbazoles et certains de leurs dérivés alkylés, certains dibenzocarbazoles. D'un point de vue géochimique, il semble évident que ces composés ne sont pas des molécules fossiles, Il est également apparu des différences de comportement de ces composés les uns par rapport aux autres vis-à-vis de l'hydrotraitement catalytique. This article describes the leading techniques for analyzing derivatives from pyrrole in oil and petroleum products. The main results obtained are described. The most effective method consists of a concentration of these compounds by liquid chromatography. The main individual components are identified by gas chromatography and its coupling with mass spectrometry. The principal compounds identified or characterized were carbazole and some of its alkylated derivatives, dibenzo(a-, -(b- and -(ccarbazoles and some of their alkylated derivates, and various dibenzocarbazoles. From the geochernical standpoint, it seems obvious that these compounds are not fossil molecules. Differences in behavior were also found for these compounds in relation to others with regard to catalytic hydrotreatment.

  7. The thermodynamic properties of 2-aminobiphenyl (an intermediate in the carbazole/hydrogen reaction network)

    Energy Technology Data Exchange (ETDEWEB)

    Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.


    Catalytic hydrodenitrogenation (HDN) is a key step in upgrading processes for conversion of heavy petroleum, shale oil, tar sands, and the products of the liquefaction of coal to economically viable products. This research program provides accurate experimental thermochemical and thermophysical properties for key organic nitrogen-containing compounds present in the range of alternative feedstocks, and applies the experimental information to thermodynamic analyses of key HDN reaction networks. This report is the first in a series that will lead to an analysis of a three-ring HDN system; the carbazole/hydrogen reaction network. 2-Aminobiphenyl is the initial intermediate in the HDN pathway for carbazole, which consumes the least hydrogen possible. Measurements leading to the calculation of the ideal-gas thermodynamic properties for 2-aminobiphenyl are reported. Experimental methods included combustion calorimetry, adiabatic heat-capacity calorimetry, comparative ebulliometry, inclined-piston gauge manometry, and differential-scanning calorimetry (d.s.c). Entropies, enthalpies, and Gibbs energies of formation were derived for the ideal gas for selected temperatures between 298.15 K and 820 K. The critical temperature and critical density were determined for 2-aminobiphenyl with the d.s.c., and the critical pressure was derived. The Gibbs energies of formation are used in thermodynamic calculations to compare the feasibility of the initial hydrogenolysis step in the carbazole/H{sub 2} network with that of its hydrocarbon and oxygen-containing analogous; i.e., fluorene/H{sub 2} and dibenzofuran/H{sub 2}. Results of the thermodynamic calculations are compared with those of batch-reaction studies reported in the literature. 57 refs., 8 figs., 18 tabs.

  8. Synthesis of two carbazole-based dyes and application of two-photon initiating polymerization

    Institute of Scientific and Technical Information of China (English)


    Two carbazole-based polymerization initiators possessing blue fluorescence emission have been synthesized via Wittig reaction in the solid phase at room temperature.Two-photon excited fluorescence(TPEF) spectra for them were investigated under 800 nm fs laser pulse and two-photon absorption cross sections were determined by the Z-scan technique.Then two-photon initiating polymerization(TPIP) microfabrication experiments were successfully carried out.Three-dimensional lattice and artificial defects were gained,indicating that they were viable candidates for the two-photon polymerization initiator in practical application of microfabrication.

  9. Synthesis, measurements, and theoretical analysis of carbazole derivatives with high-triplet-energy

    Energy Technology Data Exchange (ETDEWEB)

    Li Jianli; Mi Xiaoyun; Wan Yuchun [School of Materials Science and Engineering, Changchun University of Science and Technology, Changchun 130022 (China); Si Zhenjun, E-mail: [School of Materials Science and Engineering, Changchun University of Science and Technology, Changchun 130022 (China); Institute of Organic Chemistry and Biochemistry, Czech Academy of Science, Praha 6 16610 (Czech Republic); Sun Haiying; Duan Qian [School of Materials Science and Engineering, Changchun University of Science and Technology, Changchun 130022 (China); He Xingquan [School of Chemistry and Environmental Engineering, Changchun University of Science and Technology, Changchun 130022 (China); Yan Dong; Wan Sha [School of Materials Science and Engineering, Changchun University of Science and Technology, Changchun 130022 (China)


    In order to obtain the blue light-emitting organic materials with high triplet state energy, two 3,5-diphenyl-4H-1,2,4-triazole (Tz) containing carbazole (Cz) derivatives of 9-(4-(3,5-diphenyl-4H-1,2,4-triazol-4-yl)phenyl)-9H-carbazole (TzCz1) and 3,6-di-tert-butyl-9-(4-(3,5-diphenyl-4H-1,2,4-triazol-4-yl)phenyl) -9H-carbazole (TzCz2) are synthesized using Cz acting as the starting material, as well as characterized by the {sup 1}H NMR spectra, ultraviolet-visible (UV-vis) absorption spectra, and the IR absorption spectra. The luminescence quantum yields (LQYs) of TzCz1 and TzCz2 are measured in CH{sub 2}Cl{sub 2} solution to be 32.1% and 47.5%, respectively. The electrochemical analysis and the photophysical measurements suggest that the triplet energy levels and the energy gaps of the highest-occupied orbital and the lowest-unoccupied orbital are 2.83 eV and 3.59 eV for TzCz1, and 2.80 eV and 3.43 eV for TzCz2. At last, the theoretical analyses of their ground state geometries and the simulated UV-vis absorption spectra are carried out at B3LYP1/6-31G Low-Asterisk level. The studies mentioned above indicate that both TzCz1 and TzCz2 are suitable for the host materials of blue light-emitting diodes. - Highlights: Black-Right-Pointing-Pointer Synthesis of two blue light-emitting Carbazole derivatives. Black-Right-Pointing-Pointer Photophysical and electrochemical properties are systematically studied. Black-Right-Pointing-Pointer Theoretical analysis of geometry of the ground states and the UV-vis absorption are performed with Firefly package. Black-Right-Pointing-Pointer The triplet energy levels are measured to be ca. 2.83 eV.

  10. Synthesis of two carbazole-based dyes and application of two-photon initiating polymerization

    Institute of Scientific and Technical Information of China (English)

    HU RenTao; LU LiangFei; RUAN BanFeng; WANG Peng; ZHANG MingLiang; ZHOU HongPing; LI ShengLi; WU JieYing; TIAN YuPeng


    Two carbazole-based polymerization initiators possessing blue fluorescence emission have been synthesized via Wittig reaction in the solid phase at room temperature.Two-photon excited fluorescence (TPEF) spectra for them were investigated under 800 nm fs laser pulse and two-photon absorption cross sections were determined by the Z-scan technique.Then two-photon initiating polymerization (TPIP) microfabrication experiments were successfully carried out.Three-dimensional lattice and artificial defects were gained,indicating that they were viable candidates for the two-photon polymerization initiator in practical application of microfabrication.

  11. Antidiarrhoeal activity of carbazole alkaloids from Murraya koenigii Spreng (Rutaceae) seeds. (United States)

    Mandal, Suvra; Nayak, Anupam; Kar, Manoj; Banerjee, Samir K; Das, Ashes; Upadhyay, S N; Singh, R K; Banerji, Avijit; Banerji, Julie


    The bioassay guided fractionation of the n-hexane extract of the seeds of Murraya koenigii Spreng (Rutaceae) resulted in the isolation of three bioactive carbazole alkaloids, kurryam (I), koenimbine (II) and koenine (III). The structures of the compounds were confirmed from their (1)H-, (13)C-, and 2D-NMR spectral data. Of the three compounds (I) and (II) exhibited significant inhibitory activity against castor oil-induced diarrhoea and PGE(2)-induced enteropooling in rats. The compounds also produced a significant reduction in gastrointestinal motility in the charcoal meal test in Wistar rats.

  12. New materials based on carbazole for optoelectronic device applications:Theoretical investigation

    Institute of Scientific and Technical Information of China (English)

    K.Hasnaoui; H.Zgou; M.Hamidi; M.Bouachrine


    A quantum-chemical investigation on the structural and optoelectronic properties of two materials based on carbazole is carried out.The purpose is to display the effect of grafting the fluorine atoms on their optoelectronic and pbysico-chemical properties.In addition to solubility in the polar solvents and the modification in geometric parameters,the substitution of fluorine destabilizes the HOMO and LUMO levels,decreases the band gap energy and raises conjugation length.These properties suggest the substituted fluorine compound as a good candidate for optoelectronic applications.

  13. Miscibility and Molecular Orientation of Carbazole in Mixed Langmuir and Langrnuir-Blodgett Films

    Institute of Scientific and Technical Information of China (English)

    Md. N. Islam; D. Bhattacharjee; S. A. Hussain


    We report the miscibility and molecular orientation of carbazole (CA) molecules in the mixed Langmuir and Langmuir-Blodgett (LB) films of CA in polymethyl methacrylate (PMMA) and stearic acid (SA) matrices. The r-A isotherm confirms the formation of stable Langmuir films of CA mixed with either PMMA or SA at airwater interface. Characteristics of area per molecule versus molefraction and collapse pressure versus molefraction reveal complete demixing of CA and the matrix PMMA/SA molecules in the mixed films. Absorption spectroscopy certainly confirms the fact that CA molecules have preferred orientation on the substrate of the LB films.

  14. 3,6-Dichloro-9-(prop-2-yn-1-yl-9H-carbazole

    Directory of Open Access Journals (Sweden)

    Joel T. Mague


    Full Text Available The tricyclic aromatic ring system of the title compound, C15H9Cl2N, is essentially planar (r.m.s. deviation = 0.002 Å. The two Cl atoms lie slightly out of the plane of the carbazole ring system, with the C—Cl bonds forming angles of 1.23 (8 and 1.14 (8° with the plane. The acetylene group has a syn orientation with respect to the ring system. In the crystal, no weak hydrogen bonds nor any π–π stacking interactions are observed.

  15. Regio-selective synthesis of diversely substituted benzo[a]carbazoles through Rh(iii)-catalyzed annulation of 2-arylindoles with α-diazo carbonyl compounds. (United States)

    Li, Bin; Zhang, Beibei; Zhang, Xinying; Fan, Xuesen


    A novel synthetic approach toward benzo[a]carbazoles or 6-amino benzo[a]carbazoles containing an unprotected NH unit through Rh(iii)-catalyzed cascade reactions of 2-arylindoles or 2-arylindole-3-carbonitriles with α-diazo carbonyl compounds has been established. To our knowledge, this is the first example in which the NH unit of indole is used as a directing group for an intramolecular C(sp(2))-H bond functionalization to give benzo[a]carbazole derivatives. Notably, this method features easily obtainable substrates, good functional group tolerance, excellent regio-selectivity, and high atom-efficiency.

  16. 1,2-Di­hydro­spiro­[carbazole-3(4H),2′-[1,3]dioxolane


    Bjerrum, Janni Vester; Ulven, Trond; Bond, Andrew D.


    In the title compound, C14H15NO2, the hydrogenated six-membered ring of the carbazole unit adopts a half-chair conformation and the dioxolane ring points to one side of the carbazole plane. Neighbouring mol­ecules form edge-to-face inter­actions in which the NH group is directed towards an adjacent carbazole unit, with a shortest H⋯C contact of 2.72 Å. These inter­actions arrange the mol­ecules into one-dimensional herringbone-type motifs, which pack so that the methyl­ene groups of the dioxo...

  17. Indolo[2,3-b]carbazole synthesized from a double-intramolecular Buchwald-Hartwig reaction: its application for a dianchor DSSC organic dye. (United States)

    Su, Jia-Yi; Lo, Chun-Yuan; Tsai, Chih-Hung; Chen, Chih-Han; Chou, Shu-Hua; Liu, Shih-Hung; Chou, Pi-Tai; Wong, Ken-Tsung


    A new synthetic strategy for indolo[2,3-b]carbazole via a double-intramolecular Buchwald-Hartwig reaction has been established. The N-alkylated indolo[2,3-b]carbazole then was adopted as the geometry-fixed core for the synthesis of a new molecule (ICZDTA) bearing two bithiophene π-bridged 2-cyanoacrylic acid groups as the bidentate anchor. The bidentate anchoring together with efficient HOMO (indolo[2,3-b]carbazole) → LUMO (TiO2 nanocluster) electron transfer leads to the successful development of ICZDTA-based DSSC with a power conversion efficiency of 6.02%.

  18. Assembly of BODIPY-carbazole dyes with liposomes to fabricate fluorescent nanoparticles for lysosomal bioimaging in living cells. (United States)

    Lv, Hai-Juan; Zhang, Xiao-Tai; Wang, Shu; Xing, Guo-Wen


    Two BODIPY-carbazole dye based fluorescent probes BCA and BCAS were designed, synthesized and encapsulated by liposomes to obtain fluorescent nanoparticles BCA-FNP and BCAS-FNP. The fluorescence imaging showed that BCA-FNP was membrane-permeable and capable of localizing lysosomes in living cells.

  19. DFT and experimental studies on structure and spectroscopic parameters of 3,6-diiodo-9-ethyl-9H-carbazole

    DEFF Research Database (Denmark)

    Radula-Janik, Klaudia; Kupka, Teobald; Ejsmont, Krzysztof;


    The first report on crystal and molecular structure of 3,6-diiodo-9-ethyl-9H-carbazole is presented. Experimental room-temperature X-ray and 13C chemical shift studies were supported by advanced theoretical calculations using density functional theory (DFT). The 13C nuclear magnetic shieldings we...

  20. Smart windows application of carbazole and triazine based star shaped architecture. (United States)

    Guzel, Merve; Soganci, Tugba; Ayranci, Rukiye; Ak, Metin


    A novel triazine-based, star shape and electroactive monomer, 2,4,6-tris(2-(9H-carbazol-9-yl)ethoxy)-1,3,5-triazine (TCZ) which contains 2,4,6-trichloro-1,3,5-triazine as the core and 2-(9H-carbazol-9-yl)ethanol as the arms, was successfully synthesized. After electrochemical polymerization of the TCZ monomer, called PTCZ, the polymer shows superior optoelectronic and thermal properties due to its unique three-dimensional shape and highly-branched structure in comparison with linear analogues. Electrochromic studies exhibited that PTCZ has turquoise color in the oxidized state and is transparent in the neutral state. Due to the fact that the redox color characteristics of PTCZ are indispensable for smart windows, a PTCZ-based electrochromic device was formed with PEDOT as complementary coloring material. A potential range of -1.5 to +1.8 V was determined to be suitable for operating the PTCZ/PEDOT device between transparent and blue colors. Characterizations of the device were performed in term of switching times, optical contrast, optical memory and redox stability.

  1. Photoluminescence of donor-acceptor carbazole-based molecules in amorphous and powder forms (United States)

    Adès, D.; Boucard, V.; Cloutet, E.; Siove, A.; Olivero, C.; Castex, M. C.; Pichler, G.


    We present absorption and photoluminescence features of four samples of carbazole molecules substituted with various electron-acceptor groups. These molecules named 1-(N-ethylcarbazolyl)-2-substituted-2-cyanovinylene contain in their structure the electron-donor carbazole nucleus and cyanovinylene bearing either another nitrile function, an ethylester, a phenyl, or a para-nitrophenyl groups. It is shown that depending on the strength of the donor-acceptor internal charge transfer, both the absorption and emission spectra are more or less redshifted. It is found that the ethyl-ester derivative displays the best relative photoluminescence efficiency among all the samples and its peak is measured at 490 nm when taking amorphous thin film. The microcrystalline powder form of the same material exhibits spectral narrowing and shift of the peak emission. We obtain further narrowing of the emission band and further redshifting of the emission when we illuminate, transversely, a glass capillary containing the crystalline sample by an ultraviolet light-emitting diode.

  2. Valence one-electron and shake-up ionization bands of fluorene, carbazole and dibenzofuran

    Energy Technology Data Exchange (ETDEWEB)

    Reza Shojaei, S.H.; Morini, Filippo; Deleuze, Michael S., E-mail:


    Highlights: • The photoelectron spectra of the title compounds are assigned in details. • Shake-up lines are found to severely contaminate both π- and σ-ionization bands. • σ-ionization onsets are subject to severe vibronic coupling complications. • We compare the results of OVGF, ADC(3) and TDDFT calculations. - Abstract: A comprehensive study of the He (I) ultra-violet photoelectron spectra of fluorene, carbazole and dibenzofuran is presented with the aid of one-particle Green’s Function calculations employing the outer-valence Green’s Function (OVGF) approach and the third-order algebraic diagrammatic construction [ADC(3)] scheme, along with Dunning’s correlation consistent basis sets of double and triple zeta quality (cc-pVDZ, cc-pVTZ). Extrapolations of the ADC(3) results for the outermost one-electron π-ionization energies to the cc-pVTZ basis set enable theoretical insights into He (I) measurements within ∼0.15 eV accuracy, up to the σ-ionization onset. The lower ionization energy of carbazole is the combined result of mesomeric and electronic relaxation effects. OVGF/cc-pVDZ or OVGF/cc-pVTZ pole strengths smaller than 0.85 systematically corroborate a breakdown of the orbital picture of ionization at the ADC(3) level. Comparison is made with calculations of the lowest doublet–doublet excitation energies of the radical cation of fluorene, by means of time-dependent density functional theory (TDDFT)

  3. Solvent-dependent fluorescence enhancement and piezochromism of a carbazole-substituted naphthopyran

    Energy Technology Data Exchange (ETDEWEB)

    Liu, Lihui; Wang, Aixia [Faculty of Chemistry, Northeast Normal University, Changchun 130024 (China); Wang, Guang, E-mail: [Faculty of Chemistry, Northeast Normal University, Changchun 130024 (China); Munyentwari, Alexis [Faculty of Chemistry, Northeast Normal University, Changchun 130024 (China); Zhou, Yihan, E-mail: [National Analytical Research Center of Electrochemistry and Spectroscopy, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022 (China)


    A novel carbazole-substituted naphthopyran, 3,3-bis-(4-carbazolylphenyl)-[3H]-naphtho[2,1-b]pyran (CzNP) was designed and synthesized. The new compound exhibited normal photochromism in dichloromethane solution and the UV irradiation did not influence its fluorescence. On the contrary, the fluorescence of CzNP in N,N-dimethylformamide (DMF) was intensively enhanced to 29 times after 60 min of the UV irradiation and this enhanced fluorescence can be quenched by addition of triethylamine (TEA). The study of enhanced extent of fluorescence of CzNP in solvents with different polarities and in mixed solvents demonstrated that the enhanced fluorescence is dependent on the polarity of solvents. The larger the polarity of solvent was, the stronger was the fluorescence of CzNP. CzNP also exhibited piezochromic performance and the pressure led to the cleavage of the C–O bond of pyran ring. - Highlights: • A carbazole-substituted photochromic naphthopyran was designed and synthesized. • The fluorescence was enhanced under the existence of DMF and UV irradiation. • The polarity of solvent was the dominating factor to affect the fluorescence. • The new compound also displayed piezochromic performance.

  4. 1,2-Di­hydro­spiro­[carbazole-3(4H),2′-[1,3]dioxolane (United States)

    Bjerrum, Janni Vester; Ulven, Trond; Bond, Andrew D.


    In the title compound, C14H15NO2, the hydrogenated six-membered ring of the carbazole unit adopts a half-chair conformation and the dioxolane ring points to one side of the carbazole plane. Neighbouring mol­ecules form edge-to-face inter­actions in which the NH group is directed towards an adjacent carbazole unit, with a shortest H⋯C contact of 2.72 Å. These inter­actions arrange the mol­ecules into one-dimensional herringbone-type motifs, which pack so that the methyl­ene groups of the dioxolane ring lie over the face of a neighbouring carbazole unit with a shortest H⋯C contact of 2.85 Å. PMID:21582234

  5. 3-Methoxy-2-methyl-carbazole-1,4-quinone, carbazomycins D and F from Streptomyces sp. CMU-JT005. (United States)

    Ruanpanun, Pornthip; Dame, Zerihun Teklemariam; Laatsch, Hartmut; Lumyong, Saisamorn


    3-Methoxy-2-methyl-carbazole-1,4-quinone (1) together with carbazomycins D (2) and F (3) were isolated from the crude extract of Streptomyces CMU-JT005, an actinomycete with nematicidal activity. 3-Methoxy-2-methyl-carbazole-1,4-quinone is reported here for the first time from nature. In this paper, we describe the isolation and structure elucidation of the compounds together with the characterization of the Streptomyces strain CMU-JT005.

  6. Magnetite nanoparticle aided immobilization of Pseudomonas sp. GBS.5 for carbazole degradation

    Directory of Open Access Journals (Sweden)

    Poorva Mehndiratta


    Full Text Available Normal 0 false false false EN-US X-NONE X-NONE MicrosoftInternetExplorer4 Pseudomonas sp. GBS.5 is a newly isolated biosurfactant producing and carbazole degrading bacterium. In the present study, this bacterium was coated with magnetite nanoparticles, synthesized using co-precipitation method. Scanning electron microscopy (SEM studies confirmed the coating of the bacterial surface with these nanoparticles. Degradation activity of the coated cells obtained was 1.4 ppm/min as compared to 0.32 ppm/min for free cells and could be reused for five different cycles. These results indicate that magnetite nanoparticle can be efficiently used for the immobilization of biosurfactant producing bacteria involved in the degradation of polyaromatic compounds.

  7. Efficient fluorescent deep-blue and hybrid white emitting devices based on carbazole/benzimidazole compound

    KAUST Repository

    Yang, Xiaohui


    We report the synthesis, photophysics, and electrochemical characterization of carbazole/benzimidazole-based compound (Cz-2pbb) and efficient fluorescent deep-blue light emitting devices based on Cz-2pbb with the peak external quantum efficiency of 4.1% and Commission Internationale dÉnclairage coordinates of (0.16, 0.05). Efficient deep-blue emission as well as high triplet state energy of Cz-2pbb enables fabrication of hybrid white organic light emitting diodes with a single emissive layer. Hybrid white emitting devices based on Cz-2pbb show the peak external quantum efficiency exceeding 10% and power efficiency of 14.8 lm/W at a luminance of 500 cd/m2. © 2011 American Chemical Society.

  8. A new cytotoxic carbazole alkaloid and two new other alkaloids from Clausena excavata. (United States)

    Peng, Wen-Wen; Zeng, Guang-Zhi; Song, Wei-Wu; Tan, Ning-Hua


    One new carbazole alkaloid, excavatine A (1), and two additional new alkaloids, excavatine B (2) and excavatine C (3), were isolated from the stems and leaves of Clausena excavata Burm.f. (Rutaceae). Their structures were determined on the basis of detailed spectroscopic analyses, especially 2D-NMR and HR-EI-MS data. Compounds 1-3 were tested for their cytotoxic activities against A549, HeLa, and BGC-823 cancer cell lines, and for their antimicrobial activities against Candida albicans and Staphylococcus aureus. Only 1 exhibited cytotoxicity against A549 and HeLa cell lines with the IC50 values of 5.25 and 1.91 μg/ml, respectively.

  9. Synthesis of novel carbazole chalcones as radical scavenger, antimicrobial and cancer chemopreventive agents. (United States)

    Bandgar, Babasaheb P; Adsul, Laxman K; Lonikar, Shrikant V; Chavan, Hemant V; Shringare, Sadanand N; Patil, Sachin A; Jalde, Shivkumar S; Koti, Basawaraj A; Dhole, Nagesh A; Gacche, Rajesh N; Shirfule, Amol


    A series of novel carbazole chalcones has been synthesised and evaluated for radical scavenging activity, cytotoxicity and antimicrobial activities. Compounds 12m, 12o and 12c exhibited good 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, compounds 12e, 12m and 12d were excellent hydroxyl radical scavengers and compounds 12a, 12e, 12g, 12n and 12m have shown inhibition of oxidative DNA damage induced by 2,2'-azobis (2-amidinopropane hydrochloride). Compounds 12j, 12i, 12n, 12c, 12m and 12e were most active against the selected cancer cell lines. Compounds 12a, 12e and 12m showed good antibacterial activity and compounds 12h and 12m have shown good antifungal activity. All the compounds were subjected for absorption, distribution, metabolism and excretion (ADME) predictions by computational method and found that these molecules could be considered as potential candidates for oral drug development.

  10. Ethyl 4,9-dimethyl-9H-carbazole-3-carboxylate

    Directory of Open Access Journals (Sweden)

    Serkan Öncüoğlu


    Full Text Available In the title compound, C17H17NO2, the carbazole skeleton includes an ethoxycarbonyl group at the 3-position. The indole three-ring system is almost planar [maximum deviation = 0.065 (2 Å], and the ethyl ester group is inclined to its mean plane by 15.48 (2°. In the crystal, there are π–π stacking interactions between parallel benzene rings and between parallel benzene and pyrrole rings of adjacent molecules [centroid–centroid distances = 3.9473 (8 and 3.7758 (8 Å, respectively]. Weak C—H...π interactions are also present.

  11. Understanding the domino reaction between 3-chloroindoles and methyl coumalate yielding carbazoles. A DFT study. (United States)

    Domingo, Luis R; Sáez, José A; Emamian, Saeed R


    The molecular mechanism of the reaction between N-methyl-3-chloroindole and methyl coumalate yielding carbazole has been studied using DFT methods at the MPWB1K/6-311G(d,p) level in toluene. This reaction is a domino process that comprises three consecutive reactions: (i) a polar Diels-Alder (P-DA) reaction between indole and methyl coumalate yielding two stereoisomeric [2 + 4] cycloadducts (CAs); (ii) the elimination of HCl from these CAs affording two stereoisomeric intermediates; and (iii) the extrusion of CO2 in these intermediates, finally yielding the carbazole. This P-DA reaction proceeds in a completely regioselective and slightly exo selective fashion. In spite of the highly polar character of this P-DA reaction, it presents a high activation enthalpy of 21.8 kcal mol(-1) due to the loss of the aromatic character of the indole during the C-C bond formation. Thermodynamic calculations suggest that the P-DA reaction is the rate-determining step of this domino reaction; in addition, the initial HCl elimination in the formal [2 + 4] CAs is kinetically favoured over the extrusion of CO2. Although the P-DA reaction is kinetically and thermodynamically very unfavourable, the easier HCl and CO2 elimination from the [2 + 4] CAs together with the strong exergonic character of the CO2 extrusion makes the P-DA reaction irreversible. An ELF topological analysis of the bonding changes along the P-DA reaction supports a two-stage one-step mechanism. An analysis of the global DFT reactivity indices at the ground state of the reagents confirms the highly polar character of this P-DA reaction. Finally, the complete regioselectivity of the studied reactions can be explained using the Parr functions.

  12. Properties, theoretical study and crystal structure of 3-benzothiazole-9-ethyl carbazole. (United States)

    Gu, Yingchun; Lin, Dayong; Fei, Xuening; Wang, Cuihong; Li, Ling; Tang, Yalin; Zhou, Jianguo


    The title compound of 3-benzothiazole-9-ethyl carbazole was synthesized by the reaction of 3-aldehyde-9-ethyl carbazole and 2-aminothiophenol. The compound was characterized by (1) H nuclear magnetic resonance (NMR) and mass spectrometry (MS). Its crystal structure was obtained and determined by single crystal X-ray diffraction. The results showed that the crystal belongs to the orthorhombic crystal system and the cell parameters of space group P2(1)2(1)2(1) were a = 5.6626 (12) Å, b = 12.606 (3) Å, c = 22.639 (5) Å, α = 90°, β = 90°, γ = 90°, V = 1616.0 (6) Å(3) , Z = 4, Dc = 1.350 mg/m(3) . The UV-vis and fluorescence spectra were also studied preliminarily. The fluorescence spectra of the title compound with bovine serum albumin (BSA) showed that BSA could be marked with the compound and the stability constant between them was 0.82 × 10(7)  M(-1) . Meanwhile, the crystal and molecule were theoretically surveyed by density functional tight-binding (DFTB). The results showed that there was an orbital overlap for lowest unoccupied molecular orbital (LUMO) between the neighbouring molecules for the crystal, which is different from the molecule structure. It was also showed that the crystal structure is a non-conductor. Copyright © 2016 John Wiley & Sons, Ltd.

  13. Ferulic acid-carbazole hybrid compounds: Combination of cholinesterase inhibition, antioxidant and neuroprotection as multifunctional anti-Alzheimer agents. (United States)

    Fang, Lei; Chen, Mohao; Liu, Zhikun; Fang, Xubin; Gou, Shaohua; Chen, Li


    In order to search for novel multifunctional anti-Alzheimer agents, a series of ferulic acid-carbazole hybrid compounds were designed and synthesized. Ellman's assay revealed that the hybrid compounds showed moderate to potent inhibitory activity against the cholinesterases. Particularly, the AChE inhibition potency of compound 5k (IC50 1.9μM) was even 5-fold higher than that of galantamine. In addition, the target compounds showed pronounced antioxidant ability and neuroprotective property, especially against the ROS-induced toxicity. Notably, the neuroprotective effect of 5k was obviously superior to that of the mixture of ferulic acid and carbazole, indicating the therapeutic effect of the hybrid compound is better than the combination administration of the corresponding mixture.

  14. Synthesis and Characterization of Carbazole-Benzothiadiazole-Based Conjugated Polymers for Organic Photovoltaic Cells with Triazole in the Main Chain

    Directory of Open Access Journals (Sweden)

    Eunhee Lim


    Full Text Available We have synthesized a series of carbazole-benzothiadiazole-triazole based copolymers, poly[(N-9′-heptadecanyl-2,7-carbazole-co-(5,5-(4′,7′-di-2-thienyl-2′,1′,3′-benzothiadiazole-co-((4-(4-butylphenyl-3,5-diphenyl-4H-1,2,4]triazole] (PCz3TBTz by Suzuki coupling polymerization. The optical and electrochemical properties of the copolymers could be tuned by changing the comonomer unit of triazole from 0% to 80%. Organic photovoltaic (OPV cells were fabricated by blending the synthesized polymers as a donor and PCBM as an acceptor. The material solubility and film morphology were improved by introducing the triazole unit in the main chain. Improved OPV device performance of 1.74% was achieved in the presence of an optimal amount of triazole moieties.

  15. Determination by ultraviolet absorption spectrometry and theoretical calculation of dissociation constant of 1,2,3,9-tetrahydro-4H-carbazol-4-one. (United States)

    Zhang, Shufang; Zhang, Xiaoyan; Tang, Ke; Zhou, Zhengyu


    The dissociation constant of 1,2,3,9-tetrahydro-4H-carbazol-4-one was determined by ultraviolet absorption spectrometry method based on the absorption spectra of 1,2,3,9-tetrahydro-4H-carbazol-4-one at different pH in ethanol-water mixed solvents. The results show that the pK(b) was a good linear function of the volume fraction of ethanol in the concentration range studied. The dissociation constant of 1, 2, 3,9-tetrahydro-4H-carbazol-4-one in water were determined by extrapolation to be 14.04 under the condition of this experiment. The accurate pK(b) calculations of 1,2,3,9-tetrahydro-4H-carbazol-4-one have been investigated using the combination of the extended clusters-continuum model with the polarizable continuum solvation model (PCM). The calculations are performed at the B3LYP/6-31G levels. The formation of molecular clusters by means of the 1,2,3,9-tetrahydro-4H-carbazol-4-one wrapped up with water molecules leads to the weakness of the interaction between the polar solvents and the 1,2,3,9-tetrahydro-4H-carbazol-4-one, hence, the accuracy of pK(b) has been enhanced. The dissociation constant of 1,2,3,9-tetrahydro-4H-carbazol-4-one in water were calculated to be 14.10 and agreed well with experimental data.

  16. Transcriptomic insight into terpenoid and carbazole alkaloid biosynthesis, and functional characterization of two terpene synthases in curry tree (Murraya koenigii) (United States)

    Meena, Seema; Rajeev Kumar, Sarma; Dwivedi, Varun; Kumar Singh, Anup; Chanotiya, Chandan S.; Akhtar, Md. Qussen; Kumar, Krishna; Kumar Shasany, Ajit; Nagegowda, Dinesh A.


    Curry tree (Murraya koenigii L.) is a rich source of aromatic terpenes and pharmacologically important carbazole alkaloids. Here, M. koenigii leaf transcriptome was generated to gain insight into terpenoid and alkaloid biosynthesis. Analysis of de novo assembled contigs yielded genes for terpene backbone biosynthesis and terpene synthases. Also, gene families possibly involved in carbazole alkaloid formation were identified that included polyketide synthases, prenyltransferases, methyltransferases and cytochrome P450s. Further, two genes encoding terpene synthases (MkTPS1 and MkTPS2) with highest in silico transcript abundance were cloned and functionally characterized to determine their involvement in leaf volatile formation. Subcellular localization using GFP fusions revealed the plastidial and cytosolic localization of MkTPS1 and MkTPS2, respectively. Enzymatic characterization demonstrated the monoterpene synthase activity of recombinant MkTPS1, which produced primarily (−)-sabinene from geranyl diphosphate (GPP). Recombinant MkTPS2 exhibited sesquiterpene synthase activity and formed (E,E)-α-farnesene as the major product from farnesyl diphosphate (FPP). Moreover, mRNA expression and leaf volatile analyses indicated that MkTPS1 accounts for (−)-sabinene emitted by M. koenigii leaves. Overall, the transcriptome data generated in this study will be a great resource and the start point for characterizing genes involved in the biosynthetic pathway of medicinally important carbazole alkaloids. PMID:28272514


    Directory of Open Access Journals (Sweden)

    Felipe Sánchez-Minero


    Full Text Available En este trabajo se estudió la velocidad de reacción del carbazol sobre catalizadores NiMo soportados sobre Al2O3 modificada superficialmente con SiO2 (0 y 10 % en peso de SiO2 en el soporte. Los catalizadores fueron evaluados en un reactor intermitente a cuatro temperaturas (287, 300, 312 y 325oC, presión de 4.0 MPa y relación molar hidrogeno/carbazol de 2400. A partir de los resultados experimentales se realizó un estudio cinético utilizando ecuaciones del tipo Langmuir-Hinshelwood (L-H. Luego, los parámetros cinéticos fueron estimados mediante la minimización de Powell (programa Scientist de MicroMath. Los resultados muestran que el catalizador con sílice (NiMo-SAC 10 alcanza una mayor actividad para la HDN de carbazol debido a que presenta un mayor número de sitios activos (valor de A, así como una menor fuerza de adsorción entre el reactante y la superficie catalítica (valor de KN, lo cual posiblemente favorece una mejor regeneración de sitios activos.


    Institute of Scientific and Technical Information of China (English)

    Cheuk-lam Ho; Wai-yeung Wong


    A new luminescent and thermally stable platinum(Ⅱ) polyyne polymer trans-[-Pt(PBu3)2C≡CArC≡C-]n (P1) containing the 2,7-fluorene chromophoric spacer substituted by pendant carbazolyl group via long alkyl bridges. The regiochemical structures of these compounds were studied by various spectroscopic analyses. We report the photophysical properties of this group 10 polymetallayne and a comparison was made to its binuclear model complex trans-[Pt(Ph)(PEt3)2C≡CArC≡CPt(Ph)(PEt3)2] (M1) as well as to those with non-carbazole-containing fluorene spacer (P2 and M2). Upon photoexcitation, each of P1 and M1 emits an intense purple-blue fluorescence emission in the near-UV to visible region in dilute fluid solutions at room temperature. Harvesting of organic triplet emissions harnessed through the strong heavy-atom effects of platinum metal was examined and at 77 K, each of the metalated compounds displayed dual emission bands, viz. Both the fluorescence and the lower-lying phosphorescence. Spectroscopic results revealed that the formation of excimers was suppressed by introducing carbazole side groups. The spatial extent of the lowest singlet and triplet excitons in PI and M1 was fully elucidated. Such organometallic poly(fluorenyleneethynylene)s anchored with the carbazole pendants was found to have an improved thermal stability and suppressed aggregation.

  19. 4-Fluoro-N-methyl-N-(1,2,3,4-tetra­hydro­carbazol-3-yl)benzene­sulfonamide (United States)

    Rasmussen, Kaspar Gothardt; Ulven, Trond; Bond, Andrew D.


    In the title compound, C19H19FN2O2S, the hydrogenated six-membered ring of the carbazole unit adopts a half-chair conformation and the plane of the fluoro­phenyl ring forms a dihedral angle of 41.5 (1)° with respect to the carbazole mean plane. The crystal structure is segregated into layers containing the carbazole units and fluoro­phenyl rings in alternate (200) planes. The carbazole units form centrosymmetric face-to-face inter­actions [inter­planar separation = 4.06 (1) Å] and edge-to-face inter­actions in which the N—H group is directed towards an adjacent carbazole face, with a shortest H⋯C contact of 2.53 Å. The fluoro­phenyl rings form face-to-face contacts with an approximate inter­planar separation of 3.75 Å and a centroid–centroid distance of 4.73 (1) Å. PMID:21582475

  20. Antimicrobial activity of carbazole compounds:research advances%具有抗微生物活性咔唑类化合物的研究进展

    Institute of Scientific and Technical Information of China (English)

    颜建平; 周成合; 吉庆刚; 耿蓉霞


    咔唑类化合物是一类重要的芳杂环化合物,在抗细菌、抗真菌和抗病毒方面具有较好的应用前景,深受研究者关注.有关咔唑类化合物的研究包括天然生物碱的分离、全合成、结构修饰及其抗微生物活性研究与开发.本文结合本课题组的研究,综述了近年来咔唑类化合物的抗微生物活性及其构效关系的研究进展.%Carbazole compounds, a class of important aromatic heterocyclic compounds, possess extensive application prospect as antibacterial, antifungal and antiviral agents, and thus receive increasing attention. The researches on carbazole compounds include isolation and total synthesis of naturally carbazole alkaloids, structure modification of carbazole derivatives and investigation on their recovery of antimicrobial activities. This paper reviews recent research advances in carbazole compounds and their antimicrobial activities. The structure-activity relationship is also discussed.

  1. Neuroprotective efficacy of aminopropyl carbazoles in a mouse model of amyotrophic lateral sclerosis. (United States)

    Tesla, Rachel; Wolf, Hamilton Parker; Xu, Pin; Drawbridge, Jordan; Estill, Sandi Jo; Huntington, Paula; McDaniel, Latisha; Knobbe, Whitney; Burket, Aaron; Tran, Stephanie; Starwalt, Ruth; Morlock, Lorraine; Naidoo, Jacinth; Williams, Noelle S; Ready, Joseph M; McKnight, Steven L; Pieper, Andrew A


    We previously reported the discovery of P7C3, an aminopropyl carbazole having proneurogenic and neuroprotective properties in newborn neural precursor cells of the hippocampal dentate gyrus. We have further found that chemicals having efficacy in this in vivo screening assay also protect dopaminergic neurons of the substantia nigra following exposure to the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, a mouse model of Parkinson disease. Here, we provide evidence that an active analog of P7C3, known as P7C3A20, protects ventral horn spinal cord motor neurons from cell death in the G93A-SOD1 mutant mouse model of amyotrophic lateral sclerosis (ALS). P7C3A20 is efficacious in this model when administered at disease onset, and protection from cell death correlates with preservation of motor function in assays of walking gait and in the accelerating rotarod test. The prototypical member of this series, P7C3, delays disease progression in G93A-SOD1 mice when administration is initiated substantially earlier than the expected time of symptom onset. Dimebon, an antihistaminergic drug with significantly weaker proneurogenic and neuroprotective efficacy than P7C3, confers no protection in this ALS model. We propose that the chemical scaffold represented by P7C3 and P7C3A20 may provide a basis for the discovery and optimization of pharmacologic agents for the treatment of ALS.

  2. Oxadiazole-carbazole polymer (POC)-Ir(ppy)3 tunable emitting composites (United States)

    Bruno, Annalisa; Borriello, Carmela; Di Luccio, Tiziana; Sessa, Lucia; Concilio, Simona; Haque, Saif A.; Minarini, Carla


    POC polymer is an oxadiazole-carbazole copolymer we have previously synthetized and established as light emitting material in Organic Light Emitting Devices (OLEDs), although POC quantum yield emission efficiency and color purity still need to be enhanced. On the other hand, tris[2-phenylpyridinato-C2,N]iridium(III) (Ir(ppy)3) complexes, namely Ir(ppy)3 are among the brightest luminophores employed in green light emitting devices. Our aim, in this work, is to take advantage of Ir(ppy)3 bright emission by combining the Ir complex with blue emitting POC to obtain tunable light emitting composites over a wide range of the visible spectrum. Here we have investigated the optical proprieties POC based nanocomposites with different concentrations of Ir(ppy)3, ranging from 1 to 10 wt%. Both spectral and time resolved fluorescence measurements show an efficient energy transfer from the polymer to the dopants, resulting in white-emitting composites. The most intense and stable emission has been found when POC was doped with about 5 wt% concentration of Ir(ppy)3.


    Institute of Scientific and Technical Information of China (English)

    Ze Liu; Li-xiang Wang; Xia-bin Jing; Fo-song Wang


    Two new blue light-emitting PPV-based conjugated copolymers containing both an electron-withdrawing unit (triazole-TAZ) and electron-rich moieties (carbazole-CAR and bicarbazole-BCAR) were prepared by Wittig condensation polymerization between the triazole diphosphonium salt and the corresponding dialdehyde monomers. Their structures and properties were characterized by FT-IR, TGA, DSC, UV-Vis, PL spectroscopy and electrochemical measurements. The resulting copolymers are soluble in common organic solvents and thermally stable with a Ts of 147C for TAZ-CAR-PPV and of 157C for TAZ-BCAR-PPV. The maximum photoluminescence wavelengths of TAZ-CAR-PPV and TAZ-BCAR-PPV film appear at 460 nm and 480 nm, respectively. Cyclic voltammetry measurement demonstrates that TAZ-BCAR-PPV has good electrochemical reversibility, while TAZ-CAR-PPV exhibits the irreversible redox process. The triazole unit was found to be an effective π-conjugation interrupter and can play the rigid spacer role in determining the emission colour of the resulting copolymer.


    Institute of Scientific and Technical Information of China (English)

    Ran-sheng Liu; Wen-jin Zeng; Bin Du; Wei Yang; Qiong Hou; Wei Shi; Yong Zhang; Yong Cao


    A series of conjugated copolymers derived from 9-ethylhexyl-2,7-carbazole (Cz) and 4,7-di(4-hexylthien-2-yl)-2,1,3-benzothiadiazole (DHTBT) was synthesized by Suzuki polycondensation. The photo- and electro-luminescentproperties of these polymers were investigated. Efficient energy transfer from the Cz segment to the DHTBT unit occurseven if the DHTBT content as low as 1 mol%. PL emission was red-shifted significantly from 645 nm to 700 nm with theincrease in DHTBT content by 1-50 mol%. PL efficiencies decreased with the increase in DHTBT content in the polymersfrom 55% for PCzDHTBT1 gradually down to 7% for PCzDHTBT50. EL emission of these polymers red-shifted from640 nm to 690 nm when the DHTBT content increased from 1 mol% to 50 mol%. The highest external quantum efficiencywas 1.67% for PCzDHTBT25 with the maximum luminescence of 870 cd/m,'2 in the device configuration of ITO/PEDOT:PSS/polymer/PFN/Ba/Al. The enhancement of device performances could be due to the improved electron injection byinserting the amino-containing polyfluorene (PFN) layer. These polymers are promising candidates as a red emitter in thefull-color polymer light emitting diodes (PLEDs).

  5. Quickly Updatable Hologram Images Using Poly(N-vinyl Carbazole (PVCz Photorefractive Polymer Composite

    Directory of Open Access Journals (Sweden)

    Wataru Sakai


    Full Text Available Quickly updatable hologram images using photorefractive (PR polymer composite based on poly(N-vinyl carbazole (PVCz is presented. PVCz is one of the pioneer materials of photoconductive polymers. PR polymer composite consists of 44 wt % of PVCz, 35 wt % of 4-azacycloheptylbenzylidene-malonitrile (7-DCST as a nonlinear optical dye, 20 wt % of carbazolylethylpropionate (CzEPA as a photoconductive plasticizer and 1 wt % of 2,4,7-trinitro-9-fluorenone (TNF as a sensitizer. PR composite gives high diffraction efficiency of 68% at E = 45 V μm−1. Response speed of optical diffraction is the key parameter for real-time 3D holographic display. The key parameter for obtaining quickly updatable holographic images is to control the glass transition temperature lower enough to enhance chromophore orientation. Object image of the reflected coin surface recorded with reference beam at 532 nm (green beam in the PR polymer composite is simultaneously reconstructed using a red probe beam at 642 nm. Instead of using a coin object, an object image produced by a computer was displayed on a spatial light modulator (SLM and used for the hologram. The reflected object beam from an SLM was interfered with a reference beam on PR polymer composite to record a hologram and simultaneously reconstructed by a red probe beam.

  6. New chromophores based on combination of ethylenedioxythiophene and carbazole fragments: synthesis and optoelectronic properties (United States)

    Bakiev, A. N.; Mayorova, O. A.; Gorbunov, A. A.; Lunegov, I. V.; Shklyaeva, E. V.; Abashev, G. G.


    Two new D-π-A chromophores composed of an electron-donating carbazole unit linked through π- bridges, bearing 3,4-ethylenedioxythiophene (EDOT) moiety, with an electron withdrawing dicyanovinyl group (DCV) were successfully synthesized involving Suzuki or Heck cross-coupling and Knöevenagel reactions as the key steps. The obtained compounds absorb light over a broad spectral range, including the visible spectrum. The HOMO/LUMO energies and band gap energy values (Eg) were calculated on the basis of the experimental optical and electrochemical data: HOMO, LUMO, Eg (eV), -5.51, -3.14, 2.37 (4), -5.34, -3.14, 2.20 (7). The presence of the HC=CH unit in compound 7 resulted in the increase of the HOMO energy level, the decrease of a band gap value and red shifts of the absorption and emission bands in comparison with those of 4. Large Stokes shifts and broadband luminescence inherent to both chromophores suggest their use as materials for luminescent solar collectors (LSCs). The obtained compounds demonstrated good solubility and suitable thin-film forming properties. For this reason, they may be suitable for solution-processable photovoltaic applications.

  7. Carbazole based electrochromic polymers with benzoazole units: Effect of heteroatom variation on electrochromic performance

    Directory of Open Access Journals (Sweden)

    C. Doyranli


    Full Text Available A series of carbazole-based polymers were synthesized via Suzuki polymerization between N-(2-ethylhexylcarbazole-3,6-bis(ethyleneboronate (Cbz and dibromobenzazole unit. Three different polymers, PCBN, PCBS and PCBSe were obtained from 4,7-dibromo-2-hexyl-2H-benzotriazole (BN, 4,7-dibromo-2,1,3-benzothiadiazole- (BS and 4,7-dibromo-2,1,3-benzoselenadiazole (BSe, respectively. It is observed that, the variation of heteroatoms (N,S and Se on the benzazole unit have most important effect on electro-optic properties of the PCBX polymers. Neutral state color of the polymer films and their electrochromic performances are also influenced. Among the synthesized polymers, the PCBS bearing 2,1,3-benzothiadiazole as acceptor units has a broad absorption and 50% of ΔT in the near-IR regime at the oxidized state. This property of PCBS is a great advantage for near-IR electrochromic applications.

  8. 2-(4-Chloro-2-nitrophenyl-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde

    Directory of Open Access Journals (Sweden)

    S. Gopinath


    Full Text Available In the title compound, C25H15ClN2O6S, the carbazole ring system is essentially planar, with a maximum deviation of 0.152 (3 Å for the C atom to which the 4-chloro-2-nitrophenyl ring is attached. Its mean plane is almost orthogonal to the phenylsulfonyl and nitrophenyl rings, making dihedral angles of 82.64 (14 and 79.89 (13°, respectively. The N atom of the nitro group deviates by 0.032 (3 Å from the benzene ring to which it is attached. The molecular structure features intramolecular O—H...O and C—H...O hydrogen bonds, which generate three S(6 ring motifs. In the crystal, molecules are linked by C—H...O hydrogen bonds, which generate C(6 and C(9 chains running in the [100] and [010] directions, respectively, forming a two-dimensional network lying parallel to (001. There are also R43(28 supramolecular graph-set ring motifs enclosed within these networks.

  9. Study on the Synthesis and Spectra of a Novel Kind of Carbozole Benzothiazole Indole Styryl Cyanine Dye with a Carbazole Bridged Chain. (United States)

    Fei, Xuening; Hao, Yachao; Gu, Yingchun; Li, Chao; Yu, Lu


    Based on the frequently-used cyanine dye probe thiazole orange (TO) and Cy3, a novel kind of styryl cyanine dye was designed and synthesized. Carbazole was inserted into the structures of two cyanine dyes, TO and Cy3, to act as a bridge to link the benzothiazole and indole. This modification resulted in a novel kind of carbozole benzothiazole indole cyanine dye with a carbazole-bridged chain. The dyes were characterized by HNMR and MS. The spectra of the novel dyes were also studied and the results showed that the fluorescence wavelength of novel carbazole benzothiazole indole cyanine dye shifted red, the Stokes shift and Fluorescence quantum yields increased and the fluorescence intensity was enhanced compared to that of TO. These results indicated that the novel dye could be used as an excellent fluorescent probe in biological labeling.

  10. Novel high band gap pendant-borylated carbazole polymers with deep HOMO levels through direct +N=B- interaction for organic photovoltaics

    DEFF Research Database (Denmark)

    Brandt, Rasmus G.; Sveegaard, Steffen G.; Xiao, Manjun;


    '] dithiophene) (P(3,6-BCBDT)) and poly(3,6-(N-di(2,4,6-trimethyl)phenylboryl-carbazole)-alt-3,3 '''- didodecyl-2,2': 5',2 '': 5 '',2 '''-quaterthiophene) (P(3,6-BCQT)), which result in ambipolarity, high electron affinity, and deep HOMO levels. The quasi-donor-acceptor nature of the two polymers was confirmed......In this communication, we investigate the direct and still conjugated intramolecular +N=B- interactions in novel high band gap borylated carbazole containing polymers, namely, poly(3,6-(N-di(2,4,6-trimethyl)-phenylboryl-carbazole)-alt- 4,8-di(5-(2-ethylhexyl)thiophene-2-yl)benzo[1,2-b: 4,5-b...

  11. Synthesis and spectra of a kind of novel longer-wavelength benzoxazole indole styryl cyanine dye with a carbazole-bridged chain. (United States)

    Fei, Xuening; Gu, Yingchun; Li, Chao; Liu, Yuru; Yu, Lu


    Based on cyanine dye probe oxazole yellow (YO) and Cy(3), a series of novel styryl cyanine dyes were designed and synthesized. Carbazole was inserted into the structures of YO and Cy(3) to act as a bridge to link the benzoxazole and indole group. This modification resulted in a novel kind of benzoxazole indole styryl cyanine dye with a carbazole-bridged chain. The dyes were characterized by (1)HNMR and MS. The spectra of the novel dyes were also performed and the results showed that the maximum emission wavelength of the carbazole styryl cyanine dye was shifted red, the Stokes shift increased and the fluorescence intensity enhanced compared with those of YO and Cy(3). These results indicated that the novel dye could be used as an excellent fluorescent probe in biological labeling.

  12. 3-苯并嚼唑-6-甲酰基咔唑的合成%Synthesis of 3-benzoxazole-6-formyl Carbazole

    Institute of Scientific and Technical Information of China (English)

    杨旭; 费学宁; 谷迎春; 李超


    Two novel 3-benzoxazole-6-formyl carbazole derivatives were synthesized from carbazole by alkylation, formylation, oxidation of carbazole schiff bases and formylation. The cqmpounds' structures were characterized by 1H NMR and MS and their fluorescent spectra were preliminarily studied.%以咔唑为原料,经过烷基化、甲酰化、咔唑席夫碱氧化、甲酰化,合成了2个3-苯并嗯唑-6-甲酰基咔唑衍生物,其结构经1HNMR和MS表征,并初步研究了其荧光光谱.

  13. Synthesis of Novel 1-Substituted and 1,9-Disubstituted-1,2,3,4-tetrahydro-9H-Carbazole Derivatives as Potential Anticancer Agents

    Directory of Open Access Journals (Sweden)

    H. I. El-Diwani


    Full Text Available Condensation of 1-acetyl-1,2,3,4-tetrahydro-9H-carbazole (2 with some amino compounds furnished the corresponding imino derivatives 3a-e. Compound 3a reacted with chloroacetic acid and underwent cyclization to give the thiazolidine derivative 5. Also, treatment of 3c with thionyl chloride caused cyclization to yield the [1,2,6]thiadiazino derivative 6, which gave the corresponding N-formyl derivative 7 upon heating with ethyl formate. In addition, interaction of 3d with ethyl cyanoacetate yielded the monoamide of malonic acid derivative 8. Acylation of carbazole 1 with succinoyl chloride or phenylacetyl choride produced the corresponding azepine (11 and 1,9-diphenyl acetyl derivatives (14, respectively. Compounds 11, 14 were further reacted to give the carbazole derivatives 12, 13 and 15a,b. The cytotoxic activity for some of the prepared compounds against breast cancer B20 is discussed.

  14. Synthesis, photophysics, electrochemistry, thermal stability and electroluminescent performances of a new europium complex with bis(β-diketone) ligand containing carbazole group. (United States)

    Liu, Jian; Liang, Quan-Bin; Wu, Hong-Bin


    We synthesized a new europium complex [Eu(ecbpd)3 (Phen)] with bis(β-diketone) ligand containing a carbazole group, in which ecbpd and Phen are dehydro-3,3'-(9-ethyl-9H-carbazole-3,6-diyl)bis(1-phenylpropane-1,3-dione) and 1,10-phenanthroline, respectively. Its UV/vis and photoluminescent spectra, quantum yield, luminescence lifetime, electrochemistry, thermal stability and electroluminescent performances were studied. This europium complex showed low efficiency luminescence, which is probably due to the mismatching energy levels of its ligand and Eu(3)(+) , as well as the double Eu(3)(+) core resonance.

  15. The genes coding for the conversion of carbazole to catechol are flanked by IS6100 elements in Sphingomonas sp. strain XLDN2-5.

    Directory of Open Access Journals (Sweden)

    Zhonghui Gai

    Full Text Available BACKGROUND: Carbazole is a recalcitrant compound with a dioxin-like structure and possesses mutagenic and toxic activities. Bacteria respond to a xenobiotic by recruiting exogenous genes to establish a pathway to degrade the xenobiotic, which is necessary for their adaptation and survival. Usually, this process is mediated by mobile genetic elements such as plasmids, transposons, and insertion sequences. FINDINGS: The genes encoding the enzymes responsible for the degradation of carbazole to catechol via anthranilate were cloned, sequenced, and characterized from a carbazole-degrading Sphingomonas sp. strain XLDN2-5. The car gene cluster (carRAaBaBbCAc and fdr gene were accompanied on both sides by two copies of IS6100 elements, and organized as IS6100::ISSsp1-ORF1-carRAaBaBbCAc-ORF8-IS6100-fdr-IS6100. Carbazole was converted by carbazole 1,9a-dioxygenase (CARDO, CarAaAcFdr, meta-cleavage enzyme (CarBaBb, and hydrolase (CarC to anthranilate and 2-hydroxypenta-2,4-dienoate. The fdr gene encoded a novel ferredoxin reductase whose absence resulted in lower transformation activity of carbazole by CarAa and CarAc. The ant gene cluster (antRAcAdAbAa which was involved in the conversion of anthranilate to catechol was also sandwiched between two IS6100 elements as IS6100-antRAcAdAbAa-IS6100. Anthranilate 1,2-dioxygenase (ANTDO was composed of a reductase (AntAa, a ferredoxin (AntAb, and a two-subunit terminal oxygenase (AntAcAd. Reverse transcription-PCR results suggested that carAaBaBbCAc gene cluster, fdr, and antRAcAdAbAa gene cluster were induced when strain XLDN2-5 was exposed to carbazole. Expression of both CARDO and ANTDO in Escherichia coli required the presence of the natural reductases for full enzymatic activity. CONCLUSIONS/SIGNIFICANCE: We predict that IS6100 might play an important role in the establishment of carbazole-degrading pathway, which endows the host to adapt to novel compounds in the environment. The organization of the car

  16. One-Pot Synthesis of N-(α-Peroxy)Indole/Carbazole via Chemoselective Three-Component Condensation Reaction in Open Atmosphere

    KAUST Repository

    Wang, Xinbo


    A facile one-pot synthesis of N-(α-peroxy)indole and N-(α-peroxy)carbazole has been developed using metal-free, organo-acid-catalyzed three-component condensation reactions of indole/carbazole, aldehyde, and peroxide. Based on the reaction discovered, a new synthetic proposal for Fumitremorgin A and Verruculogen is introduced. Such a protocol could be easily handled and scaled up in an open atmosphere with a wide substrate scope, enabling the construction of a new molecule library.

  17. A New Star-shaped Carbazole Derivative with Polyhedral Oligomeric Silsesquioxane Core: Crystal Structure and Unique Photoluminescence Property. (United States)

    Xu, Zixuan; Yu, Tianzhi; Zhao, Yuling; Zhang, Hui; Zhao, Guoyun; Li, Jianfeng; Chai, Lanqin


    A new inorganic–organic hybrid material based on polyhedral oligomeric silsesquioxane (POSS) capped with carbazolyl substituents, octakis[3-(carbazol-9-yl)propyldimethylsiloxy]-silsesquioxane (POSS-8Cz), was successfully synthesized and characterized. The X-ray crystal structure of POSS-8Cz were described. The photophysical properties of POSS-8Cz were investigated by using UV–vis,photoluminescence spectroscopic analysis. The hybrid material exhibits blue emission in the solution and the solid film.The morphology and thermal stablity properties were measured by X-ray diffraction (XRD) and TG-DTA analysis.

  18. Cloning and expression of meta-cleavage enzyme (CarB of carbazole degradation pathway from Pseudomonas stutzeri

    Directory of Open Access Journals (Sweden)

    Ariane Leites Larentis


    Full Text Available In this work, the 1082bp PCR product corresponding to carBaBb genes that encode the heterotetrameric enzyme 2'-aminobiphenyl-2,3-diol 1,2-dioxygenase (CarB, involved in the Pseudomonas stutzeri ATCC 31258 carbazole degradation pathway, was cloned using the site-specific recombination system. Recombinant clones were confirmed by PCR, restriction enzyme digestion and sequencing. CarB dioxygenase was expressed in high levels and in active form in Escherichia coli BL21-SI using the His-tagged expression vector pDEST TM17 and salt induction for 4h.Carbazol e seus derivados são compostos nitrogenados aromáticos, presentes comumente em petróleo e potencialmente poluentes. A rota de biodegradação de carbazol a ácido antranílico em Pseudomonas sp. é composta por três enzimas responsáveis, respectivamente, pelas reações de dioxigenação angular, meta-clivagem e hidrólise. A segunda enzima da rota, 2'-aminobifenil-2,3-diol 1,2-dioxigenase (CarB, codificada por dois genes (carBa e carBb, é um heterotetrâmero com atividade catalítica na quebra do anel catecol do susbtrato na posição meta. Neste trabalho, foi clonado o produto de PCR de 1082pb correspondente aos genes carBaBb da bactéria degradadora de carbazol Pseudomonas stutzeri ATCC 31258. A estratégia de clonagem empregada foi a de recombinação sítio-específica e a construção dos plasmídeos foi confirmada por PCR, digestão com enzima de restrição e seqüenciamento. A enzima ativa foi expressa em altas concentrações em vetor pDEST TM17 com cauda de histidina e promotor T7 em Escherichia coli BL21-SI com indução por NaCl durante 4h.

  19. Indolo[2,3-b]carbazoles with tunable ground states: How Clar's aromatic sextet determines the singlet biradical character

    KAUST Repository

    Luo, Ding


    Polycyclic hydrocarbons (PHs) with a singlet biradical ground state have recently attracted extensive interest in physical organic chemistry and materials science. Replacing the carbon radical center in the open-shell PHs with a more electronegative nitrogen atom is expected to result in the more stable aminyl radical. In this work, two kinetically blocked stable/persistent derivatives (1 and 2) of indolo[2,3-b]carbazole, an isoelectronic structure of the known indeno[2,1-b]fluorene, were synthesized and showed different ground states. Based on variable-temperature NMR/ESR measurements and density functional theory calculations, it was found that the indolo[2,3-b]carbazole derivative 1 is a persistent singlet biradical in the ground state with a moderate biradical character (y0 = 0.269) and a small singlet-triplet energy gap (ΔES-T ≅ -1.78 kcal mol-1), while the more extended dibenzo-indolo[2,3-b]carbazole 2 exhibits a quinoidal closed-shell ground state. The difference can be explained by considering the number of aromatic sextet rings gained from the closed-shell to the open-shell biradical resonance form, that is to say, two for compound 1 and one for compound 2, which determines their different biradical characters. The optical and electronic properties of 2 and the corresponding aromatic precursors were investigated by one-photon absorption, transient absorption and two-photon absorption (TPA) spectroscopies and electrochemistry. Amphoteric redox behaviour, a short excited lifetime and a moderate TPA cross section were observed for 2, which can be correlated to its antiaromaticity and small biradical character. Compound 2 showed high reactivity to protic solvents due to its extremely low-lying LUMO energy level. Unusual oxidative dimerization was also observed for the unblocked dihydro-indolo[2,3-b]carbazole precursors 6 and 11. Our studies shed light on the rational design of persistent aminyl biradicals with tunable properties in the future. This journal

  20. Neuroprotective efficacy of aminopropyl carbazoles in a mouse model of Parkinson disease. (United States)

    De Jesús-Cortés, Héctor; Xu, Pin; Drawbridge, Jordan; Estill, Sandi Jo; Huntington, Paula; Tran, Stephanie; Britt, Jeremiah; Tesla, Rachel; Morlock, Lorraine; Naidoo, Jacinth; Melito, Lisa M; Wang, Gelin; Williams, Noelle S; Ready, Joseph M; McKnight, Steven L; Pieper, Andrew A


    We previously reported the discovery of P7C3, an aminopropyl carbazole having proneurogenic and neuroprotective properties in newborn neural precursor cells of the dentate gyrus. Here, we provide evidence that P7C3 also protects mature neurons in brain regions outside of the hippocampus. P7C3 blocks 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-mediated cell death of dopaminergic neurons in the substantia nigra of adult mice, a model of Parkinson disease (PD). Dose-response studies show that the P7C3 analog P7C3A20 blocks cell death with even greater potency and efficacy, which parallels the relative potency and efficacy of these agents in blocking apoptosis of newborn neural precursor cells of the dentate gyrus. P7C3 and P7C3A20 display similar relative effects in blocking 1-methyl-4-phenylpyridinium (MPP(+))-mediated death of dopaminergic neurons in Caenorhabditis elegans, as well as in preserving C. elegans mobility following MPP(+) exposure. Dimebon, an antihistaminergic drug that is weakly proneurogenic and neuroprotective in the dentate gyrus, confers no protection in either the mouse or the worm models of PD. We further demonstrate that the hippocampal proneurogenic efficacy of eight additional analogs of P7C3 correlates with their protective efficacy in MPTP-mediated neurotoxicity. In vivo screening of P7C3 analogs for proneurogenic efficacy in the hippocampus may thus provide a reliable means of predicting neuroprotective efficacy. We propose that the chemical scaffold represented by P7C3 and P7C3A20 provides a basis for optimizing and advancing pharmacologic agents for the treatment of patients with PD.

  1. Crystal structure of poly[[[μ4-5-(9H-carbazol-9-ylisophthalato][μ3-5-(9H-carbazol-9-ylisophthalato]bis(dimethylformamide(methanoldizinc] dimethylformamide monosolvate

    Directory of Open Access Journals (Sweden)

    Liubov M. Lifshits


    Full Text Available The structure of the polymeric title compound, {[Zn2(C20H11NO42(C3H7NO2(CH3OH]·C3H7NO}n, comprises carbazolylisophthalate moieties connecting dimetallic tetracarboxylate zinc secondary building units (SBUs parallel to [100] and [010], leading to a layer-like arrangement parallel to (001. Each SBU consists of two Zn atoms in slightly distorted tetrahedral and octahedral coordination environments [Zn...Zn = 3.5953 (6 Å]. Three carboxylate groups bridge the two Zn atoms in a μ2-O:O′ mode, whereas the fourth coordinates through a single carboxylate O atom (μ1-O. The O atoms of two dimethylformamide (DMF and one methanol molecule complete the Zn coordination spheres. The methanol ligand interacts with the noncoordinating DMF molecule via an O—H...O hydrogen bond of medium strength. Carbazoles between the layers interdigitate through weak C—H....π interactions to form a laminar solid stacked along [010]. Two kinds of C—H...π interactions are present, both with a distance of 2.64 Å, between the H atoms and the centroids, and a third C—H...π interaction, where the aromatic H atom is located above the carbazole N-atom lone pair (H...N = 2.89 Å. Several C—H...O interactions occur between the coordinating DMF molecule, the DMF solvent molecule, and ligating carboxylate O atoms.

  2. Molecular modeling and experimental studies on structure and NMR parameters of 9-benzyl-3,6-diiodo-9H-carbazole

    DEFF Research Database (Denmark)

    Radula-Janik, Klaudia; Kupka, Teobald; Ejsmont, Krzysztof;


    A combined experimental and theoretical study has been performed on 9-benzyl-3,6-diiodo-9H-carbazole. Experimental X-ray (100.0 K) and room-temperature 13C NMR studies were supported by advanced density functional theory (DFT) calculations. The non relativistic structure optimization was performe...

  3. Novel Hole Transporting Materials Based on 4-(9H-Carbazol-9-yltriphenylamine Derivatives for OLEDs

    Directory of Open Access Journals (Sweden)

    Quynh Pham Bao Nguyen


    Full Text Available During the past few years, organic light emitting diodes (OLEDs have been increasingly studied due to their emerging applicability. However, some of the properties of existing OLEDs could be improved, such as their overall efficiency and durability; these aspects have been addressed in the current study. A series of novel hole-transporting materials (HTMs 3a–c based on 4-(9H-carbazol-9-yltriphenylamine conjugated with different carbazole or triphenylamine derivatives have been readily synthesized by Suzuki coupling reactions. The resulting compounds showed good thermal stabilities with high glass transition temperatures between 148 and 165 °C. The introduction of HTMs 3b and 3c into the standard devices ITO/HATCN/NPB/HTMs 3 (indium tin oxide/dipyrazino(2,3-f:2ꞌ,3ꞌ-hquinoxaline 2,3,6,7,10,11-hexacarbonitrile/N,Nꞌ-bis(naphthalen-1-yl-N,Nꞌ-bis(phenyl-benzidine/HTMs/CBP (4,4ꞌ-Bis(N-carbazolyl-1,1ꞌ-biphenyl: 5% Ir(ppy3/Bphen/LiF/Al (tris[2-phenylpyridinato-C2,N]iridium(III/4,7-diphenyl-1,10-phenanthroline/LiF/Al resulted in significantly enhanced current, power, and external quantum efficiencies (EQE as compared to the reference device without any layers of HTMs 3.


    Institute of Scientific and Technical Information of China (English)

    Lei Ying; Yan-hu Li; Cai-hong Wei; Min-quan Wang; Wei Yang; Hong-bin Wu; Yong Cao


    Efficient white light emitting polymers were synthesized based on poly(9,9-dioctylfluorene-co-dibenzothiopheneS,S-dioxide) as blue emitter and a bisphenylamine functionalized 2,1,3-benzothiadiazole (DPABT) as red emitter.It was found that the incorporation of hole-transporting carbazole moiety into polymer main chain could effectively reduce the hole injection barriers,which can lead to distinctly improved charge balance in the emissive layer.Additionally,the holetransporting carbazole units may form efficient bipolar host with electron-transporting dibenzothiophene-S,S-dioxide units.The white light emitting diodes based on single polymer PFSOCzDPABT showed the maximum luminous efficiency of 3.3 cd/A with the maximum luminance of 10282 cd/m2,and the luminous efficiency showed only 24% roll off at current density of 400 mA/cm2.These Commission Intemationale d'Enclairage (CIE) coordinates of the devices changed slightly with the driving voltages increasing from 8 V to 12 V,and were very close to National Television System Committee (NTSC) standard white light emission of (0.33,0.33).The results indicated that the incorporating bipolar host and low band gap DPABT unit was a promising way to achieve efficient single white light emitting copolymers.

  5. Ultrafast intramolecular charge transfer with N-(4-cyanophenyl)carbazole. Evidence for a LE precursor and dual LE + ICT fluorescence. (United States)

    Galievsky, Victor A; Druzhinin, Sergey I; Demeter, Attila; Mayer, Peter; Kovalenko, Sergey A; Senyushkina, Tamara A; Zachariasse, Klaas A


    The photophysics of N-(4-cyanophenyl)carbazole (NP4CN) was investigated by using absorption and fluorescence spectra, picosecond fluorescence decays, and femtosecond transient absorption. In the nonpolar n-hexane as well as in the polar solvent acetonitrile (MeCN), a locally excited (LE) state is detected, as a precursor for the intramolecular charge transfer (ICT) state. A LE → ICT reaction time τ(2) at 22 °C of 0.95 ps in ethyl cyanide (EtCN) and 0.32 ps in MeCN is determined from the decay of the LE excited state absorption (ESA) maximum around 620 nm. In the ESA spectrum of NP4CN in n-hexane at a pump-probe delay time of 100 ps, an important contribution of the LE band remains alongside the ICT band, in contrast to what is observed in EtCN and MeCN. This shows that a LE ⇄ ICT equilibrium is established in this solvent and the ICT reaction time of 0.5 ps is equal to the reciprocal of the sum of the forward and backward ICT rate constants 1/(k(a) + k(d)). In the photostationary S(0) → S(n) absorption spectrum of NP4CN in n-hexane and MeCN, an additional CT absorption band appears, absent in the sum of the spectra of its electron donor (D) and acceptor (A) subgroups carbazole and benzonitrile. This CT band is located at an energy of ∼4000 cm(-1) lower than for N-phenylcarbazole (NPC), due to the larger electron affinity of the benzonitrile moiety of NP4CN than the phenyl subunit of NPC. The fluorescence spectrum of NP4CN in n-hexane at 25 °C mainly consists of a structured LE emission, with a small ICT admixture, indicating that a LE → ICT reaction just starts to occur under these conditions. In di-n-pentyl ether (DPeE) and di-n-butyl ether (DBE), a LE emission is found upon cooling at the high-energy edge of the ICT fluorescence band, caused by the onset of dielectric solvent relaxation. This is not the case in more polar solvents, such as diethyl ether (DEE) and MeCN, in which a structureless ICT emission band fully overlaps the strongly quenched LE

  6. Design, synthesis and biological evaluation of novel 1,2,3-triazolyl [Formula: see text]-hydroxy alkyl/carbazole hybrid molecules. (United States)

    Rad, Mohammad Navid Soltani; Behrouz, Somayeh; Behrouz, Marzieh; Sami, Akram; Mardkhoshnood, Mehdi; Zarenezhad, Ali; Zarenezhad, Elham


    The design, synthesis and biological study of several novel 1,2,3-triazolyl [Formula: see text]-hydroxy alkyl/carbazole hybrid molecules as a new type of antifungal agent has been described. In this synthesis, the N-alkylation reaction of carbazol-9-ide potassium salt with 3-bromoprop-1-yne afforded 9-(prop-2-ynyl)-9H-carbazole. The 'Click' Huisgen cycloaddition reaction of 9-(prop-2-ynyl)-9H-carbazole with diverse [Formula: see text]-azido alcohols in the presence of copper-doped silica cuprous sulphate led to target molecules in excellent yields. The in vitro antifungal and antibacterial activities of title compounds were screened against various pathogenic fungal strains, Gram-positive and/or Gram-negative bacteria. In particular, 1-(4-((9H-carbazol-9-yl) methyl)-1H-1,2,3-triazol-1-yl)-3-butoxypropan-2-ol (10e) proved to have potent antifungal activity against all fungal tests compared with fluconazole and clotrimazole as studied reference drugs. Our molecular docking analysis revealed an appropriate fitting and a potential powerful interaction between compound 10e and an active site of the Mycobacterium P450DM enzyme. The strong hydrogen bondings between [Formula: see text]-hydroxyl and ether groups in 10e were found to be the main factors that drive the molecule to fit in the active site of enzyme. The in silico pharmacokinetic studies were used for a better description of 10a-10n as potential lead antifungal agents for future investigations.

  7. DNA rearrangement has occurred in the carbazole-degradative plasmid pCAR1 and the chromosome of its unsuitable host, Pseudomonas fluorescens Pf0-1. (United States)

    Shintani, Masaki; Matsumoto, Takashi; Yoshikawa, Hirofumi; Yamane, Hisakazu; Ohkuma, Moriya; Nojiri, Hideaki


    The carbazole-degradative plasmid pCAR1 carries the class II transposon Tn4676, which contains the car and ant genes, essential for conversion of carbazole into anthranilate, and anthranilate into catechol, respectively. In our previous study, DNA rearrangements in pCAR1 were frequently detected in the host Pseudomonas fluorescens Pf0-1 in the presence of carbazole, resulting in the improvement of host survivability. Several Pf0-1 mutants harbouring pCAR1 were isolated, and deletion of DNA in the plasmid ant gene was found. Here, we compared genome sequences of the parent strain Pf0-1L(pCAR1::rfp) and one of its mutants, 5EP83, to assess whether other DNA rearrangements occurred in either the plasmid or the host chromosome. We found transposition of Tn4676 into the 5EP83 chromosome. In addition, ISPre1 had transposed into the car gene intergenic region on the pCAR1-derivative plasmid of 5EP83, which inhibited car transcription. As a result of these transpositions, 5EP83 was able to metabolize carbazole due to the Tn4676 on its chromosome, although the car genes on its plasmid were non-functional. We also found that one copy of duplicate carAa genes had been deleted, and that ISPre4 had transposed into both the host chromosome and the plasmid. Our findings suggest that Pf0-1 harbouring pCAR1 is subjected to DNA rearrangements not only on the plasmid but also on its chromosome in the presence of carbazole.

  8. Synthesis and properties of a star-shaped organic material with triphenylamine and N-vinyl carbazole units

    Institute of Scientific and Technical Information of China (English)


    A starburst triphenylamine cored N-vinyl carbazole (V-Cz) branched compound was designed and synthesized via optimized Heck reaction in a yield of 40-60%. Moderate yield came from decomposition of V-Cz and self-coupling of triiodo-triphenylamine.TCz-TPA adopts a highly twisted propeller conformation by molecular mechanical optimization. It is readily soluble for its highly twisted conformation. Transparent and pinhole free films could be easily fabricated by spin-coating for its starburst structure. It emits blue-greenish light in CH2Cl2 peaked at 460 nm with a narrow full-width at half-maximum (FWHM) of 65 nm. As compared,the absorption peaks of the spin-coated film blue shifted and emission peak red shifted to 510 nm with a FWHM of 96 nm.

  9. Photoconductivity of novel poly(N-vinyl)-3-[p-nitrophenylazo]carbazole/CdS-nanoparticle polymer composite

    Institute of Scientific and Technical Information of China (English)

    DING Li-yun; JIANG De-sheng; HUANG Jun; DAI Lei; LIU Cheng; WANG Jun-tao; LI Bin


    The photoconductive characteristic of the inorganic/organic hybridized polymer system is reported,in which a novel bi-functional photorefractive (PR) poly(N-vinyl)-3-[p-nitrophenylazo]carbazole (PVNPAK) serves as a polymeric charge-transporting and second-order nonliner optical matrix and quantum dots composed of surface passivated cadmium sulfide serve as a charge-generation sensitizer. The hybrid PVNPAK/CdS-nanoparticles polymer composites with different mass ratio of CdS to PVNPAK were prepared. The generation of photocurrent on illumination and photoconductive properties of the PVNPAK/CdS-nanoparticles polymer composites were studied. The results show that the addition of CdS nanoparticle as a photosensitizer can enhance the photoconductivity of the PVNPAK significantly because of the properties of the high quantum efficiency of photosensitization and high charge transport to conducting polymer.

  10. Microfluidic biosensor array with integrated poly(2,7-carbazole)/fullerene-based photodiodes for rapid multiplexed detection of pathogens. (United States)

    Matos Pires, Nuno Miguel; Dong, Tao


    A multiplexed microfluidic biosensor made of poly(methylmethacrylate) (PMMA) was integrated into an array of organic blend heterojunction photodiodes (OPDs) for chemiluminescent detection of pathogens. Waterborne Escherichia coli O157:H7, Campylobacter jejuni and adenovirus were targeted in the PMMA chip, and detection of captured pathogens was conducted by poly(2,7-carbazole)/fullerene OPDs which showed a responsivity over 0.20 A/W at 425 nm. The limits of chemiluminescent detection were 5 × 10(5) cells/mL for E. coli, 1 × 10(5) cells/mL for C. jejuni, and 1 × 10(-8) mg/mL for adenovirus. Parallel analysis for all three analytes in less than 35 min was demonstrated. Further recovery tests illustrated the potential of the integrated biosensor for detecting bacteria in real water samples.

  11. Novel glass-forming organic materials. 2. Structure and fluorescence of pyrene- and carbazole-containing cyclohexane, bicyclooctene, and adamantane

    Energy Technology Data Exchange (ETDEWEB)

    Mastrangelo, J.C.; Conger, B.M.; Chen, S.H. [Univ. of Rochester, NY (United States)] [and others


    A series of novel glass-forming organic materials consisting of pyrenyl and carbazolyl groups attached to cyclohexane with a 1-axial-2-equatorial configuration, bicyclo[2.2.2]oct-7-ene with an all-exo configuration, and adamantane were synthesized and characterized. On the basis of proton NMR spectra, it was found that the rotation of pendant pyrenyl and carbazolyl groups is restricted in the bicyclic system presumably because of steric hindrance in the all-exo configuration. In contrast, free rotation was found to prevail in cyclohexane- and adamantane-based systems. Fluorescence spectra gathered in solution at room temperature show evidence exclusively for intramolecular excimer formation in pyrene-containing compounds up to a concentration of 10{sup -4} M. On the contrary, carbazole-containing compounds are not prone to excimer formation in the concentration range 10{sup -6}-10{sup -3} M, presumably because of the more stringent requirements of interchromophoric distance and orientation. Although both pyrene and carbazole are highly crystalline on their own, attachment to cyclic, bicyclic, and tricyclic central cores was found to contribute to an ease of vitrification of the hybrid systems with a T{sub g} ranging from 43 to 132 {degrees}C. Moreover, the quenched glasses of all seven model systems were found to possess morphological stability in view of the absence of recrystallization upon heating from 0 to 200 {degrees}C at a heating rate ranging from 0.2 to 20{degrees}C/min. Morphological stability was further supported by the absence of recrystallization upon prolonged thermal annealing at temperatures above T{sub g}. 24 refs., 6 figs.

  12. Four new carbazole alkaloids from Murraya koenigii that display anti-inflammatory and anti-microbial activities. (United States)

    Nalli, Yedukondalu; Khajuria, Vidushi; Gupta, Shilpa; Arora, Palak; Riyaz-Ul-Hassan, Syed; Ahmed, Zabeer; Ali, Asif


    In our present study, four new, designated as murrayakonine A-D (), along with 18 known carbazole alkaloids were isolated from CHCl3 : MeOH (1 : 1) crude extracts of the stems and leaves of Murraya koenigii (Linn.) Spreng. The structures of the all isolated compounds were characterized by analysis of HR-ESI-MS and NMR (1D and 2D spectroscopy) results, and comparison of their data with the literature data. For the first time, all the isolates were evaluated for their anti-inflammatory activities, using both in vitro and in vivo experiments, against the key inflammatory mediators TNF-α and IL-6. The new compound murrayakonine A (), O-methylmurrayamine A () and mukolidine () were proven to be the most active, efficiently inhibiting TNF-α and IL-6 release in a dose-dependent manner and showing decreased LPS induced TNF-α and IL-6 production in human PBMCs. Furthermore, all the isolates were screened for their antimicrobial potential, and the compounds girinimbine () (IC50 3.4 μM) and 1-hydroxy-7-methoxy-8-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde () (IC50 10.9 μM) displayed potent inhibitory effects against Bacillus cereus. Furthermore, compounds murrayamine J () (IC50 11.7 μM) and koenimbine () (IC50 17.0 μM) were active against Staphylococcus aureus. However, none of the compounds were found to be active against Escherichia coli or Candida albicans.

  13. From Sediment to Top Predators: Broad Exposure of Polyhalogenated Carbazoles in San Francisco Bay (U.S.A.). (United States)

    Wu, Yan; Tan, Hongli; Sutton, Rebecca; Chen, Da


    The present study provides the first comprehensive investigation of polyhalogenated carbazoles (PHCZs) contamination in an aquatic ecosystem. PHCZs have been found in soil and aquatic sediment from several different regions, but knowledge of their bioaccumulation and trophodynamics is extremely scarce. This work investigated a suite of 11 PHCZ congeners in San Francisco Bay (United States) sediment and organisms, including bivalves (n = 6 composites), sport fish (n = 12 composites), harbor seal blubber (n = 18), and bird eggs (n = 8 composites). The most detectable congeners included 3,6-dichlorocarbazole (36-CCZ), 3,6-dibromocarbazole (36-BCZ), 1,3,6-tribromocarbazole (136-BCZ), 1,3,6,8-tetrabromocarbazole (1368-BCZ), and 1,8-dibromo-3,6-dichlorocarbazole (18-B-36-CCZ). The median concentrations of ΣPHCZs were 9.3 ng/g dry weight in sediment and ranged from 33.7 to 164 ng/g lipid weight in various species. Biomagnification was observed from fish to harbor seal and was mainly driven by chlorinated carbazoles, particularly 36-CCZ. Congener compositions of PHCZs differed among species, suggesting that individual congeners may be subject to different bioaccumulation or metabolism in species occupying various trophic levels in the studied aquatic system. Toxic equivalent (TEQ) values of PHCZs were determined on the basis of their relative effect potencies (REP) compared to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). The median TEQ was 1.2 pg TEQ/g dry weight in sediment and 4.8-19.5 pg TEQ/g lipid weight in biological tissues. Our study demonstrated the broad exposure of PHCZs in San Francisco Bay and their characteristics of bioaccumulation and biomagnification along with dioxin-like effects. These findings raise the need for additional research to better elucidate their sources, environmental behavior, and fate in global environments.

  14. Theoretical investigation of the broad one-photon absorption line-shape of a flexible symmetric carbazole derivative. (United States)

    Liu, Yanli; Cerezo, Javier; Santoro, Fabrizio; Rizzo, Antonio; Lin, Na; Zhao, Xian


    The one-photon absorption spectrum of a carbazole derivative has been studied by employing density functional response theory combined with a mixed quantum/classical (QC) approach to simulate the spectral shape. In a first step of our analysis we employed the vertical gradient (VG) vibronic model to investigate the role of Franck-Condon (FC) profiles of the first ten electronic excited states of the system, underlying most of the range of the experimental spectrum. We then focussed on the first six excited states covering the low-energy region of the spectrum, and investigated the effect of inter-state electronic couplings on the spectral shapes within Herzberg-Teller (HT) theory. Furthermore, in order to introduce the broadening effects due to the two inter-ring torsions, we employed a QC approach, adopting VG vibronic models for high-frequency modes and computing the contribution of the torsions to the spectrum from the distribution of the excitation energies along a two-dimensional relaxed potential energy. Finally, we estimated the solvent inhomogeneous broadening by computing the solvent reorganization energy using a polarizable continuum model. Our calculations allow us to obtain a non-phenomenological description of the low-energy part of the spectrum in semi-quantitative agreement with experiment and to dissect the relative importance of solvent, torsional flexibility, FC vibronic progressions, and inter-state couplings in determining its broad spectral shapes and the modulation of its intensity. Our analysis also clearly highlights that the investigated carbazole represents a big challenge for available methodologies due to the existence of many close-lying excited electronic states coupled by internal low-frequency and high-frequency motions and by solvent fluctuations. The study of their impact on the spectra at the HT level is only approximate and more refined treatments would require a fully quantum-dynamical calculation on the manifold of the coupled

  15. PbBr-Based Layered Perovskite Organic-Inorganic Superlattice Having Carbazole Chromophore; Hole-Mobility and Quantum Mechanical Calculation. (United States)

    Era, Masanao; Yasuda, Takeshi; Mori, Kento; Tomotsu, Norio; Kawano, Naoki; Koshimizu, Masanori; Asai, Keisuke


    We have successfully evaluated hole mobility in a spin-coated film of a lead-bromide based layered perovskite having carbazole chromophore-linked ammonium molecules as organic layer by using FET measurement. The values of hole mobility, threshold voltage and on/off ratio at room temperature were 1.7 x 10(-6) cm2 V-1 s-1, 27 V and 28 V, respectively. However, the spin-coated films on Si substrates were not so uniform compared with those on fused quartz substrates. To improve the film uniformity, we examined the relationship between substrate temperature during spin-coating and film morphology in the layered perovskite spin-coated films. The mean roughness of the spin-coated films on Si substrates was dependent on the substrate temperature. At 353 K, the mean roughness was minimized and the carrier mobility was enhanced by one order of magnitude; the values of hole mobility and threshold voltage were .estimated to be 3.4 x 10(-5) cm2 V-1 s-1, and 22 V at room temperature in a preliminary FET evaluation, respectively. In addition, we determined a crystal structure of the layered perovskite by X-ray diffraction analysis. To gain a better understanding of the observed hole transports, we conducted quantum mechanical calculations using the obtained crystal structure information. The calculated band structure of the layered organic perovskite showed that the valence band is composed of the organic carbazole layer, which confirms that.the measured hole mobility is mainly derived from the organic part of the layered perovskite. Band and hopping transport mechanisms were discussed by calculating the effective masses and transfer integrals for the 2D periodic system of the organic layer in isolation.

  16. One-pot synthesis of carbazole based 3-hydroxy-4H-chromen-4-ones by modified Algar-Flynn-Oyamada reaction and their antimicrobial activity

    Directory of Open Access Journals (Sweden)

    Ashok Dongamanti


    Full Text Available A new series of 2-(9-ethyl-9H-carbazol-3-yl-3-hydroxy-4Hchromen-4-ones have been synthesized from substituted 2-hydroxy acetophenones and 9-ethyl-9H-carbazole-3-carbaldehyde using NaOH and H2O2 by modified Algar-Flynn-Oyamada reaction. In this method flavonols are synthesized without isolating chalcones in good yields (70-82%. The structures of the compounds were established on the basis of 1H-NMR, 13CNMR, FT-IR and mass spectral and analytical data. All the compounds were evaluated for their antimicrobial activity against bacteria such as Staphylococus aureus, Bacillus subtilis, Escherichia coli and Klebsiella pneumoniae as well as fungi such as Aspergillus flavus and Fusarium oxysporum.

  17. Molecular modeling and experimental studies on structure and NMR parameters of 9-benzyl-3,6-diiodo-9H-carbazole

    DEFF Research Database (Denmark)

    Radula-Janik, Klaudia; Kupka, Teobald; Ejsmont, Krzysztof;


    A combined experimental and theoretical study has been performed on 9-benzyl-3,6-diiodo-9H-carbazole. Experimental X-ray (100.0 K) and room-temperature 13C NMR studies were supported by advanced density functional theory (DFT) calculations. The non relativistic structure optimization was performed.......57 ppm dropped to 5.6 ppm). A good linear correlation between experimental and theoretically predicted structural and NMR parameters was observed....

  18. Anion Binding Studies on Receptors Derived from the Indolo[2,3-a]carbazole Scaffold Having Different Binding Cavity Sizes

    Directory of Open Access Journals (Sweden)

    Guzmán Sánchez


    Full Text Available The indolo[2,3-a]carbazole scaffold is a fused polyheteroaromatic system bearing two NH groups which suitably converge as hydrogen bond donor sites for the recognition of anions. A simple derivatisation of the indolocarbazole system at positions 1 and 10 with different functional groups, namely alcohols and amides, has contributed to modulate the anion binding selectivity and sensibility. A particularly good response has been obtained for the benzoate anion.

  19. A novel carbazole-based fluorescent probe:3,6-Bis-[(N-ethylcarbazole-3-y1)-propene-1-keto]-N-ethylcarbazole

    Institute of Scientific and Technical Information of China (English)


    A novel carbazole-based compound 5,3,6-bis[(N-ethylcarbazole-3-yl)-propene-1-keto]-N-ethylcarbazole has been designed, synthesized and characterized.The absorption and fluorescence spectra in solvents of different polarities prove that the compound has a distinct intramolecular charge transfer character.Compound 5 can be used as a new class of fluorescent probe or biosensor due to its sensitivity to the local microenvironment such as solvent polarity.

  20. Experimental and theoretical studies on new 7-(3,6-di-tert-butyl-9H-carbazol-9-yl)-10-alkyl-10H-phenothiazine-3-carbaldehydes (United States)

    Stalindurai, Kesavan; Gokula Krishnan, Kannan; Nagarajan, Erumaipatty Rajagounder; Ramalingan, Chennan


    Synthesis of fused heterocyclic aldehydes with carbazole (CZ) structural motif linked at C-7 position on phenothiazines (PTZ), 7-(3,6-di-tert-butyl-9H-carbazol-9-yl)-10-butyl-10H-phenothiazine-3-carbaldehyde (1) and 7-(3,6-di-tert-butyl-9H-carbazol-9-yl)-10-hexyl-10H-phenothiazine-3-carbaldehyde (2) has been accomplished and are characterized through experimental and computational techniques. The optimized structure with their bonding aspects and vibrational frequencies of the same have been examined utilizing DFT-B3LYP technique with a basis set 6-311++G(d,p). In the optimized structures of 1 and 2, the bond lengths and bond angles are in accord with their corresponding reported analogous. The vibrational frequencies resulted from experimental as well as theoretical are in well accord with each other. Further, the results of polarizabilities, first order hyperpolarizabilities and dipole moment of 1 and 2 imply that these could be utilized for the preparation of NLO crystals which might generate second order harmonic waves.

  1. BC3EE2,9B, a synthetic carbazole derivative, upregulates autophagy and synergistically sensitizes human GBM8901 glioblastoma cells to temozolomide. (United States)

    Chen, Chien-Min; Syu, Jhih-Pu; Way, Tzong-Der; Huang, Li-Jiau; Kuo, Sheng-Chu; Lin, Chung-Tien; Lin, Chih-Li


    Glioblastoma multiforme (GBM) is the most fatal form of human brain cancer. Although temozolomide (TMZ), an oral alkylating chemotherapeutic agent, improves the survival rate, the prognosis of patients with GBM remains poor. Naturally occurring carbazole alkaloids isolated from curry leaves (Murraya koenigii Spreng.) have been shown to possess a wide range of anticancer properties. However, the effects of carbazole derivatives on glioblastoma cells remain poorly understood. In the present study, anti‑glioblastoma profiles of a series of synthetic carbazole derivatives were evaluated in vitro. The most promising derivative in this series was BC3EE2,9B, which showed significant anti‑proliferative effects in GBM8401 and GBM8901 cells. BC3EE2,9B also triggered cell‑cycle arrest, most prominently at the G1 stage, and suppressed glioblastoma cell invasion and migration. Furthermore, BC3EE2,9B induced autophagy‑mediated cell death and synergistically sensitized GBM cells to TMZ cytotoxicity. The possible mechanism underlying BC3EE2,9B‑induced autophagy may involve activation of adenosine monophosphate-activated protein kinase and the attenuation of the Akt and mammalian target of the rapamycin downstream signaling pathway. Taken together, the present results provide molecular evidence for the mode of action governing the ability of BC3EE2,9B to sensitize drug‑resistant glioblastoma cells to the chemotherapeutic agent TMZ.

  2. Synthesis, biological evaluation and molecular modeling study of novel tacrine-carbazole hybrids as potential multifunctional agents for the treatment of Alzheimer's disease. (United States)

    Thiratmatrakul, Supatra; Yenjai, Chavi; Waiwut, Pornthip; Vajragupta, Opa; Reubroycharoen, Prasert; Tohda, Michihisa; Boonyarat, Chantana


    New tacrine-carbazole hybrids were developed as potential multifunctional anti-Alzheimer agents for their cholinesterase inhibitory and radical scavenging activities. The developed compounds showed high inhibitory activity on acetylcholinesterase (AChE) with IC50 values ranging from 0.48 to 1.03 μM and exhibited good inhibition selectivity against AChE over butyrylcholinesterase (BuChE). Molecular modeling studies revealed that these tacrine-carbazole hybrids interacted simultaneously with the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. The derivatives containing methoxy group showed potent ABTS radical scavenging activity. Considering their neuroprotection, our results indicate that these derivatives can reduce neuronal death induced by oxidative stress and β-amyloid (Aβ). Moreover, S1, the highest potency for both radical scavenging and AChE inhibitory activity, exhibited an ability to improve both short-term and long-term memory deficit in mice induced by scopolamine. Overall, tacrine-carbazole derivatives can be considered as a candidate with potential impact for further pharmacological development in Alzheimer's therapy.

  3. Study of the pore filling fraction of carbazole-based hole-transporting materials in solid-state dye-sensitized solar cells

    Directory of Open Access Journals (Sweden)

    Marwa Ben Manaa


    Full Text Available Carbazole-based molecular glasses have emerged as a promising alternative to the widely used hole-transporting materials (HTM spiro-OMeTAD in solid-state dye-sensitized solar cells (DSSCs. The pore filling fraction (PFF of the mesoporous TiO2 layer by the HTM appears as a key parameter determining the final efficiency of a DSSC. In this work, the pore-filling properties of a family of carbazole-based HTMs are investigated for the first time and the photovoltaic behavior of DSSC devices (fabricated using the D102 dye is discussed in light of the present findings. It is found that N-aryl substituted 3,6-bis(diphenylaminyl-carbazole derivatives exhibit relatively low PFF of ca. 60%. Methoxy groups on the diphenylamine moieties have little influence on the PFF, indicating that the strong enhancement in power conversion efficiency (PCE is not related to an improved filling of the pores by the HTM. N-alkylated HTMs lead to higher PFF, increasing with the alkyl chain length, up to 78%.

  4. Theoretical Study on the Optical Properties for 2,7- and 3,6-Linked Carbazole Trimers by Time-dependent Density Functional Theory

    Institute of Scientific and Technical Information of China (English)

    WANG Han-Lu; WANG Xue-Ye; WANG Ling; WANG Heng-Liang; LIU Ai-Hong


    Electronic properties, such as HOMO and LUMO energies, band gaps, ionization potential (IP) and electron affinity (EA) of 2,7- and 3,6-linked carbazole trimers, two conjugated oligomers with different linkages of carbazole, were studied by the density functional theory with Becke-Lee-Young-Parr composite exchange correlation functional (B3LYP). The absorption spectra of these compounds were also investigated by time-dependent density functional theory (TD-DFT) with 6-31G* basis set. The calculated results indicated that the HOMO and LUMO of the 2,7- and 3,6-linked carbazole trimers are both slightly destabilized on going from methyl substitution to sec-butyl substitution. Both IP and EA exhibit their good hole-transporting but poor electron-accepting ability. The presence of alkyl groups on the nitrogen atoms does not affect the intra-chain electronic delocalization along the molecular frame. Thus no significant effect on the band gap and absorption spectra of compounds has been found.

  5. Optical biosensor with poly[N-nonyl-3,6-bis(ethylenedioxythiophene)carbazole] matrix for monitoring of phenol derivatives (United States)

    Jedrychowska, Agnieszka; Malecha, Karol; Cabaj, Joanna; Sołoducho, Jadwiga


    The aim of the research was to develop an enzymatic, optical biosensor which provides quick and convenient determination of phenolic compounds in aqueous solutions. The biosensing strategy concerns design, fabrication and testing of a miniature ceramic-based biosensor which is destined for in-situ substrate monitoring. The base of the measuring system was fabricated using low temperature co-fired ceramics (LTCC) technology. The biocatalyst - laccase- was immobilized on the thin film of poly[N-nonyl-3,6-bis(ethylenedioxythiophene)carbazole] which provided good binding of the enzyme to the substrate and positively affected on the catalytic activity of the protein. In order to evaluate properties of the designed biosensor, its response for various concentrations of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diamonnium sal (ABTS) was measured. The optical biosensor produced by presented method could find applications in many fields, i.e. for detection of phenolic compounds in food products and beverages, in industry for control of technological processes or for environmental monitoring

  6. Charge carrier mobility in conjugated organic polymers: simulation of an electron mobility in a carbazole-benzothiadiazole-based polymer (United States)

    Li, Yaping; Lagowski, Jolanta B.


    Inorganic (mostly silicon based) solar cells are important devices that are used to solve the world energy and environmental needs. Now days, organic solar cells are attracting considerable attention in the field of photovoltaic cells because of their low cost and processing flexibility. Often conjugated polymers are used in the construction of the organic solar cells. We study the conjugated polymers' charge transport using computational approach that involves the use of the density functional theory (DFT), semiempirical (ZINDO), and Monte Carlo (MC) theoretical methods in order to determine their transfer integrals, reorganization energies, transfer rates (with the use of Marcus-Hush equation) and mobilities. We employ the experimentally determined three dimensional (3D) structure of poly(9,9'-di-n-octylfluorene-alt-benzothiadiazole) (F8BT) to estimate the electron mobility in a similar co-alternating polymer consisting of carbazole and benzothiadiazole units (C8BT). In agreement with our previous work, we found that including an orientational disorder in the crystal reduces the electron mobility in C8BT. We hope that the proposed computational approach can be used to predict charge mobility in organic materials that are used in solar cells.

  7. Nitrogen-containing microporous conjugated polymers via carbazole-based oxidative coupling polymerization: preparation, porosity, and gas uptake. (United States)

    Chen, Qi; Liu, De-Peng; Luo, Min; Feng, Li-Juan; Zhao, Yan-Chao; Han, Bao-Hang


    Facile preparation of microporous conjugated polycarbazoles via carbazole-based oxidative coupling polymerization is reported. The process to form the polymer network has cost-effective advantages such as using a cheap catalyst, mild reaction conditions, and requiring a single monomer. Because no other functional groups such as halo groups, boric acid, and alkyne are required for coupling polymerization, properties derived from monomers are likely to be fully retained and structures of final polymers are easier to characterize. A series of microporous conjugated polycarbazoles (CPOP-2-7) with permanent porosity are synthesized using versatile carbazolyl-bearing 2D and 3D conjugated core structures with non-planar rigid conformation as building units. The Brunauer-Emmett-Teller specific surface area values for these porous materials vary between 510 and 1430 m(2) g(-1) . The dominant pore sizes of the polymers based on the different building blocks are located between 0.59 and 0.66 nm. Gas (H2 and CO2 ) adsorption isotherms show that CPOP-7 exhibits the best uptake capacity for hydrogen (1.51 wt% at 1.0 bar and 77 K) and carbon dioxide (13.2 wt% at 1.0 bar and 273 K) among the obtained polymers. Furthermore, its high CH4 /N2 and CO2 /N2 adsorption selectivity gives polymer CPOP-7 potential application in gas separation.

  8. Facile Synthesis and High performance of a New Carbazole-Based Hole Transporting Material for Hybrid Perovskite Solar Cells

    KAUST Repository

    Wang, Hong


    Perovskite solar cells are very promising for practical applications owing to their rapidly rising power conversion efficiency and low cost of solution-based processing. 2,2’,7,7’-tetrakis-(N,N-di-p-methoxyphenylamine) 9,9’-spirobifluorene (Spiro-OMeTAD) is most widely used as hole transporting material (HTM) in perovskite solar cells. However, the tedious synthesis and high cost of Spiro-OMeTAD inhibit its commercial-scale application in the photovoltaic industry. In this article, we report a carbazole-based compound (R01) as a new HTM in efficient perovskite solar cells. R01 is synthesized via a facile route consisting of only two steps from inexpensive commercially available materials. Furthermore, R01 exhibits higher hole mobility and conductivity than the state-of-the-art Spiro-OMeTAD. Perovskite solar cells fabricated with R01 produce a power conversion efficiency of 12.03%, comparable to that obtained in devices using Spiro-OMeTAD in this study. Our findings underscore R01 as a highly promising HTM with high performance, and its facile synthesis and low cost may facilitate the large-scale applications of perovskite solar cells.

  9. Halogen effect on structure and 13C NMR chemical shift of 3,6-disubstituted-N-alkyl carbazoles

    DEFF Research Database (Denmark)

    Radula-Janik, Klaudia; Kupka, Teobald; Ejsmont, Krzysztof


    Structures of selected 3,6-dihalogeno-N-alkyl carbazole derivatives were calculated at the B3LYP/6-311++G(3df,2pd) level of theory and their 13C NMR isotropic nuclear shieldings were predicted using density functional theory (DFT). The model compounds contained 9H-, N-methyl and N-ethyl derivatives......). The decreasing electronegativity of the halogen substituent (F, Cl, Br and I) was reflected in both nonrelativistic and relativistic NMR results as decreased values of chemical shifts of carbon atoms attached to halogen (C3 and C6) leading to a strong sensitivity to halogen atom type at 3 and 6 positions...

  10. 5′,11′-Dihydrodispiro[cyclohexane-1,6′-indolo[3,2-b]carbazole-12′,1′′-cyclohexane

    Directory of Open Access Journals (Sweden)

    Ilia A. Guzei


    Full Text Available The title compound, C28H30N2, is a symmetrical 2:2 product from the condensation of indole and cyclohexanone. It is the only reported 5,11-dihydroindolo[3,2-b]carbazole compound in which the spiro atoms are quaternary C atoms. Crystals were grown by vapor diffusion in a three-zone electric furnace. The molecule resides on a crystallographic inversion center. The cyclohexyl rings are in a slightly distorted chair conformation, whereas the indole units and the spiro-carbons are coplanar within 0.014 Å.

  11. Synthesis of novel precursors of Pfitzinger reaction: A facile one-pot strategy to the synthesis of quinoline carboxylic acid derivatives of pyrazolo-carbazoles and azacarbazoles

    Indian Academy of Sciences (India)

    Ruchi Tyagi; Bhawani Singh; D Kishore


    Interaction of 5-indazolyldiazonium chloride 2 with 2-hydroxymethylidene cyclohexanone 5 and -benzyl-3-hydroxymethylidene-4-piperidone 6 under the conditions of Japp-Klingemann reaction, followed by Fischer-indolization of the resulting hydrazones, formed the 5,7,8,9-tetrahydropyrazolo[4,3-b]carbazol- 6(1)-one 9 and 9-benzyl-5,7,8,9-tetrahydropyrido[2',3':4,5]pyrrolo[2,3-f]indazol-6(1)-one 10, respectively. Pfitzinger reaction of 9 and 10 with isatin in alkali afforded the corresponding quinoline carboxylic acid derivatives 12 and 13, respectively.

  12. Morphological, dielectric and electrical conductivity characteristics of clay-containing nanohybrids of poly(N-vinyl carbazole) and polypyrrole. (United States)

    Haldar, Ipsita; Biswas, Mukul; Nayak, Arabinda; Ray, Suprakas Sinha


    Poly(N-vinyl carbazole) (PNVC) and polypyrrole (PPY)-montmorillonite (MMT) clay hybrids were prepared by mechanical grinding of the respective monomers with MMT followed by subsequent standard processing methods. Fourier transform infrared spectroscopic studies confirmed the inclusion of the polymers in the composites. The morphologies of the hybrids were investigated by transmission electron microscopic techniques, which suggested the formation of intercalated structures. X-ray diffraction analyses indicated the enhancement of 'd001' values in MMT implying intercalation of the polymers into the nano-interlamellar spaces of MMT. The dielectric constants of PNVC-MMT hybrids were improved (60-180) relative to the homopolymer (3-6) in the frequency range 0.1-25 kHz. PPY-MMT hybrid also showed significantly higher values of dielectric constant (2000-4000) relative to the corresponding base polymers. These variations were dependent on the MMT/polymer feed ratio in the frequency range (1-25 kHz). This feature could manifest from the characteristic differences in the interfaces between the grains and grain boundaries of the composites, which control the dielectric properties of the system. Relaxation behavior for the composites was explained by considering the Maxwell-Wagner two-layered dielectric models. The ac conductivity was found to be dependent on frequency in the entire frequency range of study (100 Hz to 25 kHz), which indicated that the composites had few free charges for conduction, and frequency dependent conductivity was due to trapped charges in the grain boundary.

  13. Novel carbazole-phenothiazine dyads for dye-sensitized solar cells: a combined experimental and theoretical study. (United States)

    Marotta, Gabriele; Reddy, Marri Anil; Singh, Surya Prakash; Islam, Ashraful; Han, Liyuan; De Angelis, Filippo; Pastore, Mariachiara; Chandrasekharam, Malapaka


    We report a joint experimental and computational work on new organic donor-acceptor dye sensitizers in which a carbazole (CZ) and a phenothiazine (PTZ) units are linked together by an alkyl C6H13, while two different anchoring groups are employed: the cyanoacrylic acid (CS1A, CSORG1) and the rhodanine-3-acetic acid (CS4A, CSORG4). The CZ moiety has multiple roles of (i) acting as an extra-electron donor portion, providing more electron density on the PTZ; (ii) suppressing the back-electron transfer from TiO2 to the electrolyte by forming a compact insulating dye layer; (iii) modulating dye aggregation on the semiconductor surface; and (iv) acting as an antenna, collecting photons and, through long-range energy transfer, redirecting the captured energy to the dye sensitizer. We show that the introduction of the CZ donor remarkably enhances the photovoltaic performances of the rhodanine-based dye, compared to the corresponding simple PTZ dye, with more than a two-fold increase in the overall efficiencies, while it does not bring beneficial effects in the case of the cyanoacrylic-based sensitizer. Based on quantum mechanical calculations and experimental measurements, we show that, in addition to a favored long-range energy transfer, which increases the light absorption in the blue region of the spectrum, the presence of the CZ unit in the CSORG4 dye effectively induces a beneficial aggregation pattern on the semiconductor surface, yielding a broadened and red-shifted light absorption, accounting for the two-fold increase in the generated photocurrent.

  14. Synthesis and Characterization of Two β-Diketones with Carbazole Group%2个含咔唑基团β-二酮的合成与表征

    Institute of Scientific and Technical Information of China (English)

    唐怀军; 张梅芳; 张志国; 石青; 张克立


    以咔唑和联苯为原料合成了2个含咔唑基团的新型β-二酮,并用1H NMR、13C NMR、MS、元素分析、热分析、紫外可见吸收光谱及荧光光谱等测试技术进行了表征.2种β-二酮具有较高的热稳定性,5%失重温 度(△T5%)分别为319和356℃,荧光发射位于蓝光区,最大发射峰为443和455 nm.%Two β-diketones with carbazole group were synthesized from carbazole and biphenyl. The β-diketones were characterized by 'H NMR, 13C NMR, MS, elemental analyses, thermoanalysis, UV-Vis absorption spectra and photoluminescence ( PL) spectra. The β-diketones have high thermal stability, their 5% mass-reduction temperatures( AT5% ) are 319 °C and 356 °C, respectively. Their PL spectra lie in blue light zone with the maximum emission peaks of 443 nm and 455 nm. They are potential ligands for synthesizing metal ion complexes targeted for light-emitting materials.

  15. Doped and non-doped organic light-emitting diodes based on a yellow carbazole emitter into a blue-emitting matrix

    CERN Document Server

    Choukri, H; Forget, S; Chenais, S; Castex, M C; Geffroy, B; Ades, D; Siove, A; Choukri, Hakim; Fischer, Alexis; Forget, Sebastien; Chenais, Sebastien; Castex, Marie-Claude; Geffroy, Bernard; Ades, Dominique; Siove, Alain


    A new carbazole derivative with a 3,3'-bicarbazyl core 6,6'-substituted by dicyanovinylene groups (6,6'-bis(1-(2,2'-dicyano)vinyl)-N,N'-dioctyl-3,3'-bicarbazyl; named (OcCz2CN)2, was synthesized by carbonyl-methylene Knovenagel condensation, characterized and used as a component of multilayer organic light-emitting diodes (OLEDs). Due to its -donor-acceptor type structure, (OcCz2CN)2 was found to emit a yellow light at max=590 nm (with the CIE coordinates x=0.51; y = 0.47) and was used either as a dopant or as an ultra-thin layer in a blue-emitting matrix of 4,4'-bis(2,2'-diphenylvinyl)-1,1'-biphenyl (DPVBi). DPVBi (OcCz2CN)2-doped structure exhibited, at doping ratio of 1.5 weight %, a yellowish-green light with the CIE coordinates (x = 0.31; y = 0.51), an electroluminescence efficiency EL=1.3 cd/A, an external quantum efficiency ext= 0.4 % and a luminance L= 127 cd/m2 (at 10 mA/cm2) whereas for non-doped devices utilizing the carbazolic fluorophore as a thin n...

  16. Synthesis, photophysical and charge-transporting properties of a novel asymmetric indolo [3,2-b]carbazole derivative containing benzothiazole and diphenylamino moieties (United States)

    Shi, Heping; Yuan, Jiandong; Dong, Xiuqing; Cheng, Fangqin


    A novel asymmetric donor-π-donor-π-acceptor compound, 2-benzothiazolyl-8-diphenylamino-5,11-dihexylindolo[3,2-b]carbazole (BDDAICZ), has been successfully synthesized by introducing a benzothiazole moiety (as an electron-acceptor) and a diphenylamino moiety (as an electron-donor) to 2-position and 8-position of indolo[3,2-b]carbazole moiety (as a skeleton and an electron-donor), and characterized by elemental analysis, 1H NMR, 13C NMR and MS. The thermal, electrochemical properties of BDDAICZ were characterized by thermogravimetric analysis combined with electrochemistry. The absorption and emission spectra of BDDAICZ was experimentally determined in several solvents and computed using density functional theory (DFT) and time-dependent density functional theory (TDDFT). The calculated absorption and emission wavelengths are coincident with the measured data. The ionization potential (IP), the electron affinity (EA) and reorganization energy of BDDAICZ were also investigated using density functional theory (DFT). Charge-transporting properties of BDDAICZ were characterized by OLEDs devices fabricated by using it as charge-transport layers. The results show that BDDAICZ has excellent thermal stability, electrochemical stability and hole-transporting properties, indicating its potential application as a hole-transporting material in OLEDs devices.

  17. Indolo[3,2-b]carbazole inhibits gap junctional intercellular communication in rat primary hepatocytes and acts as a potential tumor promoter

    DEFF Research Database (Denmark)

    Herrmann, Susan; Seidelin, Michel; Bisgaard, Hanne Cathrine


    Indole-3-carbinol (I3C) is a naturally occurring substance that shows anti-carcinogenic properties in animal models. Besides its clear anti-carcinogenic effects, some studies indicate that I3C may sometimes act as a tumor promoter. Indolo[3,2-b]carbazole (ICZ), which is formed in the acidic...... environment of the stomach after intake of I3C, has a similar structure to, and shares biological effects with, the well-known tumor promoter 2,3,7,8-tetrachlorodibenzo-pdioxin (TCDD). Therefore, we hypothesized that ICZ could be responsible for the potential tumor-promoting activity of I3C. The aim...... of the present study was to investigate the effect of ICZ on gap junctional intercellular communication (GJIC) in primary cultured rat hepatocytes co-cultured with the rat liver epithelial cell line WB-F344. Indolo[3,2-b]carbazole inhibited GJIC in the rat hepatocytes in a dose- and time-dependent manner...

  18. OFF-ON-OFF Dual Emission at Visible and UV Wavelengths from Carbazole Functionalized β-Diketonate Europium(III) Complex. (United States)

    Imai, Yuki; Kawai, Tsuyoshi; Yuasa, Junpei


    This work demonstrates dual emission "OFF-ON-OFF" switching at visible and UV wavelengths of a carbazole functionalized β-diketone (LH) by a simple change of a europium(III) ion (Eu(3+)) concentration in the submicromolar concentration range. In the presence of 0.25 equiv of Eu(3+) (5 μM), LH forms a luminescent 4:1 complex ([Eu(3+)(L(-))4](-)) exhibiting dual emission at 357 and 613 nm resulting from the local excitation of the carbazole ring and ligand-sensitized luminescence from the Eu(3+)-β-diketonate unit, respectively. The 4:1 complex begins to convert into a 2:1 complex ([Eu(3+)(L(-))2](+)) via a 3:1 complex [Eu(3+)(L(-))3] above a molar ratio ([Eu(3+)]/[LH]) of 0.25, which provides the opportunity for binding of solvent methanol molecules to the vacant site of the Eu(3+) ion in the complex ([Eu(3+)(L(-))2(MeOH)n](+)). The OH oscillators of coordinated methanol molecules facilitate the nonradiative pathway of the Eu(3+) emission; hence the emission at 613 nm almost disappears above the 0.50 equivalent of Eu(3+) (11 μM), while the UV emission at 357 nm remains mostly constant over the whole concentration range.

  19. Synthesis of indolo[3,2-b]carbazole-based random copolymers for polymer solar cell applications

    Energy Technology Data Exchange (ETDEWEB)

    Chan, Li-Hsin, E-mail: [Department of Applied Materials and Optoelectronic Engineering, National Chi Nan University, Nantou, Taiwan 54561, ROC (China); Lin, Lu-Chi; Yao, Chi-Han [Department of Applied Materials and Optoelectronic Engineering, National Chi Nan University, Nantou, Taiwan 54561, ROC (China); Liu, You-Ren; Jiang, Zong-Jhih [Department of Applied Chemistry, National Chi Nan University, Nantou, Taiwan 54561, ROC (China); Cho, Ting-Yu [Department of Applied Materials and Optoelectronic Engineering, National Chi Nan University, Nantou, Taiwan 54561, ROC (China)


    In addition to preparing two indolocarbazole-based random copolymers (named as r-PICTBT1 and r-PICTBT2), this work investigated their feasibility for bulk heterojunction polymer solar cells (PSCs). These copolymers consisted of commercially available 3,9-dibromo-5,11-dioctyl-5,11-dihydroindole[3,2-b]carbazole, 2,5-bis(trimethylstannyl) thiophene and dibromobenzo[c][1,2,5]thiadiazole by varying the feed in ratios via Stille cross-coupling reactions. The photophysical and electrochemical properties of the resulting copolymers could be fine-modulated easily by adjusting the feed ratios of monomers. Both copolymers in the thin film state exhibited two obvious peaks and a vibronic shoulder in the absorption spectra. Electrochemical experiments indicated that the highest occupied molecular orbital energy levels were − 4.95, − 5.00 eV; meanwhile, the lowest unoccupied molecular orbital energy levels were − 3.38, − 3.54 eV for r-PICTBT1 and r-PICTBT2, respectively. Bulk heterojunction PSCs composed of an electron-donor copolymer blended with an electron acceptor [6,6]-phenyl-C61-butyric acid methyl ester (PC{sub 61}BM) or [6,6]-phenyl-C71-butyric acid methyl ester (PC{sub 71}BM) at a weight ratio of 1:1 or 1:3 were investigated. Moreover, the r-PICTBT2/PC{sub 71}BM-based (w/w = 1:1) PSC performed the best with an open-circuit voltage of 0.54 V, short-circuit current of 6.83 mA/cm{sup 2}, fill factor of 0.44, and power conversion efficiency of 1.63%. - Highlights: • We report two indolocarbazole-based copolymers for photovoltaic applications. • Two copolymers exhibited excellent thermal stability. • Energy levels of copolymers can be modulated by varying the monomers ratios. • Increasing of planar monomer content leads to a relatively smooth morphology. • The optimal device performance reached a power conversion efficiency of 1.63%.

  20. Novel conjugated polymers based on dithieno[3,2-b:6,7-b]carbazole for solution processed thin-film transistors. (United States)

    Chen, Yagang; Liu, Chengfang; Tian, Hongkun; Bao, Cheng; Zhang, Xiaojie; Yan, Donghang; Geng, Yanhou; Wang, Fosong


    Two conjugated polymers (CPs) P-tCzC12 and P-tCzC16 comprising alternating dithieno[3,2-b:6,7-b]carbazole and 4,4'-dihexadecyl-2,2'-bithiophene units have been designed and synthesized. Upon thermal annealing, they can form ordered thin films in which the polymer backbones dominantly adopted an edge-on orientation respective to the substrate with a lamellar spacing of ≈24 Å and a π-stacking distance of ≈3.7 Å. Organic thin-film transistors (OTFTs) were fabricated by solution casting. A hole mobility of 0.39 cm(2) V(-1) s(-1) has been demonstrated with P-tCzC16. This value is the highest among the CPs containing heteroacenes larger than 4 rings.

  1. An unusual case of OD-allotwinning: 9,9′-(2,5-dibromo-1,4-phenylene)bis[9H-carbazole (United States)

    Kautny, Paul; Schwartz, Thomas; Fröhlich, Johannes


    9,9′-(2,5-Dibromo-1,4-phenylene)bis[9H-carbazole] (1) crystallizes as a category I order–disorder (OD) structure composed of non-polar layers of one kind with B2/m(1)1 layer symmetry. The crystals are made up of the two polytypes with a maximum degree of order (MDO). The monoclinic MDO1 polytype (B21/d) possesses an orthorhombic B-centered lattice and appears in two orientations, which are related by reflection at (100). The orthorhombic MDO2 polytype (F2dd) has a doubled b-axis and appears in two orientations, which are related by inversion. The crystal structures of both polytypes were determined in a concurrent refinement. The MDO1:MDO2 ratio is 69:31.

  2. Chain folding controlled by an isomeric repeat unit: helix formation versus random aggregation in acetylene-bridged carbazole-bipyridine co-oligomers. (United States)

    Divya, Kizhmuri P; Sreejith, Sivaramapanicker; Suresh, Cherumuttathu H; Philips, Divya S; Ajayaghosh, Ayyappanpillai


    An unprecedented, positional effect of the isomeric repeat unit on chain folding in donor–acceptor-linked oligomers, which contain alternating bipyridine and carbazole moieties that are connected through an acetylinic linkage, is reported. 4,4′-Linked oligomer 1 adopts an intrachain helical conformation (CD-active) in CHCl3/MeCN (20:80 v/v), whereas oligomer 2, which contains an isomeric 6,6′-linkage, forms interchain randomly coiled aggregates (CD-inactive). The substitution position plays a significant role in controlling the variations in electronic effects and dipole moments around the bipyridyl moiety, which are responsible for this observed phenomenon. Two model compounds of oligomers 1 and 2 (3 and 4, respectively) were prepared and their properties were compared. A systematic investigation of the photophysical and CD properties of these structures, as well as theoretical studies, support our conclusions.

  3. Synthesis, spectral and third-order nonlinear optical properties of terpyridine Zn(II) complexes based on carbazole derivative with polyether group (United States)

    Kong, Ming; Liu, Yanqiu; Wang, Hui; Luo, Junshan; Li, Dandan; Zhang, Shengyi; Li, Shengli; Wu, Jieying; Tian, Yupeng


    Four novel Zn(II) terpyridine complexes (ZnLCl2, ZnLBr2, ZnLI2, ZnL(SCN)2) based on carbazole derivative group were designed, synthesized and fully characterized. Their photophysical properties including absorption and one-photon excited fluorescence, two-photon absorption (TPA) and optical power limiting (OPL) were further investigated systematically and interpreted on the basis of theoretical calculations (TD-DFT). The influences of different solvents on the absorption and One-Photon Excited Fluorescence (OPEF) spectral behavior, quantum yields and the lifetime of the chromophores have been investigated in detail. The third-order nonlinear optical (NLO) properties were investigated by open/closed aperture Z-scan measurements using femtosecond pulse laser in the range from 680 to 1080 nm. These results revealed that ZnLCl2 and ZnLBr2 exhibited strong two-photon absorption and ZnLCl2 showed superior optical power limiting property.

  4. Incorporation of Hexa-peri-hexabenzocoronene (HBC) into Carbazole-Benzo-2,1,3-thiadiazole Copolymers to Improve Hole Mobility and Photovoltaic Performance. (United States)

    Gao, Chen; Jiang, Pei; Shi, Keli; Ma, Di; Li, Yongfang; Yu, Gui; Li, Xiaoyu; Wang, Haiqiao


    Hexa-peri-hexabenzocoronene (HBC) is a discotic-shaped conjugated molecule with strong π-π stacking property, high intrinsic charge mobility, and good self-assembly properties. For a long time, however, organic photovoltaic (OPV) solar cells based on HBC demonstrated low power conversion efficiencies (PCEs). In this study, two conjugated terpolymers, poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5'-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT)-5 HBC and PCDTBT-10 HBC, were synthesized by incorporating different amounts of HBC as the third component into poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5'-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT) through Suzuki coupling polymerization. For comparison, the donor-acceptor (D-A) conjugated dipolymer PCDTBT was also synthesized to investigate the effect of HBC units on conjugated polymers. The HBC-containing polymers exhibited higher thermal stabilities, broader absorption spectra, and lower highest-occupied molecular orbital (HOMO) energy levels. In particular, the field-effect mobilities were enhanced by more than one order of magnitude after the incorporation of HBC into the conjugated polymer backbone on account of increased interchain π-π stacking interactions. The bulk heterojunction (BHJ) polymer solar cells (PSCs) fabricated with the polymers as donor and PC71 BM as acceptor demonstrated gradual improvement of open-circuit voltage (VOC ) and short-circuit current (JSC ) with the increase in HBC content. As a result, the PCEs were improved from 3.21 % for PCDTBT to 3.78 % for PCDTBT-5 HBC and then to 4.20 % for PCDTBT-10 HBC.

  5. Photophysics and non-linear absorption of Au(I) and Pt(II) acetylide complexes of a thienyl-carbazole chromophore. (United States)

    Goswami, Subhadip; Wicks, Geoffrey; Rebane, Aleksander; Schanze, Kirk S


    In order to understand the photophysics and non-linear optical properties of carbazole containing π-conjugated oligomers of the type ET-Cbz-TE (E = ethynylene, T = 2,5-thienylene, Cbz = 3,6-carbazole), a detailed investigation was carried out on a series of oligomers that feature Au(i) or Pt(ii) acetylide "end groups", as well as a Pt(ii)-acetylide linked polymer (CBZ-Au-1 and CBZ-Pt-1, CBZ-Poly-Pt). These organometallic chromophores were characterized by UV-visible absorption and variable temperature photoluminescence spectroscopy, nanosecond transient absorption spectroscopy, open aperture nanosecond z-scan and two photon absorption (2PA) spectroscopy. The Au(i) and Pt(ii) oligomers and polymer exhibit weak fluorescence in fluid solution at room temperature. Efficient phosphorescence is observed from the Pt(ii) systems below 150 K in a solvent glass; however, the Au(i) oligomer exhibits only weak phosphorescence at 77 K. Taken together, the emission results indicate that the intersystem crossing efficiency for the Pt(ii) chromophores is greater than for the Au(i) oligomer. Nonetheless, nanosecond transient absorption indicates that direct excitation affords moderately long-lived triplet states for all of the chromophores. Open aperture z-scan measurement shows effective optical attenuation can be achieved by using these materials. The 2PA cross section in the degenerate S0→S1 transition region was in the range 10-100 GM, and increased monotonically toward shorter wavelengths, reaching 800-1000 GM at 550 nm.

  6. Solar-energy production and energy-efficient lighting: photovoltaic devices and white-light-emitting diodes using poly(2,7-fluorene), poly(2,7-carbazole), and poly(2,7-dibenzosilole) derivatives. (United States)

    Beaupré, Serge; Boudreault, Pierre-Luc T; Leclerc, Mario


    World energy needs grow each year. To address global warming and climate changes the search for renewable energy sources with limited greenhouse gas emissions and the development of energy-efficient lighting devices are underway. This Review reports recent progress made in the synthesis and characterization of conjugated polymers based on bridged phenylenes, namely, poly(2,7-fluorene)s, poly(2,7-carbazole)s, and poly(2,7-dibenzosilole)s, for applications in solar cells and white-light-emitting diodes. The main strategies and remaining challenges in the development of reliable and low-cost renewable sources of energy and energy-saving lighting devices are discussed.

  7. Rh(III)-Catalyzed Cascade Annulation/C-H Activation of o-Ethynylanilines with Diazo Compounds: One-Pot Synthesis of Benzo[a]carbazoles via 1,4-Rhodium Migration. (United States)

    Guo, Songjin; Yuan, Kai; Gu, Meng; Lin, Aijun; Yao, Hequan


    A Rh(III)-catalyzed cascade annulation/C-H activation of o-ethynylanilines with diazo compounds has been developed. This concise method allows for the rapid formation of a number of benzo[a]carbazoles in high yields, exhibiting good functional group tolerance and scalability. The key to the success of this approach involves one C-N bond and two C-C bond formation, and an aryl-to-aryl 1,4-rhodium migration.

  8. Carboxylate ligands induced structural diversity of zinc(II) coordination polymers based on 3,6-bis(imidazol-1-yl)carbazole: Syntheses, structures and photocatalytic properties

    Energy Technology Data Exchange (ETDEWEB)

    Cheng, Hong-Jian, E-mail:; Tang, Hui-Xiang; Shen, Ya-Li; Xia, Nan-Nan; Yin, Wen-Yu; Zhu, Wei; Tang, Xiao-Yan; Ma, Yun-Sheng; Yuan, Rong-Xin, E-mail:


    Solvothermal reactions of Zn(NO{sub 3}){sub 2}·6H{sub 2}O with 3,6-bis(1-imidazolyl)carbazole (3,6-bmcz) and 1,4-benzenedicarboxylic acid (1,4-H{sub 2}bdc), p-phenylenediacetic acid (p-H{sub 2}pda), benzophenone-4,4-dicarboxylic acid (H{sub 2}bpda) afforded three coordination polymers [Zn(1,4-bdc)(3,6-bmcz)]{sub n} (1), {[Zn(p-pda)(3,6-bmcz)]·1.5H_2O}{sub n} (2) and {[Zn(bpda)(3,6-bmcz)]·0.25H_2O}{sub n} (3). Complexes 1–3 were characterized by elemental analysis, IR, powder X-ray diffraction, and single-crystal X-ray diffraction. Complex 1 shows 3D structure with 2D nets inclined polycatenation. Complexes 2 and 3 possess an extended 3D supramolecular architecture based on their respective 2D layers through hydrogen-bonding interactions and the π···π stacking interactions. The solid state luminescent and optical properties of 1–3 at ambient temperature were also investigated. A comparative study on their photocatalytic activity toward the degradation of methylene blue in polluted water was explored. - Graphical abstract: Reactions of Zn(NO{sub 3}){sub 2} and 3,6-(1-imidazolyl)carbazole with 1,4-benzenedicarboxylic acid, p-phenylenediacetic acid or benzophenone-4,4-dicarboxylic acid afforded three coordination polymers with different topologies and photocatalytic activity. - Highlights: • Reactions of 1,4-H{sub 2}bdc, p-H{sub 2}pda or H{sub 2}bpda with 3,6-bmcz and Zn(II) gave three CPs. • Complex 1 is a 3D entanglement. • Complex 2 or 3 is a 3D supramolecular structure based on different 2D layers. • Complex 2 exhibited good catalytic activity of methylene blue photodegradation.

  9. Substitution of Carbazole Modified Fluorenes as π-Extension in Ru(II Complex-Influence on Performance of Dye-Sensitized Solar Cells

    Directory of Open Access Journals (Sweden)

    Malapaka Chandrasekharam


    Full Text Available A new high molar extinction coefficient ruthenium(II bipyridyl complex “cis-Ru(4,4-bis(9,9-dibutyl-7-(3,6-di-tert-butyl-9H-carbazol-9-yl-9H-fluoren-2-yl-2,2-bipyridine(2,2-bipyridine-4,4-dicarboxylic acid(NCS2, BPFC” has been synthesized and characterized by FT-IR, 1H-NMR, and ESI-MASS spectroscopes. The sensitizer showed molar extinction coefficient of 18.5×103 M−1cm−1, larger as compared to the reference N719, which showed 14.4×103 M−1cm−1. The test cells fabricated using BPFC sensitizer employing high performance volatile electrolyte, (E01 containing 0.05 M I2, 0.1 M LiI, 0.6 M 1,2-dimethyl-3-n-propylimidazolium iodide, 0.5 M 4-tert-butylpyridine in acetonitrile solvent, exhibited solar-to-electric energy conversion efficiency (η of 4.65% (short-circuit current density (SC = 11.52 mA/cm2, open-circuit voltage (OC = 566 mV, fill factor = 0.72 under Air Mass 1.5 sunlight, lower as compared to the reference N719 sensitized solar cell, fabricated under similar conditions, which exhibited η-value of 6.5% (SC = 14.3 mA/cm2, OC = 640 mV, fill factor = 0.71. UV-Vis measurements conducted on TiO2 films showed decreased film absorption ratios for BPFC as compared to those of reference N719. Staining TiO2 electrodes immediately after sonication of dye solutions enhanced film absorption ratios of BPFC relative to those of N719. Time-dependent density functional theory (TD-DFT calculations show higher oscillation strengths for 4,4-bis(9,9-dibutyl-7-(3,6-di-tert-butyl-9H-carbazol-9-yl-9H-fluoren-2-yl-2,2-bipyridine relative to 2,2-bipyridine-4,4-dicarboxylic acid and increased spectral response for the corresponding BPFC complex.

  10. Structural insight into the substrate- and dioxygen-binding manner in the catalytic cycle of rieske nonheme iron oxygenase system, carbazole 1,9a-dioxygenase

    Directory of Open Access Journals (Sweden)

    Ashikawa Yuji


    Full Text Available Abstract Background Dihydroxylation of tandemly linked aromatic carbons in a cis-configuration, catalyzed by multicomponent oxygenase systems known as Rieske nonheme iron oxygenase systems (ROs, often constitute the initial step of aerobic degradation pathways for various aromatic compounds. Because such RO reactions inherently govern whether downstream degradation processes occur, novel oxygenation mechanisms involving oxygenase components of ROs (RO-Os is of great interest. Despite substantial progress in structural and physicochemical analyses, no consensus exists on the chemical steps in the catalytic cycles of ROs. Thus, determining whether conformational changes at the active site of RO-O occur by substrate and/or oxygen binding is important. Carbazole 1,9a-dioxygenase (CARDO, a RO member consists of catalytic terminal oxygenase (CARDO-O, ferredoxin (CARDO-F, and ferredoxin reductase. We have succeeded in determining the crystal structures of oxidized CARDO-O, oxidized CARDO-F, and both oxidized and reduced forms of the CARDO-O: CARDO-F binary complex. Results In the present study, we determined the crystal structures of the reduced carbazole (CAR-bound, dioxygen-bound, and both CAR- and dioxygen-bound CARDO-O: CARDO-F binary complex structures at 1.95, 1.85, and 2.00 Å resolution. These structures revealed the conformational changes that occur in the catalytic cycle. Structural comparison between complex structures in each step of the catalytic mechanism provides several implications, such as the order of substrate and dioxygen bindings, the iron-dioxygen species likely being Fe(III-(hydroperoxo, and the creation of room for dioxygen binding and the promotion of dioxygen binding in desirable fashion by preceding substrate binding. Conclusions The RO catalytic mechanism is proposed as follows: When the Rieske cluster is reduced, substrate binding induces several conformational changes (e.g., movements of the nonheme iron and the ligand

  11. D-π-A-π-A Strategy to Design Benzothiadiazole-carbazole-based Conjugated Polymer with High Solar Cell Voltage and Enhanced Photocurrent. (United States)

    Zhou, Manxi; Wang, Min; Zhu, Lei; Yang, Zhenqing; Jiang, Chao; Cao, Dapeng; Li, Qifang


    The theoretical calculations are used to find that D-π-A-π-A style conjugated polymer PC-TBTBT is more efficient for solar cells application than the D-π-A analog PC-TBT because the D-π-A-π-A structure has a narrower band gap and higher molar absorption coefficient and redshift spectrum. Motivated by the theoretical prediction, 5,6-bis(octyloxy)-2,1,3-benzothiadiazole and 2,7-carbazole are adopted to synthesize the D-π-A-π-A style PC-TBTBT (M(w) = 31.1 kDa) and D-π-A analog PC-TBT (M(w) = 87.5 kDa) by Suzuki coupling reaction. Experimental results confirm that D-π-A-π-A PC-TBTBT-based solar cell shows a power conversion efficiency (PCE) of 4.74% with high V(OC) of 0.99 V and enhanced J(SC) of 9.70 mA cm(-2). The PCE and J(SC) achieve improvements of 17% and 26%, respectively, compared to the D-π-A PC-TBT-based solar cell.

  12. Design and synthesis of new benzimidazole-carbazole conjugates for the stabilization of human telomeric DNA, telomerase inhibition, and their selective action on cancer cells. (United States)

    Maji, Basudeb; Kumar, Krishan; Kaulage, Mangesh; Muniyappa, K; Bhattacharya, Santanu


    Cell-permeable small molecules that enhance the stability of the G-quadruplex (G4) DNA structures are currently among the most intensively pursued ligands for inhibition of the telomerase activity. Herein we report the design and syntheses of four novel benzimidazole-carbazole conjugates and demonstrate their high binding affinity to G4 DNA. S1 nuclease assay confirmed the ligand mediated G-quadruplex DNA protection. Additional evidence from Telomeric Repeat Amplification Protocol (TRAP-LIG) assay demonstrated efficient telomerase inhibition activity by the ligands. Two of the ligands showed IC50 values in the sub-micromolar range in the TRAP-LIG assay, which are the best among the benzimidazole derivatives reported so far. The ligands also exhibited cancer cell selective nuclear internalization, nuclear condensation, fragmentation, and eventually antiproliferative activity in long-term cell viability assays. Annexin V-FITC/PI staining assays confirm that the cell death induced by the ligands follows an apoptotic pathway. An insight into the mode of ligand binding was obtained from the molecular dynamics simulations.

  13. New dimeric carbazole-benzimidazole mixed ligands for the stabilization of human telomeric G-quadruplex DNA and as telomerase inhibitors. A remarkable influence of the spacer. (United States)

    Maji, Basudeb; Kumar, Krishan; Muniyappa, K; Bhattacharya, Santanu


    The development of G-quadruplex (G4) DNA binding small molecules has become an important strategy for selectively targeting cancer cells. Herein, we report the design and evolution of a new kind of carbazole-based benzimidazole dimers for their efficient telomerase inhibition activity. Spectroscopic titrations reveal the ligands high affinity toward the G4 DNA with significantly higher selectivity over duplex-DNA. The electrophoretic mobility shift assay shows that the ligands efficiently promote the formation of G4 DNA even at a lower concentration of the stabilizing K(+) ions. The TRAP-LIG assay demonstrates the ligand's potential telomerase inhibition activity and also establishes that the activity proceeds via G4 DNA stabilization. An efficient nuclear internalization of the ligands in several common cancer cells (HeLa, HT1080, and A549) also enabled differentiation between normal HFF cells in co-cultures of cancer and normal ones. The ligands induce significant apoptotic response and antiproliferative activity toward cancer cells selectively when compared to the normal cells.

  14. Carboxylate ligands induced structural diversity of zinc(II) coordination polymers based on 3,6-bis(imidazol-1-yl)carbazole: Syntheses, structures and photocatalytic properties (United States)

    Cheng, Hong-Jian; Tang, Hui-Xiang; Shen, Ya-Li; Xia, Nan-Nan; Yin, Wen-Yu; Zhu, Wei; Tang, Xiao-Yan; Ma, Yun-Sheng; Yuan, Rong-Xin


    Solvothermal reactions of Zn(NO3)2·6H2O with 3,6-bis(1-imidazolyl)carbazole (3,6-bmcz) and 1,4-benzenedicarboxylic acid (1,4-H2bdc), p-phenylenediacetic acid (p-H2pda), benzophenone-4,4-dicarboxylic acid (H2bpda) afforded three coordination polymers [Zn(1,4-bdc)(3,6-bmcz)]n (1), {[Zn(p-pda)(3,6-bmcz)]·1.5H2O}n (2) and {[Zn(bpda)(3,6-bmcz)]·0.25H2O}n (3). Complexes 1-3 were characterized by elemental analysis, IR, powder X-ray diffraction, and single-crystal X-ray diffraction. Complex 1 shows 3D structure with 2D nets inclined polycatenation. Complexes 2 and 3 possess an extended 3D supramolecular architecture based on their respective 2D layers through hydrogen-bonding interactions and the π···π stacking interactions. The solid state luminescent and optical properties of 1-3 at ambient temperature were also investigated. A comparative study on their photocatalytic activity toward the degradation of methylene blue in polluted water was explored.

  15. A rectifying diode with hysteresis effect from an electroactive hybrid of carbazole-functionalized polystyrene with CdTe nanocrystals via electrostatic interaction

    Institute of Scientific and Technical Information of China (English)


    One of the strategies to tune current-voltage behaviors in organic diodes is to combine field-induced charge transfer processes with schottky barrier.According to this principle,a rectifying diode with hysteresis effect was fabricated utilizing a hybrid of electroactive polystyrene derivative covalently tethered with electron-donor carbazole moieties and electrostatic linked with electron-acceptor CdTe nanocrystals.Current-voltage characteristics show an electrical switching behavior with some hysteresis is only observed under a negative bias,with three orders of On/Off current ratio.The hybrid material based rectifier exhibits a rectification ratio of six and its maximum rectified output current is about 5 × 10-5 A.The asymmetric switching is interpreted as the result of both field induced charge transfer and schottky barrier,capable of reducing the misreading of cross-bar memory.Meanwhile,chemical doping of CdTe nanocrystals instead of physical blend favor their uniform dispersion in matrix and stable operation of device.

  16. 1,4,9,12-Tetramethoxy-14-octyl-5,8-dihydrodiindolo[3,2-b;2′,3′-h]carbazole with an unknown solvent

    Directory of Open Access Journals (Sweden)

    Norma Wrobel


    Full Text Available The title compound, 2C36H39N3O4·H2O, is a linear π-conjugated ladder oligomer with an alkyl chain on the central nitrogen atom. This diindolocarbazole, prepared via a twofold Cadogan reaction, adopts a sligthly convex shape, anti to the disordered octyl group. The unit cell contains nine molecules of the title compound and half a water molecule per main molecule. The water molecule forms hydrogen bridges, connecting the carbazole-NH and methoxy groups of different molecules. The crystal contains solvent molecules which are located in a channel parallel to the c axis. It was not possible to determine the position and nature of the solvent (a mixure of choroform, n-pentane and DMSO. The SQUEEZE [Spek (2015. Acta Cryst. C71, 9–18] option of PLATON was used to model the missing electron density. The given chemical formula and other crystal data do not take into account these solvent molecules.

  17. The Role of Porphyrin-Free-Base in the Electronic Structures and Related Properties of N-Fused Carbazole-Zinc Porphyrin Dye Sensitizers

    Directory of Open Access Journals (Sweden)

    Xing-Yu Li


    Full Text Available Dye sensitizers can significantly affect power conversion efficiency of dye-sensitized solar cells (DSSCs. Porphyrin-based dyes are promising sensitizers due to their performances in DSSCs. Here, based upon a N-fused carbazole-zinc porphyrin-free-base porphyrin triad containing an ethynyl-linkage (coded as DTBC, the novel porphyrin dyes named DTBC-MP and DTBC-TP were designed by varying the porphyrin-free-base units in the π conjugation of DTBC in order to study the effect of porphyrin-free-base in the modification of electronic structures and related properties. The calculated results indicate that, the extension of the conjugate bridge with the porphyrin-free-base unit results in elevation of the highest occupied molecular orbital (HOMO energies, decrease of the lowest unoccupied molecular orbital (LUMO energies, reduction of the HOMO-LUMO gap, red-shift of the absorption bands, and enhancement of the absorbance. The free energy changes demonstrate that introducing more porphyrin-free-base units in the conjugate bridge induces a faster rate of electron injection. The transition properties and molecular orbital characters suggest that the different transition properties might lead to a different electron injection mechanism. In terms of electronic structure, absorption spectra, light harvesting capability, and free energy changes, the designed DTBC-TP is a promising candidate dye sensitizer for DSSCs.

  18. The Tryptophan-Derived Endogenous Aryl Hydrocarbon Receptor Ligand 6-Formylindolo[3,2-b]Carbazole Is a Nanomolar UVA Photosensitizer in Epidermal Keratinocytes. (United States)

    Park, Sophia L; Justiniano, Rebecca; Williams, Joshua D; Cabello, Christopher M; Qiao, Shuxi; Wondrak, Georg T


    Endogenous UVA chromophores may act as sensitizers of oxidative stress underlying cutaneous photoaging and photocarcinogenesis, but the molecular identity of non-DNA key chromophores displaying UVA-driven photodyamic activity in human skin remains largely undefined. Here we report that 6-formylindolo[3,2-b]carbazole (FICZ), a tryptophan photoproduct and endogenous high-affinity aryl hydrocarbon receptor (AhR) agonist, acts as a nanomolar photosensitizer potentiating UVA-induced oxidative stress irrespective of AhR ligand activity. In human HaCaT and primary epidermal keratinocytes, photodynamic induction of apoptosis was elicited by the combined action of solar-simulated UVA and FICZ, whereas exposure to the isolated action of UVA or FICZ did not impair viability. In a human epidermal tissue reconstruct, FICZ/UVA cotreatment caused pronounced phototoxicity inducing keratinocyte cell death, and FICZ photodynamic activity was also substantiated in a murine skin exposure model. Array analysis revealed pronounced potentiation of cellular heat shock, endoplasmic reticulum stress, and oxidative stress response gene expression observed only upon FICZ/UVA cotreatment. FICZ photosensitization caused intracellular oxidative stress, and comet analysis revealed introduction of formamidopyrimidine-DNA glycosylase (Fpg)-sensitive oxidative DNA lesions suppressible by antioxidant cotreatment. Taken together, our data demonstrate that the endogenous AhR ligand FICZ displays nanomolar photodynamic activity representing a molecular mechanism of UVA-induced photooxidative stress potentially operative in human skin.

  19. Solvatochromic effect in absorption and emission spectra of star-shaped bipolar derivatives of 1,3,5-triazine and carbazole. A time-dependent density functional study. (United States)

    Baryshnikov, Gleb V; Bondarchuk, Sergey V; Minaeva, Valentina A; Ågren, Hans; Minaev, Boris F


    A series of three star-shaped compounds containing both donor (carbazole) and acceptor (2,4,6-triphenyl-1,3,5-triazine) moieties linked through various linking bridges was studied theoretically at the linear response TD-DFT level of theory to describe their absorption and fluorescence spectra. The concept of a localized charge-transfer excited state has been applied successfully to explain the observed strong solvatochromic effect in the emission spectra of the studied molecules, which can be utilized for the fabrication of color tunable solution-processable OLEDs. The concept is in particularly applicable to donor-acceptor species with a C 3 symmetry point group where the static dipole moment changes dramatically upon electronic excitation. An important peculiarity of the studied molecules is that they are characterized by non-zero values of the HOMO and LUMO orbitals in the same common part of molecular space that provides a large electric dipole transition moment for both light absorption and emission. Graphical abstract Star-shaped C 3 symmetry point group derivatives for color tunable OLEDs.

  20. Small Molecule Reversible Inhibitors of Bruton’s Tyrosine Kinase (BTK): Structure–Activity Relationships Leading to the Identification of 7-(2-Hydroxypropan-2-yl)-4-[2-methyl-3-(4-oxo-3,4-dihydroquinazolin-3-yl)phenyl]-9 H -carbazole-1-carboxamide (BMS-935177)

    Energy Technology Data Exchange (ETDEWEB)

    De Lucca, George V.; Shi, Qing; Liu, Qingjie; Batt, Douglas G.; Beaudoin Bertrand, Myra; Rampulla, Rick; Mathur, Arvind; Discenza, Lorell; D’Arienzo, Celia; Dai, Jun; Obermeier, Mary; Vickery, Rodney; Zhang, Yingru; Yang, Zheng; Marathe, Punit; Tebben, Andrew J.; Muckelbauer, Jodi K.; Chang, ChiehYing J.; Zhang, Huiping; Gillooly, Kathleen; Taylor, Tracy; Pattoli, Mark A.; Skala, Stacey; Kukral, Daniel W.; McIntyre, Kim W.; Salter-Cid, Luisa; Fura, Aberra; Burke, James R.; Barrish, Joel C.; Carter, Percy H.; Tino, Joseph A.


    Bruton’s tyrosine kinase (BTK) belongs to the TEC family of nonreceptor tyrosine kinases and plays a critical role in multiple cell types responsible for numerous autoimmune diseases. This article will detail the structure–activity relationships (SARs) leading to a novel second generation series of potent and selective reversible carbazole inhibitors of BTK. With an excellent pharmacokinetic profile as well as demonstrated in vivo activity and an acceptable safety profile, 7-(2-hydroxypropan-2-yl)-4-[2-methyl-3-(4-oxo-3,4-dihydroquinazolin-3-yl)phenyl]-9H-carbazole-1-carboxamide 6 (BMS-935177) was selected to advance into clinical development.

  1. Focused ion beam and field-emission microscopy of metallic filaments in memory devices based on thin films of an ambipolar organic compound consisting of oxadiazole, carbazole, and fluorene units (United States)

    Pearson, Christopher; Bowen, Leon; Lee, Myung Won; Fisher, Alison L.; Linton, Katherine E.; Bryce, Martin R.; Petty, Michael C.


    We report on the mechanism of operation of organic thin film resistive memory architectures based on an ambipolar compound consisting of oxadiazole, carbazole, and fluorene units. Cross-sections of the devices have been imaged by electron microscopy both before and after applying a voltage. The micrographs reveal the growth of filaments, with diameters of 50 nm–100 nm, on the metal cathode. We suggest that these are formed by the drift of aluminium ions from the anode and are responsible for the observed switching and negative differential resistance phenomena in the memory devices.

  2. Incorporating two different chromophores onto a silicon atom: the crystal structure and photophysical properties of 9-{4-[(9,9-dimethyl-9H-fluoren-2-yl)dimethylsilyl]phenyl}-9H-carbazole. (United States)

    Lee, Ah-Rang; Han, Won-Sik


    The crystal structure of the title bifunctional silicon-bridged compound, C(35)H(31)NSi, (I), has been determined. The compound crystallizes in the centrosymmetric space group P2(1)/c. In the crystal structure, the pairs of aryl rings in the two different chromophores, i.e. 9-phenyl-9H-carbazole and 9,9-dimethyl-9H-fluorene, are positioned orthogonally. In the crystal packing, no classical hydrogen bonding is observed. UV-Vis absorption and fluorescence emission spectra show that the central Si atom successfully breaks the electronic conjugation between the two different chromophores, and this was further analysed by density functional theory (DFT) calculations.

  3. Synthesis, characterization and properties of novel blue light emitting discrete π-functional polymer consisting of carbazole and anthracene units and their applications in polymer light emitting diodes (United States)

    Gopal, Ram; Huang, Yi-Chiang; Lee, Hsu-Feng; Chang, Ming-Sien; Huang, Wen-Yao


    A new novel blue light emitting polymer containing carbazole and anthracene derivatives has been successfully synthesized via polycondensation chemical reaction of diol and difluoro monomers. An effort has been made to raise the band gap of blue light emitter by lowering the conjugation extent in the backbone. The synthesized blue polymer exhibits decent solubility, good process ability, high thermal stability, high glass transition temperature (272 °C) and the decomposition temperature of 358 °C. The UV-vis absorption spectra and photoluminescence spectra depict that the light emission lies in blue region. The solid state photoluminescence (PL) spectra of the polymer (λPL=456 nm) shows red shift (Δλ = 37 nm) as compared with the corresponding solution PL spectra, presumably due to lower intermolecular distance in solid state. The multi-layered polymer light emitting diode was fabricated, using blue polymer with ITO/PEDOT: PSS/BP/LiF/Al architecture. The luminance-voltage (L-V) and current density-voltage (J-V) curves show a maximum luminance of 7544 cd m-2, a maximum emission efficiency of 4.2 cd A-1, a maximum current density of 453 mA cm-2 at a turn-on voltage of 4.5 V. Moreover, the PLED instigate pure blue EL emission, stable at 436 nm with outstanding CIE coordinates of (x = 0.15, y = 0.08), which is close to the pure NTSC blue coordinates of (0.14, 0.08). [Figure not available: see fulltext.

  4. Red Emission of Eu(Ⅲ) Complex Based on 1-(7-(tert-butyl)-9-ethyl-9H-carbazol-2-yl)-4,4,4-trifluorobutane-1,3-dione Excited by Blue Light

    Institute of Scientific and Technical Information of China (English)

    Sheng-gui Liu; Wen-yi Su; Rong-kai Pan; Xiao-ping Zhou


    A new Eu(Ⅲ) complex,EuL3(phen),was synthesized,where L is the abbreviation of deprotonated 1-(7-(tert-butyl)-9-ethyl-9H-carbazol-2-yl)-4,4,4-trifluorobutane-1,3-dione (HL),phen is the abbreviation of 1,10-phenanthroline.The Eu(Ⅲ) complex was characterized by element analysis,IR,1H NMR,UV-visible absorption spectroscopy,thermogravimetric analysis (TGA),and photoluminescence measurements (PL).TGA shows that thermal stability of the complex is up to 325 ℃.PL measurement indicates that the Eu(Ⅲ) complex exhibits intense red-emission and extends their excitation bands to visible region.LEDs device was successfully fabricated by precoating complex EuL3(phen) onto 460 nm blue-emitting InGaN chip.The emission of device shows that the complex can act as red phosphor in combination with 460 nm blue-emitting chips.This europium complex based on 1-(7-(tert-butyl)-9-ethyl-9H-carbazol-2-yl)-4,4,4-trifluorobutane-1,3-dione is a kind of interesting red-emitting material excited by blue light,which could avoid the damage of excitation by UV light.

  5. New carbazole-based Schiff base: Colorimetric chemosensor for Fe{sup 3+} and fluorescent turn-on chemosensor for Fe{sup 3+} and Cr{sup 3+}

    Energy Technology Data Exchange (ETDEWEB)

    Zhu, Weiju; Yang, Lianlian; Fang, Min; Wu, Zhenyu; Zhang, Qing; Yin, Fangfang; Huang, Qiang; Li, Cun, E-mail:


    Two novel carbazole-based Schiff-bases L1 and L2 have been synthesized and characterized by {sup 1}H NMR, {sup 13}C NMR, FT-IR spectroscopy and elemental analysis. L1 can selectively detect Fe{sup 3+} by UV–vis spectroscopy and Fe{sup 3+}/Cr{sup 3+} by fluorescent spectroscopy in CH{sub 3}CN among various metal ions. The addition of Fe{sup 3+} ions to a L1 solution results in a significant blue-shift from 410 nm to 378 nm accompanied with color change from yellowish green to colorless. Upon excitation at 380 nm, the addition of Fe{sup 3+} or Cr{sup 3+} causes a 13-fold or 11-fold fluorescence enhancement. The binding stoichiometry ratio of L1–Fe{sup 3+} and L1–Cr{sup 3+} is recognized as 2:1 by the method of Job's plot, and the possible binding mode of the system also proposes. The results indicate that L1 is an ideal chemosensor for Fe{sup 3+} and Cr{sup 3+} recognition. However, L2 without hydroxyl in ortho imino group cannot selectively recognize the tasted metal ions, indicating that the introduction of the appropriate coordination binding site to receptor can improve efficiently the selectivity of chemosensor. - Highlights: • We designed and synthesized two new carbazole-based Schiff bases L1 and L2. • L1 could selectively recognize Fe{sup 3+} but L2 could not, which suggested that increase recognition site helped to improve the selectivity of probe. • L1 not only could serve as a highly selective visual chemosensor for Fe{sup 3+} ion without the aid of any instruments, but also could be used as a fluorescent chemosensor for Fe{sup 3+} and Cr{sup 3+}.

  6. Spectrometric measurements and DFT studies on new complex of copper (II) with 2-((E)-9-ethyl-3-(2-(6-(4-methylpyridin-2-yl)pyridin-3-yl)vinyl)-9H-carbazole (United States)

    Zhang, Haoyang; Hu, Jie; Zhao, Jianying; Zhang, Yu


    The molecular structure of a new complex of copper (II) with (E)-9-ethyl-3-(2-(6-(4-methylpyridin-2-yl)pyridin-3-yl)vinyl)-9H-carbazole ([Cu2(emppc)2Cl2]Cl2) was optimized with B3LYP/LanL2DZ, PBE1PBE/LanL2DZ and M062X/LanL2DZ theoretical level. The ligand, (E)-9-ethyl-3-(2-(6-(4-methylpyridin-2-yl)pyridin-3-yl)vinyl)-9H-carbazole (emppc), binds to Cu(II) ions with a bi-dentate mode, two Cl- serve as bridging ligand, each Cu(II) ion has a highly distorted tetrahedron coordination geometry. With M062X/LanL2DZ theoretical level, the calculated interaction energies of Cu(II) with coordination atoms N are between 183.3-200.0 kJ mol- 1 for α spin and 319.4-324.9 kJ mol- 1 for β spin, and interaction energies of Cu(II) with coordination atoms Cl atom are 248.0-252.4 kJ mol- 1 for α spin and 332.6-333.6 kJ mol- 1 for β spin. The experimental Fourier transform infrared spectrum was assigned. The calculated IR based on B3LYP/LanL2DZ, PBE1PBE/LanL2DZ and M062X/LanL2DZ methods were performed and compared with experimental results. The UV-Vis experimental spectra of [Cu2(emppc)2Cl2]Cl2 was measured in methanol solution. The calculated electronic spectrum was performed with TD/M062X and PCM-TD/M062X methods with LanL2DZ basis set. The nature bond orbital analysis and temperature dependence of the thermodynamic properties were calculated with the same methods.

  7. 32P-postlabeling analysis of DNA adduction in mice by synthetic metabolites of the environmental carcinogen, 7H-dibenzo[c,g]carbazole: chromatographic evidence for 3-hydroxy-7H-dibenzo[c,g]carbazole being a proximate genotoxicant in liver but not skin. (United States)

    Schurdak, M E; Stong, D B; Warshawsky, D; Randerath, K


    The DNA adduction by the environmental carcinogen 7H-dibenzo[c,g]carbazole (DBC) and chemically synthesized 2-OH, 3-OH, and 4-OH metabolites of DBC was investigated in liver and skin of female CD-1 mice. After topical application to the skin of 37 mumol/kg of DBC or the phenolic metabolites, DNA adducts were measured by a 32P-post-labeling assay employing carrier-free [gamma-32P]ATP and ATP-deficient conditions. In liver, DBC produced four major and several minor chromatographically distinct adducts of as yet undetermined chemical structure. The adduct pattern elicited by 3-OH-DBC was qualitatively similar to the DBC adduct pattern, while this was not the case for 2-OH-DBC and 4-OH-DBC. On the basis of co-chromatography experiments under various conditions, the DBC and 3-OH-DBC adducts appeared identical, and the total of adduction elicited by these compounds in liver was substantial. Similar results were observed when DBC or 3-OH-DBC were administered i.p. As a major difference between the two compounds, one 3-OH-DBC adduct (no. 3) was 4.4- and 7.0-fold lower than the corresponding DBC adduct after i.p. and topical dosing, respectively. In skin, DBC produced two major adduct fractions after topical application, one of which could be chromatographically resolved into three subcomponents. Prominent adducts produced in skin DNA by each of the three metabolites were different from those elicited by DBC, and the level of adduction by the metabolites was significantly lower than that by DBC. Comparison of the skin and liver DBC-DNA adduct patterns after topical application of DBC showed that only one of the four major chromatographically resolved skin adducts corresponded to a major liver adduct (no. 3), and that total adduction in liver was 13.5-fold higher than in skin. These results suggested that activation of DBC to DNA-binding compounds in liver occurs through at least two pathways with 3-OH-DBC being a proximate carcinogen involved in the formation of most of the

  8. Synthesis, molecular structure and vibrational analysis of D-D-A based carbazole decorated phenothiazine-3-carbaldehyde: Experimental (FT-IR, UV and NMR) and density functional theory (DFT) calculations (United States)

    Karuppasamy, Ayyanar; Gokula Krishnan, Kannan; Pillai Velayutham Pillai, Muthiah; Ramalingan, Chennan


    A novel molecule, 10-(9-hexyl-9H-carbazol-3yl)-10H-phenothiazine-3-carbaldehyde (CZPTZA) has been synthesized and characterized through FT-IR, UV-Vis, NMR spectroscopic studies and molecular orbital calculations. Optimized geometrical structure, harmonic vibrational frequencies and NMR are computed with B3LYP method using 6-311++G (d,p) basis set. The geometrical parameters of the title compound obtained from Single Crystal XRD studies have been found in accord with the calculated (DFT) values. The experimentally observed vibrational frequencies are compared with the calculated ones, which were found to be in good agreement with each other. UV-Vis spectra of the title compound have also been recorded and the electronic properties, viz. excitation energies, calculated energies, oscillator strengths, frontier orbital energies and band gap energies are computed with TD-DFT/CAM-B3LYP method using 6-311++G (d,p) as the basis set. The 1H and 13C NMR chemical shifts of the molecule have been calculated by the Gauge Independent Atomic Orbital (GIAO) method and compared with the experimental outcome. Also, the values of dipole moment, polarizabilities and first order hyperpolarizabilities have been computed.

  9. Polymer light-emitting diodes based on cationic iridium(III) complexes with a 1,10-phenanthroline derivative containing a bipolar carbazole-oxadiazole unit as the auxiliary ligand (United States)

    Tang, Huaijun; Wei, Liying; Meng, Guoyun; Li, Yanhu; Wang, Guanze; Yang, Furui; Wu, Hongbin; Yang, Wei; Cao, Yong


    A 1,10-phenanthroline derivative (co-phen) containing a bipolar carbazole-oxadiazole unit was synthesized and used as the auxiliary ligand in cationic iridium(III) complexes [(ppy)2Ir(co-phen)]PF6 (ppy: 2-phenylpyridine) and [(npy)2Ir(co-phen)]PF6 (npy: 2-(naphthalen-1-yl)pyridine). Two complexes have high thermal stability with the glass-transition temperatures (Tg) of 207 °C and 241 °C, and the same 5% weight-reduction temperatures (ΔT5%) of 402 °C. Both of them were used as phosphorescent dopants in solution-processed polymer light-emitting diodes (PLEDs): ITO/PEDOT: PSS/PVK: PBD: complex (mass ratios 100: 40: x, x = 1.0, 2.0, and 4.0)/CsF/Al. The maximum luminances of the PLEDs using [(ppy)2Ir(co-phen)]PF6 and [(npy)2Ir(co-phen)]PF6 were 12567 cd m-2 and 11032 cd m-2, the maximum luminance efficiencies were 17.3 cd A-1 and 20.4 cd A-1, the maximum power efficiencies were 9.8 lm W-1 and 10.3 lm W-1, and the maximum external quantum efficiencies were 9.3% and 11.4% respectively. The CIE color coordinates were around (0.37, 0.57) and (0.44, 0.54) respectively, corresponding to the yellow green region.

  10. Sensitive and background-free determination of thiols from wastewater samples by MOF-5 extraction coupled with high-performance liquid chromatography with fluorescence detection using a novel fluorescence probe of carbazole-9-ethyl-2-maleimide. (United States)

    Lv, Zhengxian; Sun, Zhiwei; Song, Cuihua; Lu, Shuaimin; Chen, Guang; You, Jinmao


    A sensitive and background-free pre-column derivatization method for the determination of thiol compounds using metal-organic framework material (MOF-5) as dispersive solid-phase extraction (DSPE) adsorbent followed by high-performance liquid chromatography fluorescence detection (HPLC-FLD) has been developed. In this paper, a novel labeling reagent, carbazole-9-ethyl-2-maleimide(CAEM), was synthesized and reacted with thiols at 40°C for 10min in the presence of PBS buffer (0.02mol/L, pH 7.5). Interestingly, CAEM itself had no fluorescence, while its derivatives exhibited intense fluorescence with an excitation maximum at λex 274nm and an emission maximum at λem 363nm, which greatly reduced the background interference and improved the sensitivity of the method. Furthermore, the MOF-5 was prepared and used as DSPE adsorbent for the selective adsorption of thiols from wastewater sample. Under the optimized experimental conditions, an excellent linearity for all analytes over their concentration ranges of 0.01-1.0μmol/L (R(2)>0.9986)were obtained with the limit of detection (LOD) ranging from 8 to 17.1pmol/L for nine tested thiols. The feasibility of this method for the determination of thiols in wastewater samples had been evaluated and satisfactory average recoveries (n=3) were achieved with the range of 86.6-98.5%.

  11. Hole transporting material 5, 10, 15-tribenzyl-5H-diindolo[3, 2-a:3′, 2′-c]-carbazole for efficient optoelectronic applications as an active layer

    Institute of Scientific and Technical Information of China (English)

    郑燕琼; William J.Potscavage Jr; 张建华; 魏斌; 黄荣娟


    In order to explore the novel application of the transparent hole-transporting material 5,10,15-tribenzyl-5H-diindolo[3,2-a:3′,2′-c]-carbazole (TBDI), in this article TBDI is used as an active layer but not a buffer layer in a pho-todetector (PD), organic light-emitting diode (OLED), and organic photovoltaic cell (OPV) for the first time. Firstly, the absorption and emission spectra of a blend layer comprised of TBDI and electron-transporting material bis-(2-methyl-8-quinolinate) 4-phenylphenolate (BAlq) are investigated. Based on the absorption properties, an organic PD with a peak absorption at 320 nm is fabricated, and a relatively-high detectivity of 2.44×1011 cm·Hz1/2/W under 320-nm illumination is obtained. The TBDI/tris (8-hydroxyquinoline) aluminum (Alq3) OLED device exhibits a comparable external quantum efficiency and current efficiency to a traditional 4, 4-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl (α-NPD)/Alq3 OLED. A C70-based Schottky junction with 5 wt%-TBDI yields a power conversion efficiency of 5.0%, which is much higher than 1.7%for anα-NPD-based junction in the same configuration. These results suggest that TBDI has some promising properties which are in favor of the hole-transporting in Schottky junctions with low-concentration donor.

  12. Solution phase photophysics of 5,7-dimethoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one: Analysing the lineaments of a new fluorosensor to probe different micro-environments

    Energy Technology Data Exchange (ETDEWEB)

    Mitra, Amrit Krishna [Department of Clinical and Experimental Pharmacology, School of Tropical Medicine, Kolkata 700073 (India); Ghosh, Sujay; Sau, Abhishek [Chemical Sciences Division, Saha Institute of Nuclear Physics, Kolkata 700064 (India); Saha, Chandan [Department of Clinical and Experimental Pharmacology, School of Tropical Medicine, Kolkata 700073 (India); Basu, Samita, E-mail: [Chemical Sciences Division, Saha Institute of Nuclear Physics, Kolkata 700064 (India)


    We present here a detailed photophysical study of a newly synthesised fluorophore 5,7-dimethoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one (KTHC-57). Spectroscopic investigation of the compound has been carried out in 14 different protic and aprotic solvents, as well as in different binary solvent mixtures, using absorption, steady-state and time-resolved fluorescence techniques. The spectral behaviour of this compound is found to be extremely sensitive to the polarity and hydrogen bonding nature of the solvent. When considered in micelles, reverse micelles and β-cyclodextrin, KTHC-57 behaves as a reporter of its immediate microenvironment. Extent of hypsochromic shift varies as we move from cationic surfactant cetyltrimethylammonium bromide (~40 nm) to anionic surfactant sodium dodecyl sulphate (~23 nm) to non-ionic surfactant Triton X-100 (~37 nm). In case of anionic reverse micellar nanocavities composed of sodium bis(2-ethylhexyl) sulfosuccinate (AOT)/heptane with increasing water contents, a bathochromic shift of ~50 nm is observed. A quantitative assessment of the emission intensity data on Benesi–Hildebrand equation reveals a 1:1 stoichiometry for KTHC-57:β-CD complex. Triethylamine (TEA) is a simple aliphatic organic molecule that interacts with KTHC-57 in polar aprotic medium. Within β-CD environment, fluorescence quenching takes place along with a bathochromic shift. Interaction of (TEA) with KTHC-57 in β-CD nano-confinement is studied using absorption spectroscopy, steady-state as well as time-resolved fluorescence spectroscopy and laser flash photolysis in conjunction with an external magnetic field. - Highlights: • Excited state properties of KTHC-57 vary with its H-bonding environment. • KTHC-57 interacts differently in various microheterogeneous environments. • Benesi–Hildebrand equation reveals a 1:1 stoichiometry for KTHC-57:β-CD complex. • Organic base TEA quench KTHC-57 fluorescence in polar aprotic solvents. • PET takes place from

  13. Solvatomorphism of 9,9'-[1,3,4-thiadiazole-2,5-diylbis(2,3-thiophendiyl-4,1-phenylene)]bis[9H-carbazole]: isostructurality, modularity and order-disorder theory. (United States)

    Stöger, Berthold; Kautny, Paul; Lumpi, Daniel; Zobetz, Erich; Fröhlich, Johannes


    During a systematic investigation of the crystallization behaviour of 9,9'-[1,3,4-thiadiazole-2,5-diylbis(2,3-thiophendiyl-4,1-phenylene)]bis[9H-carbazole] (I), six single crystalline solvates were obtained and characterized by X-ray diffraction at 100 K. The structure of the hemi-2-butanone (MEK) solvate contains two crystallographically independent molecules of (I) related by pseudo-inversion symmetry. The structure is polytypic and composed of non-polar (I) layers and polar solvent layers. It can be described according to an extended order-disorder (OD) theory with relaxed vicinity condition. The observed polytype is of a maximum degree of order (MDO). Layer triples of the second MDO polytype are shown by twinning by inversion. The mono-benzene and mono-toluene solvates are isostructural. Whereas the (I) layers are isostructural to those of the idealized description of the hemi-MEK solvate, the solvent layers are non-polar, resulting in a fully ordered structure. The toluene molecule is ordered, the benzene molecule features disorder. The (I) layers in the sesqui-dioxane and sesqui-benzene solvates are isostructural and unrelated to those in the hemi-MEK, mono-benzene and mono-toluene solvates. The solvent layers are isopointal in both sesqui-solvates, but the stacking differs significantly. The hemi-dideuterodichloromethane (DCM-d(2)) solvate is made up of two kinds of (I) rods, spaced by DCM-d(2) molecules. Rods of one kind are similar to analogous rods in the sesqui-dioxane and the sesqui-benzene solvates, whereas rods of the other kind are only remotely related to rods in the hemi-MEK solvate.

  14. Low-band-gap conjugated polymers of dithieno[2,3-b:7,6-b]carbazole and diketopyrrolopyrrole: effect of the alkyl side chain on photovoltaic properties. (United States)

    Deng, Yunfeng; Chen, Yagang; Liu, Jian; Liu, Lihui; Tian, Hongkun; Xie, Zhiyuan; Geng, Yanhou; Wang, Fosong


    Four donor–acceptor (D–A) conjugated polymers of dithieno[2,3-b;7,6-b]carbazole (DTC) and diketopyrrolopyrrole, which have different alkyls on the nitrogen atom in the DTC unit and are named as P-C8C8, P-C5C5, P-C12, and P-C10, respectively, have been synthesized for studying the effect of the alkyl side chains on the optoelectronic properties of the polymers. All polymers are soluble in various organic solvents and exhibit identical optical band gaps (E(g)(opt)) of ~1.3 eV and highest occupied molecular orbital energy levels of ~−5.1 eV. Organic thin-film transistors and bulk heterojunction polymer solar cells (BHJ PSCs) with phenyl-C(71)-butyric acid methyl ester (PC(71)BM) as the electron-accepting material were fabricated via solution spin-casting. Compared to the polymers substituted by branched alkyl chains, the polymers with straight alkyl chains show higher hole mobility. Of these polymers, P-C10 exhibits the highest field effect mobility up to 0.011 cm(2)/V·s. The alkyl chain on the DTC unit has a strong impact on the film morphology of polymer:PC(71)BM blends. Severe phase separation was found for polymers containing branched alkyl chains, and those with straight alkyl chains formed uniform films featuring fine phase separation. An open-circuit voltage (V(oc)) of 0.72 V, a short-circuit current density (J(sc)) of 13.4 mA/cm(2), a fill factor (FF) of 62%, and a power conversion efficiency (PCE) of 5.9% were demonstrated for BHJ PSCs based on the P-C10:PC(71)BM [1:3 (w/w)] blend film.

  15. A Novel Carbazole-based Cyanine as a Fluorescent Probe for Viscosity Detection%一种新型咔唑类菁染料黏度荧光探针

    Institute of Scientific and Technical Information of China (English)

    刘飞; 吴彤; 胡明明; 彭孝军; 樊江莉


    KQ, a carbazole-based cyanine dye with aldehyde, was synthesized. Dye KQ showed lower fluorescence quantum yield and no obvious fluorescence responses to the polarity of solvents and bio-macromole-cules such as nucleic acids. Dye KQ was very sensitive to the environmental viscosity and gave strong fluorescence enhancement with the increase of the viscosity. Notably, there is a linear relationship between them. The live cell imaging experiments manifested that KQ could penetrate the cell membrane easily, detect the viscosity of the cellular micro-environment and gave bright and explicit staining image of the inner membrane system of live cells.%合成了一种带有醛基的咔唑类菁染料KQ,其自身的荧光量子产率较低,对极性的敏感性小,且荧光信号不受核酸等生物分子的干扰.KQ对环境黏度有很好的荧光响应,相对荧光强度随着环境黏度的增大而增强,并且在1×10-3 ~1.3216 Pa·s黏度范围内,染料的荧光强度与溶液的黏度呈良好的线性关系.活细胞荧光成像实验结果表明,染料KQ具有良好的细胞膜通透性,并可对细胞内不同位置的黏度检测成像.

  16. Biological effects of 6-formylindolo[3,2-b]carbazole (FICZ) in vivo are enhanced by loss of CYP1A function in an Ahr2-dependent manner. (United States)

    Wincent, Emma; Kubota, Akira; Timme-Laragy, Alicia; Jönsson, Maria E; Hahn, Mark E; Stegeman, John J


    6-Formylindolo[3,2-b]carbazole (FICZ) is a potent aryl hydrocarbon receptor (AHR) agonist that is efficiently metabolized by AHR-regulated cytochrome P4501 enzymes. FICZ is a proposed physiological AHR ligand that induces its own degradation as part of a regulatory negative feedback loop. In vitro studies in cells show that CYP1 inhibition in the presence of FICZ results in enhanced AHR activation, suggesting that FICZ accumulates in the cell when its metabolism is blocked. We used zebrafish (Danio rerio) embryos to investigate the in vivo effects of FICZ when CYP1A is knocked down or inhibited. Embryos were injected with morpholino antisense oligonucleotides targeting CYP1A (CYP1A-MO), Ahr2, or a combination of both. FICZ exposure of non-injected embryos or embryos injected with control morpholino had little effect. In CYP1A-MO-injected embryos, however, FICZ dramatically increased mortality, incidence and severity of pericardial edema and circulation failure, reduced hatching frequency, blocked swim bladder inflation, and strongly potentiated expression of Ahr2-regulated genes. These effects were substantially reduced in embryos with a combined knockdown of Ahr2 and CYP1A, indicating that the toxicity was mediated at least partly by Ahr2. Co-exposure to the CYP1 inhibitor alpha-naphthoflavone (αNF) and FICZ had similar effects as the combination of CYP1A-MO and FICZ. HPLC analysis of FICZ-exposed embryos showed increased levels of FICZ after concomitant CYP1A-MO injection or αNF co-exposure. Together, these results show that a functioning CYP1/AHR feedback loop is crucial for regulation of AHR signaling by a potential physiological ligand in vivo and further highlights the role of CYP1 enzymes in regulating biological effects of FICZ.

  17. Sustained induction of cytochrome P4501A1 in human hepatoma cells by co-exposure to benzo[a]pyrene and 7H-dibenzo[c,g]carbazole underlies the synergistic effects on DNA adduct formation

    Energy Technology Data Exchange (ETDEWEB)

    Gábelová, Alena, E-mail: [Cancer Research Institute, Slovak Academy of Sciences, Vlárska 7, 833 91 Bratislava (Slovakia); Poláková, Veronika [Cancer Research Institute, Slovak Academy of Sciences, Vlárska 7, 833 91 Bratislava (Slovakia); Prochazka, Gabriela [Department of Biosciences and Nutrition, Karolinska Institute, Novum, SE-141 83 Huddinge (Sweden); Department of Medical Epidemiology and Biostatistics, Karolinska Institute, SE-171 77 Stockholm (Sweden); Kretová, Miroslava; Poloncová, Katarína; Regendová, Eva; Luciaková, Katarína [Cancer Research Institute, Slovak Academy of Sciences, Vlárska 7, 833 91 Bratislava (Slovakia); Segerbäck, Dan [Department of Biosciences and Nutrition, Karolinska Institute, Novum, SE-141 83 Huddinge (Sweden)


    To gain a deeper insight into the potential interactions between individual aromatic hydrocarbons in a mixture, several benzo[a]pyrene (B[a]P) and 7H-dibenzo[c,g]carbazole (DBC) binary mixtures were studied. The biological activity of the binary mixtures was investigated in the HepG2 and WB-F344 liver cell lines and the Chinese hamster V79 cell line that stably expresses the human cytochrome P4501A1 (hCYP1A1). In the V79 cells, binary mixtures, in contrast to individual carcinogens, caused a significant decrease in the levels of micronuclei, DNA adducts and gene mutations, but not in cell survival. Similarly, a lower frequency of micronuclei and levels of DNA adducts were found in rat liver WB-F344 cells treated with a binary mixture, regardless of the exposure time. The observed antagonism between B[a]P and DBC may be due to an inhibition of Cyp1a1 expression because cells exposed to B[a]P:DBC showed a decrease in Cyp1a1 mRNA levels. In human liver HepG2 cells exposed to binary mixtures for 2 h, a reduction in micronuclei frequency was also found. However, after a 24 h treatment, synergism between B[a]P and DBC was determined based on DNA adduct formation. Accordingly, the up-regulation of CYP1A1 expression was detected in HepG2 cells exposed to B[a]P:DBC. Our results show significant differences in the response of human and rat cells to B[a]P:DBC mixtures and stress the need to use multiple experimental systems when evaluating the potential risk of environmental pollutants. Our data also indicate that an increased expression of CYP1A1 results in a synergistic effect of B[a]P and DBC in human cells. As humans are exposed to a plethora of noxious chemicals, our results have important implications for human carcinogenesis. - Highlights: • B[a]P:DBC mixtures were less genotoxic in V79MZh1A1 cells than B[a]P and DBC alone. • An antagonism between B[a]P and DBC was determined in rat liver WB-F344 cells. • The inhibition of CYP1a1 expression by B[a]P:DBC mixture

  18. 新型污染物卤代咔唑的环境行为及生态毒理效应%Environmental Behaviors and Ecotoxicology of the Emerging Contaminants Polyhalogenated Carbazoles

    Institute of Scientific and Technical Information of China (English)

    林坤德; 陈艳秋; 袁东星


    卤代咔唑( PHCs)是一类与多氯二苯并呋喃结构相类似的新型环境有机污染物。单种卤素取代的PHCs具有135个同系物。绝大多数PHCs不是人类合成化学品或工业品。虽然20世纪80年代即首次在环境中发现PHCs,但直到本世纪这类化合物才逐渐引起人们的关注。近年来,20余种PHCs在河流湖泊沉积物和土壤中被陆续检出。另外,PHCs具有类二英毒性、持久性和生物累积性。作为一类新型污染物,PHCs的环境行为研究目前相对较少。因此,了解PHCs的环境分布、来源和生态毒理效应对正确认识这类化合物的环境风险具有重要意义。本文综述了PHCs的环境分布、来源、分析方法和生态毒理效应,并对其未来的研究发展方向作了展望。%Polyhalogenated carbazoles ( PHCs) , with a complex chemical structure similar to polychlorinated dibenzofurans, are a class of emerging environmental organic contaminants. There are 135 congeners for PHCs with a pure halogenation. Most of PHCs are not man-made products. Although PHCs in the environment were firstly discovered in the 1980s, these emerging halogenated compounds were not seriously considered until recent years. Recently, more than 20 PHCs have been detected in sediment and soil samples. In addition, studies have shown that PHCs exhibited dioxin-like toxicity and were persistent and bioaccumulative. Therefore, it is very important to understand the distribution, origins and ecotoxicology of PHCs for a better assessment of their environmental risks. To date, research on the environmental behaviors of PHCs is relatively limited and warrants further investigations. In this review, the environmental distribution, source, analytical methods and toxicity of PHCs were summarized and future research needs were outlined.

  19. Research on Synthesis and Luminous Mechanism of a Soluble Blue-Light Luminescence Material Derived from Carbazole%一种基于咔唑的可溶性蓝光发光材料的合成与发光机理研究

    Institute of Scientific and Technical Information of China (English)

    李娟; 王华; 宋春丽; 张存; 张俊萍; 郝玉英; 许并社


    通过SN1亲核反应机理及SUZUKI偶联反应,设计并合成了一种含有咔唑及8-苄氧基喹啉基团的有机蓝光发光材料,即N-[6-(8-苄氧基喹啉基)-己基]咔唑(CzBQ).通过紫外-可见吸收光谱和荧光光谱等测试方法对其结构及光物理性能等进行了表征.研究结果表明:CzBQ为一种蓝光有机发光材料,其光学带隙为3.02 eV,在乙醇溶液中的发射峰波长为410 nm;CzBQ具有优良的溶解性和成膜性,适用于湿法制备蓝光有机电致发光器件.%In the present paper, a kind of blue light-emitting organic small molecule luminescent materials was designed and synthesized, which is composed of carbazole and 8-benzyloxyquinoline functional groups. Alkyl chain can effectively play the role of electron transfer barrier. The synthesis principle was on the basis of the mechanisms of Snlnucleophilic reaction and SUZUKI coupling reaction mechanisms. It is entitled N-[6-(8-benzylquinoline)-hexyl] carbazole(CzBQ). Its molecular structure was simulated and optimized by Gaussian03. Its chemical structure was identified by measurements of ultraviolet-visible spectra and H1 NMR spectra. It photo physical property was characterized by method of fluorescence spectra, t is indicated that CzBQ was a kind of blue-light luminescence material and its optical band gap is 3. 02 eV. Ethanol solution of CzBQ exhibits the maximal emission peak at 410 nm in photoluminescence spectra. In the luminescence process of CzBQ, carbazole groups and 8-benzylquin-oline groups were separately involved in excitation and light emission. This kind of blue-light luminescence material possesses excellent solubility, It can be dissolved in different solvents such as ethanol and ethyl acetate and dichloromethane. The test results of AFM show that CzBQ was provided with very good film formability. It is expected to be utilized in blue-light organic light-emitting device fabricated by wet method such as spin-coding method and screen

  20. Mixed-Lineage Kinase 1 and Mixed-Lineage Kinase 3 Subtype-Selective Dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-5-ones: Optimization, Mixed-Lineage Kinase 1 Crystallography, and Oral in Vivo Activity in 1-Methyl-4phenyltetrahydropyridine Models

    Energy Technology Data Exchange (ETDEWEB)

    Hudkins,R.; Diebold, J.; Tao, M.; Josef, K.; Park, C.; Angeles, T.; Aimone, L.; Husten, J.; Ator, M.; et al


    The optimization of the dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-5-one R2 and R12 positions led to the identification of the first MLK1 and MLK3 subtype-selective inhibitors within the MLK family. Compounds 14 (CEP-5104) and 16 (CEP-6331) displayed good potency for MLK1 and MLK3 inhibition with a greater than 30- to 100-fold selectivity for related family members MLK2 and DLK. Compounds 14 and 16 were orally active in vivo in a mouse MPTP biochemical efficacy model that was comparable to the first-generation pan-MLK inhibitor 1 (CEP-1347). The MLK1 structure-activity relationships were supported by the first-reported X-ray crystal structure of MLK1 bound with 16.

  1. Mixed-lineage kinase 1 and mixed-lineage kinase 3 subtype-selective dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-5-ones: optimization, mixed-lineage kinase 1 crystallography, and oral in vivo activity in 1-methyl-4-phenyltetrahydropyridine models. (United States)

    Hudkins, Robert L; Diebold, James L; Tao, Ming; Josef, Kurt A; Park, Chung Ho; Angeles, Thelma S; Aimone, Lisa D; Husten, Jean; Ator, Mark A; Meyer, Sheryl L; Holskin, Beverly P; Durkin, John T; Fedorov, Alexander A; Fedorov, Elena V; Almo, Steven C; Mathiasen, Joanne R; Bozyczko-Coyne, Donna; Saporito, Michael S; Scott, Richard W; Mallamo, John P


    The optimization of the dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-5-one R(2) and R(12) positions led to the identification of the first MLK1 and MLK3 subtype-selective inhibitors within the MLK family. Compounds 14 (CEP-5104) and 16 (CEP-6331) displayed good potency for MLK1 and MLK3 inhibition with a greater than 30- to 100-fold selectivity for related family members MLK2 and DLK. Compounds 14 and 16 were orally active in vivo in a mouse MPTP biochemical efficacy model that was comparable to the first-generation pan-MLK inhibitor 1 (CEP-1347). The MLK1 structure-activity relationships were supported by the first-reported X-ray crystal structure of MLK1 bound with 16.

  2. 9-Ethynyl-9H-carbazole

    Directory of Open Access Journals (Sweden)

    Hideyuki Tabata


    Full Text Available The title compound, C14H9N, is the second crystallographically characterized example of an ynamine with an H atom in the C-terminal position. There are two independent molecules (A and B in the asymmetric unit. The structures of both molecules are essentially planar (r.m.s. deviation = 0.0312 and 0.0152 Å. The N—Csp bond lengths are 1.353 (4 and 1.350 (4 Å, and those of the acetylene bonds are 1.189 (4 and 1.190 (4 Å. The Csp—H bond lengths are 0.95 (5 and 0.97 (4 Å. These geometries are consistent with those of the previously reported ynamine characterized by crystallography. In the crystal, the molecules stack along the c axis, forming two kinds of columnar structures. The acetylene C atoms of molecule A have a short contact [3.341 (4 Å and 3.396 (4 Å] with an adjacent molecule A at the C—C bond of the fused part, which originates in π–π stacking interaction; no remarkable spatial contact is recognized within the stacking of molecule B.

  3. Mono- and multilayers of molecular spoked carbazole wheels on graphite

    Directory of Open Access Journals (Sweden)

    Stefan-S. Jester


    Full Text Available Self-assembled monolayers of a molecular spoked wheel (a shape-persistent macrocycle with an intraannular spoke/hub system and its synthetic precursor are investigated by scanning tunneling microscopy (STM at the liquid/solid interface of 1-octanoic acid and highly oriented pyrolytic graphite. The submolecularly resolved STM images reveal that the molecules indeed behave as more or less rigid objects of certain sizes and shapes – depending on their chemical structures. In addition, the images provide insight into the multilayer growth of the molecular spoked wheels (MSWs, where the first adlayer acts as a template for the commensurate adsorption of molecules in the second layer.

  4. Microporous Polymers from a Carbazole-Based Triptycene Monomer: Synthesis and Their Applications for Gas Uptake. (United States)

    Zhai, Tian-Long; Tan, Liangxiao; Luo, Yi; Liu, Jun-Min; Tan, Bien; Yang, Xiang-Liang; Xu, Hui-Bi; Zhang, Chun


    Two kinds of novel organic microporous polymers TCPs (TCP-A and TCP-B) were prepared by two cost-effective synthetic strategies from the monomer of tricarbazolyltriptycene (TCT). Their structure and properties were characterized by FT-IR, solid (13) C NMR, powder XRD, SEM, TEM, and gas absorption measurements. TCP-B displayed a high surface area (1469 m(2)  g(-1) ) and excellent H2 storage (1.70 wt % at 1 bar/77 K) and CO2 uptake abilities (16.1 wt % at 1 bar/273 K), which makes it a promising material for potential application in gas storage.

  5. Experimental and theoretical study of three new benzothiazole-fused carbazole derivatives (United States)

    Shi, He-ping; Xu, Lei; Cheng, Ying; He, Jing-yuan; Dai, Jian-xin; Xing, Li-wen; Chen, Bai-quan; Fang, Li


    Three new D-π-A type compounds, each containing one benzothiazole ring as an electron acceptor and one N-ethylcarbazole group as electron donor, were synthesized and characterized by elemental analysis, NMR, MS and thermogravimetric analysis. The absorption and emission spectra of three compounds were experimentally determined in several solvents and were simultaneously computed using density functional theory (DFT) and time-dependent density functional theory (TDDFT). The calculated reorganization energy for hole and electron indicates that three compounds are in favor of hole transport than electron transport. The calculated absorption and emission wavelengths are well coincident with the measured data. The calculated lowest-lying absorption spectra can be mainly attributed to intramolecular charge transfer (ICT). And the calculated fluorescence spectra can be mainly described as originating from an excited state with intramolecular charge transfer (ICT) character. The results show that three compounds exhibited excellent thermal stability and high fluorescence quantum yields, indicating their potential applications as excellent optoelectronic material in optical field.

  6. Synthesis, photophysical and electrochemical properties of a carbazole dimer-based derivative with benzothiazole units (United States)

    Shi, He-ping; Dai, Jian-xin; Shi, Li-wen; Xu, Lei; Zhou, Zhao-bin; Zhang, Yan; Zhou, Wen; Dong, Chuan

    A novel A-π-D-π-D-π-A type compound, containing two benzothiazole rings as electron acceptors and two N-ethylcarbazole groups as electron donors, (E)-1,2-bis(3-(benzothiazol-2-yl)-9-ethylcarbazol-6-yl)ethene (BBECE), was synthesized and characterized by elemental analysis, NMR, MS and thermogravimetric analysis. Electrochemical property of compound BBECE was studied by cyclic voltammetry analysis. The absorption and emission spectra of BBECE was experimentally determined in several solvents and simultaneously computed using density functional theory (DFT) and time-dependent density functional theory (TDDFT). The calculated absorption and emission wavelengths are coincident with the measured data. The lowest-lying absorption spectra can be mainly attributed to intramolecular charge transfer (ICT), and the fluorescence spectra can be mainly described as originating from an excited state with intramolecular charge transfer (ICT) character. The molecular orbitals (HOMO and LUMO), the ionization potential (IP), the electron affinity (EA) and reorganization energy of compound BBECE were also investigated using density functional theory (DFT). The results show that compound BBECE exhibited excellent thermal stability and electrochemical stability as well as high fluorescence quantum yield, indicating its potential applications as an excellent optoelectronic material in optical fields.


    Institute of Scientific and Technical Information of China (English)

    Feng Jiang; Jin-qing Qu; Huan-qin Chen


    Novel 9-proparylcarbazole monomers containing amino acid moieties, 2-N-(tert-butoxycarbonyl)-L-alanine-9-proparylcarbazole ester (1), 2-N-(tert-butoxycarbonyl)-L-O-cyclohexyI-L-glutamic acid-9-proparylcarbazole ester (2) and 2-N-(tert-butoxycarbonyl)-L-phenylalanine-9-proparylcarbazole ester (3) were synthesized and polymerized with (nbd)Rh~+[η~6-C_6H_5B~-(C_6H_5)_3 ] to give the corresponding polymers with number-average molecular weights ranging from 7050 to 10500 in 70%-86% yields. The polymers were completely soluble in toluene, CHCl_3 , CH_2Cl_2, THF and DMSO, but insoluble in hexane, diethyl ether and MeOH. The specific rotation studies revealed that poly(1)-poly(3) do not took predominantly one-handed helical structures in the solvents although they possess chiral groups. The polymers emitted fluorescence in 0.40%-2.35% quantum yields. The cyclic voltammograms of the polymers indicated that the polymers exhibited electrochemical properties.


    Institute of Scientific and Technical Information of China (English)



    Novel 9-proparylcarbazole monomers containing amino acid moieties,2-N(tert-butoxycarbonyl)-L-alanine- 9-proparylcarbazole ester(1),2-N-(tert-butoxycarbonyl)-L-O-cyclohexyl-L-glutamic acid-9-proparylcarbazole ester(2) and 2-N-(tert-butoxycarbonyl)-L-phenylalanine-9-proparylcarbazole ester(3) were synthesized and polymerized with (nbd)Rh~+[η~6-C_6H_5B~-(C_6H_5)_3]to give the corresponding polymers with number-average molecular weights ranging from 7050 to 10500 in 70%-86%yields.The polymers were completely...

  9. 75 FR 52930 - Carbazole Violet Pigment 23 From India: Preliminary Results of Antidumping Duty Changed... (United States)


    ... of its sales of merchandise subject to the antidumping duty order for the 2008/09 period in a timely... case, the brackets are simply part of the chemical nomenclature. Use of Adverse Facts Available For...

  10. 75 FR 977 - Carbazole Violet Pigment 23 From India: Preliminary Results of Countervailing Duty Administrative... (United States)


    ... brackets are simply part of the chemical nomenclature. Subsidies Valuation Information Benchmark Interest... the goods to the date of realization of the proceeds from the sale to the overseas customer. Under the... sales within 180 days of shipment. Post-shipment financing is, therefore, a working capital program...

  11. 75 FR 29719 - Carbazole Violet Pigment 23 From India: Continuation of Countervailing Duty Order (United States)


    ... From the Federal Register Online via the Government Publishing Office DEPARTMENT OF COMMERCE... likely lead to continuation of countervailable subsidies, and material injury to an industry in the United States, the Department is publishing a notice of continuation of this CVD order. DATES:...

  12. Synthesis, photophysical, electrochemical and thermal studies on carbazole-based acceptor molecules for heterojunction solar cell

    Energy Technology Data Exchange (ETDEWEB)

    Banerjee, Shibdas; Ali, Farman [Department of Chemical Sciences, Tata Institute of Fundamental Research, Homi Bhabha Road, Colaba, Mumbai 400005 (India); Nayak, Pabitra K., E-mail: [Department of Chemical Sciences, Tata Institute of Fundamental Research, Homi Bhabha Road, Colaba, Mumbai 400005 (India); Department of Materials and Interfaces, Weizmann Institute of Science, Rehovot, 76100 (Israel); Agarwal, Neeraj, E-mail: [Centre for Excellence in Basic Sciences, University of Mumbai, Kalina campus, Santacruz(E), Mumbai 400098 (India)


    Five small molecules, 3-tricyanovinyl-N-alkylcarbazoles (6-10) have been synthesized in a cost-effective way and characterized. The molecules have high thermal stability, good thin film formation ability and are also air stable. The change of alkyl chain length altered the aggregation pattern in the thin film. Their photophysical and electrochemical studies promise a compatible highest occupied molecular orbital - lowest unoccupied molecular orbital energy level to be potentially useful as good electron acceptor materials in heterojunction solar cell in combination with copper(II)phthalocyanine or poly-3-hexylthiophene (P3HT) as donor. Significant photoluminescence quenching of P3HT in P3HT:6-10 blends were observed. - Highlights: Black-Right-Pointing-Pointer 3-tricyanovinyl-N-alkylcarbazoles have been synthesized and characterized. Black-Right-Pointing-Pointer Aggregation properties of these compounds in thin film showed the role of alkyl chain. Black-Right-Pointing-Pointer Photoluminescence quenching with the P3HT blends of these compounds were studied.

  13. Synthesis, supramolecular structures and luminescent properties of quinacridone derivatives bearing carbazole groups

    Institute of Scientific and Technical Information of China (English)

    ZHAO GuoLi; FAN Yan; HUO Cheng; BIAN Hang; SONG WeiFeng; ZHANG JingYing; WANG Yue


    The syntheses of three carbazyl-containing quinacridone derivatives, N,N'-di((N-carbazyl)-n-butyl)quinacridone (DCBQA), N,N'-di((N-carbazyl)-n-hexyl)quinacridone (DCHQA) and N,N'-di((N-carbazyl)-n-octyl)quinacridone (DCOQA), are reported, and the photoluminescent (PL) characteristics are pre-sented. The single crystal X-ray structures of DCBQA, DCHQA and DCOQA are investigated. The crystal of DCBQA is characterized by intermolecular TT···TT interactions between quinacridone cores and car-bezole moieties resulting in the formation of DCBQA molecule layer, in which every quinacridone core is surrounded by four cerbazole groups. In DCHQA crystal, molecules assemble into two kinds of ori-ented columns based on intermolecular TT···TT interactions between quinacridone cores. The DCOQA crystal displays intermolecular CH···TT and hydrogen bonding interactions feature. In DCOQA solid, every quinacridone core is sandwiched by two alkyl chains from two adjacent DCOQA molecules and simultaneously linked together.with two other quinacridone cores by hydrogen bonding interactions. The PL spectra of the three compounds in solution exhibit concentration-dependent properties and their PL quantum causes decrease with the increasing concentration.

  14. Synthesis, Characterization and Photophysical Properties of Pyridine-Carbazole Acrylonitrile Derivatives


    Gabriel Ramos-Ortiz; Enrique Pérez-Gutiérrez; José Luis Maldonado; Chapela, Víctor M.; Margarita Cerón; M. Judith Percino


    We synthesized three novel highly fluorescent compounds, 2-(2’-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile, 2-(3”-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile, and 2-(4-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile by Knoevenagel condensation. The first two were synthesized without solvent in the presence of piperidine as a catalyst; the third was synthesized without a catalyst and with N,N-dimethylformamide as a solvent. In solution, the molar absorption coefficients showed ab...

  15. 75 FR 38076 - Carbazole Violet Pigment 23 from India: Final Results of Antidumping Duty Administrative Review (United States)


    ... receive a request for a hearing. \\1\\ Nation Ford Chemical Company and Sun Chemical Corporation. The period... the antidumping duty order is CVP 23 identified as Color Index No. 51319 and Chemical Abstract No... dry color. Pigment dispersions in any form (e.g., pigment dispersed in oleoresins, flammable...

  16. Synthesis, Characterization and Photophysical Properties of Pyridine-Carbazole Acrylonitrile Derivatives

    Directory of Open Access Journals (Sweden)

    Gabriel Ramos-Ortiz


    Full Text Available We synthesized three novel highly fluorescent compounds, 2-(2’-pyridyl-3-(N-ethyl-(3’-carbazolylacrylonitrile, 2-(3”-pyridyl-3-(N-ethyl-(3’-carbazolylacrylonitrile, and 2-(4-pyridyl-3-(N-ethyl-(3’-carbazolylacrylonitrile by Knoevenagel condensation. The first two were synthesized without solvent in the presence of piperidine as a catalyst; the third was synthesized without a catalyst and with N,N-dimethylformamide as a solvent. In solution, the molar absorption coefficients showed absorptions at 380, 378, and 396 nm, respectively; in solid state, absorptions were at 398, 390, and 442 nm, respectively. The fluorescence emission was at 540, 540 and 604 nm, respectively, the 2-(4-pyridyl-3-(N-ethyl-(3’-carbazolylacrylonitrile showed a red shift in the emission of 64 nm compared to the other two compounds. The fluorescence quantum yield for the compounds in powder form showed values of 0.05, 0.14, and 0.006, respectively; compared with the value measured for the Alq3 reference, 2-(3”-pyridyl-3-(N-ethyl-(3’-carbazolylacrylonitrile had a lightly higher value. The third harmonic generation measurement for 2-(2’-pyridyl-3-(N-ethyl-(3’-carbazolylacrylonitrile yielded a χ(3 value of 5.5 × 10−12 esu, similar to that reported for commercial polymers.

  17. Synthesis, Characterization and Photophysical Properties of Pyridine-Carbazole Acrylonitrile Derivatives


    Pérez-Gutiérrez,Enrique; Percino, M. Judith; Chapela, Víctor M.; Cerón, Margarita; Maldonado, José Luis; Ramos-Ortiz, Gabriel


    in solid state, absorptions were at 398, 390, and 442 nm, respectively. The fluorescence emission was at 540, 540 and 604 nm, respectively, the 2-(4-pyridyl)-3-(N-ethyl-(3’-carbazolyl))acrylonitrile showed a red shift in the emission of 64 nm compared to the other two compounds. The fluorescence quantum yield for the compounds in powder form showed values of 0.05, 0.14, and 0.006, respectively

  18. Synthesis of potent, substituted carbazoles as selective androgen receptor modulators (SARMs). (United States)

    Miller, Chris P; Bhaket, Pushpal; Muthukaman, Nagarajan; Lyttle, C Richard; Shomali, Maysoun; Gallacher, Kyla; Slocum, Connie; Hattersley, Gary


    The synthesis and in vitro binding affinity for a novel series of potent androgen receptor modulators is described. One of the more potent compounds (17, RAD35010) was further characterized in vivo where it restored levator ani weight in castrated male rats to near sham level while having no significant effect on prostate weight.

  19. 75 FR 36630 - Carbazole Violet Pigment 23 from the People's Republic of China: Final Results of Antidumping... (United States)


    ...)(C) of the Act: (1) for subject merchandise exported by Trust Chem, the cash deposit rate will be 30... not listed above that have separate rates, the cash deposit rate will continue to be the exporter... have not been found to be entitled to a separate rate, the cash deposit rate will be the PRC-wide...

  20. Highly efficient multilayer organic pure-blue-light emitting diodes with substituted carbazoles compounds in the emitting layer

    CERN Document Server

    Fischer, A; Chenais, S; Castex, M C; Siove, A; Ades, D; Geffroy, B; Denis, C; Maisse, P; Fischer, Alexis; Forget, Sebastien; Chenais, Sebastien; Castex, Marie-Claude; Siove, Alain; Ades, Dominique; Geffroy, Bernard; Denis, Christine; Maisse, Pascal


    Bright blue organic light-emitting diodes (OLEDs) based on 1,4,5,8,N-pentamethylcarbazole (PMC) and on dimer of N-ethylcarbazole (N,N'-diethyl-3,3'-bicarbazyl) (DEC) as emitting layers or as dopants in a 4,4'-bis(2,2'-diphenylvinyl)-1,1'-biphenyl (DPVBi) matrix are described. Pure blue-light with the C.I.E. coordinates x = 0.153 y = 0.100, electroluminescence efficiency \\eta_{EL} of 0.4 cd/A, external quantum efficiency \\eta_{ext.} of 0.6% and luminance L of 236 cd/m2 (at 60 mA/cm2) were obtained with PMC as an emitter and the 2,9-dimethyl-4,7-diphenyl-1,10-phenantroline (BCP) as a hole-blocking material in five-layer emitting devices. The highest efficiencies \\eta_{EL.} of 4.7 cd/A, and \\eta_{ext} = 3.3% were obtained with a four-layer structure and a DPVBi DEC-doped active layer (CIE coordinates x = 0.158, y=0.169, \\lambda_{peak} = 456 nm). The \\eta_{ext.} value is one the highest reported at this wavelength for blue OLEDs and is related to an internal quantum efficiency up to 20%.

  1. Highly efficient multilayer organic pure blue light emitting diodes with substituted carbazoles compounds in the emitting layer

    Energy Technology Data Exchange (ETDEWEB)

    Fischer, A [Laboratoire de Physique des Lasers (LPL, CNRS), Institut Galilee, Universite Paris 13, 93430 Villetaneuse (France); Chenais, S [Laboratoire de Physique des Lasers (LPL, CNRS), Institut Galilee, Universite Paris 13, 93430 Villetaneuse (France); Forget, S [Laboratoire de Physique des Lasers (LPL, CNRS), Institut Galilee, Universite Paris 13, 93430 Villetaneuse (France); Castex, M-C [Laboratoire de Physique des Lasers (LPL, CNRS), Institut Galilee, Universite Paris 13, 93430 Villetaneuse (France); Ades, D [Biomateriaux et Polymeres de Specialite (BPS/B2OA, CNRS), Institut Galilee, Universite Paris 13, Villetaneuse/Faculte de Medecine Lariboisiere-St Louis, Universite Paris 7, 75010 Paris (France); Siove, A [Biomateriaux et Polymeres de Specialite (BPS/B2OA, CNRS), Institut Galilee, Universite Paris 13, Villetaneuse/Faculte de Medecine Lariboisiere-St Louis, Universite Paris 7, 75010 Paris (France); Denis, C [Laboratoire Cellules et Composants, CEA/LITEN/DSEN, CEA Saclay, 91191 Gif-sur-Yvette (France); Maisse, P [Laboratoire Cellules et Composants, CEA/LITEN/DSEN, CEA Saclay, 91191 Gif-sur-Yvette (France); Geffroy, B [Laboratoire Cellules et Composants, CEA/LITEN/DSEN, CEA Saclay, 91191 Gif-sur-Yvette (France)


    Bright blue organic light-emitting diodes (OLEDs) based on 1, 4, 5, 8, N-pentamethylcarbazole (PMC) and on dimer of N-ethylcarbazole (N, N'-diethyl-3, 3'-bicarbazyl) (DEC) as emitting layers or as dopants in a 4, 4'-bis(2, 2'-diphenylvinyl)-1, 1'-biphenyl (DPVBi) matrix are described. Pure blue light with the CIE coordinates (x = 0.153, y = 0.100), electroluminescence efficiency {eta}{sub EL} of 0.4 cd A{sup -1}, external quantum efficiency {eta}{sub ext} of 0.6% and luminance L of 236 cd m{sup -2} (at 60 mA cm{sup -2}) were obtained with PMC as an emitter and the 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenantroline (BCP) as a hole-blocking material in five-layer emitting devices. The highest efficiencies {eta}{sub EL} of 4.7 cd A{sup -1} and {eta}{sub ext} = 3.3% were obtained with a four-layer structure and a DPVBi DEC-doped active layer (CIE coordinates x = 0.158, y = 0.169, {lambda}{sub peak} = 456 nm). The {eta}{sub ext} value is one the highest reported at this wavelength for blue OLEDs and is related to an internal quantum efficiency up to 20%.

  2. Highly efficient multilayer organic pure blue light emitting diodes with substituted carbazoles compounds in the emitting layer (United States)

    Fischer, A.; Chénais, S.; Forget, S.; Castex, M.-C.; Adès, D.; Siove, A.; Denis, C.; Maisse, P.; Geffroy, B.


    Bright blue organic light-emitting diodes (OLEDs) based on 1, 4, 5, 8, N-pentamethylcarbazole (PMC) and on dimer of N-ethylcarbazole (N, N'-diethyl-3, 3'-bicarbazyl) (DEC) as emitting layers or as dopants in a 4, 4'-bis(2, 2'-diphenylvinyl)-1, 1'-biphenyl (DPVBi) matrix are described. Pure blue light with the CIE coordinates (x = 0.153, y = 0.100), electroluminescence efficiency ηEL of 0.4 cd A-1, external quantum efficiency ηext of 0.6% and luminance L of 236 cd m-2 (at 60 mA cm-2) were obtained with PMC as an emitter and the 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenantroline (BCP) as a hole-blocking material in five-layer emitting devices. The highest efficiencies ηEL of 4.7 cd A-1 and ηext = 3.3% were obtained with a four-layer structure and a DPVBi DEC-doped active layer (CIE coordinates x = 0.158, y = 0.169, λpeak = 456 nm). The ηext value is one the highest reported at this wavelength for blue OLEDs and is related to an internal quantum efficiency up to 20%.

  3. 75 FR 12497 - Carbazole Violet Pigment 23 from India and the People's Republic of China: Final Results of the... (United States)


    ... China, 69 FR 77987 (December 29, 2004); Notice of Amended Final Determination of Sales at Less Than Fair... chemical nomenclature. Analysis of Comments Received All issues raised in these reviews are addressed...

  4. 75 FR 13257 - Carbazole Violet Pigment 23 from India: Final Results of the Expedited Five-year (Sunset) Review... (United States)


    ... interested parties and Petitioners in the original investigation, Nation Ford Chemical Company and Sun... Color Index No. 51319 and Chemical Abstract No. 6358-30-1, with the chemical name of diindolo... the form of presscake and dry color. Pigment dispersions in any form (e.g., pigments dispersed...

  5. 2-{N-[(2,3,4,9-Tetrahydro-1H-carbazol-3-ylmethyl]methylsulfonamido}ethyl methanesulfonate

    Directory of Open Access Journals (Sweden)

    Mustafa Göçmentürk


    Full Text Available In the title compound, C17H24N2O5S2, the indole ring system is nearly planar [maximum deviation = 0.032 (1 Å] and the cyclohexene ring has a half-chair conformation. In the crystal, N—H...O hydrogen bonds link the molecules into a chain running along the b-axis direction. Weak C—H...O hydrogen bonds and weak C—H...π interactions are observed between the chains.

  6. Novel molecular host materials based on carbazole/PO hybrids with wide bandgap via unique linkages for solution-processed blue phosphorescent OLEDs (United States)

    Ye, Hua; Zhou, Kaifeng; Wu, Hongyu; Chen, Kai; Xie, Gaozhan; Hu, Jingang; Yan, Guobing; Ma, Songhua; Su, Shi-Jian; Cao, Yong


    A series of novel molecules with wide bandgap based on electron-withdrawing diphenyl phosphine oxide units and electron-donating carbazolyl moieties through insulated unique linkages of flexible chains terminated by oxygen or sulfur atoms as solution-processable host materials were successfully synthesized for the first time, and their thermal, photophysical, and electrochemical properties were studied thoroughly. These materials possess high triplet energy levels (ET, 2.76-2.77 eV) due to the introduction of alkyl chain to interrupt the conjugation between electron-donor and electron-acceptor. Such high ET could effectively curb the energy from phosphorescent emitter transfer to the host molecules and thus assuring the emission of devices was all from the blue phosphorescent emitter iridium (III) bis [(4,6-difluorophenyl)-pyridinate-N,C2‧]picolinate (FIrpic). Among them, the solution-processed device based on CBCR6OPO without extra vacuum thermal-deposited hole-blocking layer and electron-transporting layer showed the highest maximum current efficiency (CEmax) of 4.16 cd/A. Moreover, the device presented small efficiency roll-off with current efficiency (CE) of 4.05 cd/A at high brightness up to 100 cd/m2. Our work suggests the potential applications of the solution-processable materials with wide bandgap in full-color flat-panel displays and organic lighting.

  7. Microwave assisted synthesis, characterization and biocidal activities of some new chelates of carbazole derived Schiff bases of cadmium and tin metals. (United States)

    Yadav, Manju; Mishra, Neelima; Sharma, Nutan; Chandra, Sulekh; Kumar, Dinesh


    This study is planned to report the advancement of green microwave approach in the fabrication of a new series of biologically potent (N^X, where X=O/S) donor Schiff bases and their cadmium(II) and tin(II) complexes. The ligands and their metal complexes have been characterized in terms of elemental analysis, molar ionic conductance, magnetic moment and spectral (IR, UV-Vis, NMR ((1)H, (119)Sn), FAB-mass, thermal and XRD) data. The data revealed that the ligands coordinated to the metal center via nitrogen and oxygen/sulfur atoms and form an octahedral arrangement of the ligands around central metal atom. All compounds were evaluated for their in vitro antimicrobial activities against two pathogenic bacteria Bacillus subtilis and Escherichia coli and two fungi Aspergillus niger and Aspergillus flavus by standard disc diffusion method. The discs were stored in an incubator at 37°C. The compounds were dissolved in DMF at 500 and 1000 ppm concentrations for screening biocidal activity. The compounds were dissolved in DMF to get the 100 and 200 ppm concentration of test solutions for screening fungicidal activity. The inhibition zone around each disc was measured (in mm) after 24 h and 96 h for biocidal and fungicidal activities respectively.

  8. Tuning the spectral, morphological and photophysical properties of sonochemically synthesized poly(carbazole) using acid Orange, fluorescein and rhodamine 6G (United States)

    Riaz, Ufana; Ashraf, S. M.; Fatima, Talat; Jadoun, Sapana


    The lifetimes and quantum yields of organic dyes are widely investigated due to their potential application in organic light emitting diodes (OLEDs). With a view to explore the possibility of enhancing the fluorescent properties of organic conjugated polymers such as polycarbazole, the present preliminary study reports for the first time, dye modification of polycarbazole using as acid orange (AO), fluorescein (Fluo) and Rhodamine 6G (R6G) for improving its fluorescence properties. The modification of PCz via doping was confirmed by FTIR, UV-visible, XRD and TEM analyses. The fluorescence studies and confocal microscopy were carried out both in solution and solid states to investigate the behavior of the dye modified PCz. Doping was found to be governed by the chemical structure of the dye. PCz-AO revealed intense doping which was confirmed by FTIR and UV-visible studies. PCz-Fluo and PCz-R6G exhibited the highest quantum yield and fluorescence emission in the solid state. Hence, by tailoring the structure of these conjugated polymers, stable fluorescence emitting materials can be designed for their potential application in OLEDs.

  9. 4-Amino-3-[2-(9H-carbazol-9-ylethyl]-1H-1,2,4-triazole-5(4H-thione dimethyl sulfoxide monosolvate

    Directory of Open Access Journals (Sweden)

    Joel T. Mague


    Full Text Available In the crystal of the title compound, C16H15N5S·C2H6OS, both the 1,2,4-triazole derivative molecules and the disordered [refined occupancy ratio = 0.604 (1:0.396 (1] dimethyl sulfoxide solvent molecules form centrosymmetric dimers, by way of pairwise N—H...S and C—H...O hydrogen bonds, respectively. In the crystal, the two types of dimer are connected by N—H...O hydrogen bonds, forming infinite chains parallel to [101]. The packing is assisted by π–π stacking and C—H...π(ring and N—H...π(ring interactions.

  10. Correlating excited state and charge carrier dynamics with photovoltaic parameters of perylene dye sensitized solar cells: influences of an alkylated carbazole ancillary electron-donor. (United States)

    Li, Yang; Wang, Junting; Yuan, Yi; Zhang, Min; Dong, Xiandui; Wang, Peng


    Two perylene dyes characteristic of electron-donors phenanthrocarbazole (PC) and carbazyl functionalized PC are selected to study the complicated dynamics of excited states and charge carriers, which underlie the photovoltaic parameters of dye-sensitized solar cells (DSCs). We have combined femtosecond fluorescence up-conversion and time-resolved single-photon counting techniques to probe the wavelength-dependent photoluminescence dynamics of dye molecules not only dissolved in THF but also grafted on the surface of oxide nanoparticles. Excited state relaxation and electron injection both occur on a similar timescale, resulting in a very distributive kinetics of electron injection. It is also found that the carbazyl ancillary electron-donor causes a faster electron injection, which over-compensates the adverse impact of a slightly shorter lifetime of the equilibrium excited state. Nanosecond transient absorption and transient photovoltage decay measurements have shown that conjugating carbazyl to PC can effectively slow down the kinetics of charge recombination of electrons in titania with both photo-oxidized dye molecules and triiodide anions, improving the cell photovoltage.

  11. Synthesis of indolo[3,2-b]carbazole-based new colorimetric receptor for anions: A unique color change for fluoride ions

    Directory of Open Access Journals (Sweden)

    Ajit Kumar Mahapatra


    Full Text Available A novel indolocarbazole-based chemosensor 1 containing hydrogen bond donor moieties has been established as a selective colorimetric and fluorometric sensor for F− in CH3CN/H2O (4:1 v/v. Upon the addition of a series of tetrabutylammonium salts to receptor 1 in aqueous CH3CN, only when the counter ion was F− was a significant color change (from light violet to dark orange observed.

  12. Factors Affecting the Performance of Champion Silyl-Anchor Carbazole Dye Revealed in the Femtosecond to Second Studies of Complete ADEKA-1 Sensitized Solar Cells. (United States)

    Sobuś, Jan; Gierczyk, Błażej; Burdziński, Gotard; Jancelewicz, Mariusz; Polanski, Enrico; Hagfeldt, Anders; Ziółek, Marcin


    Record laboratory efficiencies of dye-sensitized solar cells have been recently reported using an alkoxysilyl-anchor dye, ADEKA-1 (over 14 %). In this work we use time-resolved techniques to study the impact of key preparation factors (dye synthesis route, addition of co-adsorbent, use of cobalt-based electrolytes of different redox potential, creation of insulating Al2 O3 layers and molecule capping passivation of the electrode) on the partial charge separation efficiencies in ADEKA-1 solar cells. We have observed that unwanted fast recombination of electrons from titania to the dye, probably associated with the orientation of the dyes on the titania surface, plays a crucial role in the performance of the cells. This recombination, taking place on the sub-ns and ns time scales, is suppressed in the optimized dye synthesis methods and upon addition of the co-adsorbent. Capping treatment significantly reduces the charge recombination between titania and electrolyte, improving the electron lifetime from tens of ms to hundreds of ms, or even to single seconds. Similar increase in electron lifetime is observed for homogenous Al2 O3 over-layers on titania nanoparticles, however, in this case the total solar cells photocurrent is decreased due to smaller electron injection yield from the dye. Our studies should be important for a broader use of very promising silyl-anchor dyes and the further optimization and development of dye-sensitized solar cells.

  13. The effects of linear assembly of two carbazole groups on acid-base and DNA-binding properties of a ruthenium(II) complex. (United States)

    Chen, Xi; Xue, Long-Xin; Ju, Chun-Chuan; Wang, Ke-Zhi


    A novel Ru(II) complex of [Ru(bpy)2(Hbcpip)](ClO4)2 {where bpy=2,2-bipyridine, Hbcpip=2-(4-(9H-3,9'-bicarbazol-9-yl)phenyl)-1H-imidazo[4,5-f][1,10]phenanthroline} is synthesized and characterized. Calf-thymus DNA-binding properties of the complex were studied by UV-vis absorption and luminescence titrations, steady-state emission quenching by [Fe(CN)6](4-), DNA competitive binding with ethidium bromide, thermal denaturation and DNA viscosity measurements. The results indicate that the complex partially intercalated into the DNA with a binding constant of (5.5±1.4)×10(5) M(-1) in buffered 50 mM NaCl. The acid-base properties of the complex were also studied by UV-visible and luminescence spectrophotometric pH titrations, and ground- and excited-state acidity ionization constant values were derived.

  14. Carbazole Hydrazone as Fluorescence Sensor for Nitrite%咔唑腙为荧光指示剂的亚硝酸根传感器

    Institute of Scientific and Technical Information of China (English)

    焦晨旭; 焦东旭


    合成了一种共轭的咔唑二聚体荧光载体9-乙基-3-咔唑亚甲基-咔唑腙(ECCH),用PVC包埋的方法可以将它固定在光纤传感器的表面,在溶液pH值为2.0时,亚硝酸根(NO-2)与过量的碘离子(I-)反应生成的碘三离子(I-3)能猝灭此ECCH光极膜的荧光.得到了可以检测NO-2的传感器,并讨论了此传感器的传感机理.传感器具有较好的稳定性、重现性和选择性,使用寿命长等优点.NO-2测定的线性范围为1.0×10-6~1.0×10-4mol·L-1;检出限为4.0 X10-7mol·L-1.将传感器用于水样中NO-2的直接测定,回收率在96.O%~103.6%.

  15. The tryptophan photoproduct 6-formylindolo[3,2-b]carbazole (FICZ) binds multiple AHRs and induces multiple CYP1 genes via AHR2 in zebrafish

    DEFF Research Database (Denmark)

    Jönsson, Maria E.; Franks, Diana G.; Woodin, Bruce R.;


    to FICZ is evolutionarily conserved in vertebrates by measuring FICZ binding to two zebrafish AHRs (AHR1B and AHR2) and its ability to induce zebrafish CYP1 genes (CYP1A, CYP1B1, CYP1C1, CYP1C2, and CYP1D1) in vivo. Exposure of zebrafish embryos (48 h-post-fertilization; hpf) to 10 nM FICZ for 6 h caused...... strong induction of CYP1A mRNA and a statistically significant but modest induction of CYP1B1 and CYP1C1. Neither CYP1C2 nor CYP1D1 expression was induced by FICZ under the conditions of dose, time or developmental stage examined here. CYP1A induction was significantly greater after 6 h than after 12 h...... of exposure to FICZ, suggesting a rapid degradation of inducer. The 6-h EC50 values for induction of CYP1A and CYP1B1 by FICZ were 0.6 and 0.5 nM compared to 72-h EC50 values of 2.3 and 2.7 nM for PCB126, indicating that in zebrafish embryos FICZ is a more potent inducer than PCB126. FICZ at 10 nM was able...

  16. 1,2-Bis[5-(9-ethyl-9H-carbazol-3-yl-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopentene

    Directory of Open Access Journals (Sweden)

    Koji Kubono


    Full Text Available The title compound, C43H32F6N2S2, is a new symmetrical photochromic diarylethene derivative with 9-ethylcarbazol-3-yl substituents. The molecule adopts a photoactive antiparallel conformation [Irie (2000. Chem. Rev. 100, 1685–1716; Kobatake et al. (2002. Chem. Commun. pp. 2804–2805], with a dihedral angle between the mean planes of the two thiophene rings of 56.23 (6°. The distance between the two reactive C atoms is 3.497 (3 Å. In the crystal, two molecules are associated through a pair of C—H...F intermolecular hydrogen bonds, forming a centrosymmetric dimer. Dimers are linked by weak π–π interactions [centroid–centroid distance = 3.8872 (13 Å], forming chains along the c axis.

  17. Synthesis and Characterization of Novel Chiral Carbazole Derivatives%新型手性咔唑类衍生物的合成与表征

    Institute of Scientific and Technical Information of China (English)

    邱银华; 林成刚; 吴奇; 史海健


    首次用手性Hajos酮的衍生物(2)与PCl3在Fischer条件下制得手性吲哚类化合物(3和4);3和4分别成肟后进行Beckmann裂解反应,合成了两个系列的新型的咔唑类衍生物(3~9),其结构经1H NMR, 13C NMR, IR, MS和元素分析表征.9的结构经X-射线单晶衍射分析确证.

  18. Solar cells of metal-free phthalocyanine dispersed in polyvinyl carbazole. 1: Effects of the recrystallization of H2PC on cell characteristics (United States)

    Shimura, M.; Baba, H.


    The development of an organic semiconductor solar cell and the effects of the recrystallization of metal free phthalocyanine (H2PC) on the characteristics of NESA/H2PC-PVK/Au sandwich cells were investigated. Alfa-H2PC sandwich cells showed photovoltage and photocurrent in a two direction opposite to that shown y as supplied H2PC cells, which consists mainly of beta-H2PC. Some difference was observed in the response times of the two cells. It is suggested that photocharacteristics change with the specific resistance of the H2PC, which is related to its crystal forms. In the cells with low resistance H2PC carriers are generated in H2PC by illumination, while in high resistance H2PC cells, carriers are generated in PVK which is sensitized with H2PC.

  19. Microwave assisted synthesis, characterization and biocidal activities of some new chelates of carbazole derived Schiff bases of cadmium and tin metals (United States)

    Yadav, Manju; Mishra, Neelima; Sharma, Nutan; Chandra, Sulekh; Kumar, Dinesh


    This study is planned to report the advancement of green microwave approach in the fabrication of a new series of biologically potent (N^X, where X = O/S) donor Schiff bases and their cadmium(II) and tin(II) complexes. The ligands and their metal complexes have been characterized in terms of elemental analysis, molar ionic conductance, magnetic moment and spectral (IR, UV-Vis, NMR (1H, 119Sn), FAB-mass, thermal and XRD) data. The data revealed that the ligands coordinated to the metal center via nitrogen and oxygen/sulfur atoms and form an octahedral arrangement of the ligands around central metal atom. All compounds were evaluated for their in vitro antimicrobial activities against two pathogenic bacteria Bacillus subtilis and Escherichia coli and two fungi Aspergillus niger and Aspergillus flavus by standard disc diffusion method. The discs were stored in an incubator at 37 °C. The compounds were dissolved in DMF at 500 and 1000 ppm concentrations for screening biocidal activity. The compounds were dissolved in DMF to get the 100 and 200 ppm concentration of test solutions for screening fungicidal activity. The inhibition zone around each disc was measured (in mm) after 24 h and 96 h for biocidal and fungicidal activities respectively.

  20. 4-Fluoro-N-methyl-N-(1,2,3,4-tetrahydrocarbazol-3-yl)benzenesulfonamide


    Kaspar Gothardt Rasmussen; Trond Ulven; Bond, Andrew D.


    In the title compound, C19H19FN2O2S, the hydrogenated six-membered ring of the carbazole unit adopts a half-chair conformation and the plane of the fluorophenyl ring forms a dihedral angle of 41.5 (1)° with respect to the carbazole mean plane. The crystal structure is segregated into layers containing the carbazole units and fluorophenyl rings in alternate (200) planes. The carbazole units form centrosymmetric face-to-face interactions [interplanar separation = 4.06Q...

  1. 40 CFR 437.23 - Effluent limitations attainable by the application of the best available technology economically... (United States)


    ... CENTRALIZED WASTE TREATMENT POINT SOURCE CATEGORY Oils Treatment and Recovery § 437.23 Effluent limitations..., cadmium, chromium, cobalt, copper, lead, mercury, tin, zinc, butylbenzyl phthalate, carbazole,...

  2. Oligomerization and DNA-binding capacity of Pmr, a histone-like protein H1 (H-NS) family protein encoded on IncP-7 carbazole-degradative plasmid pCAR1. (United States)

    Suzuki, Chiho; Yun, Choong-Soo; Umeda, Takashi; Terabayashi, Tsuguno; Watanabe, Kazuya; Yamane, Hisakazu; Nojiri, Hideaki


    Pmr, a histone-like protein H1 (H-NS) family protein encoded on plasmid pCAR1, is a key factor in optimizing gene transcription on both pCAR1 and the host chromosome. To clarify the mode of function of Pmr, we performed gel filtration chromatography analysis and protein-protein cross-linking, and found that Pmr forms homo-oligomers, consisting of its homodimers. We also found, by atomic force microscopy, that Pmr has DNA-bridging capacity. From these results, Pmr was deduced to have features common to H-NS family proteins. Additionally, evaluating protein-DNA affinity is important to clarify the mode of function of Pmr, and hence we performed an electrophoretic mobility shift assay. Though Pmr formed high-order protein-DNA complexes and did not show preference for nucleic acid sequences, the C-terminal region of Pmr did, suggesting that the DNA-binding affinity of Pmr can be evaluated by using its C-terminal region.

  3. Combining the rapid MTT formazan exocytosis assay and the MC65 protection assay led to the discovery of carbazole analogs as small molecule inhibitors of Abeta oligomer-induced cytotoxicity. (United States)

    Hong, Hyun-Seok; Maezawa, Izumi; Yao, Nianhuan; Xu, Bailing; Diaz-Avalos, Ruben; Rana, Sandeep; Hua, Duy H; Cheng, R Holland; Lam, Kit S; Jin, Lee-Way


    The discovery of small molecule inhibitors of cytotoxicity induced by amyloid-beta (Abeta) oligomers, either applied extracellularly or accumulated intraneuronally, is an important goal of drug development for Alzheimer's disease (AD), but has been limited by the lack of efficient screening methods. Here we describe our approach using two cell-based methods. The first method takes advantage of the unique ability of extracellularly applied Abeta oligomers to rapidly induce the exocytosis of formazan formed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). We employed a short protocol to quantify this toxicity, and quickly identified two novel inhibitors, code-named CP2 and A5, from two compound libraries. A second independent screen of the same libraries using our previously published MC65 protection assay, which identifies inhibitors of toxicity related to intracellular Abeta oligomers, also selected the same two leads, suggesting that both assays select for the same anti-Abeta oligomer properties displayed by these compounds. We further demonstrated that A5 attenuated the progressive aggregation of existing Abeta oligomers, reduced the level of intracellular Abeta oligomers, and prevented the Abeta oligomer-induced death of primary cortical neurons, effects similar to those demonstrated by CP2. Our results suggest that, when combined, the two methods would generate fewer false results and give a high likelihood of identifying leads that show promises in ameliorating Abeta oligomer-induced toxicities within both intraneuronal and extracellular sites. Both assays are simple, suitable for rapid screening of a large number of medicinal libraries, and amenable for automation.

  4. In Vitro Effects of Aminoalcohol-carbazole Compound BTB3 against Echinococcus granulosus%氨基醇咔唑化合物BTB3体外抗细粒棘球蚴效果的评价

    Institute of Scientific and Technical Information of China (English)

    刘丛珊; 张皓冰; 薛剑; 陶奕; 胡薇


    目的 观察氨基醇咔唑化合物BTB3体外抗细粒棘球蚴的效果. 方法 体外培养羊源细粒棘球蚴原头节和继发感染小鼠来源的生发层细胞,用浓度为1、2、4、8、10和20-μg/ml的BTB3作用3d后,分别采用美兰染色法和CCK-8法检测原头节和生发层细胞的活性.用扫描电镜观察10μg/ml BTB3对生发层细胞造成的损伤.体外培养细粒棘球蚴囊,用浓度为1、5和10 μg/ml的BTB3作用2周后,观察其对囊的影响,并用扫描电镜观察囊内部结构的变化. 结果 10μg/ml和20 μg/ml BTB3组原头节的死亡率分别为(100.0±0.0)%和(85.2±7.2)%.但当浓度降低后,原头节死亡率均低于10%.生发层细胞经8、10和20 μg/ml BTB3作用后,其细胞活性抑制率均达100%,其余低浓度BTB3组的抑制率随浓度的降低而降低.扫描电镜观察发现,BTB3可使生发层细胞发生脱落、皱缩以及空腔化.10μg/ml BTB3作用于棘球蚴囊14 d后,全部囊均出现塌陷.其超微结构显示,BTB3作用后棘球蚴内囊中出现了细胞脱落和不均匀的现象. 结论 BTB3对体外培养的细粒棘球蚴原头节、生发层细胞和棘球蚴囊均有较强的作用,是一种潜在的抗棘球蚴药物.

  5. 4-Fluoro-N-methyl-N-(1,2,3,4-tetrahydrocarbazol-3-yl)benzenesulfonamide

    DEFF Research Database (Denmark)

    Rasmussen, Kaspar Godhardt; Ulven, Trond; Bond, Andrew


    In the title compound, C(19)H(19)FN(2)O(2)S, the hydrogenated six-membered ring of the carbazole unit adopts a half-chair conformation and the plane of the fluoro-phenyl ring forms a dihedral angle of 41.5 (1)° with respect to the carbazole mean plane. The crystal structure is segregated into lay...

  6. Metabolic Engineering to Develop a Pathway for the Selective Cleavage of Carbon-Nitrogen Bonds

    Energy Technology Data Exchange (ETDEWEB)

    John J. Kilbane II


    The objective of the project is to develop a biochemical pathway for the selective cleavage of C-N bonds in molecules found in petroleum. Specifically a novel biochemical pathway will be developed for the selective cleavage of C-N bonds in carbazole. The cleavage of the first C-N bond in carbazole is accomplished by the enzyme carbazole dioxygenase, that catalyzes the conversion of carbazole to 2-aminobiphenyl-2,3-diol. The genes encoding carbazole dioxygenase were cloned from Sphingomonas sp. GTIN11 and from Pseudomonas resinovorans CA10. The selective cleavage of the second C-N bond has been challenging, and efforts to overcome that challenge have been the focus of recent research in this project. Enrichment culture experiments succeeded in isolating bacterial cultures that can metabolize 2-aminobiphenyl, but no enzyme capable of selectively cleaving the C-N bond in 2-aminobiphenyl has been identified. Aniline is very similar to the structure of 2-aminobiphenyl and aniline dioxygenase catalyzes the conversion of aniline to catechol and ammonia. For the remainder of the project the emphasis of research will be to simultaneously express the genes for carbazole dioxygenase and for aniline dioxygenase in the same bacterial host and then to select for derivative cultures capable of using carbazole as the sole source of nitrogen.

  7. Synthesis and photocurrent response of porphyrin-containing conjugated polymers

    Institute of Scientific and Technical Information of China (English)

    ZHAO Jinling; LI Binsong; BO Zhishan


    Porphyrin-containing conjugated polymers with fluorene or carbazole as spacer groups were prepared by Sonogashira cross-coupling reactions. The polymers were of high molecular weight and the flexible alkyl chains on fluorene or carbazole units made the conjugated polymers soluble in common organic solvents, such as THF and methylene chloride. The polymers could form high quality durable films from solution casting. Their optical and photocurrent responsive properties were investigated. It was found that the photocurrent response was directly proportional to the content of porphyrin. The incorporation of carbazole units into the polymer chains also gave positive contribution to the photocurrent generation in some extent.

  8. Solvent-free fluidic organic dye lasers. (United States)

    Choi, Eun Young; Mager, Loic; Cham, Tran Thi; Dorkenoo, Kokou D; Fort, Alain; Wu, Jeong Weon; Barsella, Alberto; Ribierre, Jean-Charles


    We report on the demonstration of liquid organic dye lasers based on 9-(2-ethylhexyl)carbazole (EHCz), so-called liquid carbazole, doped with green- and red-emitting laser dyes. Both waveguide and Fabry-Perot type microcavity fluidic organic dye lasers were prepared by capillary action under solvent-free conditions. Cascade Förster-type energy transfer processes from liquid carbazole to laser dyes were employed to achieve color-variable amplified spontaneous emission and lasing. Overall, this study provides the first step towards the development of solvent-free fluidic organic semiconducting lasers and demonstrates a new kind of optoelectronic applications for liquid organic semiconductors.

  9. Synthesis and Characterization of Organic Dyes Containing Various Donors and Acceptors

    Directory of Open Access Journals (Sweden)

    Wen-Chung Ou-Yang


    Full Text Available New organic dyes comprising carbazole, iminodibenzyl, or phenothiazine moieties, respectively, as the electron donors, and cyanoacetic acid or acrylic acid moieties as the electron acceptors/anchoring groups were synthesized and characterized. The influence of heteroatoms on carbazole, iminodibenzyl and phenothiazine donors, and cyano-substitution on the acid acceptor is evidenced by spectral, electrochemical, photovoltaic experiments, and density functional theory calculations. The phenothiazine dyes show solar-energy-to-electricity conversion efficiency (η of 3.46–5.53%, whereas carbazole andiminodibenzyl dyesshow η of 2.43% and 3.49%, respectively.

  10. Theoretical Investigation on the Electron and Energy Transfer between Peripheral Carrier Transport Groups and Central Chromophores in Electroluminescent Materials

    Institute of Scientific and Technical Information of China (English)

    潘玉钰; 刘丹丹; 许海; 刘晓冬; 孙冠楠; 杨兵; 马於光


    The molecular materials with structures of luminescent core and peripheral carrier groups (e.g. carbazoles), have exhibited high-performance in organic light-emitting diodes (OLEDs). Present work is to understand the basic process of electronic and energy exchange between the peripheral functional groups and the central core through quantum chemical analysis. As an example, 4,7-bis(9,9-bis(6-(9H-carbazol-9-yl)hexyl)-9H-fluoren-2-yl)benzo[c]- [1,2,5]thiadiazole (TCBzC) is investigated in regards to optoelectronic properties using density functional theory (DFT). The results suggest that the forbidden transition from peripheral carbazole to the central chromophore core makes for separated electrical and optical properties, and high performance electroluminescence (EL) is mainly at- tributed to the energy-transfer from carbazoles to the fluorene derivative core.

  11. Polycarbazoles microcavities: towards plastic blue lasers

    Energy Technology Data Exchange (ETDEWEB)

    Castex, M.C.; Olivero, C.; Fischer, A.; Mousel, S.; Michelon, J.; Ades, D.; Siove, A


    With the aim of developing a plastic blue laser emitting around 400 nm, we have investigated the luminescence and lasing possibilities of recently designed new polymeric materials based on carbazole chromophores. Our carbazole compounds are used either as doping organic dyes in usual polymer cast films (e.g. PMMA) or as thin layers deposited onto a quartz substrate. In both cases, by using different interferometric methods, periodic patterning of surfaces has been realised and compared. Efficient relief gratings are produced by laser irradiation at 193 nm of a phase mask ({lambda}=1090 nm) in con onto carbazolic films. We demonstrate that such patterning allows photopumping of doped PMMA films in a planar waveguide configuration with distributed feedback (DFB) even for high Bragg grating order (m=6). Monomode stimulated emission is observed for rhodamine doped PMMA film. Preliminary results concerning UV photopumping of carbazolic films are presented.

  12. Polycarbazoles microcavities: towards plastic blue lasers (United States)

    Castex, M. C.; Olivero, C.; Fischer, A.; Mousel, S.; Michelon, J.; Adès, D.; Siove, A.


    With the aim of developing a plastic blue laser emitting around 400 nm, we have investigated the luminescence and lasing possibilities of recently designed new polymeric materials based on carbazole chromophores. Our carbazole compounds are used either as doping organic dyes in usual polymer cast films (e.g. PMMA) or as thin layers deposited onto a quartz substrate. In both cases, by using different interferometric methods, periodic patterning of surfaces has been realised and compared. Efficient relief gratings are produced by laser irradiation at 193 nm of a phase mask ( Λ=1090 nm) in contact onto carbazolic films. We demonstrate that such patterning allows photopumping of doped PMMA films in a planar waveguide configuration with distributed feedback (DFB) even for high Bragg grating order ( m=6). Monomode stimulated emission is observed for rhodamine doped PMMA film. Preliminary results concerning UV photopumping of carbazolic films are presented.

  13. Mechanically induced gel formation

    NARCIS (Netherlands)

    van Herpt, Jochem T.; Stuart, Marc C. A.; Browne, Wesley R.; Feringa, Ben L.


    Mechanical triggering of gelation of an organic solution by a carbazole-based bisurea organogelator is described. Both the duration of the mechanical stimulation and the gelator concentration control the gelation process and the characteristics of the gel obtained.

  14. Ethyl 2-(1,2,3,4-tetrahydro­spiro­[carba­zole-3,2′-[1,3]dioxolan]-9-yl)acetate (United States)

    Löffler, Philipp M. G.; Ulven, Trond; Bond, Andrew D.


    In the title compound, C18H21NO4, the hydrogenated six-membered ring of the carbazole unit adopts a half-chair conformation. The dioxolane ring and ethyl­acetate substituent point to opposite sides of the carbazole plane. The ethyl­acetate substituent adopts an essentially fully extended conformation, and its mean plane forms a dihedral angle of 83.8 (1)° with respect to the carbazole mean plane. The mol­ecules are arranged into stacks in which the carbazole planes form a dihedral angle of 4.4 (1)° and have an approximate inter­planar separation of 3.6 Å. PMID:21582427

  15. Self-assembly of neuroprotective carbazolium based small molecules at octane/water interface: A simulation investigation (United States)

    Zolghadr, Amin Reza; Heydari Dokoohaki, Maryam


    The self-assembly of dibromocarbazole based small molecule (P7C3) and its analogues is studied at the octane/water interface by using molecular dynamics simulations. P7C3 protects newborn neurons from apoptotic cell death and enhances neurogenesis. The bromines on the carbazole appear particularly important, as the derivatives with dichloro and parent carbazole did not appear active at the concentrations tested. We are mainly focused on the question that why is dibromocarbazole derivative an effective neuroprotective drug, but not dichlorocarbazole or parent carbazole? It was found that P7C3 and P7C3-Cl were concentrated in the interfacial region, whereas the parent carbazole derivative were distributed throughout the water phase. The diffusion of P7C3 molecules in the interfacial region are higher than P7C3-Cl. This approach could use by experimentalist to evaluate the permeability of drug candidates prior to their synthesis.

  16. 40 CFR 437.26 - Pretreatment standards for new sources (PSNS). (United States)


    ...) EFFLUENT GUIDELINES AND STANDARDS THE CENTRALIZED WASTE TREATMENT POINT SOURCE CATEGORY Oils Treatment and...: Standards for chromium, cobalt, copper, lead, tin, zinc, carbazole, n-decane, bis(2-ethylhexyl)...

  17. A pre-Paleogene unconformity surface of the Sikeshu Sag, Junggar Basin: Lithological, geophysical and geochemical implications for the transportation of hydrocarbons

    Directory of Open Access Journals (Sweden)

    Xiaoyue Gao


    Full Text Available The unconformity surface at the bottom of the Paleogene is one of the most important migration pathways in the Sikeshu Sag of the Junggar Basin, which consists of three layers: upper coarse clastic rock, lower weathering crust and leached zone. The upper coarse clastic rock is characterized by higher density and lower SDT and gamma-ray logging parameters, while the lower weathering crust displays opposite features. The transport coefficient of the unconformity surface is controlled by its position in respect to the basal sandstone; it is higher in the ramp region but lower in the adjacent uplifted and sag areas. The content of saturated hydrocarbons increases with the decrease of the content of non-hydrocarbons and asphaltenes. The content of benzo[c] carbazole decreases as the content of benzo[a] carbazole and [alkyl carbazole]/[alkyl + benzo carbazole] increases. This suggests that the unconformity surface is an efficient medium for the transportation of hydrocarbons.

  18. Iridium complexes demonstrating broadband emission through controlled geometric distortion and applications thereof

    Energy Technology Data Exchange (ETDEWEB)

    Li, Jian; Turner, Eric


    Iridium compounds and their uses are disclosed herein. For example, carbazole containing iridium compounds are disclosed. The compounds are useful in many devices, including, but not limited to, electroluminescent devices.

  19. Phenothiazine-based CaaX competitive inhibitors of human farnesyltransferase bearing a cysteine, methionine, serine or valine moiety as a new family of antitumoral compounds. (United States)

    Dumitriu, Gina-Mirabela; Bîcu, Elena; Belei, Dalila; Rigo, Benoît; Dubois, Joëlle; Farce, Amaury; Ghinet, Alina


    A new family of CaaX competitive inhibitors of human farnesyltransferase based on phenothiazine and carbazole skeleton bearing a l-cysteine, l-methionine, l-serine or l-valine moiety was designed, synthesized and biologically evaluated. Phenothiazine derivatives proved to be more active than carbazole-based compounds. Phenothiazine 1b with cysteine residue was the most promising inhibitor of human farnesyltransferase in the current study.

  20. Spectral study, stability and protein labeling of two Carbazole–Benzothiazole derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Yu, Lu; Li, Ling; Fei, Xuening, E-mail:


    3-benzothiazole-9-ethyl-carbazole (BEC) and 3,6-di-benzothiazole-9-ethyl-carbazole (DBEC) were synthesized by using carbazole as base and then characterized by {sup 1}H NMR. The optical properties of them were investigated and compared with carbazole and 9-ethyl-carbazole. The photostability and thermostability of the compounds were studied and the results indicated they are both very stable. Effects of solvent properties including polarity, viscosity and refractive index on the spectra properties of the compounds were investigated. Quantum yield of the compounds in organic solvent was also determined and it is found the most complex compound has the highest quantum yield up to 0.68. Finally the synthesized compounds were used to label bovine serum albumin (BSA) protein and simultaneously stability constant (K{sub s}) between them is calculated and compared with other similar dyes. The results showed that the fluorescent intensity of the compound is increased significantly after labeling with BSA protein. - Highlights: • Synthesis and optical properties of two carbazole-benzothiazole derivatives. • Photostability and thermostability of the compounds and compared the results with each other. • Quantum yields of the compounds and the relationship with the structure. • Protein labeling properties of the compounds and stability constant.

  1. Effects of Biodegradation on the Distribution of Alkylcarbazoles in Crude Oils

    Institute of Scientific and Technical Information of China (English)



    We have investigated the distributions of alkylcarbazoles in a series of crude oils with different biodegradation extents, in combination with biomarker parameters, stable carbon isotopic ratios and viscosities. The analyses showed that slight biodegradation has little effect on alkylcarbazoles. The concentrations of C0-, C1-, and C2-carbazoles seem to display a slight decrease with biodegradation through the moderately biodegraded stage, and an abrupt decrease to the heavily biodegraded stage. The relative concentrations of C0-, C1-, and C2-carbazoles do not show any apparent change in the non-heavily biodegraded stages, but through non-heavily biodegraded to heavily biodegraded stages, the percentages of C0- and C1-carbazoles decrease,and those of C2-carbazoles increase significantly, which may indicate that C2-carbazoles are more resistant to biodegradation than lower homologous species. As to C2-carbazole isomers,the relative concentrations of the pyrrolic N-H-shielded, pyrrolic N-H partially shielded and pyrrolic N-H-exposed isomers do not show any obvious variation in the non-heavily biodegraded oil, but there is an abrupt change through the mid-biodegraded stage to the heavily biodegraded stage.


    Institute of Scientific and Technical Information of China (English)

    韩姝娜; 周同娜; 柴永明; 周红军; 刘晨光


    使用Ni-Mo催化剂,在固定床微型反应器上进行喹咻、吲哚和咔唑存在下的4,6-二甲基二苯并噻吩(4,6-DMDBT)加氢脱硫(HDS)反应.结果表明,含氮化合物对4,6-DMDBT HDS有强烈的抑制作用.这3种氮化物的抑制作用大小顺序是:喹啉、咔唑和吲哚.氮化物对于HDS 2条反应路径均有抑制作用,但是抑制的程度不同.喹啉对先加氢再脱硫(HYD)反应路径的影响比对直接脱硫(DDS)反应路径的强烈得多;吲哚存在下HYD反应为主要的HDS反应;咔唑对2条反应路径的抑制程度相似,使4,6-DMDBT HDS的HYD和DDS反应比例与不添加氮化物时相似.氮化物含量增加使4,6-DMDBT HDS中DDS反应比例增加.

  3. 磷光配体3-[4-(2-吡啶基)苯基]-9-(4-氟苯基)-9H-咔唑的合成%Synthesis of 3-[4-(Pyridin-2-y1)phenyl]-9-(4-fluorophenyl)-9H-carbazole

    Institute of Scientific and Technical Information of China (English)

    刘贵军; 邓锋杰; 邓阳生; 高希存


    以对溴苯胺为原料,经重氮化、Gomberg-Bachmann偶联、硼酸化反应得到4-(2-吡啶基)苯硼酸;再与对氟苯基取代的咔唑,通过四(三苯基磷)钯催化,于90℃进行Suzuki偶联合成出标题磷光配体,收率82.03%.对目标物用核磁共振氢谱和元素分析进行了表征,并测得它在二氯甲烷中的紫外吸收光谱和荧光光谱.由于受咔唑基团的影响,磷光配体最大吸收峰波长红移56 nm,且吸收的强度增加,Stokes位移154 nm,相对荧光量子效率为0.17.

  4. 4-Fluoro-N-methyl-N-(1,2,3,4-tetrahydrocarbazol-3-ylbenzenesulfonamide

    Directory of Open Access Journals (Sweden)

    Kaspar Gothardt Rasmussen


    Full Text Available In the title compound, C19H19FN2O2S, the hydrogenated six-membered ring of the carbazole unit adopts a half-chair conformation and the plane of the fluorophenyl ring forms a dihedral angle of 41.5 (1° with respect to the carbazole mean plane. The crystal structure is segregated into layers containing the carbazole units and fluorophenyl rings in alternate (200 planes. The carbazole units form centrosymmetric face-to-face interactions [interplanar separation = 4.06 (1 Å] and edge-to-face interactions in which the N—H group is directed towards an adjacent carbazole face, with a shortest H...C contact of 2.53 Å. The fluorophenyl rings form face-to-face contacts with an approximate interplanar separation of 3.75 Å and a centroid–centroid distance of 4.73 (1 Å.

  5. Fluorescent cyanine probe for DNA detection and cellular imaging (United States)

    Zheng, Yong-Chao; Zheng, Mei-Ling; Zhao, Zhen-Sheng; Duan, Xuan-Ming


    In our study, two carbazole-based cyanines, 3,6-bis[2-(1-methylpyridinium)vinyl]-9-methyl carbazole diiodide (A) and 6,6'-bis[2-(1-methylpyridinium)vinyl]-bis(9-methyl-carbazol-3yl)methane diiodide (B) were synthesized and employed as light-up probes for DNA and cell imaging. Both of the cyanine probes possess a symmetric structure and bis-cationic center. The obvious induced circular dichroism signals in circular dichroism spectra reveal that the molecules can specifically interact with DNA. Strong fluorescence enhancement is observed when these two cyanines are bound to DNA. These cyanine probes show high binding affinity to oligonucleotides but different binding preferences to various secondary structures. Confocal microscopy images of fixed cell stained by the probes exhibit strong brightness and high contrast in nucleus with a very low cytoplasmic background.

  6. One-pot synthesis and UV-Visible absorption studies of novel tricyclic heterocycle tethered Xanthene-1,8-diones

    Indian Academy of Sciences (India)

    Thirumal Yempala; Balasubramanian Sridhar; Srinivas Kantevari


    A series of new tricyclic heterocyclic xanthene-1,8-diones tethered with chromophoric dibenzo [ , ]furan, dibenzo[ , ]thiophene and 9-methyl-9-carbazoles were synthesized through one-pot condensation of dibenzo[ , ]furan-2-carbaldehyde, dibenzo[ , ] thiophene-2-carbaldehyde and 9-methyl-9-carbazole-3-carbaldehyde with cyclic 1,3-dicarbonyls in the presence of recyclable PPA-SiOM2 catalyst under solvent-free conditions. Further, UV-Visible absorption properties of all the synthesized compounds were investigated in CHCl3, THF and acetonitrile.

  7. Synthesis and properties of novel low band-gap polymers bearing squaraine units

    Institute of Scientific and Technical Information of China (English)


    Novel main-chain-conjugated poly(carbazol-alt-squaraine) and poly(dipyridyl-alt-squaraine) were successfully synthesized through direct polycondensation of 9-(2-ethylhexyl)carbazole-bridged or dipyridyl-bridged bispyrrole and squaric acid.The structures and properties of the polymers were characterized using ~1H NMR,FT-IR,UV-vis and cyclic voltammetry.Both polymers exhibit excellent solubility in common organic solvents and good thermal stability.Their UV-vis absorption spectra indicated the polymers hav...

  8. Enantioselective Palladium-Catalyzed Carbene Insertion into the N-H Bonds of Aromatic Heterocycles. (United States)

    Arredondo, Vanessa; Hiew, Stanley C; Gutman, Eugene S; Premachandra, Ilandari Dewage Udara Anulal; Van Vranken, David L


    C3-substituted indoles and carbazoles react with α-aryl-α-diazoesters under palladium catalysis to form α-(N-indolyl)-α-arylesters and α-(N-carbazolyl)-α-arylesters. The products result from insertion of a palladium-carbene ligand into the N-H bond of the aromatic N-heterocycles. Enantioselection was achieved using a chiral bis(oxazoline) ligand, in many cases with high enantioselectivity (up to 99 % ee). The method was applied to synthesize the core of a bioactive carbazole derivative in a concise manner.

  9. Controlling self-assembly of diphenylalanine peptides at high pH using heterocyclic capping groups (United States)

    Martin, Adam D.; Wojciechowski, Jonathan P.; Robinson, Andrew B.; Heu, Celine; Garvey, Christopher J.; Ratcliffe, Julian; Waddington, Lynne J.; Gardiner, James; Thordarson, Pall


    Using small angle neutron scattering (SANS), it is shown that the existence of pre-assembled structures at high pH for a capped diphenylalanine hydrogel is controlled by the selection of N-terminal heterocyclic capping group, namely indole or carbazole. At high pH, changing from a somewhat hydrophilic indole capping group to a more hydrophobic carbazole capping group results in a shift from a high proportion of monomers to self-assembled fibers or wormlike micelles. The presence of these different self-assembled structures at high pH is confirmed through NMR and circular dichroism spectroscopy, scanning probe microscopy and cryogenic transmission electron microscopy. PMID:28272523

  10. Well-ordered thin films as practical components of biosensors

    Energy Technology Data Exchange (ETDEWEB)

    Cabaj, Joanna; Idzik, Krzysztof [Faculty of Medicinal Chemistry and Microbiology, Department of Chemistry, Wroclaw University of Technology, Wyb. Wyspianskiego 27, 50-370 Wroclaw (Poland); Soloducho, Jadwiga [Faculty of Medicinal Chemistry and Microbiology, Department of Chemistry, Wroclaw University of Technology, Wyb. Wyspianskiego 27, 50-370 Wroclaw (Poland)], E-mail:; Chyla, Antoni [Institute of Physical and Theoretical Chemistry, Department of Chemistry, Wroclaw University of Technology, Wyb. Wyspianskiego 27, 50-370 Wroclaw (Poland); Bryjak, Jolanta [Faculty of Bioorganic Chemistry, Department of Chemistry, Wroclaw University of Technology, Wyb. Wyspianskiego 27, 50-370 Wroclaw (Poland); Doskocz, Jacek [Faculty of Medicinal Chemistry and Microbiology, Department of Chemistry, Wroclaw University of Technology, Wyb. Wyspianskiego 27, 50-370 Wroclaw (Poland)


    A Langmuir-Blodgett (LB) film consisting of glutaraldehyde as the binding site for enzyme molecule, an amphiphilic N-alkyl-bis(thiophene)carbazole (BTC7) as the additional electron mediator, and 22-tricosenoic acid (TA) as the matrix for these molecules were deposited on a hydrophilic substrate. Laccase was then covalently immobilized on the film via glutaraldehyde (GA). The sensitivity of this sensor was about twice as high as that of laccase sensor prepared with the same LB film as above but without the bis(thiophene)carbazole derivative. The laccase LB film exhibited enzyme activity.

  11. Carotenoids play a positive role in the degradation of heterocycles by Sphingobium yanoikuyae.

    Directory of Open Access Journals (Sweden)

    Xiaorui Liu

    Full Text Available BACKGROUND: Microbial oxidative degradation is a potential way of removing pollutants such as heterocycles from the environment. During this process, reactive oxygen species or other oxidants are inevitably produced, and may cause damage to DNA, proteins, and membranes, thereby decreasing the degradation rate. Carotenoids can serve as membrane-integrated antioxidants, protecting cells from oxidative stress. FINDINGS: Several genes involved in the carotenoid biosynthetic pathway were cloned and characterized from a carbazole-degrading bacterium Sphingobium yanoikuyae XLDN2-5. In addition, a yellow-pigmented carotenoid synthesized by strain XLDN2-5 was identified as zeaxanthin that was synthesized from β-carotene through β-cryptoxanthin. The amounts of zeaxanthin and hydrogen peroxide produced were significantly and simultaneously enhanced during the biodegradation of heterocycles (carbazole < carbazole + benzothiophene < carbazole + dibenzothiophene. These higher production levels were consistent with the transcriptional increase of the gene encoding phytoene desaturase, one of the key enzymes for carotenoid biosynthesis. CONCLUSIONS/SIGNIFICANCE: Sphingobium yanoikuyae XLDN2-5 can enhance the synthesis of zeaxanthin, one of the carotenoids, which may modulate membrane fluidity and defense against intracellular oxidative stress. To our knowledge, this is the first report on the positive role of carotenoids in the biodegradation of heterocycles, while elucidating the carotenoid biosynthetic pathway in the Sphingobium genus.

  12. 75 FR 74682 - Antidumping or Countervailing Duty Order, Finding, or Suspended Investigation; Opportunity To... (United States)


    ... (``the Department'') regulations at 19 CFR 351.213, that the Department conduct an administrative review... December for the following periods: \\1\\ Or the next business day, if the deadline falls on a weekend... Mushrooms A-337-804 12/1/09-11/30/10 India: Carbazole Violet Pigment 23 A-533-838 12/1/09-11/30/10...

  13. Synthesis, photophysical and electro-optical properties of bis-carbazolyl methane based host material for pure-blue phosphorescent OLED

    Energy Technology Data Exchange (ETDEWEB)

    Moon, Byoung-Joon; Yook, Kyoung Soo; Lee, Jun Yeob [Department of Polymer Science and Engineering and Center for Photofunctional Energy Materials, Dankook University, Yongin, Gyeonggi 448-701 (Korea, Republic of); Shin, Seunghan [Chonan R and D Center, KITECH, Chonan, Chungnam 330-825 (Korea, Republic of); Hwang, Seok-Ho, E-mail: [Department of Polymer Science and Engineering and Center for Photofunctional Energy Materials, Dankook University, Yongin, Gyeonggi 448-701 (Korea, Republic of)


    A new high triplet-energy host material, 9-(4-(bis(9-ethyl-9H-carbazol-3-yl)methyl)phenyl)-9H-carbazole (bis-CMPC), was synthesized and its device performance of phosphorescent organic light-emitting diode was investigated. This host material showed a high triplet energy ({approx}2.95 eV) and good thermal stability. Highly efficient pure-blue PHOLED was obtained when employing bis-CMPC as the host material and bis((3,5-difluoro-4-cyanophenyl)pyridine) iridium picolinate as the guest material. The maximum external quantum efficiency of the device reached as high as 13.3% with a pure-blue color coordinate of (0.14, 0.21). - Graphical abstract: Highlights: Black-Right-Pointing-Pointer Synthesis of 9-(4-(bis(9-ethyl-9H-carbazol-3-yl)methyl)phenyl)-9H-carbazole. Black-Right-Pointing-Pointer Synthesized host material showed high triplet energy level and thermal stability. Black-Right-Pointing-Pointer Maximum external quantum efficiency of the device as high as 13.3%. Black-Right-Pointing-Pointer The device showed a pure-blue color coordinate of (0.14, 0.21).

  14. Thermodynamic properties of 9-methylcarbazole and 1,2,3,4-tetrahydro-9-methylcarbazole

    Energy Technology Data Exchange (ETDEWEB)

    Steele, W.V.; Knipmeyer, S.E.; Nguyen, A.; Chirico, R.D.


    Removal of carbazole and its derivatives from heavy petroleum has proved to be particularly difficult using present technology. Studies have shown carbazole and its alkyl-homologs are the dominant nitrogen-containing components in clarified slurry oils, thereby indicating their low reactivity and/or formation during cat-cracking processes. The results reported here will point the way to the development of new methods of nitrogen removal from carbazole and its derivatives. Measurements leading to the calculation of the ideal-gas thermodynamic properties are reported for 9-methylcarbazole and 1,2,3,4-tetrahydro-9-methylcarbazole. For studies on 1,2,3,4-tetrahydro-9-methylcarbazole experimental methods included combustion calorimetry, adiabatic heat-capacity calorimetry, vibrating-tube densitometry, comparative ebulliometry, inclined-piston gauge manometry, and differential-scanning calorimetry (d.s.c.). Adiabatic heat-capacity and combustion calorimetric studies were reported previously for 9-methylcarbazole. Vapor pressures by comparative ebulliometry and inclined-piston gauge manometry, and heat-capacities for the liquid phase by d.s.c. are reported here. Entropies, enthalpies, and Gibbs energies of formation were derived for the ideal gas for both compounds for selected temperatures between 298.15 K and near 700 K. The Gibbs energies of formation will be used in a subsequent report in thermodynamic calculations to study the reaction pathway of the initial hydrogenation step in the carbazole/H{sub 2} hydrodenitrogenation network. 52 refs., 9 figs., 15 tabs.

  15. Construction of carbocyclic ring of indoles using ruthenium-catalyzed ring-closing olefin metathesis. (United States)

    Yoshida, Kazuhiro; Hayashi, Kazushi; Yanagisawa, Akira


    The selective synthesis of substituted indoles was achieved by the ring-closing olefin metathesis (RCM)/elimination sequence or the RCM/tautomerization sequence of functionalized pyrrole precursors. The RCM/elimination sequence was also applied to double ring closure to yield a substituted carbazole.

  16. Rhodium(I)-Catalyzed Benzannulation of Heteroaryl Propargylic Esters: Synthesis of Indoles and Related Heterocycles. (United States)

    Li, Xiaoxun; Xie, Haibo; Fu, Xiaoning; Liu, Ji-Tian; Wang, Hao-Yuan; Xi, Bao-Min; Liu, Peng; Xu, Xiufang; Tang, Weiping


    A de novo synthesis of a benzene ring allows for the preparation of a diverse range of heterocycles including indoles, benzofurans, benzothiophenes, carbazoles, and dibenzofurans from simple heteroaryl propargylic esters using a unified carbonylative benzannulation strategy. Multiple substituents can be easily introduced to the C4-C7 positions of indoles and related heterocycles.

  17. Malassezia-derived indoles activate the aryl hydrocarbon receptor and inhibit Toll-like receptor-induced maturation in monocyte-derived dendritic cells.

    NARCIS (Netherlands)

    Vlachos, C.; Schulte, B.M.; Magiatis, P.; Adema, G.J.; Gaitanis, G.


    Background The aryl hydrocarbon receptor (AhR) is a nuclear receptor and transcriptional regulator with pleiotropic effects. The production of potent AhR ligands by Malassezia yeasts, such as indirubin, indolo[3,2-b]carbazole (ICZ), tryptanthrin and malassezin, has been associated with the pathogene

  18. Adaptation of a Population of Fundulus heteroclitus to a Creosote-Contaminated Environment: Mechanisms, Genetic Consequences and Fitness Trade-Offs (United States)


    Comparative Biochemistry and Physiology, Part C (in press). Wassenberg, D.M., and R.T. Di Giulio. 2004a. Synergistic embryotoxicity of polycyclic...heterocycles, carbazole and dibenzothiophene, on in vivo and in vitro CYP1A activity and PAH-derived embryotoxicity . Environmental Toxicology and

  19. Smart Nanofibers Self-Assembled from Dumbbell-Shaped Rod Amphiphiles (United States)


    end-capped hexa -p-phenylene as a aromatic rod and oligo(ethylene oxide) dendrons according to previously reported similar methods and characterized...feature of 9-arylcarbazole derivatives revealing that there is a non-zero dihedral angle between the carbazole and hexa -p-phenylene unit. On the

  20. Synthesis, structures and charge-transfer complexations of 1,n-di-[3,6-di-(9-carbazolyl)-9-carbazolyl]alkanes with tetracyanoethylene and tetranitromethane (United States)

    Özgün, Selin; Asker, Erol; Zeybek, Orhan


    Synthesis and charge-transfer (CT) complexations of amorphous 3,6-di-(9-carbazolyl)-9-ethylcarbazole, 3,6-di-(9-carbazolyl)-9-hexylcarbazole and a series of 1,n-di-[3,6-di-(9-carbazolyl)-9-carbazolyl]alkanes (n = 1-5) with electron acceptors tetracyanoethylene and tetranitromethane are reported. The molar extinction coefficients (ε), equilibrium constants (Keq), enthalpies (ΔH) and entropies (ΔS) of complexations have been determined. The low Keq values (1.83-3.82 M-1 for carbazole-TCNE and 0.28-0.45 M-1 for carbazole-TNM complexes) show weak donor-acceptor associations. The negative values of ΔH determined to be between -2.09 ± 0.08 and -3.10 ± 0.21 kcal mol-1 for carbazole-TCNE complexes and -0.91 ± 0.08 and -3.31 ± 0.28 kcal mol-1 for carbazole-TNM complexes indicate that complexations are driven by the exothermic enthalpies. Computational analysis using semi-empirical and DFT methods were applied to clarify the structures of the synthesized molecules and the nature of their CT complexations.

  1. Influence of biodegradation on benzocarbazole distri-butions in reservoired oils

    Institute of Scientific and Technical Information of China (English)


    Partition coefficient difference of benzocarba-zole isomers between oil, water and mineral phase makes them auseful indicator to quantify petroleum migration distance. Because of their nitrogen-heteroatom andannelated aromatic cycles they are generally regarded asbeing more resistant and the effects of biodegradation ontheir concentrations and distributions have not previouslybeen investigated. Reservoir extracts from three wells lo-cated in the Leng43 block of the Liaohe Basin were analyzed to investigate their occurrence and the effect of biodegrada-tion. Both hydrocarbon biomarkers and benzocarbazole isomers show systematical changes with the increase extent of biodegradation in study columns. Carbazole compounds may be biodegraded in a similar way to that observed in aliphatic and aromatic hydrocarbons. The distance from oil water contact is a primary control factor for biodegradation. The concentrations of benzocarbazole isomers show a slight increase in the upper part of the columns then a sharp de-crease towards oil water contact (OWC). Among three iso-mers benzo[a]carbazole seems more susceptible to biode-gradation than other two isomers and benzo[b]carbazole has higher ability to res ist bacterial attack. Benzo[b]carba-zole/benzo- [a]carbazole ratios can sensitively indicate the degree of biodegradation and the benzocarbazole index (BCratio) cannot be directly used as a migration indicator inbiodegraded oils.

  2. Rhodanine dye-based small molecule acceptors for organic photovoltaic cells. (United States)

    Kim, Yujeong; Song, Chang Eun; Moon, Sang-Jin; Lim, Eunhee


    The solution-processable small molecules based on carbazole or fluorene containing rhodanine dyes at both ends were synthesized and introduced as acceptors in organic photovoltaic cells. The high energy levels of their lowest unoccupied molecular orbitals resulted in a power conversion efficiency of 3.08% and an open circuit voltage of up to 1.03 V.

  3. IndizolineThis paper is dedicated to Dato' Dr Chatar Singh, Foundation Dean, School of Physics, Universiti Sains Malaysia, whose 80th birthday falls on the 9th September 2009.

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun


    Full Text Available The title compound [systematic name: 1-methoxy-2-(3-methylbut-2-enyl-9H-carbazole-3-carbaldehyde], C19H19NO2, is a natural carbazole which was isolated from the twigs of Clausena lansium. The carbazole ring system is essentially planar with a mean deviation of 0.0068 (10 Å. The aldehyde substituent is approximately co-planar with the attached benzene ring with a torsion angle of −8.58 (14°, whereas the methoxy group is rotated out of the benzene plane with a torsion angle of −82.17 (11°. The dihedral angle between the mean planes of the 3-methyl-2-butenyl group and the carbazole ring is 88.06 (5°. An intermolecular N—H...O interaction connects the molecules into a chain along the a axis. The crystal is further consolidated by a C—H...O hydrogen bond and two π–π interactions with centroid–centroid distances of 3.6592 (6 and 3.7440 (6 Å.

  4. Thin films of arylenevinylene oligomers prepared by MAPLE for applications in non-linear optics

    Energy Technology Data Exchange (ETDEWEB)

    Stanculescu, A., E-mail: [National Institute of Materials Physics, Optics and Spectroscopy Laboratory, 105 bis Atomistilor Street, P.O. Box MG-7, Bucharest-Magurele 077125 (Romania); Vacareanu, L.; Grigoras, M. [P. Poni' Institute of Macromolecular Chemistry, 41 A Gr. Ghica Voda Alley, 700487 Iasi (Romania); Socol, M. [National Institute of Materials Physics, Optics and Spectroscopy Laboratory, 105 bis Atomistilor Street, P.O. Box MG-7, Bucharest-Magurele 077125 (Romania); Socol, G. [National Institute for Laser, Plasma and Radiation Physics, Str. Atomistilor, Nr. 409, P.O. Box MG-36, Magurele, Bucharest 077125 (Romania); Stanculescu, F. [Faculty of Physics, University of Bucharest, Str. Atomistilor nr.405, P.O. Box MG-11, Bucharest-Magurele 077125 (Romania); Preda, N.; Matei, E. [National Institute of Materials Physics, Optics and Spectroscopy Laboratory, 105 bis Atomistilor Street, P.O. Box MG-7, Bucharest-Magurele 077125 (Romania); Ionita, I. [Faculty of Physics, University of Bucharest, Str. Atomistilor nr.405, P.O. Box MG-11, Bucharest-Magurele 077125 (Romania); Girtan, M. [Laboratoire de Photonique d' Angers, Universite d' Angers, 2, Bd. Lavoisier, 49045 Angers (France); Mihailescu, I.N. [National Institute for Laser, Plasma and Radiation Physics, Str. Atomistilor, Nr. 409, P.O. Box MG-36, Magurele, Bucharest 077125 (Romania)


    This paper discusses two arylenevinylene oligomers with optical nonlinear properties. Their trans molecular structure was confirmed by Fourier Transform Infrared Spectroscopy and Nuclear Magnetic Resonance. Second Harmonic Generation and two-photon fluorescence have been observed on Matrix Assisted Pulsed Laser Evaporation-deposited thin films. We have seen two local maxima in UV-Vis spectra and a red shift of the photoluminescence peak for carbazole-based oligomer, which can be correlated with a higher conformational flexibility and with strong polarization interactions in the solid state. Scanning Electron Microscopy and Atomic Force Microscopy images have revealed a grainy morphology of the film deposited on titanium and a higher roughness for carbazole-based oligomer. Second harmonic measurements have shown nearly equal values of the second-order nonlinear optical coefficient for the triphenylamine and carbazole-based oligomers for P{sub laser} < 100 mW. z-Scan and x-scan representations of the carbazole-based oligomer film have shown strong two-photon fluorescence intensity inside the sample confirming a volume process, and a strong second harmonic at the surface of the sample determined by the surface morphology.

  5. Quantification of the beta-adrenoceptor ligand S-1'[F-18]fluorocarazolol in plasma of humans, rats and sheep

    NARCIS (Netherlands)

    vanWaarde, A; Posthumus, H; Elsinga, PH; Anthonio, RL; van Loenen - Weemaes, Anne-miek; Beaufort-Krol, Gertie C. M.; Paans, AMJ; Vaalburg, W; Visser, Thomas; Visser, Gerben


    Myocardial and pulmonary beta-adrenoceptors can be imaged with 2-(S)-(-)-(9H-carbazol-4-yl-oxy)-3-[1-(fluoromethyl)ethyl]amino-2-propanol (S-1'-[F-18]fluorocarazolol, I). Quantification of unmodified fluorocarazolol in plasma is necessary for analysis of PET images in terms of receptor densities. We

  6. Distribution and Catabolic Diversity of 3-Chlorobenzoic Acid Degrading Bacteria Isolated from Geographically-Separated Pristine Soils (United States)


    Prostaglandins Anthraquinones Nucleic Acids Carbazoles Pyrroles Carbolines Quinolines Dibenzodioxins Terpenes Dibenzofurans Thiophenes Furans Examples...column (E. Merck, Darmstadt, Germany) using 70% methanol:30% 1% H3 PO4 as the mobile phase. The detector was set to record absorbance at 230 nm. 14C


    Energy Technology Data Exchange (ETDEWEB)

    John J. Kilbane II


    The objective of the project is to develop biochemical pathways for the selective cleavage of C-N bonds in molecules found in petroleum. The initial phase of the project was focused on the isolation or development of an enzyme capable of cleaving the C-N bond in aromatic amides, specifically 2-aminobiphenyl. The objective of the second phase of the research will be to construct a biochemical pathway for the selective removal of nitrogen from carbazole by combining the carA genes from Sphingomonas sp. GTIN11 with the gene(s) encoding an appropriate deaminase. The objective of the final phase of the project will be to develop derivative C-N bond cleaving enzymes that have broader substrate ranges and to demonstrate the use of such strains to selectively remove nitrogen from petroleum. During the first year of the project (October, 2002-September, 2003) enrichment culture experiments resulted in the isolation of microbial cultures that utilize aromatic amides as sole nitrogen sources, several amidase genes were cloned and were included in directed evolution experiments to obtain derivatives that can cleave C-N bonds in aromatic amides, and the carA genes from Sphingomonas sp. GTIN11, and Pseudomonas resinovorans CA10 were cloned in vectors capable of replicating in Escherichia coli. During the second year of the project (October, 2003-September, 2004) enrichment culture experiments succeeded in isolating a mixed bacterial culture that can utilize 2-aminobiphenyl as a sole nitrogen source, directed evolution experiments were focused on the aniline dioxygenase enzyme that is capable of deaminating aniline, and expression vectors were constructed to enable the expression of genes encoding C-N bond cleaving enzymes in Rhodococcus hosts. The construction of a new metabolic pathway to selectively remove nitrogen from carbazole and other molecules typically found in petroleum should lead to the development of a process to improve oil refinery efficiency by reducing the


    Directory of Open Access Journals (Sweden)

    Víctor Macías


    Full Text Available From ethanol-soluble extract of the bark from Zanthoxylum fagara (L. Sargent. were isolated two novel furocarbazole alkaloids, 4-methoxy-10H-furo[3,2-a]carbazole ( and 10H-furo[3,2-a]carbazole ( , whose structures were elucidated on the basis of IR, MS and NMR (including 1D and 2D techniques. In addition, the antibacterial effect of the ethanol extract of bark was evaluated against Gram-negative bacteria Escherichia coli, Salmonella typhi, Shigella boydii, Vibrio cholerae El Tor, and Vibrio cholerae clinical lysate; and Gram-positive bacteria Bacillus subtilis and Staphylococcus epidermidis, using the Agar-well diffusion method. In above-mentioned assay was found that the ethanol extract of bark exhibited inhibition against strains B. subtilis (17mm, V. cholerae El Tor (11mm, V. cholerae clinical lysate (10mm, and S. epidermidis (9mm.

  9. Concise and efficient synthesis of calothrixin B. (United States)

    Sissouma, Drissa; Maingot, Lucie; Collet, Sylvain; Guingant, André


    A convergent synthesis of the naturally occurring alkaloid Calothrixin B is presented, which used a regioselective hetero-Diels-Alder reaction between a "push-pull" 2-aza-diene and a N-protected 3-bromo-9H-carbazole-1,4-dione to construct the five-ring skeleton of the molecule. Protection of the indole motif with a benzyl group was unattractive for delivery of sufficient target material because the removal of the protecting group had not been high yielding. We therefore elected to temporarily protect the indole motif with a more labile benzyloxycarbonyl group. Accordingly, the synthesis of calothrixin B proceeded in 17% overall yield over 9 steps from the commercially available 1,2,3,9-tetrahydro-4H-carbazol-4-one.

  10. Synthesis and photoluminescence properties of 8-hydroxyquinoline derivatives and their metallic complexes

    Institute of Scientific and Technical Information of China (English)

    OUYANG Xinhua; ZENG Heping; XIE Yan


    Three new 8-hydroxyquinoline derivatives, I.e.5-[(4-styryl-benzylidene)-amino]-quinolin-8-ol (1), 5-[(4-bromo-2-fluoro-benzylidene)-amino]-quinoline-8-ol (2) and 2-[2-(9-ethyl-9H-carbazol-2yl)-vinyl]-quinolin-8-ol (3), and their metallic complexes were synthesized and identified by ultraviolet-visible (UV-Vis), 1H nuclear magnetic resonance(1H NMR), Fourier transform infrared spectrometer (FTIR),mass spectrometry (MS) spectra and elemental analyses.Their fluorescence properties were studied by photolumines-cence, which indicated that the luminescence wavelength of 5- and 2-substitued-8-hydroxyquinoline derivatives shifted to red in comparison with that of 8-hydroxyquinoline.Meanwhile, the fluorescence lifetime of 2-[2-(9-ethyl-9H-carbazol-2yl)-vinyl]-quinolin-8-ol and its zinc complex showed long lifetime in benzene solution.

  11. Fluid Catalytic Cracking Feed Hydrotreatment and its Impact on Distribution of Sulfur and Nitrogen Compounds in FCC Diesel

    Institute of Scientific and Technical Information of China (English)

    Bai Rui; Chai Yongming; Zhang Chengtao; Liu Chenguang


    The sulfides and nitrogen compounds in FCC diesel were analyzed by gas chromatography equipped with a pulsed lfame photometric detector (GC-PFPD) and gas chromatography coupled with nitrogen chemiluminescence detection (GC-NCD). And the variation of sulifdes and nitrogen compounds in FCC diesel produced from gas oil feed hydrotreated at different temperatures was investigated. The test results showed that two main types of sulfur compounds, i.e. benzothio-phenes (BTs) and dibenzothiophenes (DBTs) were found in diesel. Nitrogen compounds are mainly composed of non-basic nitrogen compounds, and indoles and carbazoles account for about 98% of the total nitrogen contents. The sulifdes in FCC diesel obtained from hydrotreated feed are mainly BTs with a small amount of 4-MDBT and 4,6-DMDBT. With the increase in FCC feed hydrotreating temperature, indoles content in FCC diesel increases, while carbazoles content decreases.

  12. Theoretical studies on nonlinear optical properties of two newly synthesized compounds: EPVPC and OPVPC

    Institute of Scientific and Technical Information of China (English)

    孙元红; 赵珂; 王传奎; 罗毅; 延云兴; 陶绪堂; 蒋民华


    The nonlinear optical properties of two newly synthesized molecules 9-Ethyl-3-{2-[4-(2-Pyridin-4-yl-vinyl)-phenyl]-vinyl}-9H-carbazole (EPVPC) and 9-Octadecyl-3-{2-[4-(2-Pyridin-4-yl-vinyl)-phenyl]-vinyl}-9H-carbazole (OPVPC)have been studied with hybrid density functional theory (DFT/B3LYP). The generalized few-state model is employed to calculate the two-photon absorption cross sections of the compounds. The theoretical results are in good agreement with the available experimental measurements. It is found that the maximal two-photon absorption (TPA) cross sections of the compounds can be well described by a three-state model. The numerical simulation shows that both compounds have large two-photon absorption (TPA) cross sections and, furthermore, OPVPC displays a little stronger TPA activity than EPVPC in a lower frequency region.

  13. Material degradation of liquid organic semiconductors analyzed by nuclear magnetic resonance spectroscopy

    Directory of Open Access Journals (Sweden)

    Tatsuya Fukushima


    Full Text Available Liquid organic light-emitting diodes (liquid OLEDs are unique devices consisting only of liquid organic semiconductors in the active layer, and the device performances have been investigated recently. However, the device degradation, especially, the origin has been unknown. In this study, we show that material degradation occurs in liquid OLEDs, whose active layer is composed of carbazole with an ethylene glycol chain. Nuclear magnetic resonance (NMR experiments clearly exhibit that the dimerization reaction of carbazole moiety occurs in the liquid OLEDs during driving the devices. In contrast, cleavages of the ethylene glycol chain are not detected within experimental error. The dimerization reaction is considered to be related to the device degradation.

  14. Effects and uptake of polycyclic aromatic compounds in snails (Helix aspersa). (United States)

    Sverdrup, Line Emilie; De Vaufleury, Annette; Hartnik, Thomas; Hagen, Snorre B; Loibner, Andreas Paul; Jensen, John


    The International Standardization Organization recently launched a soil toxicity test with snails (Helix aspersa). We assessed the sensitivity of this test for seven polycyclic aromatic compounds. Control animals had 100% survival and low variability for growth measurements. Maximum exposure concentrations of 2800 mg/kg (4000 mg/kg for acridine) had no effect on survival. Similarly, growth (biomass and shell size) was not affected by pyrene, fluoranthene, fluorene, carbazole, phenanthrene, or acridine, whereas dibenzothiophene gave a 10% effect concentration of 1600 mg/kg. Measured internal concentrations of carbazole, dibenzothiophene, and acridine increased with increasing soil concentrations, but biota-soil accumulation factors were low (0.002-0.1). Compared to previously tested organisms, with all being exposed in the same soil type and under similar test conditions, the H. aspersa test was relatively insensitive to all substances.

  15. Synthesis, spectroscopy, and electrochemistry of ionic hosts for organic electronics (United States)

    Shavaleev, Nail M.; Nazeeruddin, Mohammad K.


    We report on charge- and ion-transport ionic hosts made from an imidazolium-cation-modified aryl-1,2,4-triazole, phosphineoxide-carbazole, and phosphineoxide. The hosts are white solids that have short-wavelength absorption cut-off at 28,200 cm-1) and that exhibit oxidation at (-2.75) V against ferrocene with a wide redox gap of >3.9 V.

  16. Effects of Self-coiling of Organic Molecules on Intramolecular Exciplex Formation and Fluorescence Quenching in DX-H2O Solvent System

    Institute of Scientific and Technical Information of China (English)

    CHEN,Ying-Qi(陈英奇); WANG,Xiao-Zhong(王晓钟); JIANG,Xi-Kui(蒋锡夔); SHI,Ji-Liang(史济良); SHI,Min(施敏); LI,Zhan-Tmg(黎占亭)


    Effects of self-coiling of organic molecules on intramolecular exciplex formation of compound I, in which the carbazole chromophore and terephthalic acid methylester acceptor group are linked by one (CH2)10 chain, and the decrease of the fluorescence intensities of compounds H, Ⅲ, and Ⅳ, in which the carbazole chromophore and 3,5-dinitrobenzoate are connected by one aliphatic chain of (CH2)10 (Ⅱ), (CH2)12 (Ⅲ),or (CH2)4 (Ⅳ), have been studied in the dioxane(DX)-H2Obinary system. The results show that self-coiling of organic molecules in DX-H2O facilitates intramolecular exciplex formation of Ⅰ and induces the decrease of fluorescence intensities of Ⅱ, because of the proximity effect brought about by selfcoiling of organic molecules under hydrophobic-lipophilic interaction (HLI) between the excited carbazole chromophore and the acceptor. Since the similar effects are observed even when the concentrations of the probes are less than their CAgCs (critical aggregate concentratons) in the DX-H2Omixture withthe same φ values, formation of the intermolecular exciplex has been excluded. The effects are found to be strongly depended on φ values, indicating that they are mainly driven by HLI. The properties of the acceptors can also affect the intrmolecular exciplex formation. With terephthalic acid methylester moiety as the acceptor, the carbazole chromophore exihibits the fluorescence spectra of the exciplex,while with 3,5- dinitrobenzoate moiety as the acceptor, only the fluorescence spectra of excited carbazolyl chromphore are observed.

  17. Synthesis of Linearly Fused Benzodipyrrole Based Organic Materials. (United States)

    Vlasselaer, Maarten; Dehaen, Wim


    The objective of this review is to give an overview of the synthetic methods to prepare different indolo[3,2-b]carbazoles and similar systems with a potential use in electro-optical devices such as OLEDs (organic light emitting diode), OPVs (organic photovoltaic) and OFETs (organic field effect transistor). Some further modifications to the core units and their implications for specific applications are also discussed.

  18. Electrochemical route to fabricate film-like conjugated microporous polymers and application for organic electronics. (United States)

    Gu, Cheng; Chen, Youchun; Zhang, Zhongbo; Xue, Shanfeng; Sun, Shuheng; Zhang, Kai; Zhong, Chengmei; Zhang, Huanhuan; Pan, Yuyu; Lv, Ying; Yang, Yanqin; Li, Fenghong; Zhang, Suobo; Huang, Fei; Ma, Yuguang


    Film-like conjugated microporous polymers (CMPs) are fabricated by the novel strategy of carbazole-based electropolymerization. The CMP film storing a mass of counterions acting as an anode interlayer provides a significant power-conversion efficiency of 7.56% in polymer solar cells and 20.7 cd A(-1) in polymer light-emitting diodes, demonstrating its universality and potential as an electrode interlayer in organic electronics.

  19. Synthesis of Linearly Fused Benzodipyrrole Based Organic Materials

    Directory of Open Access Journals (Sweden)

    Maarten Vlasselaer


    Full Text Available The objective of this review is to give an overview of the synthetic methods to prepare different indolo[3,2-b]carbazoles and similar systems with a potential use in electro-optical devices such as OLEDs (organic light emitting diode, OPVs (organic photovoltaic and OFETs (organic field effect transistor. Some further modifications to the core units and their implications for specific applications are also discussed.

  20. Organic photoredox catalysis for the oxidation of silicates: applications in radical synthesis and dual catalysis. (United States)

    Lévêque, Christophe; Chenneberg, Ludwig; Corcé, Vincent; Ollivier, Cyril; Fensterbank, Louis


    Metal free photooxidation of alkyl bis(catecholato)silicates with the organic dye 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyano-benzene (4CzIPN) allows the smooth formation of alkyl radicals. The latter can be efficiently engaged either with radical acceptors to provide homolytic addition products or in photoredox/nickel dual catalysis reactions to obtain cross-coupling products.

  1. Exploiting the Distal Reactivity of Indolyl Methylenemalononitriles: An Asymmetric Organocatalyzed [4+2] Cycloaddition with Enals Enables the Assembly of Elusive Dihydrocarbazoles. (United States)

    Rassu, Gloria; Curti, Claudio; Zambrano, Vincenzo; Pinna, Luigi; Brindani, Nicoletta; Pelosi, Giorgio; Zanardi, Franca


    An unprecedented technique for the in situ generation of indolyl ortho-quinodimethanes from 2-methylindole-based methylenemalononitriles by amine-mediated remote C(sp(3) )-H deprotonation was developed. These intermediates were efficiently trapped by diverse enals to provide a rapid entry to 2,9-dihydro-1H-carbazole-3-carboxyaldehyde structures through a formal asymmetric [4+2] eliminative cycloaddition governed by a α,α-diphenylprolinol trimethylsilyl ether catalyst.

  2. Effects of Substituents in Polyvinylcarbazole Structures on Their Optical Properties

    CERN Document Server

    Vertsimakha, Ya; Syromyatnikov, V; Savchenko, I


    Absorption, photoluminescence, and photoluminescence excitation spectra of solutions and thin films of N-vinylcarbazole polymers and copolymers with various substituents directly on the carbazole moiety and on the polymer chain were studied comprehensively. Polymers that were used previously to develop polymer composites with polymethine dyes having photosensitivity over a broad spectral range including the visible and near-IR regions were selected for the studies.

  3. Conformational control in a bipyridine linked π-conjugated oligomer: cation mediated helix unfolding and refolding. (United States)

    Divya, Kizhumuri P; Sreejith, Sivaramapanicker; Suresh, Cherumuttathu H; Ajayaghosh, Ayyappanpillai


    A chiral π-conjugated oligomer having alternate bipyridine and carbazole moieties connected through acetylinic bonds undergoes helical folding in chloroform-acetonitrile (40/60, v/v) as evident by fluorescence and circular dichroism changes. In the presence of transition metal cations such as Zn(2+) defolding of the helical conformation occurs. Upon decomplexation of the cation with EDTA, the helical conformation is regained.

  4. Assembly of metal-organic polyhedra into highly porous frameworks for ethene delivery. (United States)

    Stoeck, Ulrich; Senkovska, Irena; Bon, Volodymyr; Krause, Simon; Kaskel, Stefan


    Two new mesoporous metal-organic frameworks (DUT-75 and DUT-76) with exceptional ethene uptake were obtained using carbazole dicarboxylate based metal-organic polyhedra as supermolecular building blocks. The compounds have a total pore volume of 1.84 and 3.25 cm(3) g(-1) and a specific BET surface area of 4081 and 6344 m(2) g(-1), respectively, and high gas uptake at room temperature and high pressure.

  5. Ideal Molecular Design of Blue Thermally Activated Delayed Fluorescent Emitter for High Efficiency, Small Singlet-Triplet Energy Splitting, Low Efficiency Roll-Off, and Long Lifetime. (United States)

    Lee, Dong Ryun; Choi, Jeong Min; Lee, Chil Won; Lee, Jun Yeob


    Highly efficient thermally activated delayed fluorescent (TADF) emitters, 5-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5H-benzofuro[3,2-c]carbazole (oBFCzTrz), 5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5H-benzofuro[3,2-c]carbazole (mBFCzTrz), and 5-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5H-benzofuro[3,2-c]carbazole (pBFCzTrz), were synthesized to study the effects of ortho-, meta-, and para- linkages between donor and acceptor moieties. oBFCzTrz having ortho- linked donor and acceptor moieties showed smaller singlet-triplet energy gap, shorter excited state lifetime, and higher photoluminescence quantum yield than mBFCzTrz and pBFCzTrz which are interconnected by meta- and para- positions. The TADF device using oBFCzTrz as a blue emitter exhibited high external quantum efficiency over 20%, little efficiency roll-off, and long device lifetime.

  6. Isoindigo-Based Small Molecules with Varied Donor Components for Solution-Processable Organic Field Effect Transistor Devices. (United States)

    Patil, Hemlata; Chang, Jingjing; Gupta, Akhil; Bilic, Ante; Wu, Jishan; Sonar, Prashant; Bhosale, Sheshanath V


    Two solution-processable small organic molecules, (E)-6,6'-bis(4-(diphenylamino)phenyl)-1,1'-bis(2-ethylhexyl)-(3,3'-biindolinylidene)-2,2'-dione (coded as S10) and (E)-6,6'-di(9H-carbazol-9-yl)-1,1'-bis(2-ethylhexyl)-(3,3'-biindolinylidene)-2,2'-dione (coded as S11) were successfully designed, synthesized and fully characterized. S10 and S11 are based on a donor-acceptor-donor structural motif and contain a common electron accepting moiety, isoindigo, along with different electron donating functionalities, triphenylamine and carbazole, respectively. Ultraviolet-visible absorption spectra revealed that the use of triphenylamine donor functionality resulted in an enhanced intramolecular charge transfer transition and reduction of optical band gap, when compared with its carbazole analogue. Both of these materials were designed to be donor semiconducting components, exerted excellent solubility in common organic solvents, showed excellent thermal stability, and their promising optoelectronic properties encouraged us to scrutinize charge-carrier mobilities using solution-processable organic field effect transistors. Hole mobilities of the order of 2.2 × 10(-4) cm²/Vs and 7.8 × 10(-3) cm²/Vs were measured using S10 and S11 as active materials, respectively.

  7. Copolymères (carbazolylène-pyrrolylène) : synthèse par oxydation chimique et propriétés (United States)

    Boucard, V.; Adès, D.; Siove, A.


    Conditions in which (carbazolylene-pyrrolylene) random copolymers could be synthetized directly by chemical oxidation by FeCl3 were studied. A substantial amount of soluble copolymers is obtained after work-up in the conditions corresponding to carbazole/pyrrole/2 FeCl3 molar proportions. An important fraction of polypyrrole was obtained beside a fraction of species soluble in ethanol (carbazole and dimer) and an other fraction of products soluble in water (pyrrole accompanied by the first terms of the oligomeric series). Soluble copolymers were characterized by means of SEC, NMR and UV-Visible spectroscopies. Cyclic voltammetry analysis disclosed that these copolymers exhibit both the carbazolic and the pyrrolic features. Les conditions dans lesquelles des copolymères statistiques (carbazo lylène-pyrrolylène) pouvaient être synthétisés directement par oxydation chimique par FeCl3 ont été étudiées. Des quantités substantielles de copolymères solubles en milieu organique sont obtenues par extraction lorsque les proportions molaires en réactifs carbazole/pyrrole/2 FeCl3 sont utilisées. Une fraction importante de polypyrrole est obtenue à côté d'une fraction d'espèces solubles dans l'éthanol (carbazole et son dimère) et d'une fraction de produits solubles dans l'eau (pyrrole et les premiers termes oligomères). Les copolymères solubles ont été caractérisés par CES, spectroscopies RMN et UV-Visible. L'analyse voltampérométrique de ces matériaux révèle qu'ils possèdent à la fois les caractéristiques des entités carbazolylènes et celles des entités pyrrolylènes.

  8. Frovatriptan salts of aliphatic carboxylic acids. (United States)

    Ravikumar, Krishnan; Sridhar, Balasubramanian; Nanubolu, Jagadeesh Babu; Hariharakrishnan, Venkatasubramanian; Rao, Bandi Venugopal


    The interaction of the antimigraine pharmaceutical agent frovatriptan with acetic acid and succinic acid yields the salts (±)-6-carbamoyl-N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-aminium acetate, C14H18N3O(+)·C2H3O2(-), (I), (R)-(+)-6-carbamoyl-N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-aminium 3-carboxypropanoate monohydrate, C14H18N3O(+)·C4H5O4(-)·H2O, (II), and bis[(R)-(+)-6-carbamoyl-N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-aminium] succinate trihydrate, 2C14H18N3O(+)·C4H4O4(2-)·3H2O, (III). The methylazaniumyl substitutent is oriented differently in all three structures. Additionally, the amide group in (I) is in a different orientation. All the salts form three-dimensional hydrogen-bonded structures. In (I), the cations form head-to-head hydrogen-bonded amide-amide catemers through N-H···O interactions, while in (II) and (III) the cations form head-to-head amide-amide dimers. The cation catemers in (I) are extended into a three-dimensional network through further interactions with acetate anion acceptors. The presence of succinate anions and water molecules in (II) and (III) primarily governs the three-dimensional network through water-bridged cation-anion associations via O-H···O and N-H···O hydrogen bonds. The structures reported here shed some light on the possible mode of noncovalent interactions in the aggregation and interaction patterns of drug molecule adducts.

  9. Hybrid polymer/TiO{sub 2} films by in situ hydrolysis condensation of titanium alkoxide precursors for photovoltaic transparent windows

    Energy Technology Data Exchange (ETDEWEB)

    Davenas, Joel; Barlier, Vincent; Legare, Veronique-Bounor [Polymer Engineering, Universite Lyon 1, CNRS UMR 5223, 43 Bd du 11 novembre, 69622 Villeurbanne (France); Canut, Bruno [Lyon Institute of Nanotechnology, INSA de Lyon, CNRS UMR 5270, 20 Av. A. Einstein, 69621 Villeurbanne (France); Rybak, Andrzej [Polymer Engineering, Universite Lyon 1, CNRS UMR 5223, 43 Bd du 11 novembre, 69622 Villeurbanne (France); Department of Molecular Physics, Technical University of Lodz, Zeromskiego 116, 90-924 Lodz (Poland); Slazak, Agnieszka; Jung, Jaroslaw [Department of Molecular Physics, Technical University of Lodz, Zeromskiego 116, 90-924 Lodz (Poland)


    Poly(vinylcarbazole)/TiO{sub 2} hybrid thin films have been produced by the hydrolysis condensation of titanium alkoxide precursors dispersed in a polymer layer deposited on ITO substrates. Common alkoxide precursors like titanium isopropoxide [Ti({sup i}OPr){sub 4}] show a fast hydrolysis beginning during film deposition, which leads to early phase separation. A new TiO{sub 2} precursor precursor bearing carbazole groups: titanium tetrakis 9H-carbazole-9-yl-ethyl-oxy [Ti(OeCarb){sub 4}] has been used to slow down the reactivity of the precursor by a steric hindrance effect. Improved precursor dispersion in the polymer solution is obtained for this new precursor leading to an homogeneous dispersion of the TiO{sub 2} phase at the nanoscale in the hybrid film. Rutherford Backscattering Spectrometry has shown that the hydrolysis condensation was effective with the production of carbazol alcohol remaining trapped in the bulk of the film. This residual alcohol leads to an increase of the UV optical absorption of the PVK/TiO{sub 2} hybrid films. Improvement of the balance between the two types of photogenerated charges has been shown by surface potential decay experiments upon the formation of a TiO{sub 2} conduction network for the transport of electrons. The film is almost transparent above 350 nm opening a new route for the elaboration of semi-transparent photovoltaic glasses, which can find application on the growing market of energy efficient buildings. (Abstract Copyright [2010], Wiley Periodicals, Inc.)

  10. Total alkyl dibenzothiophenes content tracing the filling pathway of condensate reservoir in the Fushan Depression,South China Sea

    Institute of Scientific and Technical Information of China (English)


    The condensates are generally characterized by high maturity,low concentration of steranes and ter-panes biomarkers and low content of non-hydrocarbon fraction. In this case commonly used steranes,terpanes and carbazoles parameters cannot be effectively applied in the reservoir-filling tracing. The hydrogen bond formed by sulfur atom in the dibenzothiophenes (DBTs) results in molecule adsorption and fractionation during oil migration in reservoir. Like carbazoles,total DBTs content decreases with the increasing of oil migration distance. Therefore,a new parameter——total DBTs content is proposed to be used to trace the oil migration orientation and filling pathway. In present study,total DBTs con-tents of condensates and light oils are obtained by adding internal standard——eight deuterium atoms substituted DBT during Gas Chromatography-Mass Spectrometry analysis of aromatic fraction. Except for a few samples with much lower content of non-hydrocarbon fraction,the total DBTs content shows a fine positive correlation with that of carbazoles. Large errors can be caused in the process of pyrrolic nitrogen compounds separation. The application of this new parameter in the Fushan Depression of Beibu Gulf Basin,South China Sea indicates that this parameter is a reliable one to trace filling pathway in condensate reservoirs. Combined with other DBTs-related parameters,such as 4-/1-methydibenzo-thiophene and 2,4-/1,4-dimethyldibenzothiophene,oil migration orientation and filling pathway of the Fushan Depression was determined. The accumulations of Huachang oil field in the Fushan Depres-sion are mainly migrated and charged from northeast to southeast along the Huachang uplift. It can be predicated that the light oil and condensates in the Huachang oil field should be sourced from the source kitchen at the Bailian Sag. It shows that total DBTs content is an effective parameter to tracing oil migration orientation and filling pathway.

  11. Synthesis and Spectral Properties of 6-bromo-3-(2,2'-dinitrilevinyl)-N-butylcarbazole%6-溴-3-(2,2'-二氰基乙烯基)-N-正丁基咔唑的合成及其光谱性能

    Institute of Scientific and Technical Information of China (English)

    王永涛; 赵赫; 陈婷婷; 张鹏波; 代斌; 刘志勇


    咔唑衍生物已被广泛应用于有机电致发光材料,为提高咔唑的电子传输和空穴传输性能,本文以咔唑为起始原料,经N-烷基化、NBS亲电取代、甲酰化、丙二腈缩合反应,合成得到未见文献报道的双氰基功能性化合物6-溴-3-(2,2’-二氰基乙烯基)-N-正丁基咔唑,目标化合物经核磁(1H-NMR)、质谱(MS)、元素分析、紫外可见分光光度计(UV-Vis)、荧光光谱和热重(TG)表征,结果表明该化合物有希望被用作蓝色有机电致发光材料.%Carbazole derivatives have been widely used as organic electroluminescence material. In order to improve the carbazole electronic and hole transport efficiency,carbazole was used as starting material, via N-alkylation,NBS electrophilic substitution, formylatign,malononitrile condensation reaction, to prepare 6-bromo-3-(2, 2'-dinitrile vinyl)-N-butylcarbazo-le, an unreported dicyano functionalized compound. The structure and spectral properties of target compound were characterized by 1H-NMR, MS,elemental analysis,UV-Vis,fluorescence spectrum and thermo-gravimetric analysis. The results show that the compound is a potential blue organic electroluminescent material.

  12. Dynamic quenchers in fluorescently labeled membranes. Theory for quenching in a three-phase system. (United States)

    Omann, G M; Glaser, M


    The theory for quenching of fluorescently labeled membranes by dynamic quenchers is described for a three-phase system: a fluorescently labeled membrane, a nonlabeled membrane, and an aqueous phase. Two different experimental protocols are possible to determine quenching parameters. Using the first protocol, partition coefficients and bimolecular quenching constants were determined for a hydrophobic quencher in carbazole-labeled membranes in the presence of an unlabeled reference membrane. These parameters determined for 1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene (DDE) using this three-phase analysis were in good agreement with values determined by a two-phase analysis without the reference lipid. Hence, the theory was verified. In the second protocol, the quencher partition coefficient was determined for unlabeled membranes in the presence of a carbazole-labeled reference membrane. Partition coefficients for DDE determined by this method were the same as partition coefficients determined for carbazole-labeled membranes using the two-phase analysis. The greater ease in determining partition coefficients and bimolecular quenching constants by the three-phase analysis and, in particular, the ability to determine the partition coefficient in unlabeled membranes make the three-phase analysis especially useful. This method was used to study the effect varying the membrane lipid composition has on the partition coefficient. The data indicate that partition coefficients of DDE in fluid membranes are not dramatically dependent upon polar head group composition, fatty acid composition, or cholesterol content. However, partitioning into gel-phase lipids is at least 100-fold less than fluid-phase lipids.

  13. Blue electroluminescence of ZnSe thin film in an organic-inorganic heterostructures device

    Energy Technology Data Exchange (ETDEWEB)

    Yu Wenge [Institute of Optoelectronics, Beijing Jiaotong University, Beijing 100044 (China) and Changchun Institute of Optics and Fine Mechanics and Physics, CAS, Changchun 130021 (China) and Shenyang Institute of Aeronautical Engineering, Shenyang 110034 (China)]. E-mail:; Xu Zheng [Institute of Optoelectronics, Beijing Jiaotong University, Beijing 100044 (China); Teng, Feng [Institute of Optoelectronics, Beijing Jiaotong University, Beijing 100044 (China); Yang Shengyi [Institute of Optoelectronics, Beijing Jiaotong University, Beijing 100044 (China); Hou Yanbing [Institute of Optoelectronics, Beijing Jiaotong University, Beijing 100044 (China); Qian Lei [Institute of Optoelectronics, Beijing Jiaotong University, Beijing 100044 (China); Qu Chong [Institute of Optoelectronics, Beijing Jiaotong University, Beijing 100044 (China); Quan Sanyu [Institute of Optoelectronics, Beijing Jiaotong University, Beijing 100044 (China); Xu Xurong [Institute of Optoelectronics, Beijing Jiaotong University, Beijing 100044 (China); Changchun Institute of Optics and Fine Mechanics and Physics, CAS, Changchun 130021 (China)


    Blue light emission of ZnSe thin film from the ZnSe/poly-(N-vinyl-carbazole) (PVK) heterostructures was obtained. The threshold voltage is about 10 V and the brightness of 12 cd/m{sup 2} was obtained at 17 V. From the electroluminescence (EL), the photoluminescence (PL), the transient electroluminescence and the dependence of EL intensity on the applied voltage and current, we attribute the EL of ZnSe to carrier injection and recombination. This new phenomenon not only opens a new mechanism of II-IV compounds in low voltage injection EL but also provides a new way of obtaining blue emission.

  14. Chemical Constituents from Stem Bark and Roots of Clausena anisata

    Directory of Open Access Journals (Sweden)

    Etienne Dongo


    Full Text Available Phytochemical investigations on the stem bark and roots of the tropical shrub Clausena anisata led to the isolation and characterization three carbazole alkaloids: girinimbine, murrayamine-A and ekeberginine; two peptide derivatives: aurantiamide acetate and N-benzoyl-l-phenylalaninyl-N-benzoyl-l-phenylalaninate; and a mixture of two phytosterols: sitosterol and stigmasterol. The structures of these compounds were established by nuclear magnetic resonance (1H-NMR, 13C-NMR, COSY, HSQC, HMQC, HMBC and NOESY spectroscopy and electrospray ionization mass spectrometry (MS.

  15. High Efficiency Polymer Solar Cells with Long Operating Lifetimes

    KAUST Repository

    Peters, Craig H.


    Organic bulk-heterojunction solar cells comprising poly[N-9\\'-hepta-decanyl- 2,7-carbazole-alt-5,5-(4\\',7\\'-di-2-thienyl-2\\', 1\\',3\\'-benzothiadiazole) (PCDTBT) are systematically aged and demonstrate lifetimes approaching seven years, which is the longest reported lifetime for polymer solar cells. An experimental set-up is described that is capable of testing large numbers of solar cells, holding each device at its maximum power point while controlling and monitoring the temperature and light intensity. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  16. Novel fluorene-carzazole-based conjugated copolymers containing pyrazoline and benzothiazole segments for blue light-emitting materials

    Institute of Scientific and Technical Information of China (English)


    A series of novel fluorene-carbazole-based copolymers with pyrazoline and benzothiazole units were synthesized successfully through Suzuki coupling reactions. The molecular structures and thermal properties of these polymers were characterized by FT-IR,1H NMR, DSC and TGA. GPC results indicated that the weight-average molecular weight (Mw) and polydispersity of these polymers were in range (12,000-14,000) and (1.8-2.0), respectively. The two resulting polymers have high photoluminescence quantum efficiency implying that they may be promising candidates for polymer light-emitting diodes (PLEDs).

  17. 基于分子对接研究吲哚咔唑类小分子对Tie-2/VEGFR2的双效抑制作用模式%Studies on Interactions between Tie-2/VEGFR2 and Dihydroindazolocarbazole Dual Inhibitors via Molecular Docking

    Institute of Scientific and Technical Information of China (English)

    田元新; 张贤祚; 安林坤


    Dihydroindazolocarbazoles (DHI-carbazoles) are the potent dual inhibitors to VEGFR2 and Tie-2. In this work, the mechanism of interaction between VEGFR2/Tie-2 and DHI-carbazoles was performed with Surflex-dock. The results from molecular docking indicated that DHI-carbazoles competitively bound to the active site, which was the substrate ATP in VEGFR2/Tie-2 with high affinity. The differences of activity between VEGFR2 and Tie-2 resulted from the minor difference of active pockets. Hydro-phobic effect played a key role in the formation and stability. Hydrogen bond and electrostatic effect also contributed to the difference. This work elucidated the antitumor mechanism of the DHI-carbazoles as a dual potent inhibitor and provided theoretical basis for the design of tyrosine kinase inhibitors.%运用分子对接技术研究了吲哚咔唑类小分子对人血管内皮生长因子受体2 (VEGFR2)和人血管生成素受体Tie-2 (ANG-R-Tie-2)的双效抑制作用模式.研究结果表明,吲哚咔唑类小分子的双效抑制作用主要源于两种受体相似的活性口袋,小分子与两者的铰链区均可形成氢键,使其催化活性受到抑制,从而抑制肿瘤细胞的生长.抑制活性的差异主要源于活性口袋的细微差异所导致疏水、静电等相互作用的不同.其中,疏水作用的差异是影响配体选择性的主要原因,静电作用、氢键及空间位阻对结合稳定也有一定影响.该文的研究结果为多靶点酪氨酸激酶小分子抑制剂的设计及提高激酶抑制剂的选择性提供了重要的理论依据.

  18. Design and analysis of optically pumped semiconductor VECSEL with ANECz optical control layer

    Institute of Scientific and Technical Information of China (English)

    Yuqi Zhou; Dapeng Zhao; Yajuan Li; Qingxin Yang


    Through the reversible isomerization of trans-cis-trans under the linear polarization light, the molecules of azo materials have the same tropism which is vertical to the polarization of light. This means that azo materials have photo-induced birefringence which is related to optical power and polarization angle of the light. Based on the photo-induced birefringence of azo materials, we design a new type of optically pumped semiconductor vertical external cavity surface emitting laser (OPS-VECSEL) which can control the polarization and frequency of the ejection laser. The functional molecules of azo materials are [3-azo- (4'nitro)]-(9-ethyl)-carbazole (ANECz).

  19. Largely enhanced efficiency with a PFN/Al bilayer cathode in high efficiency bulk heterojunction photovoltaic cells with a low bandgap polycarbazole donor

    Energy Technology Data Exchange (ETDEWEB)

    He, Zhicai; Zhang, Chen; Xu, Xiaofeng; Zhang, Lianjie; Huang, Liang; Chen, Junwu; Wu, Hongbin; Cao, Yong [Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Physics and Chemistry of Luminescence, South China University of Technology, Guangzhou 510640 (China)


    Quinoxaline-containing poly(4,5-ethylene-2,7-carbazole) (PECz-DTQx) shows a high efficiency of 6.07% in solar cells with a PFN/Al bilayer cathode. This is higher than the efficiency achieved with sole Al (3.99%) or with Ca/Al (4.52%) cathodes. A bilayer cathode could be valuable in device configurations to achieve high efficiency in combination with a high-performance polymer donor. (Copyright copyright 2011 WILEY-VCH Verlag GmbH and Co. KGaA, Weinheim)

  20. Quantitation of heparosan with heparin lyase III and spectrophotometry. (United States)

    Huang, Haichan; Zhao, Yingying; Lv, Shencong; Zhong, Weihong; Zhang, Fuming; Linhardt, Robert J


    Heparosan is Escherichia coli K5 capsule polysaccharide, which is the key precursor for preparing bioengineered heparin. A rapid and effective quantitative method for detecting heparosan is important in the large-scale production of heparosan. Heparin lyase III (Hep III) effectively catalyzes the heparosan depolymerization, forming unsaturated disaccharides that are measurable using a spectrophotometer at 232 nm. We report a new method for the quantitative detection of heparosan with heparin lyase III and spectrophotometry that is safer and more specific than the traditional carbazole assay. In an optimized detection system, heparosan at a minimum concentration of 0.60 g/L in fermentation broth can be detected.

  1. Cyanines as new fluorescent probes for DNA detection and two-photon excited bioimaging. (United States)

    Feng, Xin Jiang; Wu, Po Lam; Bolze, Frédéric; Leung, Heidi W C; Li, King Fai; Mak, Nai Ki; Kwong, Daniel W J; Nicoud, Jean-François; Cheah, Kok Wai; Wong, Man Shing


    A series of cyanine fluorophores based on fused aromatics as an electron donor for DNA sensing and two-photon bioimaging were synthesized, among which the carbazole-based biscyanine exhibits high sensitivity and efficiency as a fluorescent light-up probe for dsDNA, which shows selective binding toward the AT-rich regions. The synergetic effect of the bischromophoric skeleton gives a several-fold enhancement in a two-photon absorption cross-section as well as a 25- to 100-fold enhancement in two-photon excited fluorescence upon dsDNA binding.

  2. Chemical physics behind formation of efficient charge-separated state for complexation between PC70BM and designed diporphyrin in solution. (United States)

    Ray, Anamika; Banerjee, Shrabanti; Ghosh, Shalini; Bauri, Ajoy K; Bhattacharya, Sumanta


    The present work reports supramolecular interaction of [6,6]-phenyl C71 butyric acid methyl ester (PC70BM) with two designed diporphyrin molecules having dithiophene (1) and carbazole (2) spacer in solvent having varying polarity. Studies on complex formation reveal relatively higher binding constant for PC70BM/2 complex in all the solvent studied. Solvent dependence of charge separation and charge recombination processes in PC70BM/diporphyrin non-covalent complexes has been well established in present work. Donor-acceptor geometry and stabilization of the singlet excited state of the diporphyrin during charge recombination are considered to be the possible reasons for this behavior.

  3. Effect of Low Molecule Polyamide and Nano-SiO2 on Properties of the Poly (MMA/BA/MAA)

    Institute of Scientific and Technical Information of China (English)

    Wenjun ZOU; Bo LIAO; Jin PENG; Linqi ZHANG; Yun YANG; Furen XIAO


    Effects of Iow molecule polyamide (LMPA) and namometer SiO2 particles on the properties of the poly (MMA/BA/MAA) adhesive for wearable and nonskid PVC (polyvinyl carbazole) materials were investigated. The experimental results show that the shear strength of poly (MMA/BA/MAA)/LMPA is increased, when the LMPA is added into poly (MMA/BA/MAA). The optimum addition of LMPA is about 4 wt pct. By adding 3 wt pct nano-SiO2 into poly (MMA/BA/MAA)/LMPA adhesive, its properties such as the shear strength,thermal stability, wear resistance and sea waterproof resistance are increased too.

  4. Is organic photovoltaics promising for indoor applications? (United States)

    Lee, Harrison K. H.; Li, Zhe; Durrant, James R.; Tsoi, Wing C.


    This work utilizes organic photovoltaics (OPV) for indoor applications, such as powering small electronic devices or wireless connected Internet of Things. Three representative polymer-based OPV systems, namely, poly(3-hexylthiophene-2,5-diyl), poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)], and poly[[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl][3-fluoro-2-[(2-ethylhexyl)carbonyl]thieno[3,4-b]thiophenediyl

  5. Conformational and Molecular Structures of α,β-Unsaturated Acrylonitrile Derivatives: Photophysical Properties and Their Frontier Orbitals


    María Judith Percino; Margarita Cerón; Oscar Rodríguez; Guillermo Soriano-Moro; María Eugenia Castro; Chapela, Víctor M.; Siegler, Maxime A.; Enrique Pérez-Gutiérrez


    We report single crystal X-ray diffraction (hereafter, SCXRD) analyses of derivatives featuring the electron-donor N-ethylcarbazole or the (4-diphenylamino)phenyl moieties associated with a -CN group attached to a double bond. The compounds are (2Z)-3-(4-(diphenylamino)-phenyl)-2-(pyridin-3-yl)prop-2-enenitrile (I), (2Z)-3-(4-(diphenylamino)phenyl)-2-(pyridin-4-yl)-prop-2-enenitrile (II) and (2Z)-3-(9-ethyl-9H-carbazol-3-yl)-2-(pyridin-2-yl)enenitrile (III). SCXRD analyses reveal that I and I...

  6. 8-THP-DHI analogs as potent Type I dual TIE-2/VEGF-R2 receptor tyrosine kinase inhibitors. (United States)

    Hudkins, Robert L; Zulli, Allison L; Underiner, Ted L; Angeles, Thelma S; Aimone, Lisa D; Meyer, Sheryl L; Pauletti, Daniel; Chang, Hong; Fedorov, Elena V; Almo, Steven C; Fedorov, Alexander A; Ruggeri, Bruce A


    A novel series of 8-(2-tetrahydropyranyl)-12,13-dihydroindazolo[5,4-a]pyrrolo[3,4-c]carbazoles (THP-DHI) was synthesized and evaluated as dual TIE-2 and VEGF-R2 receptor tyrosine kinase inhibitors. Development of the structure-activity relationships (SAR) with the support of X-ray crystallography led to identification of 7f and 7g as potent, selective dual TIE-2/VEGF-R2 inhibitors with excellent cellular potency and acceptable pharmacokinetic properties. Compounds 7f and 7g were orally active in tumor models with no observed toxicity.

  7. Synthesis and Electrochemical Characterization of Azomethine Containing N-Ethylcarbazole Group

    Institute of Scientific and Technical Information of China (English)

    LI Ya-peng; SUN Li-min; SUN Ming-hao; LI Hong-tu; ZHANG Hong-wen; WANG Jing-yuan


    Conjugated aromatic azomethines containing a carbazole group were synthesized. Their structures have been confirmed by IR, MS and UV spectrometries. When iodine was used as the dope to the conjugated compounds, the electrical conductivities (EC) of the doped conjugated compounds were increased by several orders of magnitude. The thermal stability of these two compounds investigated by TGA shows a good result, which guarantees the correct result of EC when the compounds are heated. As can be seen from the CV characterization of the electrochemical properties .of these two compounds, the azomethine diamine and p-aminophenyl-9-ethylcarbazolyl azomethine possess electrochemical activity, which arises from the heteroatom of molecules.

  8. One-Pot Synthesis of Tetraphene and Construction of Expanded Conjugated Aromatics. (United States)

    Wang, Jianbo; Yao, Jinzhong; Wang, Hailong; Chen, Hao; Dong, Jingcheng; Zhou, Hongwei


    Acene derivatives as a class of polycyclic aromatic hydrocarbons have attracted considerable interest because of their outstanding semiconductor properties. We developed a one-pot synthesis for fully conjugated tetraphene via a sequence of propargyl-allenyl isomerization, phosphine addition, intramolecular Wittig reactions, and Diels-Alder cyclization reactions. The derivative-conjugated aromatic compounds including carbazole or triphenylamine have been constructed via Pd-catalyzed coupling reaction with dibromotetraphene. These compounds show superior photophysical and electrochemical properties, which make them possible candidates for optoelectronic conjugated materials.

  9. 1,3-Diphenylethenylcarbazolyl-Based Monomer for Cross-Linked Hole Transporting Layers

    Directory of Open Access Journals (Sweden)

    Maryte Daskeviciene


    Full Text Available A new cross-linkable monomer containing 1,3-diphenylethenylcarbazolyl-based hole-transporting moieties and four reactive epoxy groups, was prepared by a multistep synthesis route from 1,3-bis(2,2-diphenylethenyl-9H-carbazol-2-ol and its application for the in situ formation of cross-linked hole transporting layers was investigated. A high concentration of flexible aliphatic epoxy chains ensures good solubility and makes this compound an attractive cross-linking agent. The synthesized compounds were characterized by various techniques, including differential scanning calorimetry, xerographic time of flight, and electron photoemission in air methods.

  10. Liquid-crystalline rigid-core semiconductor oligothiophenes: influence of molecular structure on phase behaviour and thin-film properties. (United States)

    Melucci, Manuela; Favaretto, Laura; Bettini, Christian; Gazzano, Massimo; Camaioni, Nadia; Maccagnani, Piera; Ostoja, Paolo; Monari, Magda; Barbarella, Giovanna


    The design, synthesis and properties of liquid-crystalline semiconducting oligothiophenes containing dithienothiophene (DTT), benzothiadiazole (BTZ) and carbazole (CBZ) rigid cores are described. The effect of molecular structure (shape, size and substitution) on their thermal behaviour and electrical properties has been investigated. Polarised optical microscopy (POM) and differential scanning calorimetry (DSC) analyses have revealed highly ordered smectic mesophases for most of the newly synthesised compounds. X-ray diffraction (XRD) studies performed at various temperatures have shown that the smectic order is retained in the crystalline state upon cooling across the transition temperature, affording cast films with a more favourable morphology for FET applications.

  11. Optical and THz reflectance investigations of organic solar cells (United States)

    Sporea, Dan; Mihai, Laura; Sporea, Adelina; Galagan, Yulia


    Two Organic Photovoltaic devices having a photoactive layer containing Poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5- (4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT) and [6,6]-phenyl C61-butyric acid methyl ester (PCBM, 99%), and the layer sequences - glass/ITO/ZnO/PAL/PEDOT:PSS/Ag/encapsulation were non-destructively investigated by diffuse optical spectral reflectance, THz spectroscopy and THz imaging. The proposed methods proved to be powerful tools to support quality assurance in organic solar cells development, facilitating both the localization of manufacturing defects and the device degradation, as they are combined with "classical" evaluation means.

  12. QTAIM investigation of bis(pyrazol-1-yl)methane derivative and its Zn(II) complexes (ZnLX2, X=Cl, Br or I)


    Dehestani Maryam; Zeidabadinejad Leila


    Topological analyses of the electron density using the quantum theory of atoms in molecules (QTAIM) have been carried out at the B3PW91/6-31g (d) theoretical level, on bis(pyrazol-1-yl)methanes derivatives 9-(4-(di (1H-pyrazol-1-yl)-methyl)phenyl)-9H-carbazole (L) and its zinc(II) complexes: ZnLCl2 (1), ZnLBr2 (2) and ZnLI2 (3). The topological parameters derived from Bader theory were also analyzed; these are characteristics of Zn-bond critical points and ...


    Institute of Scientific and Technical Information of China (English)

    ZHANG Lina; DING Qiong


    A method of determining branching parameter of lacquer polysaccharide was established by acid-base back-titration of terminal uronic acid of branches. The branching factors obtained are in agreement with the values determined by colorimetric method with carbazole and the results estimated by using Zimm-Stockmayer equation from viscosity data. Influences of molecular weights and branching factors of five fractions of lacquer polysaccharide on the bioactivities were studied. The results show that the polysaccharides have bioactivities in motivating the growth of leucocytes, and the effect increases with the decrease of molecular weight and branching factor in the range studied(17×104>Mw>4×104).

  14. Synthesis, Reactivity, and Characterization of (-Hexacarbocyclic) Manganese Dicarbonyl Complexes with Sulfur and Phosphorus Ligands (United States)


    strained ring systems, fluorene 12,13c or carbazole, 13c or heteroatoms (0, S, or N) 13c was found to stabilize the deprotonated CpFe(arene) complexes...carbon atom rather than beneath the saturated ring carbon atom and is discussed in more detail in Chapter V.8 In 2b, the near random positioning of the...formation of d2 -cyclopropane observed in the MS analysis with peaks at 6 1.29 and 6 0.88 assigned to the two methyl groups and the ring protons

  15. Phytochemical screening and antimicrobial activity of roots of Murraya koenigii (Linn. Spreng. (Rutaceae

    Directory of Open Access Journals (Sweden)

    Manisha Vats


    Full Text Available Murraya koenigii, family Rutaceae, commonly known as Curry leaf plant is a highly valued plant for its medicinal value and characteristic aroma. The plant is a rich source of carbazole alkaloids. The petroleum ether, chloroform, ethyl acetate and ethanol extracts of roots of the plant were screened for phytochemical properties and antimicrobial activity for Staphylococcus aureus, Micrococcus luteus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa, Candida albicans and Aspergillus niger. Phytochemical screening showed the presence of carbohydrates, alkaloids, steroids and flavonoids in the root extracts of the plant. The study shows that all the extracts possess remarkable antibacterial activity. Additionally, petroleum ether and chloroform extracts also had antifungal activity.

  16. Toxicity of eight polycyclic aromatic compounds to red clover (Trifolium pratense), ryegrass (Lolium perenne), and mustard (Sinapsis alba). (United States)

    Sverdrup, Line E; Krogh, Paul Henning; Nielsen, Torben; Kjaer, Christian; Stenersen, Jørgen


    The effect of eight polycyclic aromatic compounds (PACs) on the seed emergence and early life-stage growth of three terrestrial plants (Sinapsis alba, Trifolium pratense and Lolium perenne) were studied in a greenhouse, using a Danish agricultural soil with an organic carbon content of 1.6%. After three weeks of exposure, seed emergence and seedling weight (fresh weight and dry weight) were determined. Exposure concentrations were verified with chemical analysis. The substances tested were four polycyclic aromatic hydrocarbons (fluoranthene, pyrene, phenanthrene and fluorene), the N-, S-, and O-substituted analogues of fluorene (carbazole, dibenzothiophene and dibenzofuran, respectively), and the quinoline representative acridine. Seedling growth was a far more sensitive endpoint than seed emergence for all substances. Concentrations estimated to give a 20% reduction of seedling fresh weight (EC20-values) ranged from 36 to 290 mgkg(-1) for carbazole, 43 to 93 mgkg(-1) for dibenzofuran, 37 to 110 mgkg(-1) for dibenzothiophene, 140 to 650 mgkg(-1) for fluoranthene, 55 to 380 mgkg(-1) for fluorene, 37 to 300 mgkg(-1) for phenanthrene, and 49 to 1300 mgkg(-1) for pyrene. For acridine, no toxicity was observed within the concentration range tested (1-1000 mgkg(-1)). As illustrated by the EC20-values, there was a rather large difference in sensitivity between the species, and T. pratense was the most sensitive of the species tested.

  17. Synthesis of Soluble Host Materials for Highly Efficient Red Phosphorescent Organic Light-Emitting Diodes. (United States)

    Suh, Min Chul; Park, So-Ra; Cho, Ye Ram; Shin, Dong Heon; Kang, Pil-Gu; Ahn, Dong A; Kim, Hyung Suk; Kim, Chul-Bae


    New soluble host materials with benzocarbazole and triphenyltriazine moieties, 11-[3-(4,6-diphenyl-[1,3,5]triazin-2-yl)-phenyl]-11H-benzo[a]carbazole and 11-[3'-(4,6-diphenyl-[1,3,5]triazin-2-yl)-biphenyl-4-yl]-11H-benzo[a]carbazole, were synthesized for highly efficient red phosphorescent organic light-emitting diodes (PHOLED). Hole-transporting benzocarbazole moiety and electron transporting triphenyltriazine moiety, which are severely twisted each other enhance the solubility of those materials in common organic solvent. The improved solubility from this molecular design could be due to a reduced π-π stacking interaction, which gives a very uniform film morphology after spin coating of those materials. As a result, we obtained highly efficient soluble PHOLEDs combined with an evaporated blue common layer structure. The resultant red PHOLED exhibited the maximum current efficiency as well as external quantum efficiency values up to 23.7 cd/A and 19.0%.

  18. Synthesis, fluorescence properties of Eu(Ⅲ) complexes with novel carbazolefunctionalized β-diketone ligand

    Institute of Scientific and Technical Information of China (English)

    TANG Ruiren; ZHANG Wei; LUO Yiming; LI Jun


    A novel carbazole functionalized β-diketone, methyl 6-(9-ethylcarbazole-3-yl)-oxoacetyl-2-pyridinecarboxylate (MEP), and its Corresponding Corresponding binary Eu(Ⅲ) complexes Eu(MEP)32H2O and ternary complex Eu(MEP)3Phen with 1,10-Phenanthroline (Phen) were pre-pared. The ligand was characterized based on elemental analysis, FT-IR, and 1H NMR, and the complexes were characterized with elemental analysis, FT-IR and thermogravimetric and differential thermal analysis (TG-DTA). The investigation of fluorescence properties of the com-plexes Eu(MEP)32H2O and Eu(MEP)3Phen showed that the Eu(Ⅲ) ion could be sensitized efficiently by the ligand to some extent, in par-titular, in the ternary system, the secondary ligand Phen acting as a light-harvesting center was involved in the highly efficient energy transfer process, and the emission was stronger than the binary complex. In addition, the introduction of the carbazole moiety enlarged the π-conjugated system of the ligand and enhanced the luminescent intensity of the complexes.

  19. Synthesis and Crystal Structure of 3,6-Bis(4,4,4-trifluorobutane-1,3-dione)-9-n-butylcarbazole

    Institute of Scientific and Technical Information of China (English)

    YANG Lin; ZHAO Xiang-Hua; ZHOU Hong-Ping; WU Jie-Ying; YANG Jia-Xiang; SHAO Guo-Quan; CHENG Le-Hua; TIAN Yu-Peng


    A novel bis(β-diketonate)derivate,3,6-bis(4,4,4-trifluorobutane-l,3-dione)-9-n-butylcarbazole 1,was synthesized and structurally characterized by single-crystal X-ray diffrac-tion.The crystal belongs to the monoclinic system,space group P21/c with a=10.961(6),b=22.942(13),C=9.408(6)(A),α=90,β=109.663(9),γ=90°, V=2228(2)(A)3,Z=4,Dc=1.489g/cm3,C24H19F6NO4,Mr=499.40,F(000)=1024 and μ=0.134mm-1.The structure was refined to the final R=0.0699 and wR=0.1627 for 3744 independent reflections(Rint=0.1288)and 1349observed reflections(I>2o(I)).Compound 1 consists of carbazole unit and two terminal diketonate groups,in which carbazole and its two adjacent diketonate rings are almost coplanar.Moreover,compound 1 was characterized with IR,elemental analysis,1H NMR,MS,electronic absorption,and single-photon fluorescence.

  20. Synthesis, crystal structure and photoluminescence of phosphorescent copper (I) complexes containing hole-transporting carbazoly moiety. (United States)

    Yu, Tianzhi; Chai, Haifang; Zhao, Yuling; Zhang, Chengcheng; Liu, Peng; Fan, Duowang


    Two new mononuclear Cu(I) complexes based on 2-(2'-pyridyl)benzimidazolyl derivative ligand containing hole-transporting carbazole (L), [Cu(L)(DPEphos)](BF4) and [Cu(L)(PPh3)2](BF4), where L=(4-(9H-carbazol-9-yl)phenyl)methyl-2-(2'-pyridyl)benzimidazole; DPEphos=bis[2-(diphenylphosphino)phenyl]ether and PPh3=triphenylphosphine, have been synthesized and characterized on the basis of elemental analysis, (1)H NMR and FT-IR spectra. The structures of the ligand L and the Cu(I) complexes were characterized by single crystal X-ray diffraction. The results reveal that in the Cu(I) complexes the central Cu(I) ions assume the irregular distorted tetrahedral geometry and are tetra-coordinated by the two nitrogen atoms from L ligand and two phosphorus atoms from ancillary ligands. The photophysical properties of the complexes were examined by using UV-vis, photoluminescence spectroscopic analysis. The complexes exhibit weak MLCT absorption bands ranging from 360 to 480 nm, and display strong orange phosphorescence in the solid states at room temperature, which is completely quenched in solutions.

  1. Hyperbranched red light-emitting phosphorescent polymers based on iridium complex as the core

    Energy Technology Data Exchange (ETDEWEB)

    Guo, Ting; Yu, Lei; Yang, Yong; Li, Yanhu; Tao, Yun [Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640 (China); Hou, Qiong [School of Chemistry & Environment, South China Normal University, Guangzhou 510006 (China); Ying, Lei, E-mail: [Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640 (China); Yang, Wei; Wu, Hongbin; Cao, Yong [Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640 (China)


    A series of hyperbranched π-conjugated light-emitting polymers containing an iridium complex as the branched core unit and polyfluorene or poly(fluorene-alt-carbazole) as the branched segments were synthesized via a palladium catalyzed Suzuki polymerization. Apparent Förster energy transfer in the photoluminescent spectra as thin films was observed, while no discernible characteristic absorbance and photoluminescence of the iridium complex can be realized in dilute solutions. Copolymers based on poly(fluorene-alt-carbazole) as the branched segments demonstrated enhanced highest occupied molecular orbital energy levels relative to those based on polyfluorene. The electroluminescent spectra of these copolymers exclusively showed the characteristic emission of the iridium complex, with corresponding CIE coordinates of (0.67±0.01, 0.31). All devices exhibited relatively slow roll-off of efficiency, and the best device performance with the maximum luminous efficiency of 5.33 cd A{sup −1} was attained by using PFCzTiqIr3 as the emissive layer. These results indicated that the hyperbranched conjugated architectures can be a promising molecular design strategy for efficient electrophosphorescent light-emitting polymers. - Highlights: • Hyperbranched red light-emitting polymers are synthesized. • Red light-emitting iridium complex is used as the branched core unit. • Hyperbranched polymers based on PFCz exhibit higher luminescence. • The highest luminous efficiency of 5.33 cd A{sup −1} is attained.

  2. Synthesis and property of polymer nanospheres with Pd/P4VP shells via surface RAFT polymerization

    Directory of Open Access Journals (Sweden)


    Full Text Available A reversible addition-fragmentation chain transfer (RAFT agent with carbazole as Z-group was immobilized on the surfaces of the cross-linked poly (4-vinylbenzyl chloride-co-styrene (PVBCS nanospheres with a diameter of about 70 nm by the reaction of benzyl chloride groups in the PVBCS between carbazole and carbon sulfide. Then surface RAFT polymerization of 4-vinylpyridine (4VP was used to modify the nanospheres to produce a well-defined and covalently tethered P4VP shell. By surface activation in a PdCl2 solution and then reduction by hydrazine hydrate (N2H4•H2O, the P4VP composite shells were obtained containing densely palladium metal nanoparticles. The chemical composition of the nanosphere surfaces at various stages of the surface modification was characterized by X-ray photoelectron spectroscopy (XPS. Transmission electron microscopy (TEM was used to characterize the morphology of the hybrid nanospheres. The Pd/P4VP shell nanospheres were also applied to the catalytic reaction and proved to be efficient and reusable for the Heck reaction.

  3. Highly efficient exciplex organic light-emitting diodes using thermally activated delayed fluorescent emitters as donor and acceptor materials. (United States)

    Jeon, Sang Kyu; Yook, Kyoung Soo; Lee, Jun Yeob


    Highly efficient exciplex type organic light-emitting diodes were developed using thermally activated delayed fluorescent emitters as donors and acceptors of an exciplex. Blue emitting bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (DMAC-DPS) was a donor and 9,9'-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole) (DDCzTrz) and 9,9',9″-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)benzene-1,2,3-triyl)tris(9H-carbazole) (TCzTrz) were acceptor materials. The exciplexes of DMAC-DPS:TCzTrz and DMAC-DPS:DDCzTrz resulted in high photoluminescence quantum yield and high quantum efficiency in the green exciplex organic light-emitting diodes. High quantum efficiencies of 13.4% and 15.3% were obtained in the DMAC-DPS:DDCzTrz and DMAC-DPS:TCzTrz exciplex devices.

  4. External Heavy-Atom Effect via Orbital Interactions Revealed by Single-Crystal X-ray Diffraction. (United States)

    Sun, Xingxing; Zhang, Baicheng; Li, Xinyang; Trindle, Carl O; Zhang, Guoqing


    Enhanced spin-orbit coupling through external heavy-atom effect (EHE) has been routinely used to induce room-temperature phosphorescence (RTP) for purely organic molecular materials. Therefore, understanding the nature of EHE, i.e., the specific orbital interactions between the external heavy atom and the luminophore, is of essential importance in molecular design. For organic systems, halogens (e.g., Cl, Br, and I) are the most commonly seen heavy atoms serving to realize the EHE-related RTP. In this report, we conduct an investigation on how heavy-atom perturbers and aromatic luminophores interact on the basis of data obtained from crystallography. We synthesized two classes of molecular systems including N-haloalkyl-substituted carbazoles and quinolinium halides, where the luminescent molecules are considered as "base" or "acid" relative to the heavy-atom perturbers, respectively. We propose that electron donation from a π molecular orbital (MO) of the carbazole to the σ* MO of the C-X bond (π/σ*) and n electron donation to a π* MO of the quinolinium moiety (n/π*) are responsible for the EHE (RTP) in the solid state, respectively.

  5. Synthesis, crystal structure and photoluminescence of phosphorescent copper (I) complexes containing hole-transporting carbazoly moiety (United States)

    Yu, Tianzhi; Chai, Haifang; Zhao, Yuling; Zhang, Chengcheng; Liu, Peng; Fan, Duowang


    Two new mononuclear Cu(I) complexes based on 2-(2'-pyridyl)benzimidazolyl derivative ligand containing hole-transporting carbazole (L), [Cu(L)(DPEphos)](BF4) and [Cu(L)(PPh3)2](BF4), where L = (4-(9H-carbazol-9-yl)phenyl)methyl-2-(2'-pyridyl)benzimidazole; DPEphos = bis[2-(diphenylphosphino)phenyl]ether and PPh3 = triphenylphosphine, have been synthesized and characterized on the basis of elemental analysis, 1H NMR and FT-IR spectra. The structures of the ligand L and the Cu(I) complexes were characterized by single crystal X-ray diffraction. The results reveal that in the Cu(I) complexes the central Cu(I) ions assume the irregular distorted tetrahedral geometry and are tetra-coordinated by the two nitrogen atoms from L ligand and two phosphorus atoms from ancillary ligands. The photophysical properties of the complexes were examined by using UV-vis, photoluminescence spectroscopic analysis. The complexes exhibit weak MLCT absorption bands ranging from 360 to 480 nm, and display strong orange phosphorescence in the solid states at room temperature, which is completely quenched in solutions.

  6. Ferrocenyl Chalcone with 2-Anthracenyl Group (2-Anth-C(O)CH=CHFc): Electrochemical and Fluorescent Properties

    Energy Technology Data Exchange (ETDEWEB)

    Lee, Su Kyung; Lim, Chae Mi; Lee, Ji Yeon; Noh, Dong Youn [Seoul Women' s University, Seoul (Korea, Republic of)


    In this study, a ferrocenyl chalcone with a 2-anthracenyl group, an analogue of was prepared. Unlike is fluorescent and its fluorescence was investigated in relation to its solvent's polarity. Its electrochemical properties were also studied and the local geometry of is suggested from {sup 1}H NMR results. Ferrocenyl chalcones, in which ferrocenyl and aromatic groups are linked by an enone bridge, are versatile compounds exhibiting antiplasmodial and antitumor activities, fluorescent and electrochemical properties, and molecular chemosensor activity. Ferrocenyl chalcones bearing the fluorophores such as 2-naphthalene, 9-anthracene, 1-pyrene, and N-ethyl carbazole, are regarded as good candidates for new fluorescent material. However, ferrocenyl chalcones containing 9-anthracene and 2-naphthalene derivatives have been reported as being not fluorescent, while those containing 1-pyrene and N-ethyl carbazole derivatives are fluorescent. It means that the ferrocenyl group, known as an effective quencher of exited states, is therefore not the only reason why they are non-fluorescent. Some derivatization of fluoro-phores can also disable fluorescence, as demonstrated by 2-acetylanthracene being fluorescent while 9-acetylanthracene is not.

  7. Highly Efficient PCDTBT:PC71 BM Based Photovoltaic Devices without Thermal Annealing Treatment

    Institute of Scientific and Technical Information of China (English)

    杨少鹏; 孔伟光; 刘博雅; 郑文耀; 李保民; 刘贤豪; 傅广生


    We propose an effective method to fabricate highly efficient organic photovoltaic cells based on poly [N-9"-hepta-decanyl-2, 7-carbazole-alt-5,5-(4'7'-di-2-thienyl-2'l '3'-b-enzothiadiazole):[6,6]-phenyl Cji-butyric acid methyl ester (PCDTBT.PC71BM). A power conversion efficiency of as high as 5.6% and a fill factor of 53.7% are achieved from the optimized cells. The influence of surface morphology of the active layer on the performance of the cells is also investigated.%We propose an effective method to fabricate highly efficient organic photovoltaic cells based on poly[N-9”-hepta-decanyl-2,7-carbazole-alt-5,5-(4'7'-di-2-thienyl-2'1 '3'-b-enzothiadiazole):[6,6]-phenyl C71-butyric acid methyl ester(PCDTBT:PC71BM).A power conversion efficiency of as high as 5.6% and a fill factor of 53.7% are achieved from the optimized cells.The influence of surface morphology of the active layer on the performance of the cells is also investigated.

  8. Hydrogenation of heteroaromatics by high pressure DTA techniques. 3; Koatsu DTA ho ni yoru hokozoku kagobutsu no suisoka (rutenium tanji shokubai ni yoru kakusuisoka datsu hetero hanno)

    Energy Technology Data Exchange (ETDEWEB)

    Yamamoto, M.; Yoshida, T. [Hokkaido National Industrial Research Institute, Sapporo (Japan); Kotanigawa, T. [Japan International Cooperation Agency, Tokyo (Japan)


    Ring-opening of heteroaromatics and heteroatom-removal reaction were studied experimentally using the acidic catalyst containing phosphoric acid for improvement of an upgrading method of coal derived oils. In experiment, some Ru-carrying metal oxide catalysts such as RMZ, RML and RMN catalyst, and MNP catalyst containing phosphoric acid were used as specimens. Nuclear hydrogenation reaction and hydro-denitrogenation reaction of dibenzothiophene and carbazole were compared with each other. The experimental results are as follows. Both RMN and RMNP catalysts offer a superior selectivity in nuclear hydrogenation reaction and hydro-denitrogenation reaction of carbazole. Although both catalysts offer an extremely high nuclear hydrogenation activity at 360{degree}C, these offer the high selectivity of denitrogenation products at 430{degree}C. In comparison of the activities of MN and MNP catalysts with the same Mn2O3:NiO ratio, MNP catalyst offers the higher denitrogenation activity than MN catalyst at 430{degree}C. 1 ref., 3 tabs.


    Institute of Scientific and Technical Information of China (English)

    Guo-xin Jiang; Chun-lei Bian; Jun-qiao Ding; Li-xiang Wang


    Novel blue light-emitting poly(aryl ether)s comprising of bipolar oligofluorene pendants as chromophores have been designed and synthesized,in which pyrimidine and arylamine moieties are utilized as the electron acceptor and electron donor,respectively.Through varying π bridge length from monofluorene to bifluorene and end-cappers from hydrogen to carbazole and diphenylamine,the emission color of the resulting polymers covers from deep blue to greenish blue,and their HOMO and LUMO levels can be modulated to facilitate charge injection to improve the device performance.Polymer lightemitting diodes (PLEDs) are fabricated with the device structure of ITO/poly(3,4-ethylenedioxythiophene):poly(styrene sulfonic acid) (PEDOT:PSS) (50 nm)/polymer (80 nm)/Ca (10 nm)/A1 (200 nm).Among these polymers,P2Cz5F-Py with bifluorene bridge and carbazole end-capper shows excellent trade-off between the efficiency and emission wavelength,having a peak luminous efficiency as high as 1.26 cd/A and Commission Internationale de L'Eclairage (CIE) coordinates of (0.17,0.17).

  10. Synthesis and properties of acrylic copolymers for ocular implants (United States)

    Reboul, Adam C.

    There is a need for flexible polymers with higher refractive index and extended UV absorbing properties for improved intraocular lenses (IOLs). This research was devoted to the synthesis of new acrylic copolymers for foldable IOLs and to studies concerning IOL polymer properties. New polymers were synthesized from phenylated acrylates copolymerized with N-vinyl carbazole derivatives using bulk free radical addition methods. The copolymers had low Tg values, high refractive index, and were flexible. The N-vinyl carbazole derivatives were characterized by NMR and copolymers were characterized by DSC, UV-Vis, and refractometry. New phenothiazine based UV absorbers with high extinction coefficients were also synthesized for incorporation into ocular materials. Patent disclosures on UV absorbers and high refractive index polymers were prepared. A so called "glistening" phenomenon that occurs in all foldable intraocular lenses currently in clinical use is poorly understood and was studied. Research on this microvoid forming behavior included studies and development of methods to inhibit glistening in low Tg acrylic based copolymers. Glistenings were characterized using SEM and optical microscopy. A novel technique for inhibiting glistening was found and a patent disclosure was prepared.

  11. 6H-Indolo[2,3-b]quinoxaline-based organic dyes containing different electron-rich conjugated linkers for highly efficient dye-sensitized solar cells (United States)

    Qian, Xing; Gao, Huan-Huan; Zhu, Yi-Zhou; Lu, Lin; Zheng, Jian-Yu


    A new class of organic dyes based on 6H-indolo[2,3-b]quinoxaline are synthesized and applied as photosensitizers for dye-sensitized solar cells. Different electron-rich π-conjugated bridges such as oligothiophene, thienyl carbazole, and furyl carbazole are introduced to cooperate with 6H-indolo[2,3-b]quinoxaline and cyanoacrylic acid anchoring group to give the dyes JY01, JY02, and JY03, respectively. Their photophysical, electrochemical, and photovoltaic properties are further investigated. All three dyes show good performances as photosensitizers. In particular, DSSC based on JY01 shows the best photovoltaic performance with a short-circuit photocurrent density of 16.0 mA cm-2, an open-circuit photovoltage of 708 mV and a fill factor of 0.67, corresponding to an overall power conversion efficiency of 7.62% under AM 1.5 irradiation (100 mW cm-2).

  12. Effect of Mangiferin and Mahanimbine on Glucose Utilization in 3T3-L1 cells (United States)

    Kumar, B Dinesh; Krishnakumar, K; Jaganathan, Saravana Kumar; Mandal, Mahitosh


    Background: Stem barks of Mangifera indica contain a rich content of mangiferin (xanthone glucoside), whereas Murraya koenigii leaves contain rich sources of mahanimbine (carbazole alkaloid) and used traditionally for the treatment of diabetes. Objective: To investigate the effects of mangiferin (xanthone glucoside) and mahanimbine (carbazole alkaloid) on glucose utilization in 3T3-L1 cells. Materials and Methods: Mangiferin was isolated from stem barks of Mangifera indica and mahanimbine was isolated from Murraya koenigii leaves. These isolated compounds were subjected to MTT assay and glucose utilization test with 3T3-L1 cells. Results: Treatment of the 3T3-L1 cells with mangiferin and mahanimbine increased the glucose utilization in a dose-dependent manner. At a concentration of 1 mM, mangniferin showed 2-fold increase in glucose utilization compared with untreated control. In case of mahanimbine, the observed effect at 1 mM was almost equivalent to positive control (insulin at 1 μM). Moreover, MTT assay showed that both of these compounds were less toxic at a concentration of 1 mM (nearly 75% cells are viable). Conclusion: The present results indicated that these natural products (mangiferin and mahanimbine) exhibited potential ethnomedical uses in management of diabetes. PMID:23661997

  13. The distribution of dimethylcarbazoles in oils from the Pearl River Mouth Basin, South China Sea

    Institute of Scientific and Technical Information of China (English)

    ZHANG Chunming; ZHAO Hongjing; GAO Kunshun; YANG Shaokun


    C2-carbazole isomers have been investigated in crude oils from the Hui-Liu Structure Ridge (HLSR) in the Pearl River Mouth Basin (PRMB), South China Sea. The NH shielded isomer, as well as the NH partially shielded isomers, was detected in high abundance and the NH exposed isomers in lower abundance. A small-enrichment trend of 1,8-dimethylcarbazole (DMC) was observed in crude oils along the western part of HLSR (WPHLSR), which may indicate little effect of migration on the C2-carbazole distributions. Two strikingly different distribution patterns of NH partially shielded isomers were observed in the reservoirs along the WPHLSR: one with a preference of 1,3- and 1,6-DMCs and the other with a preference of 1,4- and 1,5-DMCs. All of the oils occurring in the Upper reservoirs have a preference of 1,3- and 1,6-DMCs, whereas those trapped in the Lower reservoirs show a preference of 1,4- and 1,5-DMCs, which may indicate there are two petroleum migration systems in the WPHLSR.

  14. Quantification of alginate by aggregation induced by calcium ions and fluorescent polycations. (United States)

    Zheng, Hewen; Korendovych, Ivan V; Luk, Yan-Yeung


    For quantification of polysaccharides, including heparins and alginates, the commonly used carbazole assay involves hydrolysis of the polysaccharide to form a mixture of UV-active dye conjugate products. Here, we describe two efficient detection and quantification methods that make use of the negative charges of the alginate polymer and do not involve degradation of the targeted polysaccharide. The first method utilizes calcium ions to induce formation of hydrogel-like aggregates with alginate polymer; the aggregates can be quantified readily by staining with a crystal violet dye. This method does not require purification of alginate from the culture medium and can measure the large amount of alginate that is produced by a mucoid Pseudomonas aeruginosa culture. The second method employs polycations tethering a fluorescent dye to form suspension aggregates with the alginate polyanion. Encasing the fluorescent dye in the aggregates provides an increased scattering intensity with a sensitivity comparable to that of the conventional carbazole assay. Both approaches provide efficient methods for monitoring alginate production by mucoid P. aeruginosa.

  15. Strong emissive nanofibers of organogels for the detection of volatile acid vapors. (United States)

    Xue, Pengchong; Sun, Jiabao; Yao, Boqi; Gong, Peng; Zhang, Zhenqi; Qian, Chong; Zhang, Yuan; Lu, Ran


    Two L-phenylalanine derivatives with 5,8-bis(2-(carbazol-3-yl)vinyl)quinoxaline (PCQ) and 5,8-bis[2-(carbazol-3-yl)]-2,3-dimethylquinoxaline (DCQ) as fluorophores were synthesized, and their photophysical properties were measured and compared. The two compounds were found to gelate some organic solvents and self-assemble into 1D nanofibers in gels. The wet gel of PCQ emitted a weak orange fluorescence, but the DCQ gel had a strong green one. This result can be due to the presence of two methyl groups and the nonplanar conformation of fluorophore in DCQ. The gel film of DCQ also showed significantly stronger fluorescence than that of PCQ. Thus, the wet gel and xerogel film of DCQ were selected to study their sensing properties to acids. The yellow wet gel of DCQ transformed into a brown sol upon the addition of 0.2 equiv trifluoroacetic acid (TFA), accompanied by emission quenching. The xerogel film of DCQ rapidly responded to volatile acids, such as TFA, HCl, and HOAc. The fluorescence of the xerogel film was gradually quenched with increased concentration of volatile acid vapors. The fibrous film exhibited low detection limits for volatile acid. The detection limits of the thin films for TFA, HCl, and HOAc reached 43, 122, and 950 ppb, respectively.

  16. Hybrid AgNP–TiO2 thin film based photoanode for dye sensitized solar cell

    Directory of Open Access Journals (Sweden)

    Jayraj V. Vaghasiya


    Full Text Available This article addresses two major issues in the plasmonic dye solar cell; (i protection of plasmonic nanoparticles from electrolyte attack and (ii design of appropriate molecular dye to harvest photon near the plasmonic resonance. This report reveals the synthesis of D-π-A carbazole dye and incorporation of plasmonic Ag nanoparticles (AgNPs into TiO2 film using Ag–TiO2 gel. We have designed and synthesized an efficient D-π-A carbazole dye molecule whose absorption maxima matches the plasmonic resonance of AgNPs leading to augmented near field effect, enhancing photon harvesting property of dye molecule. This article also describes a strategy to incorporate AgNPs into the TiO2 photoelectrode by Ag–TiO2 gel. The plasmonic photoanode was characterized using SEM and optical spectroscopy. Dye solar cells were characterized by J–V characteristics and electrochemical impedance technique in order to take insight into photovoltaic performance and electron transfer kinetic. This engineered DSSC achieves 45% enhancement in current due to the plasmon enhanced near field effect at thin film (3 μm.

  17. Intramolecular Charge Transfer and Solvation of Photoactive Molecules with Conjugated Push-Pull Structures. (United States)

    Zhu, Huaning; Wang, Xian; Ma, Renjun; Kuang, Zhuoran; Guo, Qianjin; Xia, Andong


    A comparative investigation on the photophysical properties and solvation-related ICT dynamics of three push-pull compounds containing different donors including carbazole, triphenylamine and phenothiazine, was performed. The steady-state spectra and theoretical calculations show the charge transfers from the central donors to the acceptors at each side. The characterization of the extent of charge transfer was determined by various means, including estimation of the dipole moment, the electron density distribution of HOMO and LUMO, CDD and change in Gibb's free energy, which show the charge transfer strength to be in the order PDHP > BDHT > PDHC. This suggests that the electron-donating ability of the donor groups plays a crucial role in the charge transfer in these compounds. The TA data show the excited-state relaxation dynamics follow a sequential model: FC→ICT→ICT'→S0 , and are affected by the solvent polarity. The results presented here demonstrate that the compound with a higher degree of ICT characteristic interacts more strongly with stronger polar solvent molecules, which can accelerate the solvation and spectral evolution to lower energy levels. The A-π-D-π-A architectures with prominent ICT characteristics based on carbazole, triphenylamine and phenothiazine might be potential scaffolds for light-harvesting and photovoltaic devices. These results are of value for understanding structure-property relationships and the rational design of functional materials for photoelectric applications.

  18. Novel Aryne Chemistry in Organic Synthesis

    Energy Technology Data Exchange (ETDEWEB)

    Liu, Zhijian [Iowa State Univ., Ames, IA (United States)


    Arynes are among the most intensively studied systems in chemistry. However, many aspects of the chemistry of these reactive intermediates are not well understood yet and their use as reagents in synthetic organic chemistry has been somewhat limited, due to the harsh conditions needed to generate arynes and the often uncontrolled reactivity exhibited by these species. Recently, o-silylaryl triflates, which can generate the corresponding arynes under very mild reaction conditions, have been found very useful in organic synthesis. This thesis describes several novel and useful methodologies by employing arynes, which generate from o-silylaryl triflates, in organic synthesis. An efficient, reliable method for the N-arylation of amines, sulfonamides and carbamates, and the O-arylation of phenols and carboxylic acids is described in Chapter 1. Amines, sulfonamides, phenols, and carboxylic acids are good nucleophiles, which can react with arynes generated from a-silylaryl triflates to afford the corresponding N- and O-arylated products in very high yields. The regioselectivity of unsymmetrical arynes has also been studied. A lot of useful, functional groups can tolerate our reaction conditions. Carbazoles and dibenzofurans are important heteroaromatic compounds, which have a variety of biological activities. A variety of substituted carbazoles and dibenzofwans are readily prepared in good to excellent yields starting with the corresponding o-iodoanilines or o-iodophenols and o-silylaryl triflates by a treatment with CsF, followed by a Pd-catalyzed cyclization, which overall provides a one-pot, two-step process. By using this methodology, the carbazole alkaloid mukonine has been concisely synthesized in a very good yield. Insertion of an aryne into a σ-bond between a nucleophile and an electrophile (Nu-E) should potentially be a very beneficial process from the standpoint of organic synthesis. A variety of substituted ketones and sulfoxides have been synthesized in good


    Energy Technology Data Exchange (ETDEWEB)

    John J. Kilbane III


    The objective of the project is to develop biochemical pathways for the selective cleavage of C-N bonds in molecules found in petroleum. The initial phase of the project will focus on the isolation or development of an enzyme capable of cleaving the C-N bond in aromatic amides, specifically 2-aminobiphenyl. The objective of the second phase of the research will be to construct a biochemical pathway for the selective removal of nitrogen from carbazole by combining the carA genes from Sphingomonas sp. GTIN11 with the gene(s) encoding an appropriate amidase. The objective of the final phase of the project will be to develop derivative CN bond cleaving enzymes that have broader substrate ranges and to demonstrate the use of such strains to selectively remove nitrogen from petroleum. The project is on schedule and no major difficulties have been encountered. During the first year of the project (October, 2002-September, 2003) enrichment culture experiments have resulted in the isolation of promising cultures that may be capable of cleaving C-N bonds in aromatic amides, several amidase genes have been cloned and are currently undergoing directed evolution to obtain derivatives that can cleave C-N bonds in aromatic amides, and the carA genes from Sphingomonas sp. GTIN11, and Pseudomonas resinovorans CA10 were cloned in vectors capable of replicating in Escherichia coli. Future research will address expression of these genes in Rhodococcus erythropolis. Enrichment culture experiments and directed evolution experiments continue to be a main focus of research activity and further work is required to obtain an appropriate amidase that will selectively cleave C-N bonds in aromatic substrates. Once an appropriate amidase gene is obtained it must be combined with genes encoding an enzyme capable of converting carbazole to 2'aminobiphenyl-2,3-diol: specifically carA genes. The carA genes from two sources have been cloned and are ready for construction of C-N bond cleavage

  20. Cytotoxic Constituents from the Stems of Clausena lansium (Lour. Skeels

    Directory of Open Access Journals (Sweden)

    Shu Shan Du


    Full Text Available Six compounds were isolated from the stems of Clausena lansium (Lour. Skeels by repeated sillica gel column chromatography. Their chemical structures were elucidated on the basic of physicochemical and spectroscopic data. Among them, 8-geranyloxypsolaren (3 and 2-methoxy-1-(3-methyl-buten-1-yl-9H-carbazole-3-carbaldehyde (6 were isolated for the first time from this plant. These compounds were screened for cytotoxicity in human cervical cancer (Hela, leukemia (K562, lung cancer (A549, non-small lung carcinoma (H1299 and liver cancer (SMMC-7721. Within the series of cytotoxic tests, compounds 4–6 displayed potent cytotoxic activity against H1299 and SMMC-7721, with the IC50 values of 6.19 to 26.84 μg/mL.

  1. Aqueous solubility data for pressurized hot water extraction for solid heterocyclic analogs of anthracene, phenanthrene and fluorene. (United States)

    Karásek, Pavel; Planeta, Josef; Roth, Michal


    We report the aqueous solubilities of phenanthrene and several solid three-ring aromatic heterocycles (phenanthridine, acridine, phenazine, thianthrene, phenothiazine, phenoxathiin, phenoxazine, carbazole, dibenzofuran, dibenzothiophene, and 4,6-dimethyldibenzothiophene) at temperatures ranging from 313K to the solute melting point and at a pressure of 5MPa. The data were measured by dynamic saturation method using an in-house-assembled apparatus for pressurized hot water extraction (PHWE). The solute from a known mass of the saturated aqueous solution was transferred to an organic solvent (hexane or toluene), and the organic phase was analyzed by GC/MS. In any of the solutes, the GC/MS records did not indicate any noticeable decomposition within the temperature range of the measurements. The resultant solubilities were converted to activity coefficients of the individual solutes in saturated aqueous solutions, and the results are discussed in terms of temperature and type/number of heteroatoms.

  2. Simple synthesis of P(Cbz-alt-TBT) and PCDTBT by combining direct arylation with suzuki polycondensation of heteroaryl chlorides. (United States)

    Lombeck, Florian; Matsidik, Rukiya; Komber, Hartmut; Sommer, Michael


    Direct arylation (DA) of 2-chlorothiophene and 2-chloro-3-hexylthiophene with 4,7-dibromo-2,1,3-benzothiadiazole is used to synthesize 4,7-bis(5-chloro-2-thienyl)-2,1,3-benzothiadiazole (TBTCl2) and 4,7-bis(5-chloro-4-hexyl-2-thienyl)-2,1,3-benzothiadiazole (DH-TBTCl2) in one step. Suitable conditions of the Suzuki polycondensations (SPC) of TBTCl2 and DH-TBTCl2 with the carbazole comonomer CbzPBE2 are established, furnishing PCDTBT and P(Cbz-alt-TBT) with high molecular weight and yield. Compared with control samples made from the corresponding dibromides, high-temperature NMR and UV-vis spectroscopy indicate similar properties for PCDTBT but an increased content of Cbz-Cbz homocouplings for P(Cbz-alt-TBT).

  3. Highly Efficient Sky-Blue Fluorescent Organic Light Emitting Diode Based on Mixed Cohost System for Thermally Activated Delayed Fluorescence Emitter (2CzPN). (United States)

    Sun, Jin Won; Kim, Kwon-Hyeon; Moon, Chang-Ki; Lee, Jeong-Hwan; Kim, Jang-Joo


    The mixed cohosts of 1,3-bis(N-carbazolyl)benzene and 2,8-bis(diphenylphosphoryl)dibenzothiophene have been developed for a highly efficient blue fluorescent oragnic light emitting diode (OLED) doped with a thermally activated delayed fluorescence (TADF) emitter [4,5-di (9H-carbazol-9-yl) phthalonitrile (2CzPN)]. We have demonstrated one of the highest external quantum efficiency of 21.8% in blue fluorescent OLEDs, which is identical to the theoretically achievable maximum electroluminescence efficiency using the emitter. Interestingly, the efficiency roll-off is large even under the excellent charge balance in the device and almost the same as the single host based devices, indicating that the efficiency roll-off in 2CzPN based TADF host is related to the material characteristics, such as low reverse intesystem crossing rate rather than charge imbalance.

  4. Synthesis and mixed lineage kinase activity of pyrrolocarbazole and isoindolone analogs of (+)K-252a. (United States)

    Hudkins, Robert L; Johnson, Neil W; Angeles, Thelma S; Gessner, George W; Mallamo, John P


    Structural modification of the indolecarbazole natural product (+)K-252a identified structural requirements for MLK activity and a novel series of potent fused pyrrolocarbazole MLK1/3 inhibitors. The SAR revealed that the lactam regiochemistry, the shape of the heterocycle, and aryl rings B and F are important to MLK activity. Heteroatom and alkyl replacement of the N-12 and/or N-13 indole nitrogen atoms identified the nonplanar dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-7-one (8) and corresponding 5,7-dione (7) as potent cell-permeable MLK1/3 family-selective leads with in vitro activity comparable to that of (+)K-252a and determined them to be 2- to 3-fold more potent than the aglycone natural product K-252c.

  5. CO{sub 2} removal potential of carbons prepared by co-pyrolysis of sugar and nitrogen containing compounds

    Energy Technology Data Exchange (ETDEWEB)

    Arenillas, A.; Drage, T.C.; Smith, K.; Snape, C.E. [University of Nottingham, Fuel Science Group, School of Chemical, Environmental and Mining Engineering, University Park, Nottingham NG7 2RD (United Kingdom)


    The nitrogen enrichment of active carbons is reported to be effective in enhancing the specific adsorbate-adsorbent interactions for CO{sub 2}. In this work, nitrogen-enriched carbons were prepared by co-pyrolysis of sugar and a series of nitrogen compounds with different nitrogen functionalities. The results show that although the amount of nitrogen incorporated to the final adsorbent is important, the N-functionality seems to be more relevant for increasing CO{sub 2} uptake. Thus, the adsorbent obtained from urea co-pyrolysis presents the highest nitrogen content but the lowest CO{sub 2} adsorption capacity. However, the adsorbent obtained from carbazole co-pyrolysis, despite the lower amount of N incorporated, shows high CO{sub 2} uptake, up to 9wt.%, probably because the presence of more basic functionalities as determined by XPS analysis.

  6. Surface electronic structure and molecular orientation of poly(9-vinylcarbazole) thin film: ARUPS and NEXAFS

    CERN Document Server

    Okudaira, K K; Hasegawa, S; Ishii, H; Azuma, Y; Imamura, M; Shimada, H; Seki, K; Ueno, N


    The molecular orientation at the surfaces of poly(9-vinylcarbazole) (PvCz) thin films was studied by angle-resolved ultraviolet photoelectron spectroscopy and near-edge X-ray absorption fine structure (NEXAFS) spectroscopy. The observed take-off angle (theta) dependence of photoelectron intensities from top pi band peaks clearly at larger theta than the calculated one for the three-dimensional isotropic random orientation model. The results indicate that there are more pendant groups with large tilt angles than the three-dimensional isotropic random orientation model, which is in good agreement with the result obtained from NEXAFS spectroscopy. The surface electronic states of PvCz may be rather dominated by sigma(C-H) states at the pendant carbazole group than pi states

  7. 中间层对白色全磷光有机电致发光器件性能的影响%Effect of Interlayer on Phosphorescent White Organic Light-emitting Diodes

    Institute of Scientific and Technical Information of China (English)

    朱映光; 梁春军; 刘姝; 刘淑洁; 何志群


    Phosphorescent white organic light-emitting diodes with double light-emitting layers were fabricated based on phosphorescent blue emittor bis[3,5-difluoro-2-(2-pridyl) phenyl-(2-earboxy-pyribyl)iridumⅢ] (FIrpic) and red emittor bis(2-methyldibenzo[f,h]quinoxaline)(acetylaceto-nate) iridium(Ⅲ)(Ir(MDQ)2acac). FIrpic was doped in an ultra wide band-gap host 1,3-bis(tri-phenylsilyl)benzene (UGH3), and Ir(MDQ)2acac was doped in the host 4,4’,4"-tris(carbazol-9-yl)triphenylamine(TCTA). A hole transporting wide-band-gap material 1,3-bis(carbazol-9-yl)ben-zene (mCP) was introduced between the emitting layers. The device structure was ITO/NPB(40 nm)/TCTA:Ir(MDQ)2acac 7%(10 nm)/mCP(x nm)/UGH3: Firpic 8%(30 nm)/BPhen(30 nm)/LiF(0. 8 nm)/Al(200 nm). The results show that the interlayer plays an important role of balancing charge carriers, and blocking energy transfer between the emitting layers. With an appro-priate thickness of the interlayer, the device performances can be significantly enhanced. Compared with the device without interlayer, the maximum current efficiency can be enhanced from 3. 4 cd/A to 13. 2 cd/A.%制备了基于蓝色磷光材料bis[3,5-difluoro-2-(2-pridyl)phenyl-(2-earboxypyribyl)iridum芋](FIrpic)、红色磷光材料bis(2-methyldibenzo[f,h]quinoxaline)(acetylacetonate)iridium (芋)(Ir(MDQ)2acac)的双波段白光有机电致发光器件。蓝色磷光材料 FIrpic被掺杂在一种宽带隙的主体材料1,3-bis(triphenylsilyl)benzene (UGH3)之中,红色磷光材料Ir(MDQ)2acac被掺杂在主体材料4,4忆,4义-tris(carbazol-9-yl)triphenylamine(TC-TA)之中,并在两发光层之间加入一种宽带隙的空穴传输材料1,3-bis( carbazol-9-yl) benzene( mCP)作为中间层。制备的器件结构为ITO/NPB(40 nm)/TCTA.Ir(MDQ)2acac 7%(10 nm)/mCP(x nm)/UGH3.Firpic 8%(30 nm)/BPhen (30 nm)/LIF(0.8 nm)/AL(200 nm)。实验结果表明,中间层的加入促进了发光层中电子和空穴的平衡并抑制了发光层之间的能量转移。加入

  8. Synthesis and Characterization of Quinoxaline-Based Low-Bandgap Copolymers for Bulk Heterojunction Solar Cells (United States)

    Lee, Yoonkyoo; Jo, Won Ho


    A series of low-bandgap alternating copolymers consisting of quinoxaline derivatives and electron-donating carbazole or fluorene were synthesized via the Suzuki coupling reaction. For the purpose to improve the molecular packing of polymer chains and to enhance the charge carrier mobility in the packing direction, a new quinoxaline derivative, 5,8-dithien-2-yl-dibenzophenazine which has perfectly planar polycyclic structure, was synthesized and introduced as a new building block for alternating copolymers instead of frequently-used 5,8-dithien-2-yl-2,3-diphenylquinoxaline. The use of planar quinoxaline derivative exhibited better optical, electrochemical, and structural properties of the resulting copolymers as compared to those of polymers with less planar quinoxaline derivatives. Charge transport and photovoltaic properties of these two classes of copolymers are compared and discussed.

  9. Efficient light-emitting devices based on platinum-complexes-anchored polyhedral oligomeric silsesquioxane materials

    KAUST Repository

    Yang, Xiaohui


    The synthesis, photophysical, and electrochemical characterization of macromolecules, consisting of an emissive platinum complex and carbazole moieties covalently attached to a polyhedral oligomeric silsesquioxane (POSS) core, is reported. Organic light-emitting devices based on these POSS materials exhibit a peak external quantum efficiency of ca. 8%, which is significantly higher than that of the analogous devices with a physical blend of the platinum complexes and a polymer matrix, and they represent noticeable improvement in the device efficiency of solution-processable phosphorescent excimer devices. Furthermore, the ratio of monomer and excimer/aggregate electroluminescent emission intensity, as well as the device efficiency, increases as the platinum complex moiety presence on the POSS macromolecules decreases. © 2010 American Chemical Society.

  10. Multifunctional Composites Obtained by Incorporating Nanocrystals into Decorated PVK Polymers

    Directory of Open Access Journals (Sweden)

    Haizhu Sun


    Full Text Available Poly(vinylcarbazole (PVK was decorated with surfactant group to achieve amphiphilic polymer with luminescent property. The composition and properties of the polymers were systematically investigated using FTIR, EA, TGA, UV-Vis, and PL characterizations. Different CdTe nanocrystals (NCs prepared in aqueous medium were directly transferred to organic phase using the PVK-based polymers. The quantum yield of NCs in the composites had been improved by 50% compared with their parent aqueous solution due to the short distance from carbazole moieties to NCs, which facilitated the Förster resonant energy transfer (FRET between them. Moreover, efficient electron transfer at the interface of NCs and polymers had been confirmed which also indicated the application in photovoltaic cell for such composites.

  11. Surface modification of low cost carbons for their application in the environmental protection (United States)

    Arenillas, A.; Rubiera, F.; Parra, J. B.; Ania, C. O.; Pis, J. J.


    In this work, the CO 2 capture capacity of a series of activated carbons derived from recycled polyethylene terephtalate (PET) was tested, facing two problems at the same time: minimising plastic waste and developing an adsorbent for CO 2 capture. The PET raw material, obtained from post-consumer soft-drink bottles, was chemically activated with KOH. In addition, a series of nitrogen-enriched activated carbons was obtained by mixing the raw material with different nitrogen compounds (i.e., acridine, carbazole and urea). The influence of temperature on the CO 2 capture capacity of the adsorbents was evaluated in a thermogravimetric system. The CO 2 uptake was also related to the chemical and textural characteristics of the samples.

  12. Modification of silicone sealant to improve gamma radiation resistance, by addition of protective agents (United States)

    González-Pérez, Giovanni; Burillo, Guillermina


    Poly (dimethylsiloxane) (PDMS) sealant (SS) was modified with the addition of different protective compounds to conserve its physical-chemical properties during gamma irradiation. 2-Vinyl naphthalene (2-VN), bisphenol-A (BPA) and poly (vinyl carbazole) (PVK) were used to evaluate radiation protection through the crosslinking effect of radiation. The samples were irradiated with doses from 100 kGy to 500 kGy at room temperature in air, with a 60Co gamma source, and the changes in molecular weight, thermal behavior, elastic properties and infrared spectra (FTIR-ATR) absorbance analysis were determined. The molecular weight of unmodified silicone sealant increases with the absorbed dose because of crosslinking as predominant effect. However, the crosslinking effect was inhibited with the addition of protective agent due to the aromatic compounds present. Modified silicone sealant films present better radiation resistance than unmodified system.

  13. Bacterial Degradation of Aromatic Compounds

    Directory of Open Access Journals (Sweden)

    Qing X. Li


    Full Text Available Aromatic compounds are among the most prevalent and persistent pollutants in the environment. Petroleum-contaminated soil and sediment commonly contain a mixture of polycyclic aromatic hydrocarbons (PAHs and heterocyclic aromatics. Aromatics derived from industrial activities often have functional groups such as alkyls, halogens and nitro groups. Biodegradation is a major mechanism of removal of organic pollutants from a contaminated site. This review focuses on bacterial degradation pathways of selected aromatic compounds. Catabolic pathways of naphthalene, fluorene, phenanthrene, fluoranthene, pyrene, and benzo[a]pyrene are described in detail. Bacterial catabolism of the heterocycles dibenzofuran, carbazole, dibenzothiophene, and dibenzodioxin is discussed. Bacterial catabolism of alkylated PAHs is summarized, followed by a brief discussion of proteomics and metabolomics as powerful tools for elucidation of biodegradation mechanisms.

  14. A novel femtosecond-laser formation of CdS nanocrystallites in zirconia matrices

    Energy Technology Data Exchange (ETDEWEB)

    Raulin, Katarzyna, E-mail:; Cristini-Robbe, Odile [Universite des Sciences et Technologies de Lille, Laboratoire de Spectrochimie Infrarouge et Raman (CNRS, UMR 8516), Bat. C-5, Centre d' Etudes et de Recherches Lasers et Applications (CERLA-FR CNRS 2416) (France); Baldeck, Patrice; Stephan, Olivier [Universite Joseph-Fourier-CNRS, Laboratoire de Spectrometrie Physique (CNRS, UMR 5588) (France); Kinowski, Christophe; Turrell, Sylvia [Universite des Sciences et Technologies de Lille, Laboratoire de Spectrochimie Infrarouge et Raman (CNRS, UMR 8516), Bat. C-5, Centre d' Etudes et de Recherches Lasers et Applications (CERLA-FR CNRS 2416) (France); Capoen, Bruno; Bouazaoui, Mohamed [Universite des Sciences et Technologies de Lille, Laboratoire de Physique des Lasers, Atomes et Molecules (CNRS, UMR 8523), Bat. P-5, Centre d' Etudes et de Recherches Lasers et Applications (CERLA-FR CNRS 2416) (France)


    A novel method for direct laser writing of two-dimensional cadmium sulfide (CdS) semiconductor nanoparticle microstructures is reported. A two photon or a higher-order multiphoton absorption process, originating from femtosecond laser pulses, was used to decompose CdS precursors dispersed in a zirconia thin film previously dip-coated on a glass substrate. The kinetics of nanoparticle formation as a function of laser power were monitored in situ by photoluminescence spectroscopy. Raman spectroscopy was also performed to characterize the structural changes of the zirconia matrix under irradiation and to verify the formation of CdS nanoparticles. Results show that CdS nanoparticles were formed by two-photon absorption (TPA) with or without the help of an additional carbazole photoinitiator.

  15. Charge Transport in Dendrimer Melt using Multiscale Modeling Simulation

    CERN Document Server

    Bag, Saientan; Maiti, Prabal K


    In this paper we present a theoretical calculation of the charge carrier mobility in two different dendrimeric melt system (Dendritic phenyl azomethine with Triphenyl amine core and Dendritic Carbazole with Cyclic Phenylazomethine as core), which have recently been reported1 to increase the efficiency of Dye-Sensitized solar cells (DSSCs) by interface modification. Our mobility calculation, which is a combination of molecular dynamics simulation, first principles calculation and kinetic Monte Carlo simulation, leads to mobilities that are in quantitative agreement with available experimental data. We also show how the mobility depends on the dendrimer generation. Furthermore, we examine the variation of mobility with external electric field and external reorganization energy. Physical mechanisms behind observed electric field and generation dependencies of mobility are also explored.

  16. Multifunctional conjugated polymers with main-chain donors and side-chain acceptors for dye sensitized solar cells (DSSCs) and organic photovoltaic cells (OPVs). (United States)

    Chang, Dong Wook; Ko, Seo-Jin; Kim, Jin Young; Park, Su-Moon; Lee, Hyo Joong; Dai, Liming; Baek, Jong-Beom


    A novel multifunctional conjugated polymer (RCP-1) composed of an electron-donating backbone (carbazole) and an electron-accepting side chain (cyanoacetic acid) connected through conjugated vinylene and terthiophene has been synthesized and tested as a photosensitizer in two major molecule-based solar cells, namely dye sensitized solar cells (DSSCs) and organic photovoltaic cells (OPVs). Promising initial results on overall power conversion efficiencies of 4.11% and 1.04% are obtained from the basic structure of DSSCs and OPVs based on RCP-1, respectively. The well-defined donor (D)-acceptor (A) structure of RCP-1 has made it possible, for the first time, to reach over 4% of power conversion efficiency in DSSCs with an organic polymer sensitizer and good operation stability.

  17. Electrical Bistability and Erasable Memory Effect of a Functional Polyimide Film: Synthesis and Investigation of Mechanism (United States)

    Tian, Guofeng; Jia, Nanfang; Qi, Shengli; Wu, Dezhen


    A functional polyimide (PI) film, (hexafluoroisopropylidene)diphthalic anhydride-2-(9 H-carbazol-9-yl)ethyl 3,5-diaminobenzoate (6FDA-DADBC), in which DADBC serves as electron donor and 6FDA as electron acceptor, was synthesized in this work. The PI has electrical bistability and the sandwich device ITO‖6FDA-DADBC-PI‖Au made by using this functional PI as the active layer has nonvolatile memory-storage properties. It can be changed between the insulating state (Off state) and the conducting state (On state) by application of potentials of approximately 0.5 V and -2.5 V, respectively, with an On/Off current ratio of approximately 102, which is suitable for use as flash memory. Mechanisms of the charge transfer occurring in the materials were investigated, and are thoroughly discussed on the basis of molecular simulation. The PI has good thermal stability up to 400°C.

  18. Selective Patterning of Organic Light-Emitting Diodes by Physical Vapor Deposition of Photosensitive Materials (United States)

    Muroyama, Masakazu; Saito, Ichiro; Yokokura, Seiji; Tanaka, Kuniaki; Usui, Hiroaki


    A novel method of patterning polymeric thin films by the vapor deposition of a photosensitive layer followed by photopolymerization and development was proposed. This method was applied to the patterning of the emissive layer (EML) of an organic light-emitting diode (OLED). For the hole transport layer (HTL), N,N,N'-triphenyl-N'-(4-vinylphenyl)-biphenyl-4,4'-diamine (vTPD) and a zinc acrylate (ZnAc) crosslinker were coevaporated. The film was polymerized by postdeposition annealing to yield a polymeric HTL with a high resistance to organic solvents. On this HTL, the photosensitive EML was prepared by coevaporating a 9H-carbazole-9-ethylmethacrylate (CEMA) host material and 4-(dimethylamino)benzophenone (DABP) photoinitiator. UV irradiation on the EML through a photomask initiated radical polymerization, leaving a negative pattern of the irradiated region after immersion in tetrahydrofuran (THF). The photopatterning process was found to cause no damage to the film morphology or the device characteristics.

  19. A novel and facile synthesis of 3-(2-benzofuroyl- and 3,6-bis(2-benzofuroylcarbazole derivatives

    Directory of Open Access Journals (Sweden)

    Wentao Gao


    Full Text Available A facile synthesis of hitherto unreported 3-(2-benzofuroylcarbazoles 3a–k, 3,6-bis(2-benzofuroylcarbazoles 5a–k, and naphtho[2,1-b]furoylcarbazoles 3l and 5l is described. The synthesis mainly relies on the ultrasound-assisted Rap–Stoermer reaction of 3-chloroacetyl- (1 or 3,6-dichloroacetyl-9-ethyl-9H-carbazole (4 with various salicylaldehydes 2a–k as well as 2-hydroxy-1-naphthaldehyde (2l in CH3CN with the presence of PEG-400 as catalyst. The procedure offers easy access to benzofuroylcarbazoles in short reaction times and the products are obtained in moderate to good yields.

  20. Narrow bandgap host material for high quantum efficiency yellow phosphorescent organic light-emitting diodes doped with iridium(III) bis(4-phenylthieno[3,2-c]pyridine)acetylacetonate

    Energy Technology Data Exchange (ETDEWEB)

    Yook, Kyoung Soo; Lee, Jun Yeob, E-mail:


    A narrow bandgap host material, 4,5-di(9H-carbazol-9-yl)phthalonitrile (2CzPN), was used as a bipolar host material to improve the device performances of yellow phosphorescent organic light-emitting diodes(PHOLEDs). The device performances of the yellow PHOLEDs were optimized at a low doping concentration of 1%. A low turn-on voltage of 3.0 V and high quantum efficiency of 19.3% were achieved using the 2CzPN host material and no efficiency roll-off of the device was observed up to 1000 cd/m{sup 2} compared with 25% of reference device. - Highlights: • High quantum efficiency in yellow phosphorescent organic light-emitting diodes. • Narrow bandgap host material with donor–acceptor structure for low driving voltage. • Low optimum doping concentration of 1% for high quantum efficiency and power efficiency.

  1. Effect of uniaxial compression on traps of excitons and charge carriers in poly(9-vinylcarbazole) films (United States)

    Skryshevski, Yu. A.


    The effect of uniaxial pressure (1 × 108 Pa) on the photoluminescence spectra and thermally stimulated luminescence curves of poly(9-vinylcarbazole) has been investigated in the temperature range of 5-295 K. The thermally stimulated luminescence curve of crystalline carbazole has been measured for comparison. The high-temperature wings of the thermally stimulated luminescence curves are approximated by a Gaussian function, the half-width of which characterizes the disorder of energy states of deep structural traps. It is concluded that the pressure inhibits conformational changes of polymer chains of poly(9-vinylcarbazole), which leads to the formation of sandwich-like excimers as well as to an ordering of the spatial arrangement of the side carbazolyl groups. As a result, the concentration of "excimer-forming" centers increases, whereas the degree of disorder of energy states of deep structural traps of charge carriers is reduced by almost half and remains unchanged after the depressurization.

  2. Synthesis of Stable Diarylpalladium(II) Complexes: Detailed Study of the Aryl-Aryl Bond-Forming Reductive Elimination. (United States)

    Gensch, Tobias; Richter, Nils; Theumer, Gabriele; Kataeva, Olga; Knölker, Hans-Joachim


    The synthesis of diarylpalladium(II) complexes by twofold aryl C-H bond activation was developed. These intermediates of oxidative cyclization reactions are stabilized by chelation with acetyl groups while still maintaining sufficient reactivity to study their reductive elimination. Four distinct triggers were found for the reductive elimination of these complexes to dibenzofurans and carbazoles. Thermal elimination occurs at very high temperatures, whereas ligand-promoted and oxidatively induced reductive eliminations proceed readily at room temperature. Under these conditions, no isomerization occurs. In contrast, weak Brønsted acids, such as acetic acid, lead to a sequence of proto-demetalation, isomerization to a κ(3) -diarylpalladium(II) complex, and reductive elimination to non-symmetrical cyclization products.

  3. Development and characterization of PCDTBT:CdSe QDs hybrid solar cell

    Energy Technology Data Exchange (ETDEWEB)

    Dixit, Shiv Kumar, E-mail:; Bhatnagar, Chhavi, E-mail:; Kumari, Anita, E-mail:; Madhwal, Devinder, E-mail:; Bhatnagar, P. K., E-mail:; Mathur, P. C., E-mail: [Department of Electronic Science, University of Delhi South Campus, Benito Juarez Road, New Delhi, 110021 (India)


    Solar cell consisting of low band gap polymer poly[N-900-hepta-decanyl-2,7-carbazole-alt-5,5-(40,70-di-2-thienyl-20,10, 30-benzothiadiazole)] (PCDTBT) as donor and cadmium selenide/zinc sulphide (CdSe/ZnS) core shell quantum dots (QDs) as an acceptor has been developed. The absorption measurements show that the absorption coefficient increases in bulk heterojunction (BHJ) structure covering broad absorption spectrum (200nm–700nm). Also, the photoluminescence (PL) of the PCDTBT:QDs film is found to decrease by an order of magnitude showing a significant transfer of electrons to the QDs. With this approach and under broadband white light with an irradiance of 8.19 mW/cm{sup 2}, we have been able to achieve a power conversion efficiency (PCE) of 3.1 % with fill factor 0.42 for our typical solar cell.

  4. A sensitive fluorescence reagent for the determination of aldehydes from alcoholic beverage using high-performance liquid chromatography with fluorescence detection and mass spectrometric identification

    Energy Technology Data Exchange (ETDEWEB)

    You Jinmao [Northwest Plateau Institute of Biology, Chinese Academy of Sciences, Xining 810001 (China)], E-mail:; Yan Tao; Zhao Huaixin [Key Laboratory of Life-Organic Analysis, College of Chemistry Science, Qufu Normal University, Qufu Shandong 273165 (China); Sun Zhiwei; Xia Lian; Suo Yourui; Li Yulin [Northwest Plateau Institute of Biology, Chinese Academy of Sciences, Xining 810001 (China)


    A pre-column derivatization method for the sensitive determination of aldehydes using the tagging reagent 2-[2-(7H-dibenzo[a,g] carbazol-7-yl)-ethoxy] ethyl carbonylhydrazine (DBCEEC) followed by high-performance liquid chromatography with fluorescence detection and APCI-MS identification has been developed. The chromophore of fluoren-9-methoxy-carbonylhydrazine (Fmoc-hydrazine) reagent was replaced by 2-[2-(7H-dibenzo[a,g] carbazol-7-yl)-ethoxy] ethyl functional group, which resulted in a sensitive fluorescence tagging reagent DBCEEC. DBCEEC could easily and quickly labeled aldehydes. The maximum excitation (300 nm) and emission (400 nm) wavelengths did not essentially change for all the aldehyde derivatives. Derivatives were sufficiently stable to be efficiently analyzed by high-performance liquid chromatography. The derivatives showed an intense protonated molecular ion corresponding m/z [M + (CH{sub 2}){sub n}]{sup +} in positive-ion mode (M: molecular weight of DBCEEC, n: corresponding aldehyde carbon atom numbers). The collision-induced dissociation of protonated molecular ion formed fragment ions at m/z 294.6, m/z 338.6 and m/z 356.5. Studies on derivatization demonstrated excellent derivative yields in the presence of trichloroacetic acid (TCA) catalyst. Maximal yields close to 100% were observed with a 10 to 15-fold molar reagent excess. Separation of the derivatized aldehydes had been optimized on ZORBAX Eclipse XDB-C{sub 8} column with aqueous acetonitrile as mobile phase in conjunction with a binary gradient elution. Excellent linear responses were observed at the concentration range of 0.01-10 nmol mL{sup -1} with coefficients of >0.9991. Detection limits obtained by the analysis of a derivatized standard containing 0.01 nmol mL{sup -1} of each aldehyde, were from 0.2 to 1.78 nmol L{sup -1} (at a signal-to-noise ratio of 3)

  5. Electroluminescent properties of three ternary europium complexes with different phenanthroline derivatives

    Institute of Scientific and Technical Information of China (English)

    BIAN Zuqiang; GAO Deqing; GUAN Min; XIN Hao; LI Fuyou; HUANG Chunhui; WANG Kezhi; JIN Linpei


    Three ternary Eu(Ⅲ) complexes with general formula of Eu(DBM)3LN (DBM =dibenzoylmethanate, and LN (N= 1-3 ) stand for three different 1,1 0-phenanthroline derivatives)have been synthesized for vacuum deposition films-based electroluminescent devices. The complex Eu(DBM)3L3 (L3 = 2-phenyl-3-[3-(carbazol-9-yl)propyl]imidazo[4,5-f]1,10-phenanthroline) was designed with an effort to combine the electron-transporting phenanthroline platform and the hole-transporting carbazole group into one molecule expecting to improve both electron and hole transporting properties simultaneously. The results show that the variation of the neutral ligands in Eu(Ⅲ) mixed ligand complexes is a simple and effective approach to the improvement in the thermal stability, PL and EL properties of materials. A double-layer device with the configuration of ITO/TPD (50 nm)/Eu(DBM)3L3 (50 nm)/Mgo.9Ago.1 (200 nm)/Ag (100 nm)exhibited Eu(Ⅲ)-based pure red emission with a maximum brightness of 561 cd/m2 at 16 V, and an onset driving voltage of 8 V. A device with the configuration of ITO/TPD (50 nm)/[Eu(DBM)3L3(5 nm):BCP (5 nm)]4/BCP (20 nm)/AIQ (10 nm) Mgo.gAgo.1 (110 nm)/Ag (100 nm) gave high efficient and pure red light emission with a luminance of 1419 cd/m2.

  6. Synthesis, characterization and hydrotreating performance of supported tungsten phosphide catalysts

    Institute of Scientific and Technical Information of China (English)


    Supported tungsten phosphide catalysts were prepared by temperature-programmed reduction of their precursors (supported phospho-tungstate catalysts) in H2 and characterized by X-ray diffraction (XRD),BET,temperature-programmed desorption of ammonia (NH3-TPD) and X-ray photoelectron spectroscopy (XPS).The reduction-phosphiding processes of the precursors were investigated by thermogravimetry and differential thermal analysis (TG-DTA) and the suitable phosphiding temperatures were defined.The hydrodesulfurization (HDS) and hydrodenitrogenation (HDN) activities of the catalysts were tested by using thiophene,pyridine,dibenzothiophene,carbazole and diesel oil as the feed-stock.The TiO2,γ-Al2O3 supports and the Ni,Co promoters could remarkably increase and stabilize active W species on the catalyst surface.A suitable amount of Ni (3%-5%),Co (5%-7%) and V (1%-3%) could increase dispersivity of the W species and the BET surface area of the WP/γ-Al2O3 catalyst.The WP/γ-Al2O3 catalyst possesses much higher thiophene HDS and carbazole HDN activities and the WP/TiO2 catalyst has much higher dibenzothiophene (DBT) HDS and pyridine HDN activities.The Ni,Co and V can obviously promote the HDS activity and inhibit the HDN activity of the WP/γ-Al2O3 catalyst.The G-Ni5 catalyst possesses a much higher diesel oil HDS activity than the sulphided industrial NiW/γ-Al2O3 catalyst.In general,a support or promoter in the WP/γ-Al2O3 catalyst which can increase the amount and dispersivity of the active W species can promote its HDS and HDN activities.

  7. New electroactive polymers with electronically isolated 3,6,9-triarylcarbazole units as efficient hole transporting materials for organic light emitting diodes (United States)

    Griniene, R.; Tavgeniene, D.; Baranauskyte, U.; Xie, Z.; Zhang, B.; Gelzinis, A.; Grigalevicius, S.


    Polyethers containing electronically isolated 3,6,9-triarylcarbazole moieties have been synthesized by the multi-step synthetic procedures. A polymer containing unsubstituted carbazole rings was also prepared for comparison of properties. Full characterization of the materials is presented. The new polymers represent materials of high thermal stability with initial thermal degradation temperatures exceeding 367 °C. The high glass transition temperatures of the amorphous materials were in the rage of 133-146 °C. The electron photoemission spectra of thin layers of the polymers showed ionization potentials in the range of 5.52-5.6 eV. Hole-transporting properties of the electroactive materials were tested in the structures of organic light emitting diodes (OLEDs) with tris(quinolin-8-olato)aluminium as the green emitter and electron transporting material. The OLED devices in general exhibited rather low turn-on voltages of 3.2-4.2 V, high maximum brightness of 4910-7500 cd/m2 and luminous efficiency of 1.7-3.1 cd/A. It was confirmed that the devices containing the polymers with 3,6,9-triarylcarbazole moieties demonstrate considerably better OLED performance than that of device with polymer containing unsubstituted carbazole rings due to its higher ionization potential and accordingly worse hole injecting properties. The device containing hole-transporting layer of polymer with 3,6-di(1-naphthyl)-9-phenylcarbazole units exhibited the best overall performance with rather low turn on voltage of 4.4 V, maximum photometric efficiency exceeding 3.1 cd/A and maximum brightness of about 7500 cd/m2.

  8. Spectral, stoichiometric ratio, physicochemical, polarity and photostability studies of newly synthesized chalcone dye in organized media

    Energy Technology Data Exchange (ETDEWEB)

    Marwani, Hadi M., E-mail: [Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia); Center of Excellence for Advanced Materials Research, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia); Asiri, Abdullah M. [Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia); Center of Excellence for Advanced Materials Research, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia); Khan, Salman A. [Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia)


    The main focus of this study was to investigate spectroscopic properties, stoichiometric ratios, physicochemical parameters, polarity and photostability behaviors of newly synthesized chalcone dye in organized media. The chalcone dye, 1-(2,5-Dimethyl-thiophen-3-yl)-3-(9-etnyl-9H-carbazol-3-yl)-propenone (DTEP), was prepared by the reaction of carbazole aldehyde with 3-acetyl-2,5-dimethythiophene. Data obtained from FT-IR, {sup 1}H-–NMR, {sup 13}C-NMR and elemental analysis were consistent with chemical structure of newly prepared DTEP. Increases in fluorescence intensities of DTEP with cetyltrimethyl ammonium bromide (CTAB) were observed. In comparison of fluorescence intensities for DTEP with CTAB, reductions in fluorescence intensities for DTEP with sodium dodecyl sulfate (SDS) were noticed under the same experimental and instrumental conditions. Additionally, Benesi–Hildebrand method was applied to determine stoichiometric ratios and association constants of DTEP with CTAB and SDS. Stern–Volmer plot was used in order to further confirm the stoichiometric ratio and association constant of DTEP with SDS. Physicochemical parameters such as singlet absorption, molar absorptivity, oscillator strength, dipole moment and fluorescence quantum yield of DTEP were also determined. Fluorescence polarity study displayed that DTEP was sensitive to the polarity of the microenvironment provided by different solvents. Finally, fluorescence steady-state measurements revealed that DTEP has high photostability against photobleaching. -- Highlights: ► Mechanistic understanding of molecular structure of newly synthesized chalcone dye. ► Exploring spectral behaviors and physicochemical parameters of chalcone dye. ► Determination of stoichiometric ratios and association constants of chalcone dye. ► Determination of fluorescence quantum yield in different solvents. ► High photostability against photobleaching of chalcone dye was observed.

  9. Determination of alcohols by HPLC with 1,4-dimethylcarbazole-9-y1-propionic acid as fluorescence derivative reagent%以1,4-二甲基咔唑-9-丙酸为荧光衍生化试剂高效液相色谱法测定醇

    Institute of Scientific and Technical Information of China (English)

    劳文剑; 宋翠华; 尤进茂; 欧庆瑜


    1,4-二甲基咔唑-9-丙酸与间苯二磺酰氯反应生成混合酸酐,该混合酸酐能够衍生化18个碳以下的直链脂肪伯醇、6个碳以下的仲醇,以及叔丁醇和胆固醇;将荧光衍生物用反相C18液相色谱柱进行分离,在室温下10 min完成衍生化反应,衍生物24 h内基本稳定.基于此,建立了血清中醇的高效液相色谱测定方法.%Pre-column derivative reagent 1,4-dimethyl-carbazole-9-yl-propionic acid was allowed to couple with benzenedisulfonyl dichloride affording the mixed acidic anhydride. Resultant mixed acidic anhydride was used to derivate straight-chain aliphatic primary alcohols with less than 18 carbons and secondary alcohols with less than 6 carbons, as well as tert-butanol and cholesterol. As-obtained fluorescence derivatives were separated on reversed-phase C18 high-performance liquid chromatography (HPLC) column, with which the derivatization was finished in 10 min at room temperature and relevant derivatives were stable within 24 h. This makes it feasible to establish a HPLC method to determine alcohols in human serum with 1,4-dimethyl-carbazole-9-yl-propionic acid as the fluorescence derivative reagent.

  10. Study of a new derivatizing reagent that improves the analysis of amino acids by HPLC with fluorescence detection: application to hydrolyzed rape bee pollen. (United States)

    You, Jinmao; Liu, Lingjun; Zhao, Wenchen; Zhao, Xianen; Suo, Yourui; Wang, Honglun; Li, Yulin


    A simple and sensitive method for evaluating the chemical compositions of protein amino acids, including cystine (Cys)(2) and tryptophane (Try) has been developed, based on the use of a sensitive labeling reagent 2-(11H-benzo[alpha]-carbazol-11-yl) ethyl chloroformate (BCEC-Cl) along with fluorescence detection. The chromophore of the 1,2-benzo-3,4-dihydrocarbazole-ethyl chloroformate (BCEOC-Cl) molecule was replaced with the 2-(11H-benzo[alpha]-carbazol-11-yl) ethyl functional group, yielding the sensitive fluorescence molecule BCEC-Cl. The new reagent BCEC-Cl could then be substituted for labeling reagents commonly used in amino acid derivatization. The BCEC-amino acid derivatives exhibited very high detection sensitivities, particularly in the cases of (Cys)(2) and Try, which cannot be determined using traditional labeling reagents such as 9-fluorenyl methylchloroformate (FMOC-Cl) and ortho-phthaldialdehyde (OPA). The fluorescence detection intensities for the BCEC derivatives were compared to those obtained when using FMOC-Cl and BCEOC-Cl as labeling reagents. The ratios I (BCEC)/I (BCEOC) = 1.17-3.57, I (BCEC)/I (FMOC) = 1.13-8.21, and UV(BCEC)/UV(BCEOC) = 1.67-4.90 (where I is the fluorescence intensity and UV is the ultraviolet absorbance). Derivative separation was optimized on a Hypersil BDS C(18) column. The detection limits calculated from 1.0 pmol injections, at a signal-to-noise ratio of 3, ranged from 7.2 fmol for Try to 8.4 fmol for (Cys)(2). Excellent linear responses were observed, with coefficients of >0.9994. When coupled with high-performance liquid chromatography, the method established here allowed the development of a highly sensitive and specific method for the quantitative analysis of trace levels of amino acids including (Cys)(2) and Try from bee-collected pollen (bee pollen) samples.

  11. Concentrations of Polycyclic Aromatic Hydrocarbons (PAHs) and Azaarenes in Runoff from Freshly Applied Coal-Tar-Based Pavement Sealcoat (United States)

    Mahler, B. J.; Van Metre, P. C.


    Coal-tar-based sealcoat (CT-sealcoat) is extensively applied to asphalt parking lots and driveways in the U.S. and Canada. Toxicity to fish and invertebrates of runoff from pavement to which CT-sealcoat has been freshly applied has been reported, but relatively little is known about how concentrations of chemicals in runoff change in the hours to days following sealcoat application. We measured the concentrations of 16 U.S. Environmental Protection Agency Priority Pollutant polycyclic aromatic hydrocarbons (PAHs) and 7 azaarenes in 9 samples of simulated runoff from a coal-tar-sealed test plot collected at increasing intervals from 5 hours to 16 weeks following application. Azaarenes, several of which are common constituents in coal-tar pitch, and their oxidized derivatives, azaarones, are an emerging group of little-studied heterocyclic chemicals. Runoff samples were collected by spraying 25 L of a diluted groundwater to 10 m2 on sealed pavement and retrieving the runoff downgradient where the runoff pooled against spill berms. Unfiltered samples were analyzed by GC/MS following liquid-liquid extraction. In the first sample (t=5 hr), phenanthrene had the highest concentration (130 μg/L) among the 16 PAHs. Concentrations of the lower molecular weight (LMW) PAHs (2 and 3 ring) decreased during the 16 weeks following application, and concentrations of the higher molecular weight (HMW) PAHs (4 to 6 ring) increased, coincident with an increase in the concentration of suspended particulates. In the final sample (t=16 weeks), fluoranthene had the highest concentration (36 μg/L) among the 16 PAHs. Of the azaarenes measured, concentrations of acridine and carbazole (107 and 750 μg/L, respectively) in the initial sample exceeded those of any of the PAHs measured except phenanthrene; acridine and carbazole concentrations decreased over the 5 weeks to <5% of their initial values. Samples of dried sealcoat were analyzed the day of application and 5 weeks later. Samples were

  12. 邻-吡啶苯并噻二唑衍生物的合成与双光子荧光传感性能%Two-Photon Sensors for Proton Derived from 7-Pyridinylbenzo[c][1,2,5]thiadiazole Receptor

    Institute of Scientific and Technical Information of China (English)

    赵维峰; 王筱梅; 罗建芳; 陶绪堂


    Two new chromophores with carbazole as molecular focal point bearing either one o-pyridine-benzothiadiazole unit or two o-pyridine-benzothiadiazole units at the periphery respectively, named as 2,8-(o-pyridine-benzothiadiazole)-N-ethyl-carbazole (CPTZ1) and 2,8-bis(o-pyridine-benzothiadiazole)-N-ethyl-carbazole (CPTZ2), were synthesized and characterized by IR spectra, 1H NMR spectra and MS. The influence of proton upon one-photon and two-photon fluorescence about these two compounds was discussed. Stern-Volmer equation gives that the S-V constants (kg) of one-photon fluorescence (1PF) of CPTZ1 and CPTZ2 are 0.04 and 0. 10 L · mol-1 , respectively; white the k2psv of two-photon fluorescence (2PF) of CPTZ1 and CPTZ2 are 0. 20 and 0. 22 L · mol-1, respectively. Obviously, two-photon (2P) fluorescence detection presented more sensitivity than one-photon (1P) fluorescence response, which exhibits the potential application of two-photon sensor in PH detection.%以吡啶苯并噻二唑基元为荧光传感"接受体(齿)",将其与咔唑"核"键合获得单齿和双齿两个化合物:2,8-(2-吡啶苯并噻二唑)-N-乙基氮杂笏(CPTZ1)和2,8-双(2-吡啶苯并噻二唑)-N-乙基氮杂芴(CPTZ2),并通过红外光谱、核磁共振谱、质谱表征.通过稳态/瞬态单光子荧光测试和飞秒钛宝石激光器泵浦探测,探讨了CPTZ1和CPTZ2化合物对质子[H+]的敏感性.Stern-Volmer方程给出CPTZ1的单、双光子荧光的猝灭常数分别为:k1PSV=0.04 L·mol-1,k2PSV=0.20 L·moL-1;而CPTZ2的猝灭常数则分别为k1PSV=0.10 L·moL-1,k2PSV(CPTZ2)=0.22 L·moL-1.研究结果表明,双光子荧光(TPF)检测表现出对质子更高的敏感性,其灵敏度是相应的单光子荧光(OPF)的2~5倍.

  13. Simulations of charge transport in organic compounds

    Energy Technology Data Exchange (ETDEWEB)

    Vehoff, Thorsten


    We study the charge transport properties of organic liquid crystals, i.e. hexabenzocoronene and carbazole macrocycle, and single crystals, i.e. rubrene, indolocarbazole and benzothiophene derivatives (BTBT, BBBT). The aim is to find structure-property relationships linking the chemical structure as well as the morphology with the bulk charge carrier mobility of the compounds. To this end, molecular dynamics (MD) simulations are performed yielding realistic equilibrated morphologies. Partial charges and molecular orbitals are calculated based on single molecules in vacuum using quantum chemical methods. The molecular orbitals are then mapped onto the molecular positions and orientations, which allows calculation of the transfer integrals between nearest neighbors using the molecular orbital overlap method. Thus we obtain realistic transfer integral distributions and their autocorrelations. In case of organic crystals the differences between two descriptions of charge transport, namely semi-classical dynamics (SCD) in the small polaron limit and kinetic Monte Carlo (KMC) based on Marcus rates, are studied. The liquid crystals are investigated solely in the hopping limit. To simulate the charge dynamics using KMC, the centers of mass of the molecules are mapped onto lattice sites and the transfer integrals are used to compute the hopping rates. In the small polaron limit, where the electronic wave function is spread over a limited number of neighboring molecules, the Schroedinger equation is solved numerically using a semi-classical approach. The carbazole macrocycles form columnar structures arranged on a hexagonal lattice with side chains facing inwards, so columns can closely approach each other allowing inter-columnar and thus three-dimensional transport. We are able to show that, on the time-scales of charge transport, static disorder due to slow side chain motions is the main factor determining the mobility. The high mobility of rubrene is explained by two main

  14. Synthesis and Spectral Properties of 1-(6-acetyi-9-butylcarbazole-3-yl)-3-phenylpropane-1,3-dione%1-(6-乙酰基-9-正丁基咔唑-3-基)-3-苯丙基-1,3-二酮的合成及其光谱性能

    Institute of Scientific and Technical Information of China (English)

    王永涛; 赵赫; 张鹏波; 刘志勇; 代斌


    The β-diketone compounds are widely used as ligand in organic rare earth complexes. The matching degree between the lowest triplet energy level of ligand and the lowest excited state energy level of rare earth directly influences the fluorescence intensity of organic rare earth complexes. In order to improve the fluorescence intensity of organic rare earth complexes, the design and synthesis of new β-diketone become more and more important. In this paper, l-(6-acetyl-9-butyl-9H-carbazol-3-yl)-3-phen-yl-propane-l,3-diketone was gained by N-alkylation,acetylation and condensation reaction from carbazole as raw material. Target compound was characterized by mass spectrometry (1H-NMR), MS-ESI and Infrared Spectroscopy (IR). The ultraviolet absorption spectrum,thermo-gravimetric analysis and Differential Scanning Calorimeter were recorded. The results show that the compound is suitable to be used as ligand in the organic rare earth complexes.%β-二酮化合物被广泛应用于有机稀土配合物的配体,配体的最低三重态能级与稀土的最低激发态能级的匹配程度直接影响有机稀土配合物的荧光强度,为了提高有机稀土配合物的荧光强度,设计合成新的β-二酮化合物变的尤为重要.本文以咔唑为原料,经N-烷基化、乙酰化和缩合反应得到1-(6-乙酰基-9-正丁基-9H-咔唑基)-3-苯丙基-1,3-二酮.经氢核磁共振谱(1 H-NMR)、质谱(MS-ESI)和红外光谱(IR)确认,目标化合物结构正确,并测定了化合物的紫外吸收光谱、热重(TG)、示差扫描量热曲线(DSC),结果表明该化合物适合用于有机稀土配合物的配体.

  15. Precursor polymer approach towards functional conjugated polymer networks and ultrathin film electro-optical applications (United States)

    Taranekar, Prasad

    Conjugated polymers are organic semiconductors which are of interest to a wide variety of optical, electronic, opto-electronic, and sensory applications; including light emitting diodes, thin film transistors, photovoltaic cells, and chemical sensors. While conducting polymers have some similarities to conventional polymeric materials, it is clearly the extensive main chain pi-conjugated structure and its implicit electro-optical properties that make it distinct. The same structure, however, gives it "chain stiffness" that affects its physical behavior. As a direct consequence of this, virtually all unsubstituted conducting polymers are found to be intractable and insoluble. This dissertation details the issue of tailoring the electro-optical properties and processability of conjugated polymers via a novel "precursor polymer approach". In this approach, electroactive side group units of either similar or different kind are tethered to a polymeric backbone. This combination determines the eventual electro-optical and electrochemical properties of these polymers including their ability to form ultrathin films. Thus, the desired macroscopic property is transformed by designing new precursor polymer structures, manipulating polymer-based compositions and blends, and the exploration and exploitation of their electrochemical processing conditions. In Chapters 2, 3, and 4, we have used single or binary electroactive compositions of species such as pyrrole, thiophene, carbazole and terthiophene are tethered to a linear polymeric backbone. Besides, the linear approach, in Chapters 5 and 6, we have also explored the use of generational dendrimers as backbone with carbazole units attached as peripheral electroactive groups. These precursor polymers were then subjected to electrochemical cross-linking to generate high optical quality ultrathin films on a conducting substrate such as indium tin oxide (ITO) or Au surfaces. The reaction of such electroactive species inimically

  16. New Palladium-Catalyzed Approaches to Heterocycles and Carbocycles

    Energy Technology Data Exchange (ETDEWEB)

    Huang, Qinhua [Iowa State Univ., Ames, IA (United States)


    The tert-butylimines of o-(1-alkynyl)benzaldehydes and analogous pyridinecarbaldehydes have been cyclized under very mild reaction conditions in the presence of I2, ICl, PhSeCl, PhSCl and p-O2NC6H4SCl to give the corresponding halogen-, selenium- and sulfur-containing disubstituted isoquinolines and naphthyridines, respectively. Monosubstituted isoquinolines and naphthyridines have been synthesized by the metal-catalyzed ring closure of these same iminoalkynes. This methodology accommodates a variety of iminoalkynes and affords the anticipated heterocycles in moderate to excellent yields. The Pd(II)-catalyzed cyclization of 2-(1-alkynyl)arylaldimines in the presence of various alkenes provides an efficient way to synthesize a variety of 4-(1-alkenyl)-3-arylisoquinolines in moderate to excellent yields. The introduction of an ortho-methoxy group on the arylaldimine promotes the Pd-catalyzed cyclization and stabilizes the resulting Pd(II) intermediate, improving the yields of the isoquinoline products. Highly substituted naphthalenes have been synthesized by the palladium-catalyzed annulation of a variety of internal alkynes, in which two new carbon-carbon bonds are formed in a single step under relatively mild reaction conditions. This method has also been used to synthesize carbazoles, although a higher reaction temperature is necessary. The process involves arylpalladation of the alkyne, followed by intramolecular Heck olefination and double bond isomerization. This method accommodates a variety of functional groups and affords the anticipated highly substituted naphthalenes and carbazoles in good to excellent yields. Novel palladium migratiodarylation methodology for the synthesis of complex fused polycycles has been developed, in which one or more sequential Pd-catalyzed intramolecular migration processes involving C-H activation are employed. The chemistry works best with electron-rich aromatics, which is in agreement

  17. New Palladium-Catalyzed Approaches to Heterocycles and Carbocycles

    Energy Technology Data Exchange (ETDEWEB)

    Qinhua Huang


    The tert-butylimines of o-(1-alkynyl)benzaldehydes and analogous pyridinecarbaldehydes have been cyclized under very mild reaction conditions in the presence of I{sub 2}, ICl, PhSeCl, PhSCl and p-O{sub 2}NC{sub 6}H{sub 4}SCl to give the corresponding halogen-, selenium- and sulfur-containing disubstituted isoquinolines and naphthyridines, respectively. Monosubstituted isoquinolines and naphthyridines have been synthesized by the metal-catalyzed ring closure of these same iminoalkynes. This methodology accommodates a variety of iminoalkynes and affords the anticipated heterocycles in moderate to excellent yields. The Pd(II)-catalyzed cyclization of 2-(1-alkynyl)arylaldimines in the presence of various alkenes provides an efficient way to synthesize a variety of 4-(1-alkenyl)-3-arylisoquinolines in moderate to excellent yields. The introduction of an ortho-methoxy group on the arylaldimine promotes the Pd-catalyzed cyclization and stabilizes the resulting Pd(II) intermediate, improving the yields of the isoquinoline products. Highly substituted naphthalenes have been synthesized by the palladium-catalyzed annulation of a variety of internal alkynes, in which two new carbon-carbon bonds are formed in a single step under relatively mild reaction conditions. This method has also been used to synthesize carbazoles, although a higher reaction temperature is necessary. The process involves arylpalladation of the alkyne, followed by intramolecular Heck olefination and double bond isomerization. This method accommodates a variety of functional groups and affords the anticipated highly substituted naphthalenes and carbazoles in good to excellent yields. Novel palladium migratiodarylation methodology for the synthesis of complex fused polycycles has been developed, in which one or more sequential Pd-catalyzed intramolecular migration processes involving C-H activation are employed. The chemistry works best with electron-rich aromatics, which is in agreement with the idea that

  18. 过氧化叔戊醇对苯并噻吩类衍生物的氧化%Oxidation of benzothiophenes using tert-amyl hydroperoxide

    Institute of Scientific and Technical Information of China (English)

    周新锐; 盖洪涛; 王静; 张珊珊; 杨锦宗; 张淑芬


    Homogeneous oxidation using an oil-soluble oxidant,tert-amyl hydroperoxide(TAHP).for ultra-deep desulfurizmion was performed under mild conditions in the presence of molybdenum oxide catalysts.Dibenzothio phene(DBT),benzothiophcne(BT)and 4,6-dimethyl-dibenzothiophene(DMDBT),which are the refractory sulfur compounds for hydrodesulfurization(HDS),were employed as model substrates for a simulated diesel fuel.Activ ity of molybdenum oxide supported on a macroporous weak acidic resin was investigated.The mass conversion of DBT reached near 100%at 90°C and a TAHP,DBT molar ratio of 3 with 1% of molybdenum oxide supported on Amberlite IRC-748 resin for l h.It was further found that the activities of the model Substrates decreasca rin the order of DMDBT>DBT>B T.In the flow oxidation using TAHP as the oxidant,mass conversion of DBT increased remarkably from 61.3%to 98.5%when dropping the weight hourly space velocity(WHSV)from 40 h1 to 10 h-1.A series of experiments dealt with selectivity of this oxidation using TAHP revealed that the model unsaturated compounds,i.e.4,6,8-trimethyl-2-nonylene,and 2-methylnaphthaIene did not affect the oxidation of DBT.Carbazole had nearly no effect on the conversion of DBT using TAHP.but had some influence on the one using tert-butyl hydroperoxide(TBHP).The mass conversion of DBT decreased remarkably from 75.2%to 3.6%when the content of carbazole increased from 0 to 500 ug.g-1.In the flow oxidation using TAHP as the oxidant.the concentration of.DBT in model fuels was reduced from 500 ug.g-1 to 7.2 ug.g-1 at WHSV of 10 h-1,and then reduced to 3.8 ug.g-1 by adsorption of Al2O3.

  19. Structure-based design of selective inhibitors of dihydrofolate reductase: synthesis and antiparasitic activity of 2, 4-diaminopteridine analogues with a bridged diarylamine side chain. (United States)

    Rosowsky, A; Cody, V; Galitsky, N; Fu, H; Papoulis, A T; Queener, S F


    As part of a larger search for potent as well as selective inhibitors of dihydrofolate reductase (DHFR) enzymes from opportunistic pathogens found in patients with AIDS and other immune disorders, N-[(2,4-diaminopteridin-6-yl)methyl]dibenz[b,f]azepine (4a) and the corresponding dihydrodibenz[b,f]azepine, dihydroacridine, phenoxazine, phenothiazine, carbazole, and diphenylamine analogues were synthesized from 2, 4-diamino-6-(bromomethyl)pteridine in 50-75% yield by reaction with the sodium salts of the amines in dry tetrahydrofuran at room temperature. The products were tested for the ability to inhibit DHFR from Pneumocystis carinii (pcDHFR), Toxoplasma gondii (tgDHFR), Mycobacterium avium (maDHFR), and rat liver (rlDHFR). The member of the series with the best combination of potency and species selectivity was 4a, with IC(50) values against the four enzymes of 0. 21, 0.043, 0.012, and 4.4 microM, respectively. The dihydroacridine, phenothiazine, and carbazole analogues were also potent, but nonselective. Of the compounds tested, 4a was the only one to successfully combine the potency of trimetrexate with the selectivity of trimethoprim. Molecular docking simulations using published 3D structural coordinates for the crystalline ternary complexes of pcDHFR and hDHFR suggested a possible structural interpretation for the binding selectivity of 4a and the lack of selectivity of the other compounds. According to this model, 4a is selective because of a unique propensity of the seven-membered ring in the dibenz[b,f]azepine moiety to adopt a puckered orientation that allows it to fit more comfortably into the active site of the P. carinii enzyme than into the active site of the human enzyme. Compound 4a was also evaluated for the ability to be taken up into, and retard the growth of, P. carinii and T. gondii in culture. The IC(50) of 4a against P. carinii trophozoites after 7 days of continuous drug treatment was 1.9 microM as compared with previously observed IC(50

  20. Tailoring the color of electrochromic polymer devices by stoichiometric control of blends and copolymers (United States)

    Meeker, David Lloyd

    A systematic study of the color and optical properties of electrochromic devices using stoichiometric combinations of polymer blends and copolymers is presented. Monomers of N-phenyl-2-(5/sp /prime-vinyl-2/sp /prime- thienyl)-5-(2/prime'-thienyl)-pyrrole (SNPhS) and N-vinyl carbazole (NVC) are combined into two forms: homopolymer blends, and copolymers. The homopolymers poly N-phenyl-2-(5 /sp /prime-vinyl-2 /sp/prime-thienyl)- 5-(2 /prime'-thienyl)-pyrrole (PSNPhS) and poly (N-vinylcarbazole) (PVK) were blended together according to the stoichiometric mass ratios (1:4), (3:2) and (4:1) of (PSNPhS:PVK) respectively. Copolymers were prepared using feed stock ratios identical to the polymer blends, which produced the respective stoichiometric ratios (3:7), (3:2) and (7:3) of (PSNPhS:PVK). Photoluminescence (PL) and photoluminescence excitation spectroscopy (PLE) allowed the identification of excimer formation in dilute solutions of the blends and copolymers. Two excimer emission bands at 373 nm and 420 nm in were attributed to poly(N-vinyl carbazole), in the partial overlap and sandwich configuration. Analysis of the PL data indicated that the effects of these excimers on the color of the electrochromic devices was minimized by avoiding (1:1) stoichiometric combinations of PVK and PSNPhS. Films of the polymeric materials were characterized by optical absorption, and spectroelectrochemistry. Solid state devices were assembled and their spectrocolorimetery measurements correlated with the stoichiometric ratios of copolymers and polymer blends. Analysis using Commission International de l'Eclairage (CIE) L*a*b* color coordinates determined that stoichiometric adjustment of polymer blends and copolymers yields a strong correlation (R2 = 0.99) with the amount of SNPhS present in the device. It was found that blends access the widest range of color adjustments, while copolymers provide the most precise means of tailoring color over a narrow range.

  1. 三芳基咪唑富勒烯吡咯烷衍生物的合成及在CdSe量子点敏化太阳能电池中的应用%Synthesis of Fulleropyrrolidine Derivatives with Aromatic Substituted Imidazoles and Their Application in CdSe-Quantum Dot Solar Cells

    Institute of Scientific and Technical Information of China (English)

    赵爱婷; 熊艳玲; 曾和平


    设计合成了2个三芳基咪唑类化合物Im(5)和Bn-Im(6),进一步通过1,3-偶极化反应合成了C吡咯烷衍生物Im-C(7)和Bn-Im-C(8),采用FTIR,H NMR,C NMR和MALDI-TOF-MS等方法对其结构进行了表征.实验组装了7个太阳能电池,结构分别为FTO/TiO:/CdSe/Pt,FTO/TiO/C/Pt,FTO/TiO/Im-C/Pt,FTO/TiO/Bn-Im-C/Pt,FTO/TiO/C-CdSe/Pt,FTO/TiO/Im-C-CdSe/Pt和FTO/TiO/Bn-lm-CCdSe/Pt,对其光电性能进行了表征.结果表明,与CdSe敏化太阳能电池相比,以Im-C-CdSe和Bn-Im-C-CdSe为敏化剂的电池效率分别增加了5.28%和40.08%.%Two novel aromatic substituted imidazole compounds including 4-(4,5-bis (3-nitrophenyl)-1Himidazole-2-yl ) -3,6-biacetyl-9-ethyl-carbazole ( 5 ) and 4-( 1 -benzyl-4,5-bis ( 3-nitrophenyl ) - imidazol-2-yl )3,6-biacetyl-9-ethyl-carbazole(6) were synthesized by the optimized Debus' method. Fulleropyrrolidine derivatives 7 and 8 were successfully synthesized by 1,3-dipolar cycloaddition. The structures of these moleculars were confirmed by FTIR, 1H NMR, 13C NMR and MALDI-TOF-MS. Seven solar cells, FTO/TiO2/CdSe/Pt,FTO/TiO2/C60/Pt, FTO/TiO2/Im-C60/Pt, FrO/TiO2/Bn-Im-C60/Pt, FrO/TiO2/C60-CdSe/Pt, FTO/TiO2/ Im-C60-CdSe/Pt and FTO/TiO2/Bn-Im-C60-CdSe/Pt, were fabricated. The results show that the observed energy conversion efficiency with Im-C60-Cdse films and Bn-Im-C60-Cdse films increased by 5.28% and 40. 08% compared with CdSe QDs sensitized solar cell, respectively.

  2. Simultaneous determination of six triterpenic acids in some Chinese medicinal herbs using ultrasound-assisted dispersive liquid-liquid microextraction and high-performance liquid chromatography with fluorescence detection. (United States)

    Wu, Hongliang; Li, Guoliang; Liu, Shucheng; Liu, Di; Chen, Guang; Hu, Na; Suo, Yourui; You, Jinmao


    A novel analytical method was developed for simultaneous determination of six triterpenic acids using ultrasound-assisted dispersive liquid-liquid microextraction (UA-DLLME) follow by high-performance liquid chromatography (HPLC) with fluorescence detection. Six triterpenic acids (ursolic acid, oleanolic acid, betulinic acid, maslinic acid, betulonic acid and corosolic acid) were extracted by UA-DLLME using chloroform and acetone as the extraction and disperser solvents, respectively. After the extraction and nitrogen flushing, the extracts were rapidly derivatized with 2-(12,13-dihydro-7H-dibenzo[a,g]carbazol-7-yl)ethyl4-methylbenzenesulfonate. The main experimental parameters affecting extraction efficiency and derivatization yield were investigated and optimized by response surface methodology (RSM) combined with Box-Behnken design (BBD). The limits of detection (LODs) and the limits of quantification (LOQs) were in the range of 0.95-1.36 ng mL(-1) and 3.17-4.55 ng mL(-1), respectively. Under the optimum conditions, the method has been successfully applied for the analysis of triterpenic acids in six different traditional Chinese medicinal herbs.

  3. Deep processing status and research progress of anthracene oil fractions%蒽油馏分深加工工艺现状及研究进展

    Institute of Scientific and Technical Information of China (English)



    Two kinds of anthracene oil processing are introduced in this paper. It mainly describes the status and research progress of the refined separation of anthracene oil to extract fine anthracene, phenanthrene and carbazole. The research progress, technological principle and technological process of anthracene oil hydrogenation to produce light fuel oil are described. Finally, constructive suggestions are put forward for Shanxi Coking Group Co. , Ltd. to construct anthracene oil deep processing project in the future.%介绍了蒽油馏分深加工的2种工艺、蒽油精制分离提取精蒽、菲、咔唑工艺的现状及研究进展,阐述了蒽油馏分加氢生产轻质燃料油工艺研究进展、工艺原理、工艺流程等。对山西焦化集团有限公司未来建设蒽油深加工项目提出了建议。

  4. An efficient 2-linked carbazolyl β-diketonate europium(III) complex as red phosphor applied in LED (United States)

    He, P.; Wang, H. H.; Liu, S. G.; Shi, J. X.; Gong, M. L.


    An efficient 2-linked carbazolyl β-diketonate europium(III) complex Eu(ETFMCTFBD)3phen was designed and synthesized, where ETFMCTFBD was 1-(9-ethyl-7-(trifluoromethyl)-9H-carbazol-2-yl)-4,4,4-trifluorobutane-1,3-dione and phen was 1,10-phenanthroline. Eu(ETFMCTFBD)3phen exhibits high thermal stability and excellent photoluminescence properties. The CIE chromaticity coordinates ( x=0.668, y=0.331) are close to the National Television Standard Committee (NTSC) standard values for red. The lowest triplet energy was measured and suggests the photoluminescence process as a ligand-sensitized luminescence process (antenna effect). A bright red light-emitting diode was fabricated by coating the complex phosphor onto a ˜395 nm-emitting InGaN chip. All the results indicate that Eu(ETFMCTFBD)3phen is a good candidate as a red component in the fabrication of white LEDs with a high color-rendering index.

  5. Cooperative effects of solvent and polymer acceptor co-additives in P3HT:PDI solar cells: simultaneous optimization in lateral and vertical phase separation. (United States)

    Li, Mingguang; Wang, Lei; Liu, Jiangang; Zhou, Ke; Yu, Xinhong; Xing, Rubo; Geng, Yanhou; Han, Yanchun


    In this work, solvent chloronaphthalene (CN) and polymer acceptor an alternating copolymer of perylene diimide and carbazole (PCPDI) were utilized as co-additives to optimize the nanoscale phase-separated morphology and photovoltaic properties of bulk-heterojunction (BHJ) polymer solar cells based on the poly(3-hexyl thiophene) (P3HT)/N,N'-bis(1-ethylpropyl)-perylene-3,4,9,10-tetracarboxylic diimide (EP-PDI) system. The domain size of EP-PDI molecules together with that of P3HT distinctly decreased by adding a 0.75 vol% CN additive. The optimized lateral phase separation increased the donor-acceptor interfacial area and facilitated the exciton dissociation process, leading to 5-fold enhancement of short-circuit current (JSC). Furthermore, when PCPDI was employed as a co-additive, acceptor materials (including PCPDI and EP-PDI) were prone to aggregation towards the top surface of blend films, improving vertical phase separation of active layers. PCPDI incorporation, which improved the percolation pathways for electron carriers, suppressed the crystallinity of P3HT distinctly. Thus, much more balanced charge transport was achieved by PCPDI addition, which resulted in almost 1-fold enhancement of open-circuit voltage (VOC) by reducing nongeminate recombination. As a consequence, cooperative effects of CN and PCPDI additives improved the nanoscale phase-separated morphology in lateral and vertical directions simultaneously, achieving the enhancement in both VOC and JSC.

  6. Synthesis and design of organic light-emitting devices containing lanthanide-cored complexes (United States)

    Phelan, Gregory D.; Carlson, Brenden; Lawson, Rhys; Rowe, Daniel; Allen, Kolby; Dalton, Larry; Jiang, Xuezhong; Kim, Joo H.; Jen, Alex K.


    There is a considerable interest in the use of metal centered materials as a light source in the growing field of organic light emitting devices (OLED's). In these devices, a polymeric host matrix containing either a carbazole type polymer or polyfluorene derivatives is used to help facilitate energy transfer to the luminophore. We have shown that by using a gadolinium complex that consist of three equivalents of a chelated dibenzoylmethane b-diketone ligand and one equivalent of a phenanthroline type ligand as a component in the host matrix, the performance of a double layer type OLED is improved. We have studied OLED systems that contain tris chelated europium compounds that contain three equivalents of partially fluorinated β-diketone type ligands and an equivalent of a phenanthroline type ligand. In these devices, the external efficiency has shown a 30-fold increase. We have also shown there is an increase for Osmium based OLED's that use the gadolinium complex as part of the polymer matrix. In these devices, the maximum quantum efficiency increased from 2.1% to a value of 3.8%.

  7. Photoluminescence characteristics of dye-doped polymer nanofibers excited by surface plasmon polaritons (United States)

    Kaminose, Ryohei; Ishii, Yuya; Aihara, Takuma; Takeda, Ayumi; Fukuda, Mitsuo


    Grating inscription in azo-dye doped polymers is an interesting phenomenon because of its high diffraction performance and applicability to real-time 3D displays. Although some of these materials were investigated under no external electric field with symmetric optical alignments in preceding studies, they often showed a phase shift of periodic modulation of refractive index from the interference fringe formed by irradiation beams, resulting in asymmetric energy exchange between two coupled beams. The mechanism of the behavior has been usually attributed to the molecular motions triggered by trans-cis isomerization, but their details are still unknown. Therefore, studies on temporal evolution of the process and their translation into physical meaning are necessary. In order to investigate the evolution of grating inscription and phase shift, several methods have been developed. In this study, we analyzed the coupled wave equations proposed by Kogelnik, and derived general solution applicable to the system with both phase and amplitude gratings with arbitrary phase relationship. We showed that the analysis based on the equation can give a direct evidence of the phase shift between the phase and amplitude gratings if it exists. This method was applied to the fringe pattern inscribed in thick films of PMMA doped with an azo-carbazole dye, showing that observed signals indicated the phase deviation between two types of gratings.

  8. Understanding polycarbazole-based polymer:CdSe hybrid solar cells. (United States)

    Lek, Jun Yan; Lam, Yeng Ming; Niziol, Jacek; Marzec, Mateusz


    We report for the first time the fabrication and characterization of organic-inorganic bulk heterojunction (BHJ) hybrid solar cells made of poly[N-9″-hepta-decanyl-2,7-carbazole-alt-5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT) and pyridine-capped CdSe nanorods. By optimizing both CdSe loading and active layer film thickness, the power conversion efficiencies (PCEs) of PCDTBT:CdSe hybrid solar cells were able to reach 2%, with PCDTBT:CdSe devices displaying an open-circuit voltage (V(OC )) that is 35% higher than P3HT:CdSe devices due to the deeper HOMO level of PCDTBT polymer. The performance of PCDTBT:CdSe devices is limited by its morphology and also its lower LUMO energy offset compared to P3HT:CdSe devices. Hence, the performance of PCDTBT:CdSe solar cells could be further improved by modifying the morphology of the films and also by including an interlayer to generate a built-in voltage to encourage exciton dissociation. Our results suggest that PCDTBT could be a viable alternative to P3HT as an electron donor in hybrid BHJ solar cells for high photovoltage application.

  9. The role of local environment on the electronic properties of a novel blue-emitting donor-acceptor compound (United States)

    Legaspi, Christian M.; Stubbs, Regan E.; Yaron, David J.; Peteanu, Linda A.; Kemboi, Abraham; Picker, Jesse; Fossum, Eric


    With the rising popularity of organic light-emitting diodes (OLEDs) in display applications, demand for more efficient blue emitters has increased. We have recently synthesized a novel blue-emitting, donor-acceptor system employing carbazole as the donor and a benzothiazole derivative as the acceptor, BTZ-CBZ. We find that the solution-phase emission of BTZ-CBZ is highly dependent on solvent polarity, both in lineshape and emission maximum, showing a Stokes shift of 50 nm in methylcyclohexane and 150 nm in acetonitrile. This is expected behavior for donor-acceptor compounds due to the presence of a charge-transfer excited state. However, the solid state properties are more important for OLED devices. Using time-dependent density functional theory calculations employing the linear-response (LR) and state-specific (SS) polarizable continuum model (PCM), we explore the effects of solvent reorganization on the emission properties of BTZ-CBZ. SS-PCM reproduces the solvatochromism behavior of BTZ-CBZ in solution, but LR-PCM shows effectively no shift with solvent polarity. We surmise that this is because solvent reorganization is necessary for the solvatochromic effect to occur. The effect of rigid matrices on the emission of BTZ-CBZ has direct implications on its viability as a blue emitter in solid-state OLEDs and which molecular environments will be ideal for devices.

  10. Switching and memory effects in composite films of semiconducting polymers with particles of graphene and graphene oxide (United States)

    Krylov, P. S.; Berestennikov, A. S.; Aleshin, A. N.; Komolov, A. S.; Shcherbakov, I. P.; Petrov, V. N.; Trapeznikova, I. N.


    The effects of switching were investigated in composite films based on multifunctional polymers. i.e., derivatives of carbazole (PVK) and fluorene (PFD), as well as based on particles of graphene (Gr) and graphene oxide (GO). The concentration of Gr and GO particles in the PVK(PFD) matrix was varied in the range of 2-3 wt %, which corresponded to the percolation threshold in these systems. The atomic composition of the composite films PVK: GO was examined using X-ray photoelectron spectroscopy. It was found that the effect of switching in structures of the form Al/PVK(PFD): GO(Gr)/ITO/PET manifests itself in a sharp change of the electrical resistance of the composite film from a low-conducting state to a relatively high-conducting state when applying a bias to Al-ITO electrodes of ˜0.1-0.3 V ( E ˜ 3-5 × 104 V/cm), which is below the threshold switching voltages for similar composites. The mechanism of resistance switching, which is associated with the processes of capture and accumulation of charge carriers by Gr (GO) particles introduced into the matrices of the high-molecular-weight (PVK) and relatively low-molecular-weight (PFD) polymers, was discussed.

  11. Mulifunctional Dendritic Emitter: Aggregation-Induced Emission Enhanced, Thermally Activated Delayed Fluorescent Material for Solution-Processed Multilayered Organic Light-Emitting Diodes (United States)

    Matsuoka, Kenichi; Albrecht, Ken; Yamamoto, Kimihisa; Fujita, Katsuhiko


    Thermally activated delayed fluorescence (TADF) materials emerged as promising light sources in third generation organic light-emitting diodes (OLED). Much effort has been invested for the development of small molecular TADF materials and vacuum process-based efficient TADF-OLEDs. In contrast, a limited number of solution processable high-molecular weight TADF materials toward low cost, large area, and scalable manufacturing of solution processed TADF-OLEDs have been reported so far. In this context, we report benzophenone-core carbazole dendrimers (GnB, n = generation) showing TADF and aggregation-induced emission enhancement (AIEE) properties along with alcohol resistance enabling further solution-based lamination of organic materials. The dendritic structure was found to play an important role for both TADF and AIEE activities in the neat films. By using these multifunctional dendritic emitters as non-doped emissive layers, OLED devices with fully solution processed organic multilayers were successfully fabricated and achieved maximum external quantum efficiency of 5.7%.

  12. QTAIM investigation of bis(pyrazol-1-ylmethane derivative and its Zn(II complexes (ZnLX2, X=Cl, Br or I

    Directory of Open Access Journals (Sweden)

    Dehestani Maryam


    Full Text Available Topological analyses of the electron density using the quantum theory of atoms in molecules (QTAIM have been carried out at the B3PW91/6-31g (d theoretical level, on bis(pyrazol-1-ylmethanes derivatives 9-(4-(di (1H-pyrazol-1-yl-methylphenyl-9H-carbazole (L and its zinc(II complexes: ZnLCl2 (1, ZnLBr2 (2 and ZnLI2 (3. The topological parameters derived from Bader theory were also analyzed; these are characteristics of Zn-bond critical points and also of ring critical points. The calculated structural parameters are the frontier molecular orbital energies highest occupied molecular orbital energy (EHOMO, lowest unoccupied molecular orbital energy (ELUMO, hardness (η, softness (S, the absolute electronegativity (χ, the electrophilicity index (ω and the fractions of electrons transferred (ΔN from ZnLX2 complexes to L. The numerous correlations and dependencies between energy terms of the Symmetry Adapted Perturbation Theory approach (SAPT, geometrical, topological and energetic parameters were detected and described.

  13. How the Molecular Packing Affects the Room Temperature Phosphorescence in Pure Organic Compounds: Ingenious Molecular Design, Detailed Crystal Analysis, and Rational Theoretical Calculations. (United States)

    Xie, Yujun; Ge, Yuwei; Peng, Qian; Li, Conggang; Li, Qianqian; Li, Zhen


    Long-lived phosphorescence at room temperature (RTP) from pure organic molecules is rare. Recent research reveals various crystalline organic molecules can realize RTP with lifetimes extending to the magnitude of second. There is little research on how molecular packing affecting RTP. Three compounds are designed with similar optical properties in solution, but tremendously different solid emission characteristics. By investigating the molecular packing arrangement in single crystals, it is found that the packing style of the compact face to face favors of long phosphorescence lifetime and high photoluminescence efficiency, with the lifetime up to 748 ms observed in the crystal of CPM ((9H-carbazol-9-yl)(phenyl)methanone). Theoretical calculation analysis also reveals this kind of packing style can remarkably reduce the singlet excited energy level and prompt electron communication between dimers. Surprisingly, CPM has two very similar single crystals, labeled as CPM and CPM-A, with almost identical crystal data, and the only difference is that molecules in CPM-A crystal take a little looser packing arrangement. X-ray diffraction and cross-polarization under magic spinning (13) C NMR spectra double confirm that they are different crystals. Interestingly, CPM-A crystal shows negligible RTP compared to the CPM crystal, once again proving that the packing style is critical to the RTP property.

  14. Surfactant-free, low band gap conjugated polymer nanoparticles and polymer:fullerene nanohybrids with potential for organic photovoltaics. (United States)

    Wang, Suxiao; Singh, Amita; Walsh, Nichola; Redmond, Gareth


    Stable, aqueous dispersions of nanoparticles based on the low band gap polymers poly [2,7-(9,9-dioctyl-fluorene)-alt-5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (APFO-3) and poly [N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT) were prepared, using a flexible, surfactant-free reprecipitation method, and characterized by a variety of optical techniques. Light scattering measurements indicated average nanoparticle hydrodynamic diameters of approximately 40 nm. The particles presented wide-bandwidth absorption and photoluminescence excitation spectra with high absorption cross-sections on the order of 10(-12) cm(2). Nanoparticle emission spectra were significantly red-shifted, with decreased emission quantum yields and lifetimes, consistent with increased inter-polymer chain interactions in the condensed phase. Single particle photoluminescence studies highlighted the multi-chromophoric nature of the polymer nanoparticles and confirmed their favorable photostabilities. When the nanoparticles were doped with [6,6]-phenyl-C61-butyric acid methyl ester (PCBM), the correspondence of photoluminescence emission quenching, quantum yield decreases, emission lifetime shortening, and increased non-radiative rates with increasing PCBM concentration suggested efficient photo-induced donor-to-acceptor charge transfer between the conjugated polymers and the fullerene dopants co-localized in the nanoparticle cores. Taken together, the data suggest that these surfactant-free hybrid nanomaterials may be useful for integration with future nanostructured organic photovoltaics technologies.

  15. Improved photovoltaic performance of inverted polymer solar cells through a sol-gel processed Al-doped ZnO electron extraction layer. (United States)

    Kim, Jun Young; Cho, Eunae; Kim, Jaehoon; Shin, Hyeonwoo; Roh, Jeongkyun; Thambidurai, Mariyappan; Kang, Chan-mo; Song, Hyung-Jun; Kim, SeongMin; Kim, Hyeok; Lee, Changhee


    We demonstrate that nanocrystalline Al-doped zinc oxide (n-AZO) thin film used as an electron-extraction layer can significantly enhance the performance of inverted polymer solar cells based on the bulk heterojunction of poly[[9-(1-octylnonyl)-9H-carbazole-2,7-diyl]-2,5-thiophenediyl-2,1,3-benzothiadiazole-4,7-diyl-2,5-thiophenediyl] (PCDTBT) and [6,6]-phenyl C(71)-butyric acid methyl ester (PC(70)BM). A synergistic study with both simulation and experiment on n-AZO was carried out to offer a rational guidance for the efficiency improvement. As a result, An n-AZO film with an average grain size of 13 to 22 nm was prepared by a sol-gel spin-coating method, and a minimum resistivity of 2.1 × 10(-3) Ω·cm was obtained for an Al-doping concentration of 5.83 at.%. When an n-AZO film with a 5.83 at.% Al concentration was inserted between the ITO electrode and the active layer (PCDTBT:PC(70)BM), the power conversion efficiency increased from 3.7 to 5.6%.

  16. Time-resolved neutron reflectometry and photovoltaic device studies on sequentially deposited PCDTBT-fullerene layers. (United States)

    Clulow, Andrew J; Tao, Chen; Lee, Kwan H; Velusamy, Marappan; McEwan, Jake A; Shaw, Paul E; Yamada, Norifumi L; James, Michael; Burn, Paul L; Gentle, Ian R; Meredith, Paul


    We have used steady-state and time-resolved neutron reflectometry to study the diffusion of fullerene derivatives into the narrow optical gap polymer poly[N-9″-hepta-decanyl-2,7-carbazole-alt-5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT) to explore the sequential processing of the donor and acceptor for the preparation of efficient organic solar cells. It was found that when [6,6]-phenyl-C61-butyric-acid-methyl-ester (60-PCBM) was deposited onto a thin film of PCDTBT from dichloromethane (DCM), a three-layer structure was formed that was stable below the glass-transition temperature of the polymer. When good solvents for the polymer were used in conjunction with DCM, both 60-PCBM and [6,6]-phenyl-C71-butyric-acid-methyl-ester (70-PCBM) were seen to form films that had a thick fullerene layer containing little polymer and a PCDTBT-rich layer near the interface with the substrate. Devices composed of films prepared by sequential deposition of the polymer and fullerene had efficiencies of up to 5.3%, with those based on 60-PCBM close to optimized bulk heterojunction (BHJ) cells processed in the conventional manner. Sequential deposition of pure components to form the active layer is attractive for large-area device fabrication, and the results demonstrate that this processing method can give efficient solar cells.

  17. Application Progress of the Narrow Band-gap Conjugated Polymer Base on Carbazolyl Materials for Solar Cells%咔唑基窄带隙共轭聚合物太阳能电池材料的研究进展

    Institute of Scientific and Technical Information of China (English)

    苏雪花; 夏德强; 王守伟


    基于咔唑基窄带隙共轭聚合物的太阳能电池材料的研究取得突破性的进展,成为当前聚合物光伏器件研究的热点课题之一。概述了咔唑基窄带隙共轭聚合物作为电子给体材料的研究进展及存在的问题,提出了光谱响应更宽、光电转换效率更高的咔唑基共轭聚合物研究的发展前景。%The study of the narrow band-gap conjugated polymer base on carbazolyl materials for application in solar cells gained breakthrough progress,and became one of hotspot issue of the polymer photovoltaic device research at present.The research progress and its main existing problems of the narrow band-gap conjugated polymers base on carbazolyl as electron donor materials were summarized,the study development prospects of the conjugated polymers based on carbazole with broader spectral response and higher incident photon-to-current conversion efficiency were proposed.

  18. Long-Range Energy Transfer and Singlet-Exciton Migration in Working Organic Light-Emitting Diodes (United States)

    Ingram, Grayson L.; Nguyen, Carmen; Lu, Zheng-Hong


    Rapid industrialization of organic light-emitting devices for flat-panel displays and solid-state lighting makes a deep understanding of device physics more desirable than ever. Developing reliable experimental techniques to measure fundamental physical properties such as exciton diffusion lengths is a vital part of developing device physics. In this paper, we present a study of exciton diffusion and long-range energy transfer in working organic light-emitting devices, and a study of the interplay between these two tangled processes through both experimental probes and simulations. With the inclusion of multiple factors including long-range energy transfer, exciton boundary conditions, and the finite width of the exciton generation zone, we quantify exciton migration based on emission characteristics from rubrene sensing layers placed in working organic light-emitting devices. This comprehensive analysis is found to be essential to accurately measuring exciton diffusion length, and in the present case the measured singlet-exciton diffusion length in the archetype material 4' -bis(carbazol-9-yl)biphenyl is 4.3 ±0.3 nm with a corresponding diffusivity of (2.6 ±0.3 )×10-4 cm2/s .

  19. Monitoring the contents of six steroidal and phenolic endocrine disrupting chemicals in chicken, fish and aquaculture pond water samples using pre-column derivatization and dispersive liquid-liquid microextraction with the aid of experimental design methodology. (United States)

    Wu, Hongliang; Li, Guoliang; Liu, Shucheng; Hu, Na; Geng, Dandan; Chen, Guang; Sun, Zhiwei; Zhao, Xianen; Xia, Lian; You, Jinmao


    This research established a sensitive and efficient pre-column derivatization HPLC method based on dispersive liquid-liquid microextraction (DLLME) for the simultaneous determination of six steroidal and phenolic endocrine disrupting chemicals (EDCs). In this study, EDCs were firstly labeled by the derivatization reagent 2-(11H-benzo[a]carbazol-11-yl) ethyl carbonochloridate (BCEC-Cl) and then extracted by DLLME. The response surface methodology was employed to investigate the key parameters of pre-column derivatization and DLLME. Under the optimal conditions, a good linear relationship between the peak area and the concentration of analytes was observed with correlation coefficients of >0.9991. Limits of detection for all EDCs derivatives were achieved within the range of 0.02-0.07 μg L(-1). The proposed method has the advantages of simple operation, low consumption of organic solvent, saving time, low output limit and good selectivity. When applied to several food and water samples analysis, it demonstrated good applicability for the determination of EDCs.

  20. 2-D Metal Organic Structure Based on Dipyrazolate Ligand through Ni...N and Ni...H-N Interactions

    Institute of Scientific and Technical Information of China (English)

    SHAO Ying; QIN Lin; YUShu-Yan


    By employing functional ligand 3,6-bis(3,5-dimethyl-lH-pyrazol-4-yl)-9-methyl- 9H-carbazole, a novel luminescent Ni complex has been obtained. Its structure was characterized by single-crystal X-ray diffraction analysis. Crystal data: monoclinic, space group P2/c, a = 13.4224(18), b = 13.759(2), c = 8.0633(17)/~, fl = 96.448(3)~, C23H23NsNi(NO3)2, M,. = 552.19, V = 1479.7(4) A3, Z = 2, Dc = 1.239 g/cm3,/ffMoKa) = 0.700 mm-1, F(000) = 572, the final R = 0.0566 and wR = 0.1336 for 1638 observed reflections with I 〉 2a(/). X-ray analysis indicates that each metal center coordinates with two N and two H atoms in tetrahedral interaction geometry. Weak interaction between Ni and N atom of pyrazole ligand and agostic bond (Ni...H-N interaction) play important roles in the formation of the 2-dimension framework. Significantly, this framework could pack into a tubular channel with NO3 anions trapped inside.

  1. S-shaped current-voltage characteristics of polymer composite films containing graphene and graphene oxide particles (United States)

    Krylov, P. S.; Berestennikov, A. S.; Fefelov, S. A.; Komolov, A. S.; Aleshin, A. N.


    The resistive switching effects in composite films containing polyfunctional polymers, such as derivatives of carbazole (PVK), fluorene (PFD), and polyvinyl chloride (PVC), and also graphene particles (Gr) and graphene oxide (GO), the concentration of which in the polymer matrices varied in the range from 1 to 3 wt % corresponding to the percolation threshold in such systems, have been studied. The analysis of the elemental composition of the investigated composites by means of X-ray photoelectron spectroscopy have shown that the oxidation degree of Gr in GO is about 9 to 10%. It has been established that a sharp conductivity jump characterized by S-shaped current-voltage curves and the presence of their hysteresis occurs upon applying a voltage pulse to the Au/PVK (PFD; PVC): Gr (GO)/ITO/PET structures, where ITO is indium tin oxide, and PET is poly(ethylene terephthalate), with the switching time, t, in the range from 1 to 30 μs. The observed effects are attributed to the influence of redox reactions taking place on the Gr and GO particles enclosed in the polymer matrix, and the additional influence of thermomechanical properties of the polymer constituent of the matrix.

  2. Synthesis of an A-D-A type of molecule used as electron acceptor for improving charge transfer in organic solar cells (United States)

    Zhang, Chao-Zhi; Gu, Shu-Duo; Shen, Dan; Yuan, Yang; Zhang, Mingdao


    Electron-accepting molecules play an important role in developing organic solar cells. A new type of A-D-A molecule, 3,6-di([7-(5-bromothiophen-2-yl)-1,5,2,4,6,8-dithiotetrazocin-3-yl]thiophen-2-yl)-9-(2-ethylhexyl)carbazole, was synthesized. The lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) energy levels are -3.55 and -5.85 eV, respectively. Therefore, the A-D-A type of compound could be used as electron acceptor for fabricating organic solar cell with a high open circuit voltage. Gibbs free energy (-49.2 kJ/mol) reveals that the process of A-D-A acceptor accepting an electron from poly(3-hexylthiophene) at excited state is spontaneous. The value of entropy (118 J/mol) in the process of an electron transferring from P3HT to the A-D-A acceptor at organic interface suggests that electrons generated from separation of electron-hole pairs at donor/acceptor interface would be delocalized efficiently. Therefore, the A-D-A molecule would be a potential acceptor for efficient organic BHJ solar cells.

  3. Synthesis and fluorescent properties of poly(arylpyrazoline)'s for organic-electronics (United States)

    Vandana, T.; Ramkumar, V.; Kannan, P.


    The present work focuses on the synthesis and characterization of poly(arylchalcone)'s (PCH I-IV) by reacting acetone with various dialdehydes for the first time at below ambient temperature followed by cyclization with phenylhydrazinehydrochloride to yield luminescent poly(arylpyrazoline)'s (PPY I-IV). The synthesized polymers were characterized by standard techniques such as, GPC, SEM, TGA, FT-IR, 1H NMR, UV-Vis absorption and fluorescence spectroscopy, and electrochemical studies by cyclic voltammetry analyses. The Pyrazoline group hooked with different aryl donors such as benzene, thiophene, carbazole, triphenylamine, thus results a series of blue and green emitting materials. The obtained optical bandgap energy of the polymers (PPY I-IV) were 2.53, 3.41, 3.07, 3.10 eV respectively, suggest that all the polymers belongs to semiconducting category. The solvent effect of polymers was thoroughly studied and explained by Lippert-Mataga equation. The polymers I & IV display large degree of intra-molecular charge transfer in excited state evidenced from solvatochromic shift on the emission spectra. The obtained results demonstrate that they are promising materials for organic electronics applications.

  4. Selective Removal of Nitrogen-Containing Heterocyclic Compounds from Transportation Diesel Fuels with Reactive Adsorbent

    Institute of Scientific and Technical Information of China (English)

    YANG Lei; WANG Shengqiang; WANG Ruicong; YU Hongbing


    This paper presents a new selective adsorbent to remove nitrogen-containing heterocyclic compounds from model and commercial transportation diesel fuels based on characteristic reaction designed to occur in the pores of substrate.This reactive adsorbent is composed of formaldehyde,phosphotungstic acid and Santa Barbara USA (SBA)-15.The experiment was based on assumed hydroxymethylation reaction of nitrogen-containing heterocyclic compounds with formaldehyde using phosphotungstic acid as catalyst in batch and fixed-bed systems.The nitrogen concentration in the model fuel was 237.33 ng·μl-1,carbazole and toluene were used as model nitrogen-containing heterocyclic compound and solvent,respectively.The effectiveness of reactive adsorbent for removal of nitrogen-containing heterocyclic compounds from commercial 0# diesel fuel containing 224.86 ng· μl-1 nitrogen was examined in a fixed-bed reactor at 70 ℃.The results showed that nitro1gen in the model fuel was very low and the nitrogen concentration in the commercial diesel reduced to 2.44 ng· μl-1.The demand for transportation fuel with ultra-low nitrogen is satisfied.

  5. Evaluation of a Direct Rapid Immunohistochemical Test (dRIT) for Rapid Diagnosis of Rabies in Animals and Humans

    Institute of Scientific and Technical Information of China (English)

    Shampur Narayan Madhusudana; Sundaramurthy Subha; Ullas Thankappan; Yajaman Belludi Ashwin


    Presently the gold standard diagnostic technique for rabies is the direct immunofluorescence assay (dFA) which is very expensive and requires a high level of expertise.There is a need for more economical and user friendly tests,particularly for use in developing countries.We have established one such test called the direct rapid immunohistochemical test (dRIT) for diagnosis of rabies using brain tissue.The test is based on capture of rabies nucleoprotein (N) antigen in brain smears using a cocktail of biotinylated monoclonal antibodies specific for the N protein and color development by streptavidin peroxidase-amino ethyl carbazole and counter staining with haematoxollin.The test was done in parallel with standard FAT dFA using 400 brain samples from different animals and humans.The rabies virus N protein appears under light microscope as reddish brown particles against a light blue background.There was 100 % correlation between the results obtained by the two tests.Also,interpretation of results by dRIT was easier and only required a light microscope.To conclude,this newly developed dRIT technique promises to be a simple,cost effective diagnostic tool for rabies and will have applicability in field conditions prevalent in developing countries.

  6. Antimicrobial applications of electroactive PVK-SWNT nanocomposites. (United States)

    Ahmed, Farid; Santos, Catherine M; Vergara, Regina Aileen May V; Tria, Maria Celeste R; Advincula, Rigoberto; Rodrigues, Debora F


    The antibacterial properties of a nanocomposite containing an electroactive polymer, polyvinyl-N-carbazole (PVK) (97 wt %), and single-walled carbon nanotubes (SWNT) (3 wt %) was investigated as suspensions in water and as thin film coatings. The toxic effects of four different PVK-SWNT (97:3 wt %) nanocomposite concentrations (1, 0.5, 0.05, and 0.01 mg/mL) containing 0.03, 0.015, 0.0015, and 0.0003 mg/mL of SWNT, respectively, were determined for planktonic cells and biofilms of Escherichia coli (E. coli) and Bacillus subtilis (B. subtilis). The results showed that the nanocomposite PVK-SWNT had antibacterial activity on planktonic cells and biofilms at all concentration levels. Higher bacterial inactivation (94% for E. coli and 90% for B. subtilis) were achieved in planktonic cells at a PVK-SWNT concentration of 1 mg/mL. Atomic force microscopy (AFM) imaging showed significant reduction of biofilm growth on PVK-SWNT coated surfaces. This study established for the first time that the improved dispersion of SWNTs in aqueous solutions in the presence of PVK enhances the antimicrobial effects of SWNTs at very low concentrations. Furthermore, PVK-SWNT can be used as an effective thin film coating material to resist biofilm formation.

  7. Antimicrobial PVK:SWNT nanocomposite coated membrane for water purification: performance and toxicity testing. (United States)

    Ahmed, Farid; Santos, Catherine M; Mangadlao, Joey; Advincula, Rigoberto; Rodrigues, Debora F


    This study demonstrated that coated nitrocellulose membranes with a nanocomposite containing 97% (wt%) of polyvinyl-N-carbazole (PVK) and 3% (wt%) of single-walled carbon nanotubes (SWNTs) (97:3 wt% ratio PVK:SWNT) achieve similar or improved removal of bacteria when compared with 100% SWNTs coated membranes. Membranes coated with the nanocomposite exhibited significant antimicrobial activity toward Gram-positive and Gram-negative bacteria (≈ 80-90%); and presented a virus removal efficiency of ≈ 2.5 logs. Bacterial cell membrane damage was considered a possible mechanism of cellular inactivation since higher efflux of intracellular material (Deoxyribonucleic acid, DNA) was quantified in the filtrate of PVK-SWNT and SWNT membranes than in the filtrate of control membranes. To evaluate possible application of these membrane filters for drinking water treatment, toxicity of PVK-SWNT was tested against fibroblast cells. The results demonstrated that PVK-SWNT was non toxic to fibroblast cells as opposed to pure SWNT (100%). These results suggest that it is possible to synthesize antimicrobial nitrocellulose membranes coated with SWNT based nanocomposites for drinking water treatment. Furthermore, membrane filters coated with the nanocomposite PVK-SWNT (97:3 wt% ratio PVK:SWNT) will produce more suitable coated membranes for drinking water than pure SWNTs coated membranes (100%), since the reduced load of SWNT in the nanocomposite will reduce the use of costly and toxic SWNT nanomaterial on the membranes.

  8. Screening and selection of wild strains for L-arabinose isomerase production

    Directory of Open Access Journals (Sweden)

    R. M. Manzo


    Full Text Available The majority of L-arabinose isomerases have been isolated by recombinant techniques, but this methodology implies a reduced technological application. For this reason, 29 bacterial strains, some of them previously characterized as L-arabinose isomerase producers, were assayed as L-arabinose fermenting strains by employing conveniently designed culture media with 0.5% (w/v L-arabinose as main carbon source. From all evaluated bacterial strains, Enterococcus faecium DBFIQ ID: E36, Enterococcus faecium DBFIQ ID: ETW4 and Pediococcus acidilactici ATCC ID: 8042 were, in this order, the best L-arabinose fermenting strains. Afterwards, to assay L-arabinose metabolization and L-arabinose isomerase activity, cell-free extract and saline precipitated cell-free extract of the three bacterial cultures were obtained and the production of ketoses was determined by the cysteine carbazole sulfuric acid method. Results showed that the greater the L-arabinose metabolization ability, the higher the enzymatic activity achieved, so Enterococcus faecium DBFIQ ID: E36 was selected to continue with production, purification and characterization studies. This work thus describes a simple microbiological method for the selection of L-arabinose fermenting bacteria for the potential production of the enzyme L-arabinose isomerase.

  9. Very large photoconduction enhancement upon self-assembly of a new triindole derivative in solution-processed films

    Energy Technology Data Exchange (ETDEWEB)

    Gallego-Gomez, Francisco; Villalvilla, Jose M.; Quintana, Jose A.; Diaz-Garcia, Maria A. [Instituto Universitario de Materiales de Alicante and Dpto. Fisica Aplicada, Universidad de Alicante, 03080 Alicante (Spain); Garcia-Frutos, Eva M.; Gutierrez-Puebla, Enrique; Monge, Angeles; Gomez-Lor, Berta [Instituto de Ciencia de Materiales de Madrid, CSIC, C/Sor Juana Ines de la Cruz 3, 28049 Madrid (Spain)


    A new carbazole-related small molecule exhibiting self-assembly into ordered nanostructures in solution-processed cast films has been synthesized and its charge-photogeneration and -transport properties have been investigated. Large photoconductivity was measured in the amorphous state while an enormous improvement in the photoconduction properties was observed when the molecules spontaneously organized. Photocurrents increased upon self-assembly by up to four orders of magnitude, mostly due to the drastic enhancement of the charge photogeneration. A greatly favorable arrangement of the aromatic cores in the resulting nanostructures, which were characterized by X-ray analysis, may explain these improvements. Photocurrents of mA cm{sup -2}, on/off ratios of 10{sup 4} and quantum efficiencies of unity at low field and light intensity, which are among the best values reported to date, along with the simplicity of fabrication, give this readily-available organic system great potential for use in plastic optoelectronic devices. (Copyright copyright 2011 WILEY-VCH Verlag GmbH and Co. KGaA, Weinheim)

  10. Push-Pull Type Porphyrin Based Sensitizers: The Effect of Donor Structure on the Light-Harvesting Ability and Photovoltaic Performance

    KAUST Repository

    Qi, Qingbiao


    Push-pull type porphyrin-based sensitizers have become promising candidates for high-efficiency dye sensitized solar cells (DSCs). It is of importance to understand the fundamental structure-physical property-photovoltaic performance relationships by varying the donor and acceptor moieties. In this work, two new porphyrin-based sensitizers, WW-7 and WW-8, were synthesized and compared with the known sensitizer YD20. All the three dyes have the same porphyrin core and acceptor group (ethynylbenzoic acid) but their donor groups vary from the triphenylamine in YD20 to meso-diphenylaminoanthracene in WW-7 to N-phenyl carbazole in WW-8. Co(II/III)-based DSC device characterizations revealed that WW-7 showed enhanced light harvesting ability in comparison to YD20 with improved incident photon-to-collected electron conversion efficiencies (IPCEs). As a result, WW-7 displayed much higher short circuit current (Jsc: 13.54 mA cm-2) and open-circuit voltage (Voc: 0.829 V), with a power conversion efficiency (η) as high as 7.7%. Under the same conditions, YD20 cell exhibited a power conversion efficiency of 6.6% and the dye WW-8 showed even lower efficiency (η = 4.6%). Detailed physical measurements and theoretic calculations were conducted to understand the difference and reveal how three different donor structures affect their molecular orbital profile, light-harvesting ability, energy level alignment, and eventually the photovoltaic performance.

  11. Lignin Peroxidase Oxidation of Aromatic Compounds in Systems Containing Organic Solvents (United States)

    Vazquez-Duhalt, Rafael; Westlake, Donald W. S.; Fedorak, Phillip M.


    Lignin peroxidase from Phanerochaete chrysosporium was used to study the oxidation of aromatic compounds, including polycyclic aromatic hydrocarbons and heterocyclic compounds, that are models of moieties of asphaltene molecules. The oxidations were done in systems containing water-miscible organic solvents, including methanol, isopropanol, N, N-dimethylformamide, acetonitrile, and tetrahydrofuran. Of the 20 aromatic compounds tested, 9 were oxidized by lignin peroxidase in the presence of hydrogen peroxide. These included anthracene, 1-, 2-, and 9-methylanthracenes, acenaphthene, fluoranthene, pyrene, carbazole, and dibenzothiophene. Of the compounds studied, lignin peroxidase was able to oxidize those with ionization potentials of <8 eV (measured by electron impact). The reaction products contain hydroxyl and keto groups. In one case, carbon-carbon bond cleavage, yielding anthraquinone from 9-methylanthracene, was detected. Kinetic constants and stability characteristics of lignin peroxidase were determined by using pyrene as the substrate in systems containing different amounts of organic solvent. Benzyl alkylation of lignin peroxidase improved its activity in a system containing water-miscible organic solvent but did not increase its resistance to inactivation at high solvent concentrations. PMID:16349176

  12. High-efficiency diphenylsulfon derivatives-based organic light-emitting diode exhibiting thermally activated delayed fluorescence

    CERN Document Server

    Lee, Geon Hyeong


    Novel thermally activated delayed fluorescence (TADF) material with diphenyl sulfone (DPS) as an electron acceptor and 3,6-dimethoxycarbazole (DMOC) and 1,3,6,8-Tetramethyl-9H-carbazole (TMC) as electron donors were investigated theoretically for a blue organic light emitting diode (OLED) emitter. We calculate the energies of the first singlet (S1) and first triplet (T1)-excited states of TADF materials by performing density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations on the ground state using a dependence on charge transfer amounts for the optimal Hartree-Fock percentage in the exchange-correlation of TD-DFT. The calculated {\\Delta}EST values of TMC-DPS (0.094 eV) was smaller than DMOC-DPS (0.386 eV) because of the large dihedral angles between the donor and accepter moieties. We show that TMC-DPS would have a suitable blue OLED emitter, because it has a large dihedral angle that creates a small spatial overlap between the HOMO and the LUMO and, consequently, the small {\\Delta}EST an...

  13. Au@Ag core-shell nanocubes for efficient plasmonic light scattering effect in low bandgap organic solar cells. (United States)

    Baek, Se-Woong; Park, Garam; Noh, Jonghyeon; Cho, Changsoon; Lee, Chun-Ho; Seo, Min-Kyo; Song, Hyunjoon; Lee, Jung-Yong


    In this report, we propose a metal-metal core-shell nanocube (NC) as an advanced plasmonic material for highly efficient organic solar cells (OSCs). We covered an Au core with a thin Ag shell as a scattering enhancer to build Au@Ag NCs, which showed stronger scattering efficiency than Au nanoparticles (AuNPs) throughout the visible range. Highly efficient plasmonic organic solar cells were fabricated by embedding Au@Ag NCs into an anodic buffer layer, poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS), and the power conversion efficiency was enhanced to 6.3% from 5.3% in poly[N-9-hepta-decanyl-2,7-carbazole-alt-5,5-(4,7-di-2-thienyl-2,1,3-benzothiadiazole)] (PCDTBT):[6,6]-phenyl C71-butyric acid methyl ester (PC70BM) based OSCs and 9.2% from 7.9% in polythieno[3,4-b]thiophene/benzodithiophene (PTB7):PC70BM based OSCs. The Au@Ag NC plasmonic PCDTBT:PC70BM-based organic solar cells showed 2.2-fold higher external quantum efficiency enhancement compared to AuNPs devices at a wavelength of 450-700 nm due to the amplified plasmonic scattering effect. Finally, we proved the strongly enhanced plasmonic scattering efficiency of Au@Ag NCs embedded in organic solar cells via theoretical calculations and detailed optical measurements.

  14. First-principles study of Carbz-PAHTDDT dye sensitizer and two Carbz-derived dyes for dye sensitized solar cells

    CERN Document Server

    Mohammadi, Narges


    Two new carbazole-based organic dye sensitizers are designed and investigated in silico. These dyes are designed through chemical modifications of the conjugated bridge of a reference organic sensitizer known as Carbz-PAHTDDT (S9) dye. The aim of designing these dyes was to reduce the energy gap between their highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and to red-shift their absorption response compared to those of the reference S9 dye sensitizer. This reference dye has a reported promising efficiency when coupled with ferrocene-based electrolyte composition. To investigate geometric and electronic structure, density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations were conducted on the new dyes as well as the reference dye. The present study indicated that the long-range correction to the theoretical model in the TD-DFT simulation is important to produce accurate absorption wavelengths.The theoretical studies have shown a reduced HOMO-LUMO gap ...

  15. Ultrathin ammonium heptamolybdate films as efficient room-temperature hole transport layers for organic solar cells. (United States)

    Qiu, Weiming; Hadipour, Afshin; Müller, Robert; Conings, Bert; Boyen, Hans-Gerd; Heremans, Paul; Froyen, Ludo


    Ammonium heptamolybdate (NH4)6Mo7O24·4H2O (AHM) and its peroxo derivatives are analyzed as solution-processed room temperature hole transport layer (HTL) in organic solar cells. Such AHM based HTLs are investigated in devices with three different types of active layers, i.e., solution-processed poly(3-hexylthiophene)/[6,6]-phenyl C61-butyric acid methyl ester(P3HT/PC60BM), poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)]/[6,6]-phenyl C70-butyric acid methyl ester(PCDTBT/PC70BM) and evaporated small molecule chloro(subphthalocyaninato)boron(III) (SubPc)/C60. By virtue of their high work functions, AHM based HTLs outperform the commonly used poly(3,4-ethylenedioxythiophene):polystyrenesulfonate (PEDOT:PSS) HTL for devices employing deep HOMO level active materials. Moreover, devices using AHM based HTLs can achieve higher short circuit current (Jsc) than the ones with evaporated molybdenum oxide(eMoO3), and thus better power conversion efficiency (PCE). In addition, P3HT/PC60BM devices with AHM based HTLs show air stability comparable to those with eMoO3, and much better than the ones with PEDOT:PSS.

  16. Development of analytical procedures for coprocessing

    Energy Technology Data Exchange (ETDEWEB)

    Vogh, J.W.; Anderson, R.P.


    Maya crude residue and Illinois No. 6 coal have been processed together over a range of reactant ratios to produce material for study of the product composition and of the coprocessing chemistry. The reaction conditions have been described in previous reports. Acid fractions have been derivatized to produce {sup 13}C tagged products suitable for NMR analysis. The acids have been identified as phenols and other oxygen acids, nitrogen acids including carbazoles, and benzylic and sulfur acids. All of the acid fractions appear to be essentially monofunctional. Base fractions were analyzed by nonaqueous titration and were shown to consist of azaarenes and arylamines. Two of the distillates boiling below 175{degrees}C were analyzed by PIANO capillary gas chromatography. Maya crude petroleum fractions similar to those obtained from coprocessing products have been analyzed for carbon isotope ratios. These fractions were prepared directly from the Maya crude without application of hydrogenation or other processing chemistry. Trends indicating isotopic fractionation coprocessing to that reported earlier for coprocessing products were observed. 14 figs., 13 tabs.


    Directory of Open Access Journals (Sweden)

    C. S. ROSA


    Full Text Available

    Hyaluronic acid (HA is part of the connective tissue. The polymer is composed of alternating units of ß-d-glucuronic acid and N-acetyl-ß-d-glucosamine linked, respectively, via 1-3 and 1-4 bonds. The chicken crest is one of the richest tissues in this polysaccharide. Since Brazil is one of the main chicken exporters in the world, the utilization of the crests of abated animals for the HA obtaining is particularly attractive. The present work sought to extract HA from chicken crest and to determine the molar mass of the extracted acid. Extraction was accomplished by proteolytic digestion with papain during 24 h at 60oC, followed by precipitation with cetylpyridinium chloride (CPC. Hexuronic acid content was determined via the carbazole method, the intrinsic viscosity was measured using the ball viscosimeter, and the molar mass was calculated by extrapolating the calibration line to zero. In addition, qualitative infrared spectroscopy was carried out on the sample using the Bomem MB spectrophotometer. The results show that the extraction method was effective: the extracted acid possesses a large molecular mass, and the extract contains a signifi cant amount of HA.

  18. Isolation and Quantification of Glycosaminoglycans from Human Hair Shaft (United States)

    Bonovas, Stefanos; Sitaras, Nikolaos


    Background There is evidence that glycosaminoglycans (GAGs) are present in the hair shaft within the follicle but there are no studies regarding GAGs isolation and measurement in the human hair shaft over the scalp surface, it means, in the free hair shaft. Objective The purpose of our research was to isolate and measure the total GAGs from human free hair shaft. Methods Seventy-five healthy individuals participated in the study, 58 adults, men and women over the age of 50 and 17 children (aged 4~9). GAGs in hair samples, received from the parietal and the occipital areas, were isolated with 4 M guanidine HCl and measured by the uronic acid-carbazole reaction assay. Results GAGs concentration was significantly higher in the occipital area than in the parietal area, in all study groups. GAG levels from both areas were significantly higher in children than in adults. GAG levels were not associated with gender, hair color or type. Conclusion We report the presence of GAGs in the human free hair shaft and the correlation of hair GAG levels with the scalp area and participants' age. PMID:27746630

  19. Photovoltaic Small Molecules of TPA(FxBT-T-Cz)3: Tuning Open-Circuit Voltage over 1.0 V for Their Organic Solar Cells by Increasing Fluorine Substitution. (United States)

    Wang, Qiong; Duan, Linrui; Tao, Qiang; Peng, Wenhong; Chen, Jianhua; Tan, Hua; Yang, Renqiang; Zhu, Weiguo


    To simultaneously improve both open-circuit voltage (Voc) and short-circuit current density (Jsc) for organic solar cells, a novel D(A-π-Ar)3 type of photovoltaic small molecules of TPA(FxBT-T-3Cz)3 was designed and synthesized, which contain central triphenylamine (TPA), terminal carbazole (Cz), armed fluorine-substituted benzothiadiazole (FxBT, where x = 1 or 2), and bridged thiophene (T) units. A narrowed ultraviolet-visible absorption and a decreasing highest occupied molecular orbital energy level were observed from TPA(F1BT-T-3Cz)3 to TPA(F2BT-T-3Cz)3 with increasing fluorine substitution. However, the TPA(F2BT-T-3Cz)3/PC71BM-based solar devices showed a rising Voc of 1.01 V and an enhanced Jsc of 10.84 mA cm(-2) as well as a comparable power conversion efficiency of 4.81% in comparison to the TPA(F1BT-T-3Cz)3/PC71BM-based devices. Furthermore, in comparison to the parent TPA(BT-T-3Cz)3 molecule without fluorine substitution, the fluorine-substituted TPA(FxBT-T-3Cz)3 molecules exhibited significantly incremental Voc and Jsc values in their bulk heterojunction organic solar cells, owing to fluorine incorporation in the electron-deficient benzothiadiazole unit.

  20. The AhR is involved in the regulation of LoVo cell proliferation through cell cycle-associated proteins. (United States)

    Yin, Jiuheng; Sheng, Baifa; Han, Bin; Pu, Aimin; Yang, Kunqiu; Li, Ping; Wang, Qimeng; Xiao, Weidong; Yang, Hua


    Some ingredients in foods can activate the aryl hydrocarbon receptor (AhR) and arrest cell proliferation. In this study, we hypothesized that 6-formylindolo [3, 2-b] carbazole (FICZ) arrests the cell cycle in LoVo cells (a colon cancer line) through the AhR. The AhR agonist FICZ and the AhR antagonist CH223191 were used to treat LoVo cells. Real-time PCR and Western blot analyses were performed to detect the expression of the AhR, CYP1A1, CDK4, cyclinD1, cyclin E, CDK2, P27, and pRb. The distribution and activation of the AhR were detected with immunofluorescence. A 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay and flow cytometric analysis were performed to measure cell viability, cell cycle stage, and apoptosis. Our results show that FICZ inhibited LoVo cell proliferation by inducing G1 cell cycle arrest but had no effect on epithelial apoptosis. Further analysis found that FICZ downregulated cyclinD1 and upregulated p27 expression to arrest Rb phosphorylation. The downregulation of cyclinD1 and upregulation of p27 were abolished by co-treatment with CH223191. We conclude that the AhR, when activated by FICZ (an endogenous AhR ligand), can arrest the cell cycle and block LoVo cell proliferation.


    Directory of Open Access Journals (Sweden)

    Wei Wei


    Full Text Available Indole-based receptors such as biindole, carbazole, and indolocarbazole are regarded as some of the most favorable anion receptors in molecular recognition. This is because indole groups possess N–H groups as hydrogen-bonding donors. The introduction of amide groups in the indole framework can induce strong binding properties and good water solubility. In this study, we designed and synthesized a series of N-(indol-3-ylglyoxylylbenzylamine derivatives as novel and simple anion receptors. The receptors derived by aryl and aliphatic amines can selectively recognize F– based on a color change from colorless-to-yellow in DMSO. The receptors derived by hydrazine hydrate can recognize F–, AcO–, and H2PO4– by similar color changes in DMSO and can even enable the selective recognition of F– in a DMSO–H2O binary solution by the naked eye. Spectrographic data indicate that complexes are formed between receptors and anions through multiple hydrogen-bonding interactions in dual solutions.

  2. Power generating reflective-type liquid crystal displays using a reflective polariser and a polymer solar cell (United States)

    Ho Huh, Yoon; Park, Byoungchoo


    We herein report the results of a study of a power generating reflective-type liquid crystal display (LCD), composed of a 90° twisted nematic (TN) LC cell attached to the top of a light-absorbing polymer solar cell (PSC), i.e., a Solar-LCD. The PSC consisted of a polymer bulk-heterojunction photovoltaic (PV) layer of poly[[9-(1-octylnonyl)-9H-carbazole-2,7-diyl]-2,5-thiophenediyl-2,1,3-benzothiadiazole-4,7-diyl-2,5-thiophenediyl] and [6,6]-phenyl C71 butyric acid methyl ester (PCDTBT:PCBM70), and showed a high power conversion efficiency of about 5%. In order to improve the visibility of the Solar-LCD, between the TN-LC and the PV cells we inserted a reflective polariser of a giant birefringent optical (GBO) film. The reflectivity from the Solar-LCD was observed to be considerably increased by more than 13-15% under illumination by visible light. The Solar-LCD also exhibited a significantly improved contrast ratio of more than 17-19. We believe there is a clear case for using such Solar-LCDs in new power-generating reflective-type displays; taken as a whole these results also demonstrate the possibility of their application in a number of energy-harvesting opto-electrical display devices.

  3. Murrayafoline A attenuates the Wnt/{beta}-catenin pathway by promoting the degradation of intracellular {beta}-catenin proteins

    Energy Technology Data Exchange (ETDEWEB)

    Choi, Hyuk; Gwak, Jungsug; Cho, Munju; Ryu, Min-Jung [PharmacoGenomics Research Center, Inje University, Busan 614-735 (Korea, Republic of); Lee, Jee-Hyun; Kim, Sang Kyum; Kim, Young Ho [College of Pharmacy, Chungnam National University, Daejeon 305-764 (Korea, Republic of); Lee, Gye Won [Department of Pharmaceutical Engineering, Konyang University, Nonsan 320-711 (Korea, Republic of); Yun, Mi-Young [Department of Beauty Health Care, Daejeon University, Daejeon 305-764 (Korea, Republic of); Cuong, Nguyen Manh [Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, Hanoi (Viet Nam); Shin, Jae-Gook [PharmacoGenomics Research Center, Inje University, Busan 614-735 (Korea, Republic of); Song, Gyu-Yong, E-mail: [College of Pharmacy, Chungnam National University, Daejeon 305-764 (Korea, Republic of); Oh, Sangtaek, E-mail: [PharmacoGenomics Research Center, Inje University, Busan 614-735 (Korea, Republic of)


    Molecular lesions in Wnt/{beta}-catenin signaling and subsequent up-regulation of {beta}-catenin response transcription (CRT) occur frequently during the development of colon cancer. To identify small molecules that suppress CRT, we screened natural compounds in a cell-based assay for detection of TOPFalsh reporter activity. Murrayafoline A, a carbazole alkaloid isolated from Glycosmis stenocarpa, antagonized CRT that was stimulated by Wnt3a-conditioned medium (Wnt3a-CM) or LiCl, an inhibitor of glycogen synthase kinase-3{beta} (GSK-3{beta}), and promoted the degradation of intracellular {beta}-catenin without altering its N-terminal phosphorylation at the Ser33/37 residues, marking it for proteasomal degradation, or the expression of Siah-1, an E3 ubiquitin ligase. Murrayafoline A repressed the expression of cyclin D1 and c-myc, which is known {beta}-catenin/T cell factor (TCF)-dependent genes and thus inhibited the proliferation of various colon cancer cells. These findings indicate that murrayafoline A may be a potential chemotherapeutic agent for use in the treatment of colon cancer.

  4. Decreased Expression of the Aryl Hydrocarbon Receptor in Ocular Behcet’s Disease

    Directory of Open Access Journals (Sweden)

    Chaokui Wang


    Full Text Available Recent studies show that the aryl hydrocarbon receptor (AhR is involved in immune responses. AhR is activated following interaction with its ligands, such as 6-formylindolo[3,2-b]carbazole (FICZ and 2-(1′H-indole-3′-carbonyl-thiazole-4-carboxylic acid methyl ester (ITE. In this study, we investigated the role of AhR activation by its endogenous ligands in the pathogenesis of ocular Behcet’s disease (BD. The expression of AhR was significantly decreased in active BD patients as compared to inactive BD patients and normal controls. Both FICZ and ITE inhibited Th1 and Th17 polarization and induced the expression of IL-22 by PBMCs and by CD4+T cells in active BD patients and normal controls. Stimulation of purified CD4+T cells with FICZ or ITE caused a decreased expression of RORC, IL-17, IL-23R, and CCR6 and an increased phosphorylation of STAT3 and STAT5. The present study suggests that a decreased AhR expression is associated with disease activity in BD patients. The activation of AhR by either FICZ or ITE was able to inhibit Th1 and Th17 cell polarization. Further studies are needed to investigate whether modulation of AhR might be used in the treatment of BD.

  5. Decreased expression of the aryl hydrocarbon receptor in ocular Behcet's disease. (United States)

    Wang, Chaokui; Ye, Zi; Kijlstra, Aize; Zhou, Yan; Yang, Peizeng


    Recent studies show that the aryl hydrocarbon receptor (AhR) is involved in immune responses. AhR is activated following interaction with its ligands, such as 6-formylindolo[3,2-b]carbazole (FICZ) and 2-(1'H-indole-3'-carbonyl)-thiazole-4-carboxylic acid methyl ester (ITE). In this study, we investigated the role of AhR activation by its endogenous ligands in the pathogenesis of ocular Behcet's disease (BD). The expression of AhR was significantly decreased in active BD patients as compared to inactive BD patients and normal controls. Both FICZ and ITE inhibited Th1 and Th17 polarization and induced the expression of IL-22 by PBMCs and by CD4(+)T cells in active BD patients and normal controls. Stimulation of purified CD4(+)T cells with FICZ or ITE caused a decreased expression of RORC, IL-17, IL-23R, and CCR6 and an increased phosphorylation of STAT3 and STAT5. The present study suggests that a decreased AhR expression is associated with disease activity in BD patients. The activation of AhR by either FICZ or ITE was able to inhibit Th1 and Th17 cell polarization. Further studies are needed to investigate whether modulation of AhR might be used in the treatment of BD.

  6. Macroscopic birefringence in liquid crystals from novel cyanobacterial polysaccharide with an extremely high molecular weight (United States)

    Okajima-Kaneko, Maiko; Hayasaka-Kaneko, Daisaku; Miyazato, Shinji; Kaneko, Tatsuo


    We report an efficient method for extraction of anionic polysaccharides (PS) from cyanobacteria, Aphanothece sacrum; we used a hot alkaline solution (0.01 N NaOH) as an elution solvent in the first step of the extraction and isopropanol as a precipitation solvent in the last step. Thin fibers of PS were obtained at a high yield (50-80 % to the weight of the raw cyanobacterial sample). The spectroscopy and elemental analyses indicated the PS contains fucose, uronic acids (14.2 % by a carbazole-sulfuric acid method), a sugar unit containing amides. The solution of PS with a concentration of 1 wt% showed a very high viscosity (80 000cps) implying a high molecular weight, and a strong macroscopic birefringence with a texture typical of nematic liquid crystals was confirmed by crossed-polarizing microscopy (more than 0.5 wt%). The PS from A. sacrum may form a special structure rigid-rod enough to show LC phase and macroscopic birefringence.

  7. Extraction of Pectin from Sugar Beet Pulp%甜菜压粕中果胶的提取工艺研究

    Institute of Scientific and Technical Information of China (English)

    王文婷; 朱思明; 陈志江; 杨永军; 高卫军; 于淑娟


    Pectin was extracted from the sugar beet pulp by using an acid extraction and alcohol precipitation technique. Ratio of gaining pectin for solid-to-liquid ratio, temperature, pH and time of extraction were discussed. The optimal conditions for the extraction were determined as solid-to-liquid ratio 1:20, temperature 90 ℃, pH 1.0 and time 3.5 h. In the best conditions, the average yield was 27.10%, with carbazole colorimetric determination of galacturonic acid content and pectin purity being of 17.82% and 65.76%, respectively.%探讨了料液比、提取温度、提取液pH值以及提取时间对酸提醇析法提取甜菜压粕中果胶得率的影响,结果表明,甜菜压粕中果胶的最佳提取工艺为:料液比1∶20,浸提温度90℃,提取液pH 1.0,提取时间3.5 h;在最佳条件下,果胶平均得率为27.10%,用咔唑比色法测定半乳糖醛酸的含量为17.82%,果胶纯度为65.76%.

  8. National Institute for Petroleum and Energy Research quarterly technical report, January 1--March 31, 1990

    Energy Technology Data Exchange (ETDEWEB)


    Fuels research is discussed in the following areas: (1) Department of Analytical Methodology for Analysis of Heavy Crudes; and (2) thermochemistry and thermophysical properties of organic nitrogen-, and diheteroatom-containing compounds. This quarter for project (1), inspection analysis of five 1000{degree}F+ resids employed in the carbonization study were completed. Also, subfractionation of Cerro Negro neutrals fraction was carried out. Progress on Project 2 consisted of: a thermodynamic analysis for the key hydrogen-consuming steps in the hydrodenitrogenation (HDN) reaction network for quinoline; heat-capacity and enthalpy measurements were completed for the diheteroatom-containing compound, thianthrene. Following completion measurements on thianthrene, the heat capacity of the empty calorimeter was determined, and in another calorimeter, heat-capacity and enthalpy studies were started on benzoxazole. Methods to convert benzoxazole to its low-temperature form were developed, and measurements were completed between 80 and 240 K; and high-temperature heat capacities were determined for phenoxathin and carbazole. 1 ref., 14 figs., 11 tabs.

  9. Identification of sulfur heterocycles in coal liquids and shale oils. Technical progress report, August 1, 1980-May 1, 1981

    Energy Technology Data Exchange (ETDEWEB)

    Lee, M. L.; Castle, R. N.


    The sulfur heterocycle separation scheme which was described in the last progress report was evaluated for quantitative recovery of individual components. The results indicate that recoveries can range from 10% to approx. 30% depending on the structure of the compound. During this period, 23 unsubstituted sulfur-containing heterocyclic ring systems were synthesized in oder to confirm GC/MS identifications and for biological testing. The four possible 3-ring heterocycles and the thirteen possible 4-ring heterocycles were tested for mutagenic activity in the histidine reversion (Ames assay) system. One of the 3-ring isomers, naphtho(1,2-b)-thiophene, and six of the 4-ring isomers induced mutations in Salmonella test strains. One of these compounds, phenanthro(3,4-b)thiophene, displayed approximately the same mutagenic activity as benzo(a)pyrene. A two-step adsorption chromatographic procedure was developed in order to fractionate synthetic fuels into various chemical-type classes for studying the relative concentrations and mutagenic activities of the various types. An SRC-II Heavy Distillate was fractionated into aliphatic hydrocarbons, polycyclic aromatic hydrocarbons, sulfur heterocycles, indoles and carbazoles, azaarenes, and amino polycyclic aromatic hydrocarbons. It was found that the amino-PAH fraction contained most of the mutagenic activity. A survey was made for compounds containing both nitrogen and sulfur heteroatoms in their structures. A number of these compounds were detected by GC using nitrogen- and sulfur-selective detection.

  10. Reactivity and Synthetic Applications of 4,5-Dicyanopyridazine: An Overview

    Directory of Open Access Journals (Sweden)

    Donatella Giomi


    Full Text Available Despite the poor reputation of electron-deficient pyridazines in intermolecular Hetero Diels-Alder (HDA reactions, 4,5-dicyanopyridazine (DCP showed a surprising reactivity as a heterocyclic azadiene in inverse electron-demand HDA processes with different dienophiles. The use of alkenes, alkynes and enamines as 2p electron counterparts afforded dicyanocyclohexa-1,3-dienes and substituted phthalonitriles, respectively, while the use of suitable bis-dienophiles provides a general strategy for the one-pot synthesis of polycyclic carbo- and hetero-cage systemsthrough pericyclic three-step homodomino processes. HDA reactions with heterocyclic dienophiles allowed direct benzoannelation: in particular, pyrrole and indole derivatives were converted to dicyano-indoles and -carbazoles. In addition an unprecedented reactivity of DCP as a very reactive heterocyclic electrophile at the C-4 carbon was also evidenced: by changing the experimental conditions, cyanopyrrolyl- and cyanoindolyl-pyridazines were obtained through reactions of pyrrole and indole systems as carbon nucleophiles in formal SNAr2 processes where a CN group of DCP acts as leaving group. Thus, careful control of the reaction conditions allows exploitation of both pathways for the synthesis of different classes of heterocyclic derivatives.

  11. Oil biodegradation by Bacillus strains isolated from the rock of an oil reservoir located in a deep-water production basin in Brazil

    Energy Technology Data Exchange (ETDEWEB)

    Duarte da Cunha, C.; Rosado, A.S.; Seldin, L.; Weid, I. von der [Universidade Federal do Rio de Janeiro (Brazil). Dept. de Microbiologia Geral; Sebastian, G.V. [CENPES, Petrobras, Ilha do Fundao, Rio de Janeiro (Brazil)


    Sixteen spore forming Gram-positive bacteria were isolated from the rock of an oil reservoir located in a deep-water production basin in Brazil. These strains were identified as belonging to the genus Bacillus using classical biochemical techniques and API 50CH kits, and their identity was confirmed by sequencing of part of the 16S rRNA gene. All strains were tested for oil degradation ability in microplates using Arabian Light and Marlin oils and only seven strains showed positive results in both kinds of oils. They were also able to grow in the presence of carbazole, n-hexadecane and polyalphaolefin (PAO), but not in toluene, as the only carbon sources. The production of key enzymes involved with aromatic hydrocarbons biodegradation process by Bacillus strains (catechol 1,2-dioxygenase and catechol 2,3-dioxygenase) was verified spectrophotometrically by detection of cis,cis-muconic acid and 2-hydroxymuconic semialdehyde, and results indicated that the ortho ring cleavage pathway is preferential. Furthermore, polymerase chain reaction (PCR) products were obtained when the DNA of seven Bacillus strains were screened for the presence of catabolic genes encoding alkane monooxygenase, catechol 1,2-dioxygenase, and/or catechol 2,3-dioxygenase. This is the first study on Bacillus strains isolated from an oil reservoir in Brazil. (orig.)

  12. Electrospinning fabrication and oxygen sensing properties of Cu(I) complex-polystyrene composite microfibrous membranes

    Energy Technology Data Exchange (ETDEWEB)

    Wang Liyan, E-mail: [Department of Orthodontics, School of Stomatology, Fourth Military Medical University, XiAn (China); Xu Yun [Department of Orthodontics, School of Stomatology, KunMing Medical College, Kunming (China); Lin Zhu [Department of Orthodontics, School of Stomatology, Fourth Military Medical University, XiAn (China); Zhao Ning [Department of Orthodontics, School of Stomatology, West China College, SiChuan University, ChengDu (China); Xu Yanhua [Department of Orthodontics, School of Stomatology, KunMing Medical College, Kunming (China)


    In this paper, a phosphorescent Cu(I) complex of [Cu(POP)(ECI-Phen)]BF{sub 4}, where POP=bis[2-(diphenylphosphino)phenyl]ether, and ECI-Phen=1-ethyl-2-(N-ethyl-carbazole-yl-4-)imidazo[4,5-f]1,10-phenanthroline, is incorporated into a polystyrene matrix of polystyrene (PS) to form microfibers membranes. The possibility of using the resulted composite microfibrous membranes as an optical oxygen sensor is explored. Good linearity and short response time are obtained with a sensitivity of 9.8. These results suggest that phosphorescent [Cu(POP)(ECI-Phen)]BF{sub 4} is a promising candidate for oxygen-sensors and PS is an excellent matrix for oxygen sensing material because it owns a large surface-area-to-volume ratio and can supply a homogeneous matrix for probe molecules. Further analysis suggests that the molecular structure of diamine ligand in Cu(I) complexes is critical for sensitivity due to the characteristic electronic structure of excited state Cu(I) complexes. - Highlights: {yields} Cu(I) complex is incorporated into polystyrene matrix to form nanofibers. {yields} Resulted sample exhibit good linearity and short response time. {yields} PS is an excellent matrix for oxygen sensing material for probe molecules. {yields} Molecular structure of diamine ligand is critical for sensitivity.

  13. A large dipole moment to promote gelation for 4-nitrophenylacrylonitrile derivatives with gelation-induced emission enhancement properties. (United States)

    Xue, Pengchong; Yao, Boqi; Zhang, Yuan; Chen, Peng; Li, Kechang; Liu, Baijun; Lu, Ran


    A series of 4-nitrophenylacrylonitrile and phenylacrylonitrile derivatives consisting of a carbazole moiety was synthesized. Some of these derivatives with longer alkyl chains and a nitro group could gelatinize some organic solvents, such as ethanol, n-butanol, ethyl acetate, and DMSO. By contrast, phenylacrylonitrile derivatives did not form gels in measured solvents. This result proved that the electron-withdrawing nitro moiety was important for gel formation because it conferred the molecules with large dipole moments, which enhanced the intermolecular interaction. Analyses by UV-vis absorption, X-ray diffraction, and scanning electron microscopy showed that the gelator molecules could self-assemble into one-dimensional nanofibers with layer packing, which further twisted into thicker fibers and formed three-dimensional networks in the gel phase. The single crystal structure of C4CNPA implied that the gelators might adopt an anti-parallel molecular stacking because of their larger ground-state dipole moment. Interestingly, the organogels had enhanced fluorescence relative to solutions at the same concentrations.

  14. Exploring the size adaptability of the B ring binding zone of the colchicine site of tubulin with para-nitrogen substituted isocombretastatins. (United States)

    Jiménez, Carmen; Ellahioui, Younes; Álvarez, Raquel; Aramburu, Laura; Riesco, Alejandra; González, Myriam; Vicente, Alba; Dahdouh, Abdelaziz; Ibn Mansour, Ahmed; Jiménez, Carlos; Martín, Diego; Sarmiento, Rogelio G; Medarde, Manuel; Caballero, Esther; Peláez, Rafael


    We have synthesized and assayed dimethylaminophenyl, pyrrolidin-1-ylphenyl and carbazole containing phenstatins and isocombretastatins as analogues of the highly potent indoleisocombretastatins with extended or reduced ring sizes. This is an attempt to explore beyond the structural constraints of the X-ray crystal structures the zone of the colchicine site where the tropolone ring of colchicine binds to tubulin (zone 1). The isocombretastatins display up to 30 fold increased water solubility when compared with combretastatin A-4, potent inhibition of tubulin polymerization, and nanomolar cytotoxicities against several human cancer cell lines irrespective of the size of the B ring. On the other hand, substitutions ortho to the nitrogen cause an important reduction in potency. We have also shown that representative compounds inhibit autophagy. These results show that zone 1 can adapt to systems of different size as far as they stay in a common plane, but does not tolerate substituents protruding above or below it. These results can help in the understanding of the binding modes of structures with similar systems and in the design of new colchicine site ligands.

  15. Studies of the effect of selected nondonor solvents on coal liquefaction yields

    Energy Technology Data Exchange (ETDEWEB)

    Jolley, R. L.; Rodgers, B. R.; Benjamin, B. M.; Poutsma, M. L.; Douglas, E. C.; McWhirter, D. A.


    The objective of this research program was to evaluate the effectiveness of selected nondonor solvents (i.e., solvents that are not generally considered to have hydrogen available for hydrogenolysis reactions) for the solubilization of coals. Principal criteria for selection of candidate solvents were that the compound should be representative of a major chemical class, should be present in reasonable concentration in coal liquid products, and should have the potential to participate in hydrogen redistribution reactions. Naphthalene, phenanthrene, pyrene, carbazole, phenanthridine, quinoline, 1-naphthol, and diphenyl ether were evaluated to determine their effect on coal liquefaction yields and were compared with phenol and two high-quality process solvents, Wilsonville SRC-I recycle solvent and Lummus ITSL heavy oil solvent. The high conversion efficacy of 1-naphthol may be attributed to its condensation to binaphthol and the consequent availability of hydrogen. The effectiveness of both the nitrogen heterocycles and the polycyclic aromatic hydrocarbon (PAH) compounds may be due to their polycyclic aromatic nature (i.e., possible hydrogen shuttling or transfer agents) and their physical solvent properties. The relative effectiveness for coal conversion of the Lummus ITSL heavy oil solvent as compared with the Wilsonville SRC-I process solvent may be attributed to the much higher concentration of 3-, 4-, and 5-ring PAH and hydroaromatic constituents in Lummus solvent. The chemistry of coal liquefaction and the development of recycle, hydrogen donor, and nondonor solvents are reviewed. The experimental methodology for tubing-bomb tests is outlined, and experimental problem areas are discussed.

  16. Naphthalene degradation by bacterial consortium (DV-AL) developed from Alang-Sosiya ship breaking yard, Gujarat, India. (United States)

    Patel, Vilas; Jain, Siddharth; Madamwar, Datta


    Naphthalene degrading bacterial consortium (DV-AL) was developed by enrichment culture technique from sediment collected from the Alang-Sosiya ship breaking yard, Gujarat, India. The 16S rRNA gene based molecular analyzes revealed that the bacterial consortium (DV-AL) consisted of four strains namely, Achromobacter sp. BAB239, Pseudomonas sp. DV-AL2, Enterobacter sp. BAB240 and Pseudomonas sp. BAB241. Consortium DV-AL was able to degrade 1000 ppm of naphthalene in Bushnell Haas medium (BHM) containing peptone (0.1%) as co-substrate with an initial pH of 8.0 at 37°C under shaking conditions (150 rpm) within 24h. Maximum growth rate and naphthalene degradation rate were found to be 0.0389 h(-1) and 80 mg h(-1), respectively. Consortium DV-AL was able to utilize other aromatic and aliphatic hydrocarbons such as benzene, phenol, carbazole, petroleum oil, diesel fuel, and phenanthrene and 2-methyl naphthalene as sole carbon source. Consortium DV-AL was also efficient to degrade naphthalene in the presence of other pollutants such as petroleum hydrocarbons and heavy metals.

  17. Neat C₇₀-based bulk-heterojunction polymer solar cells with excellent acceptor dispersion. (United States)

    Gasparini, Nicola; Righi, Sara; Tinti, Francesca; Savoini, Alberto; Cominetti, Alessandra; Po, Riccardo; Camaioni, Nadia


    The replacement of common fullerene derivatives with neat-C70 could be an effective approach to restrain the costs of organic photovoltaics and increase their sustainability. In this study, bulk-heterojunction solar cells made of neat-C70 and low energy-gap conjugated polymers, PTB7 and PCDTBT, are thoroughly investigated and compared. Upon replacing PC70BM with C70, the mobility of positive carriers in the donor phase is roughly reduced by 1 order of magnitude, while that of electrons is only slightly modified. It is shown that the main loss mechanism of the investigated neat-C70 solar cells is a low mobility-lifetime product. Nevertheless, PCDTBT:C70 devices undergo a limited loss of 7.5%, compared to the reference PCDTBT:PC70BM cells, reaching a record efficiency (4.44%) for polymer solar cells with unfunctionalized fullerenes. The moderate efficiency loss of PCDTBT:C70 devices, due to an unexpected excellent miscibility of PCDTBT:C70 blends, demonstrates that efficient solar cells made of neat-fullerene are possible. The efficient dispersion of C70 in the PCDTBT matrix is attributed to an interaction between fullerene and the carbazole unit of the polymer.

  18. Material optimization for electro-optic modulation and cascading (United States)

    Reyes, Jorge; Darracq, Bruno; Canva, Michael; Blanchard-Desce, Mireille H.; Chaput, Frederic; Lahlil, Khalid; Boilot, Jean-Pierre; Brun, Alain; Levy, Yves


    A large effort has been devoted to the preparation of organic polymeric materials for electro-optic modulation and more recently for cascading based processes. These materials contain push-pull chromophores either incorporated as guest in a high Tg polymeric matrix (doped polymers) or grafted onto the polymeric matrix. These systems present several advantages but require significant improvement at the molecular level- by designing optimized chromophores with very large molecular figure of merit specific to each application targeted. The sol-gel route was used to prepare hybrid organic-inorganic materials, for the fabrication of amorphous solids of various shapes (bulk, think films...). The results obtained on optimized chromophore-doped poled thin films emphasize that intermolecular interactions have to be taken into account, as already pointed out by Dalton and coworkers. By combining a molecular engineering strategy for getting large molecular figure of merit and by controlling the intermolecular dipole-dipole interactions via both tuning the push-pull chromophore concentration and the incorporation screening carbazole moieties in high concentration. This strategy allows us to obtain a r33 of about 50 pm/V at 831 nm for a new optimized chromophore structure. In parallel, these thin films are being processed to be used as passive components for integrated optics.

  19. Epigenetically Mediated Pathogenic Effects of Phenanthrene on Regulatory T Cells

    Directory of Open Access Journals (Sweden)

    Jing Liu


    Full Text Available Phenanthrene (Phe, a polycyclic aromatic hydrocarbon (PAH, is a major constituent of urban air pollution. There have been conflicting results regarding the role of other AhR ligands 2,3,7,8- tetrachlorodibenzo-p-dioxin (TCDD and 6-formylindolo [3,2-b]carbazole (FICZ in modifying regulatory T cell populations (Treg or T helper (Th17 differentiation, and the effects of Phe have been understudied. We hypothesized that different chemical entities of PAH induce Treg to become either Th2 or Th17 effector T cells through epigenetic modification of FOXP3. To determine specific effects on T cell populations by phenanthrene, primary human Treg were treated with Phe, TCDD, or FICZ and assessed for function, gene expression, and phenotype. Methylation of CpG sites within the FOXP3 locus reduced FOXP3 expression, leading to impaired Treg function and conversion of Treg into a CD4+CD25lo Th2 phenotype in Phe-treated cells. Conversely, TCDD treatment led to epigenetic modification of IL-17A and conversion of Treg to Th17 T cells. These findings present a mechanism by which exposure to AhR-ligands mediates human T cell responses and begins to elucidate the relationship between environmental exposures, immune modulation, and initiation of human disease.

  20. Using Geochemical Method to Distinguish Lateral Migration and Vertical Migration in Rifted Basin: A Case Study from Eastern Lujiapu Depression in the Kailu Basin, NE China

    Institute of Scientific and Technical Information of China (English)

    ZHOU Shuqing; HUANG Haiping; LIU Yuming


    Migration fractionation diagnosis is complicated in rifted basins where migration distance is generally short and lateral migration in sandy beds and vertical migration along faults are co-existed. Quantitative data from GC-MS analysis makes it possible to distinguish lateral and vertical migration effects. Oils discovered from the Jiaolige oilfield, eastern Lujiapu Depression are derived from single source rock with similar maturity, which is an ideal case to study the migration fractionation effects. Compositional differences among oils are largely caused by the migration fractionation either laterally in sand beds or vertically along the faults. Subtle maturity differences are assessed by the classic saturated hydrocarbon parameters which have certain influence on nitrogen compounds. In a certain maturity range, the ratios of shield and semi-shield isomers to the exposed isomers of alkylcarbazoles change with maturity in an opposite direction with migration fractionation, which may conceal the migration influence. However, migration and maturation have the same effects on absolute concentrations of aikylated carbazoles and benzocarhazole [a]/([a]+[c]) ratios, which provides an ideal tool for migration direction assessment. Continuous variations among different samples reflect increased migration distance in sandy beds, while abrupt changes may indicate the change of migration conduit systems. Integrated both geochemical interpretation and geological constrains, not only migration direction can be determined, but also the conduit systems through the sandy beds or the. faults can be recognized.

  1. Alkyl chain length-dependent surface reaction of dodecahydro-N-alkylcarbazoles on Pt model catalysts

    Energy Technology Data Exchange (ETDEWEB)

    Gleichweit, Christoph; Amende, Max; Bauer, Udo; Schernich, Stefan; Höfert, Oliver; Lorenz, Michael P. A.; Zhao, Wei; Bachmann, Philipp; Papp, Christian, E-mail: [Lehrstuhl für Physikalische Chemie II, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany); Müller, Michael; Koch, Marcus [Lehrstuhl für Chemische Reaktionstechnik, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany); Wasserscheid, Peter [Lehrstuhl für Chemische Reaktionstechnik, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany); Erlangen Catalysis Resource Center, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany); Libuda, Jörg; Steinrück, Hans-Peter [Lehrstuhl für Physikalische Chemie II, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany); Erlangen Catalysis Resource Center, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany)


    The concept of liquid organic hydrogen carriers (LOHC) holds the potential for large scale chemical storage of hydrogen at ambient conditions. Herein, we compare the dehydrogenation and decomposition of three alkylated carbazole-based LOHCs, dodecahydro-N-ethylcarbazole (H{sub 12}-NEC), dodecahydro-N-propylcarbazole (H{sub 12}-NPC), and dodecahydro-N-butylcarbazole (H{sub 12}-NBC), on Pt(111) and on Al{sub 2}O{sub 3}-supported Pt nanoparticles. We follow the thermal evolution of these systems quantitatively by in situ high-resolution X-ray photoelectron spectroscopy. We show that on Pt(111) the relevant reaction steps are not affected by the different alkyl substituents: for all LOHCs, stepwise dehydrogenation to NEC, NPC, and NBC is followed by cleavage of the C–N bond of the alkyl chain starting at 380–390 K. On Pt/Al{sub 2}O{sub 3}, we discern dealkylation on defect sites already at 350 K, and on ordered, (111)-like facets at 390 K. The dealkylation process at the defects is most pronounced for NEC and least pronounced for NBC.

  2. Using cyclopenta[2,1-b:3,4-c']dithiophene-4-one as a building block for low-bandgap conjugated copolymers applied in solar cells. (United States)

    Zhang, Wei; Cao, Jiamin; Liu, Ying; Xiao, Zuo; Zhu, Weiguo; Zuo, Qiqun; Ding, Liming


    A novel electron-accepting unit cyclopenta[2,1-b:3,4-c']dithiophene-4-one (CPDTO-c'), which is an isomer of CPDTO-b' was developed. CPDTO-c' can be incorporated into the D-A backbone through 5, 7 positions. The 2 position of CPDTO-c' can be easily functionalized with an electron-withdrawing chain. By copolymerizing CPDTO-c' with four different donor units: benzo[1,2-b:4,5-b']dithiophene (BDT), dithieno[3,2-b:2',3'-d]silole (DTS), carbazole, and fluorene, four new conjugated copolymers P1-P4 were obtained. All these polymers have good solubility and low-lying HOMO energy levels (-5.41 ∼ -5.92 eV). Among them, P1 and P2 exhibit broad absorption and narrow optical bandgaps of 1.91 and 1.72 eV, respectively. Solar cells based on P1/PC(71) BM afforded a PCE up to 2.72% and a high V(oc) up to ∼0.9 V.

  3. Synthesis, optical and electrochemical study of bipolar heterocyclic systems, including 1,2,4-oxadiazole moiety (United States)

    Selivanova, D. G.; Mayorova, O. A.; Gorbunov, A. A.; Vasyanin, A. N.; Dmitriev, M. V.; Shklyaeva, E. V.; Abashev, G. G.


    Two new 3,5-dihetarylsubstituted 1,2,4- oxadiazoles 8 a,b, including N-alkyl substituted carbazole and thiophene moieties, were synthesized as potential components of materials for organic electronics devices. Optical and electrochemical properties of all new compounds were investigated. On the basis of the experimental UV absorption data, the values of bandgap energies equal to 3.44 eV (8a) and 3.05 eV (8b) were determined. The values of their ionization potentials, HOMO levels (-5.62 eV for 8a, -5.46 eV - for 8b), as well as their electron affinity levels, LUMO levels (-2.2 eV for 8a, -2.4 eV - for 8b), were calculated from the results of electrochemical studies. The energy of the triplet excited states of 8 a,b was defined with the help of time-dependent density functional theory (TD-DFT), comprising 2.68 eV (8a) and 2.32 eV (8b), where the greatest value of this parameter was for the compound with a shorter conjugation chain.

  4. Isolation of oxygenase genes for indigo-forming activity from an artificially polluted soil metagenome by functional screening using Pseudomonas putida strains as hosts. (United States)

    Nagayama, Hirofumi; Sugawara, Tomonori; Endo, Ryo; Ono, Akira; Kato, Hiromi; Ohtsubo, Yoshiyuki; Nagata, Yuji; Tsuda, Masataka


    Metagenomes contain the DNA from many microorganisms, both culturable and non-culturable, and are a potential resource of novel genes. In this study, a 5.2-Gb metagenomic DNA library was constructed from a soil sample (artificially polluted with four aromatic compounds, i.e., biphenyl, phenanthrene, carbazole, and 3-chlorobenzoate) in Escherichia coli by using a broad-host-range cosmid vector. The resultant library was introduced into naphthalene-degrading Pseudomonas putida-derived strains having deficiencies in their naphthalene dioxygenase components, and indigo-forming clones on the indole-containing agar plates were screened. Cosmids isolated from 29 positive clones were classified by their various properties (original screening hosts, hosts showing indigo-forming activity, and digestion patterns with restriction enzymes), and six representative cosmids were chosen. Sequencing and in vitro transposon mutagenesis of the six cosmids resulted in the identification of genes encoding putative class B and D flavoprotein monooxygenases, a multicomponent hydroxylase, and a reductase that were responsible for the indigo-forming activity in the host cells. Among them, the genes encoding the multicomponent hydroxylase were demonstrated to be involved in phenol degradation. Furthermore, two genes encoding ring-cleavage dioxygenases were also found adjacent to the genes responsible for the indigo formation, and their functions were experimentally confirmed.

  5. Charge generation and recombination in PCDTBT:PCBM photovoltaic blends

    Energy Technology Data Exchange (ETDEWEB)

    Etzold, Fabian; Howard, Ian; Mauer, Ralf; Meister, Michael; Laquai, Frederic [Max-Planck-Institute for Polymer Research, Mainz (Germany)


    Low-bandgap donor-acceptor copolymers have recently demonstrated their potential in bulk heterojunction organic solar cells. Among them, poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT) blended with fullerene derivatives proved to be very efficient, yielding power conversion efficiencies in excess of 3 % even without postproduction annealing, which is typically applied to polythiophene:fullerene blends. We investigate exciton dynamics in pristine PCDTBT and charge carrier dynamics in as-cast and annealed blends with [6,6]-phenyl C{sub 61} butyric acid methyl ester (PCBM) by transient absorption and time-resolved photoluminescence spectroscopy. We find that in PCDTBT:PCBM blends a large fraction of excitons undergoes ultrafast generation of free charge carriers as previously observed for other material systems including P3HT:PCBM. However, a fraction of interfacial charge transfer states is also created, which recombine geminately with a lifetime of 2.5 ns. By monitoring the recombination dynamics over the previously unobserved time range from 1 ns to 1 ms, we conclude that the device efficiency must be limited by geminate recombination and charge extraction.

  6. Synthesis, structure, photophysical and electroluminescent properties of a blue-green self-host phosphorescent iridium(III) complex

    Energy Technology Data Exchange (ETDEWEB)

    Sun, Jing; Wang, Hua [Key Laboratory of Interface Science and Engineering in Advanced Materials, Taiyuan University of Technology, Taiyuan 030024 (China); Xu, Huixia, E-mail: [Key Laboratory of Interface Science and Engineering in Advanced Materials, Taiyuan University of Technology, Taiyuan 030024 (China); Li, Jie; Wu, Yuling; Du, Xiaogang [Key Laboratory of Interface Science and Engineering in Advanced Materials, Taiyuan University of Technology, Taiyuan 030024 (China); Xu, Bingshe, E-mail: [Key Laboratory of Interface Science and Engineering in Advanced Materials, Taiyuan University of Technology, Taiyuan 030024 (China); College of Materials Science and Engineering, Taiyuan University of Technology, Taiyuan 030024 (China)


    A kind of blue-green self-host phosphorescent iridium(III) complex, (CzPhBI){sub 2}Ir(tfmptz) [CzPhBI = 9-(6-(2-phenyl-1-benzimidazolyl)hexyl)-9-carbazole; tfmptz = 2-(5-trifluoromethyl-1,2,4-triazolyl)pyridine], was designed and synthesized. The synthesized iridium(III) complex was characterized by {sup 1}H NMR, {sup 19}F NMR, FT-IR, elemental analysis and X-ray single-crystal diffraction, respectively. Its thermal properties, optical properties and electrochemical properties were also investigated. The host-free organic electroluminescent devices with the configuration of ITO/MoO{sub 3} (3 nm)/NPB (30 nm)/TAPC (15 nm)/(CzPhBI){sub 2}Ir(tfmptz) (30 nm)/TBPI (30 nm)/LiF (1 nm)/Al (100 nm) had been fabricated. The devices exhibited excellent performance indicating that (CzPhBI){sub 2}Ir(tfmptz) was a promising phosphorescent material. - Highlights: • A blue-green self-host phosphorescent iridium(III) complex was synthesized. • The molecular structure, and photophysical properties were investigated. • Electroluminescent performance in host-free devices were discussed. • The maximum current efficiency 8.2 cd A{sup −1} and the maximum brightness 5420 cd m{sup −2} were achieved.

  7. Synthesis, cytostatic evaluation and structure activity relationships of novel bis-indolylmethanes and their corresponding tetrahydroindolocarbazoles. (United States)

    El Sayed, Mardia T; Ahmed, Khadiga M; Mahmoud, Kazem; Hilgeroth, Andreas


    BIMs (bis-indolylmethanes) (1a-n) were synthesized using glacial acetic acid as a protic acid for promotion of the condensation reaction of indoles with aldehydes in high yields (86-98 %). Corresponding tetrahydroindolo[2,3-b]carbazoles (2a-m) were synthesized via condensation of BIMs with aldehydes. Ten synthesized compounds have been submitted to the national cancer institute in the USA where all the submitted samples have been selected for one dose screening. As a result of the one dose screening of BIMs (1e,f,h,i,n) and of the indolocarbazoles (2e,f,h,i,j) the average highest cytostatic effects was recorded here for the BIM 1h and the indolocarbazole (2e) that showed the lowest mean values of "47.39%" and of "21.63%" respectively. Both compounds (1h and 2e) were further tested in five dose screening with the tested substance (1h) being significantly more sensitive for several cancers cell line as corresponding to their GI50 values. Furthermore, the basically substituted derivative 2e showed the highest antipoliferative activity in a nanomolar scale towards the three selected cancers cell lines Non small lung cell NCI-H460 with GI50 "616 nM", Ovarian Cancer cell line OVCAR-4 with GI50 "562 nM" and Breast Cancer cell line MCF7 with GI50 "930 nM".

  8. Detection of avian influenza virus H5N1 subtype in organs of chicken affected by higly pathogenic avian infuenza in East and West Java by using immunohistochemical technique

    Directory of Open Access Journals (Sweden)

    R Damayanti


    Full Text Available The study was conducted to detect antigen H5N1 of highly pathogenic Avian Influenza (HPAI virus in various farms in East and West Java. The immunohistochemical technique was applied due to Hematoxilin-eosin (H&E staining was impossible to visualize the antigen in tissue. Immunohistochemical staining was applied for some visceral organs collected from the areas where the outbreaks occurred in September-October 2003. The specimens were processed as histopathological paraffin blocks using standard method. The blocks that were suspected to have antigen H5N1 were cut and rabbit antisera to H5N1 produced from the local isolate was applied as the primary antibody. Biotinylated secondary antibody and avidin biotin peroxidase from a commercial kit were administered. The antigen present in the tissues were visualized by adding a substrate called Amino Ethyl Carbazole (AEC resulting in reddish brown colour. This immunostaining proved to be accurate and reliably quick method to detect H5N1 antigen present in the avian tissues. In conclusion, the outbreak of bird flu was caused by H5N1 strain and the antigen could be found in wattles, combs, brain, trachea, lungs, heart, proventriculus, liver, spleen, kidney and ovary.

  9. Hydropyrolysis: A new technique for the analysis of macromolecular material in meteorites (United States)

    Sephton, Mark A.; Love, Gordon D.; Meredith, Will; Snape, Colin E.; Sun, Cheng-Gong; Watson, Jonathan S.


    The carbonaceous chondrite meteorites are fragments of asteroids that have remained relatively unprocessed since the formation of the Solar System 4.56 billion years ago. The major organic component in these meteorites is a macromolecular phase that is resistant to solvent extraction. The information contained within macromolecular material can be accessed by degradative techniques such as pyrolysis. Hydropyrolysis refers to pyrolysis assisted by high hydrogen gas pressures and a dispersed sulphided molybdenum catalyst. Hydropyrolysis of the Murchison macromolecular material successfully releases much greater quantities of hydrocarbons than traditional pyrolysis techniques (twofold greater than hydrous pyrolysis) including significant amounts of high molecular weight polyaromatic hydrocarbons (PAH) such as phenanthrene, carbazole, fluoranthene, pyrene, chrysene, perylene, benzoperylene and coronene units with varying degrees of alkylation. When hydropyrolysis products are collected using a silica trap immersed in liquid nitrogen, the technique enables the solubilisation and retention of compounds with a wide range of volatilities (i.e. benzene to coronene). This report describes the hydropyrolysis method and the information it can provide about meteorite macromolecular material constitution.

  10. Synthesis of main-chain metallo-copolymers containing donor and acceptor bis-terpyridyl ligands for photovoltaic applications. (United States)

    Padhy, Harihara; Ramesh, Mohan; Patra, Dhananjaya; Satapathy, Rudrakanta; Pola, Murali Krishna; Chu, Hsuan-Chih; Chu, Chih-Wei; Wei, Kung-Hwa; Lin, Hong-Cheu


    Two random (Zn(II)-based P1-P2) and two alternating (Ru(II)-based P3-P4) metallo-copolymers containing bis-terpyridyl ligands with various central donor (i.e., fluorene or carbazole) and acceptor (i.e., benzothiadiazole) moieties were synthesized. The effects of electron donor-acceptor interactions with metal (Zn(II) and Ru(II)) ions on their thermal, optical, and electrochemical properties were investigated. Because of the strong ICT transitions between donor and acceptor ligands in both Zn(II)- and Ru(II)-based metallo-coplymers and MLCT transitions in Ru(II)-based metallo-coplymers, the absorption spectra covered a broad range of 260-750 nm with the band gaps of 1.57-1.77 eV. In addition, the introduction of Ru(II)-based metallo-coplymer P4 mixed with PC(60)BM as an active layer of the BHJ solar cell device exhibited the highest PCE value up to 0.90%.

  11. Preparation of active layers in polymer solar cells by aerosol jet printing. (United States)

    Yang, Chunhe; Zhou, Erjun; Miyanishi, Shoji; Hashimoto, Kazuhito; Tajima, Keisuke


    Active layers of polymer solar cells were prepared by aerosol jet printing of organic inks. Various solvents and additives with high boiling points were screened for the preparation of high-quality polymer films. The effects on device performance of treating the films by thermal and solvent vapor annealing were also investigated. The components of the solvent were important for controlling the drying rate of the liquid films, reducing the number of particle-like protrusions on the film surface, and realizing high molecular ordering in the polymer phases. The optimized solar cell device with poly(3-hexylthiophene) and a C(60) derivative showed a high fill factor of 67% and power conversion efficiency of 2.53% without thermal annealing. The combination of poly[N-9-heptadecanyl-2,7-carbazole-alt-3,6-bis(thiophen-5-yl)-2,5-diethylhexyl-2,5-dihydropyrrolo-[3,4-]pyrrole-1,4-dione] and a C(70) derivative led to power conversion efficiency of 3.92 and 3.14% for device areas of 0.03 and 1 cm(2), respectively.

  12. In situ KPFM imaging of local photovoltaic characteristics of structured organic photovoltaic devices. (United States)

    Watanabe, Satoshi; Fukuchi, Yasumasa; Fukasawa, Masako; Sassa, Takafumi; Kimoto, Atsushi; Tajima, Yusuke; Uchiyama, Masanobu; Yamashita, Takashi; Matsumoto, Mutsuyoshi; Aoyama, Tetsuya


    Here, we discuss the local photovoltaic characteristics of a structured bulk heterojunction, organic photovoltaic devices fabricated with a liquid carbazole, and a fullerene derivative based on analysis by scanning kelvin probe force microscopy (KPFM). Periodic photopolymerization induced by an interference pattern from two laser beams formed surface relief gratings (SRG) in the structured films. The surface potential distribution in the SRGs indicates the formation of donor and acceptor spatial distribution. Under illumination, the surface potential reversibly changed because of the generation of fullerene anions and hole transport from the films to substrates, which indicates that we successfully imaged the local photovoltaic characteristics of the structured photovoltaic devices. Using atomic force microscopy, we confirmed the formation of the SRG because of the material migration to the photopolymerized region of the films, which was induced by light exposure through photomasks. The structuring technique allows for the direct fabrication and the control of donor and acceptor spatial distribution in organic photonic and electronic devices with minimized material consumption. This in situ KPFM technique is indispensable to the fabrication of nanoscale electron donor and electron acceptor spatial distribution in the devices.

  13. 脱氮吸附剂深度脱除模拟含氮油中氮化物的研究%Deep removal of nitrogen-containing compounds from vehicle fuels using denitrogenation adsorbent

    Institute of Scientific and Technical Information of China (English)

    王胜强; 梁燚; 杨磊; 于宏兵


    Highly efficient denitrogenation adsorbent was prepared by loading phosphotungstic acid (PTA) and formaldehyde gases on mesoporous molecular SBA-15. The mass ratio of SBA-15 : PTA : formaldehyde gases was 10 : 7 : 3. Quinoline, indole and carbazole were used as the target nitrogen-containing compounds in vehicle fuels in which xylene or the mixture of xylene and dodecane was used as the solvents. The effect of temperature and concentration of nitrogen-containing compounds on denitrogenation rate was investigated; the deep denitrogenation mechanism of PTA and formaldehyde was also studied. The results showed that the basic nitrogen-containing compounds and non-basic compounds with low-concentration in model fuels can be deeply removed by adsorbent without loading formaldehyde. The selectivity of the adsorbent in the removal of non-basic nitrogen-containing compounds and the reaction rate benefited from the existence of formaldehyde in the pores. Model fuels with ultra-low concentration nitrogen were obtained in 90 min at 70 ℃ when the mass proportion between adsorbent and model fuels containing quinoline,indole and carbazole was 2. 0 : 30. 0. The mechanism of basic nitrogen-containing compounds removal by PTA was the formation of charge-transfer complexes and acid-base reaction; while the non-basic nitrogen-containing compounds were removed by the condensation reaction with formaldehyde under the control of PTA. The regenerated denitrogenation adsorbent was recycled and the efficiency declined according with the increase of the basicity of nitrogen-containing compounds.%将磷钨酸、甲醛气体负载于介孔分子筛SBA-15中制备脱氮吸附剂,其中SBA-15、磷钨酸、甲醛的质量比为10∶7∶3.以喹啉、吲哚和咔唑为目标氮化物,二甲苯及二甲苯和十二烷的混合液为溶剂配制模拟含氮油,考察了反应温度、氮化物类型对脱氮反应速率的影响以及磷钨酸、甲醛的脱氮机制.结果表明,磷钨酸可以

  14. Anticancer and anti-inflammatory activities of girinimbine isolated from Murraya koenigii

    Directory of Open Access Journals (Sweden)

    Iman V


    Full Text Available Venoos Iman,1 Syam Mohan,2 Siddig Ibrahim Abdelwahab,2 Hamed Karimian,1 Noraziah Nordin,1 Mehran Fadaeinasab,3 Mohamad Ibrahim Noordin,1 Suzita Mohd Noor4 1Department of Pharmacy, Faculty of Medicine, University of Malaya, Kuala Lumpur, Malaysia; 2Medical Research Center, Jazan University, Jazan, Saudi Arabia; 3Department of Chemistry, 4Department of Biomedical Science, Faculty of Medicine, University of Malaya, Kuala Lumpur, Malaysia Abstract: Therapy that directly targets apoptosis and/or inflammation could be highly effective for the treatment of cancer. Murraya koenigii is an edible herb that has been traditionally used for cancer treatment as well as inflammation. Here, we describe that girinimbine, a carbazole alkaloid isolated from M. koenigii, induced apoptosis and inhibited inflammation in vitro as well as in vivo. Induction of apoptosis in human colon cancer cells (HT-29 by girinimbine revealed decreased cell viability in HT-29, whereas there was no cytotoxic effect on normal colon cells. Changes in mitochondrial membrane potential, nuclear condensation, cell permeability, and cytochrome c translocation in girinimbine-treated HT-29 cells demonstrated involvement of mitochondria in apoptosis. Early-phase apoptosis was shown in both acridine orange/propidium iodide and annexin V results. Girinimbine treatment also resulted in an induction of G0/G1 phase arrest which was further corroborated with the upregulation of two cyclin-dependent kinase proteins, p21 and p27. Girinimbine treatment activated apoptosis through the intrinsic pathway by activation of caspases 3 and 9 as well as cleaved caspases 3 and 9 which ended by triggering the execution pathway. Moreover, apoptosis was confirmed by downregulation of Bcl-2 and upregulation of Bax in girinimbine-treated cells. In addition, the key tumor suppressor protein, p53, was seen to be considerably upregulated upon girinimbine treatment. Induction of apoptosis by girinimbine was also

  15. Yellow Organic Light-Emitting Devices Based on NPBX Doped CzHQZn%基于NPBX掺杂CzHQZn的黄色有机电致发光器件

    Institute of Scientific and Technical Information of China (English)

    高永慧; 姜文龙; 丁桂英; 丛林; 孟昭晖; 欧阳新华; 曾和平


    The performance of yellow organic light emitting devices (OLEDs) based on a no vel material [(E)- 2- (2-(9-ethyl-9H-carbazol-3-yl)vinyl) quinolato- zinc (CzHQZn)]with an emitting/hole- transporting layer as an acceptor was investigated.These devices were fabrica ted as follows: ITO/2T- NATA(30 nm)/NPBX: 25% CzHQZn(x nm)/BCP(10 nm)/Alq3(60- x) nm/LiF(0.5 nm)/Al(x: the thickness of doping layer).The x is 15,20,25,30 nm,respectively, the thickness of Alq3 is correspondingly changed, the total thickness of doping layer and Alq3 is a constant of 60 nm.When x is 20 nm, the thickness of Alq3 is 40 nm, a yellow OLED can be obtained with the CIE coordinates of (0.514 6,0.470 5), the luminance of 1.078 cd/m2 at 4 V.The maximum luminance is 449 0 cd/m2 at 14 V, and the maximum luminous efficiency is 0.98 cd/A.%利用一种既具有空穴传输特性又具有发光特性的新型荧光染料N-乙基咔唑-2-乙烯基-8-羟基喹啉锌[(E)-2-(2-(9-ethyl-9H-carbazol-3-yl)vinyl)quinolato-zinc,CzHQZn]掺杂在NPBX中作为空穴传输层,CzHQZn同时还作为发光的主体,制备了结构为ITO/2T-NATA(30 nm)/NPBX:25%CzHQZn(x nm)/BCP(10 nm)/Alq3(60-x)nm/LiF(0.5 nm)/Al的有机发光器件(x为掺杂发光层的厚度),掺杂发光层的厚度按照15,20,25,30 nm进行变化,相应改变Alq3的厚度,使得这两者的总厚度为60 nm保持不变.当掺杂发光层的厚度是20 nm,Alq3的厚度是40 nm,其他层厚度保持不变时,器件在4 V电压下实现了黄光发射,色坐标为(0.514 6,0.470 5),亮度是1.078 cd/m2.在14 V的电压下,器件最大发光亮度为449 0 cd/m2,最大发光效率为0.98 cd/A.

  16. Molecular Engineering, Photophysical and Electrochemical Characterizations of Novel Ru(II) and BODIPY Sensitizers for Mesoporous TiO2 Solar Cells (United States)

    Cheema, Hammad Arshad

    precludes coplanarity of the naphthalene moiety, thus decreasing the extracted photocurrent response from solar device. The findings were published in Dyes and Pigments (doi:10.1016/j.dyepig.2014.08.005). For HD-7 and HD-8, intriguing difference caused by structural isomerization based on anthracene and phenanthrene stilbazole type ancillary ligands, respectively in Ru (II) sensitizers was investigated using femtosecond transient absorption spectroscopy. It was found that the excited electrons in HD-7 are prone to ISC (intersystem crossing) much more than that in HD-8 and those triplet electrons are not being injected in TiO2 efficiently as discussed in Chapter 5. To achieve long term stability, we combined the strong electron donor characteristics of carbazole and the hydrophobic nature of long alkyl chains, C7 (HD-14 ), C18 (HD-15) and C2 (NCSU-10), tethered to N-carbazole. HD-15 showed strikingly good long term light soaking stability and maintained up to 98% of initial efficiency value compared to 92% for HD-14 and 78% for NCSU-10, as discussed in Chapter 6. Boron dipyromethene (BODIPY) dyes HB-1, HB-2 and HB-3 were synthesized and fully characterized for dye solar cells. It was found that having long alkyl chains tethered to the donor groups alone are not sufficient for achieving highly efficient photovoltaic response from BODIPY dyes (Chapter 7). Thus, replacement of fluorines from BODIPY core with long alkoxy chains has been suggested for future work.

  17. Importance of heterocylic aromatic compounds in monitored natural attenuation for coal tar contaminated aquifers: A review (United States)

    Blum, Philipp; Sagner, Anne; Tiehm, Andreas; Martus, Peter; Wendel, Thomas; Grathwohl, Peter


    NSO heterocycles (HET) are typical constituents of coal tars. However, HET are not yet routinely monitored, although HET are relatively toxic coal tar constituents. The main objectives of the study is therefore to review previous studies and to analyse HET at coal tar polluted sites in order to assess the relevance of HET as part of monitored natural attenuation (MNA) or any other long-term monitoring programme. Hence, natural attenuation of typical HET (indole, quinoline, carbazole, acridine, methylquinolines, thiophene, benzothiophene, dibenzothiophene, benzofuran, dibenzofuran, methylbenzofurans, dimethylbenzofurans and xanthene) were studied at three different field sites in Germany. Compound-specific plume lengths were determined for all main contaminant groups (BTEX, PAH and HET). The results show that the observed plume lengths are site-specific and are above 250 m, but less than 1000 m. The latter, i.e. the upper limit, however mainly depends on the level of investigation, the considered compound, the lowest measured concentration and/or the achieved compound-specific detection limit and therefore cannot be unequivocally defined. All downstream contaminant plumes exhibited HET concentrations above typical PAH concentrations indicating that some HET are generally persistent towards biodegradation compared to other coal tar constituents, which results in comparatively increased field-derived half-lives of HET. Additionally, this study provides a review on physicochemical and toxicological parameters of HET. For three well investigated sites in Germany, the biodegradation of HET is quantified using the centre line method (CLM) for the evaluation of bulk attenuation rate constants. The results of the present and previous studies suggest that implementation of a comprehensive monitoring programme for heterocyclic aromatic compounds is relevant at sites, if MNA is considered in risk assessment and for remediation.

  18. Polyphasic approach for assessing changes in an autochthonous marine bacterial community in the presence of Prestige fuel oil and its biodegradation potential. (United States)

    Jiménez, Núria; Viñas, Marc; Guiu-Aragonés, Cèlia; Bayona, Josep M; Albaigés, Joan; Solanas, Anna M


    A laboratory experiment was conducted to identify key hydrocarbon degraders from a marine oil spill sample (Prestige fuel oil), to ascertain their role in the degradation of different hydrocarbons, and to assess their biodegradation potential for this complex heavy oil. After a 17-month enrichment in weathered fuel, the bacterial community, initially consisting mainly of Methylophaga species, underwent a major selective pressure in favor of obligate hydrocarbonoclastic microorganisms, such as Alcanivorax and Marinobacter spp. and other hydrocarbon-degrading taxa (Thalassospira and Alcaligenes), and showed strong biodegradation potential. This ranged from >99% for all low- and medium-molecular-weight alkanes (C(15)-C(27)) and polycyclic aromatic hydrocarbons (C(0)- to C(2)- naphthalene, anthracene, phenanthrene, dibenzothiophene, and carbazole), to 75-98% for higher molecular-weight alkanes (C(28)-C(40)) and to 55-80% for the C(3) derivatives of tricyclic and tetracyclic polycyclic aromatic hydrocarbons (PAHs) (e.g., C(3)-chrysenes), in 60 days. The numbers of total heterotrophs and of n-alkane-, aliphatic-, and PAH degraders, as well as the structures of these populations, were monitored throughout the biodegradation process. The salinity of the counting medium affects the counts of PAH degraders, while the carbon source (n-hexadecane vs. a mixture of aliphatic hydrocarbons) is a key factor when counting aliphatic degraders. These limitations notwithstanding, some bacterial genera associated with hydrocarbon degradation (mainly belonging to α- and γ-Proteobacteria, including the hydrocarbonoclastic Alcanivorax and Marinobacter) were identified. We conclude that Thalassospira and Roseobacter contribute to the degradation of aliphatic hydrocarbons, whereas Mesorhizobium and Muricauda participate in the degradation of PAHs.

  19. Probing the carbonyl functionality of a petroleum resin and asphaltene through oximation and schiff base formation in conjunction with N-15 NMR (United States)

    Thorn, Kevin A.; Cox, Larry G.


    Despite recent advances in spectroscopic techniques, there is uncertainty regarding the nature of the carbonyl groups in the asphaltene and resin fractions of crude oil, information necessary for an understanding of the physical properties and environmental fate of these materials. Carbonyl and hydroxyl group functionalities are not observed in natural abundance 13C nuclear magnetic resonance (NMR) spectra of asphaltenes and resins and therefore require spin labeling techniques for detection. In this study, the carbonyl functionalities of the resin and asphaltene fractions from a light aliphatic crude oil that is the source of groundwater contamination at the long term USGS study site near Bemidji, Minnesota, have been examined through reaction with 15N-labeled hydroxylamine and aniline in conjunction with analysis by solid and liquid state 15N NMR. Ketone groups were revealed through 15N NMR detection of their oxime and Schiff base derivatives, and esters through their hydroxamic acid derivatives. Anilinohydroquinone adducts provided evidence for quinones. Some possible configurations of the ketone groups in the resin and asphaltene fractions can be inferred from a consideration of the likely reactions that lead to heterocyclic condensation products with aniline and to the Beckmann reaction products from the initially formed oximes. These include aromatic ketones and ketones adjacent to quaternary carbon centers, β-hydroxyketones, β-diketones, and β-ketoesters. In a solid state cross polarization/magic angle spinning (CP/MAS) 15N NMR spectrum recorded on the underivatized asphaltene as a control, carbazole and pyrrole-like nitrogens were the major naturally abundant nitrogens detected.

  20. Enhancement of contraction and L-type Ca(2+) current by murrayafoline-A via protein kinase C in rat ventricular myocytes. (United States)

    Chidipi, Bojjibabu; Son, Min-Jeong; Kim, Joon-Chul; Lee, Jeong Hyun; Toan, Tran Quoc; Cuong, Nguyen Manh; Lee, Byung Ho; Woo, Sun-Hee


    We previously reported that murrayafoline-A (1-methoxy-3-methyl-9H-carbazole, Mu-A) increases the contractility of ventricular myocytes, in part, via enhancing Ca(2+) influx through L-type Ca(2+) channels, and that it increases the Ca(2+) transients by activation of protein kinase C (PKC). In the present study, we further examined the cellular mechanisms for the enhancement of contractility and L-type Ca(2+) current (ICa,L) by Mu-A. Cell shortening and ICa,L were measured in rat ventricular myocytes using a video edge detection method and perforated patch-clamp technique, respectively. We found that the positive inotropic effect of Mu-A was not affected by pre-exposure to the β-adrenoceptor antagonist propranolol, the protein kinase A (PKA) inhibitors KT5720 or H-89, or the phospholipase C inhibitor U73122. Interestingly, the Mu-A-mediated increases in cell shortening and in the rate of contraction were completely suppressed by pre-treatment with the PKC inhibitor GF109203X. The stimulatory effect of Mu-A on ICa,L was not altered by inhibition of PKA (KT5720), G-protein coupled receptors (suramin), or α1-adrenoceptor (prazosin). However, pre-exposure to the PKC inhibitor, GF109203X or chelerythrine, abolished the Mu-A-induced increase in ICa,L. Pre-exposure to the Ca(2+)-calmodulin-dependent protein kinase II (CaMKII) inhibitor KN93 slightly reduced the stimulatory effects on contraction and ICa,L by Mu-A. Phosphorylation of PKC was enhanced by Mu-A in ventricular myocytes. These data suggest that Mu-A increases contraction and ICa,L via PKC in rat ventricular myocytes, and that the PKC-mediated responses in the presence of Mu-A may be partly mediated by CaMKII.

  1. Towards highly efficient red thermally activated delayed fluorescence materials by the control of intra-molecular π-π stacking interactions (United States)

    Zhang, Yunge; Zhang, Dongdong; Cai, Minghan; Li, Yilang; Zhang, Deqiang; Qiu, Yong; Duan, Lian


    Thermally activated delayed fluorescence (TADF) materials have attracted much attention as they can achieve 100% theoretical internal quantum efficiency without using expensive noble metals. However, efficient red TADF emitters are hard to realize according to the energy gap law. Here, three donor-acceptor-donor type TADF emitters with the same acceptor of o-phthalodinitrile (PN) but different donors (9, 9-dimethyl-9, 10-dihydroacridine (DMAC), phenoxazine (PXZ), and phenothiazine (PTZ) for DMAC-PN, PXZ-PN, and PTZ-PN, respectively) have been synthesized, and it is observed that the performance of the emitters can be improved by reducing the intra-molecular π-π stacking. DMAC-PN with reduced intra-molecular π-π stacking shows a photoluminescence quantum yield (PLQY) of 20.2% in degassed toluene solution, much higher than those of PXZ-PN, and PTZ-PN (0.8%, 0.2%, respectively). An organic light-emitting diode (OLED) employing DMAC-PN doped into 4,4‧-bis(9H-carbazol-9-yl)biphenyl (CBP) as the emitting layer exhibits a maximum external quantum efficiency (EQE) of 10.2% with the emission peak at 564 nm. Moreover, when DMAC-PN is doped into a polar host, bis[2-(diphenylphosphino)phenyl] ether oxide (DPEPO), the OLED shows a large redshift of the emission maximum to 594 nm, while maintaining a peak EQE as high as 7.2%, indicating that efficient red TADF OLEDs can be fabricated by doping orange TADF emitters into hosts with proper polarity.

  2. Aryl hydrocarbon receptor agonists trigger avoidance of novel food in rats. (United States)

    Mahiout, Selma; Pohjanvirta, Raimo


    The aryl hydrocarbon receptor (AHR) is a ligand-activated transcription factor that mediates the toxicity of dioxins, but also plays important physiological roles, which are only beginning to unfold. Previous studies have surprisingly unveiled that low doses of the potent AHR agonist TCDD induce a strong and persistent avoidance of novel food items in rats. Here, we further examined the involvement of the AHR in the avoidance response in Sprague-Dawley rats with three established AHR agonists: 6-formylindolo(3,2-b)carbazole (FICZ), β-naphthoflavone (BNF) and benzo[a]pyrene (BaP); with a novel selective AHR modulator (C2); and with an activator of another nuclear receptor, CAR: 2,4,6-tryphenyldioxane-1,3 (TPD). As sensitive indices of AHR or CAR activity, we used Cyp1a1 and Cyp2b1 gene expression, as they are, respectively, the drug-metabolizing enzymes specifically regulated by them. We further attempted to address the roles played by enhanced neophobia and conditioned taste aversion (CTA) in the avoidance behaviour. All AHR agonists triggered practically total avoidance of novel chocolate, but the durations varied. Likewise, acutely subtoxic doses of C2, differing by 25-fold, all elicited a similar outcome. In contrast, TPD did not influence chocolate consumption at all. If rats were initially accustomed to chocolate for 6h after single FICZ or BNF exposure, avoidance was still clearly present two weeks later when chocolate was offered again. Hence, the avoidance response appears to specifically involve the AHR instead of being triggered by induction of intestinal or hepatic nuclear receptor signalling in general. It is also shared by both endogenous and exogenous AHR activators. Moreover, this behavioural change in rats seems to contain elements of both CTA and enhanced neophobia, but further clarification of this is still required.

  3. Claulansine F promoted the neuronal differentiation of neural stem and progenitor cells through Akt/GSK-3β/β-catenin pathway. (United States)

    Huang, Ju-Yang; Ma, Yin-Zhong; Yuan, Yu-He; Zuo, Wei; Chu, Shi-Feng; Liu, Hang; Du, Guan-Hua; Zhang, Dong-Ming; Chen, Nai-Hong


    The persistence of neurogenesis raises the idea that neurons produced by the resident or transplanted neural stem cells could replace the neurons lost from brain injury or neurodegenerative disease. Therefore, compounds or methods for promoting neuronal differentiation become the focus of neurodegenerative disease therapy research. Claulansine F (Clau F), a newly discovered carbazole alkaloid, has been showed to induce neuritogenesis in PC12 cells. Herein, we studied the effect of Clau F on neuronal differentiation of neural stem/progenitor cells (NS/PCs). The current study demonstrated that Clau F initiated neuronal differentiation with a significant increase of TuJ1-positive cells and TuJ1 protein levels. We also found that Clau F promoted the maturity and sustainability of neurons by increasing MAP2-positive cells and MAP2 protein levels. At the same time, Clau F significantly inhibited the proliferation of NS/PCs. The underlying mechanism of Clau F was preliminary explored. Clau F treatment resulted in a profound increase of phosphorylation of Akt and GSK-3β, which led to GSK-3β inhibition and subsequently the nuclear accumulation of β-catenin. Further, the interaction between β-catenin and p300 in the nucleus was enhanced and the transcription of p300/β-catenin responsive genes were increased significantly (c-jun, fra-1) by Clau F. Importantly, the positive effect of Clau F on neuronal differentiation was abolished by Akti-1/2, a specific inhibitor of Akt-1/2 kinase, which indicated the involvement of Akt/GSK-3β in Clau F-mediated neuronal differentiation. In conclusion, these data suggested that Clau F promoted neuronal differentiation through Akt/GSK-3β/β-catenin signaling pathway in NS/PCs.

  4. Padronização da técnica de imunoperoxidase para detecção do vírus da diarréia bovina a vírus em cultura de células: Standardization of immunoperoxidase test to detection bovine viral diarrhea virus in cell culture

    Directory of Open Access Journals (Sweden)

    G.I. Andrade


    Full Text Available Este estudo teve como objetivo a padronização do ensaio de imunoperoxidase em monocamada de células (IPM para o diagnóstico etiológico da diarréia bovina a vírus (DBV. O teste foi padronizado em monocamada de cultivo primário de pulmão fetal bovino (PFB inoculada com as amostras clássicas, citopatogênica (CP e não citopatogênica (NCP, do vírus da DBV e testado em amostras biológicas suspeitas processadas no teste clássico de isolamento viral (IV. O método de IPM identificou o vírus da DBV, apresentando melhores resultados com a utilização do calor como agente fixador, a soroalbumina bovina a 4% em PBS como bloqueador e a revelação com o cromógeno 3-amino-9-etil-carbazol (AEC. Como anticorpos primários, tanto o anticorpo policlonal como o monoclonal forneceram bons resultados.The aim of this study was to standardize the immunoperoxidase in cell monolayer assay (IPMA for the etiological diagnosis of bovine viral diarrhea (BVD. The method was standardized in monolayer of primary bovine fetal lung culture inoculated with cytophatic and non-cytophatic classical strains of BVD virus and tested using samples that were considered suspected in the classical technique of viral isolation. The IPMA successfully identified BVD virus and presented better results when heat was used for fixation, BSA 4% solution in PBS was used for blocking and AEC chromogen was used for revelation. Both monoclonal and polycloral antibodies gave good results when used as primary antibodies.

  5. A Photosensitizer-Loaded DNA Origami Nanosystem for Photodynamic Therapy. (United States)

    Zhuang, Xiaoxi; Ma, Xiaowei; Xue, Xiangdong; Jiang, Qiao; Song, Linlin; Dai, Luru; Zhang, Chunqiu; Jin, Shubin; Yang, Keni; Ding, Baoquan; Wang, Paul C; Liang, Xing-Jie


    Photodynamic therapy (PDT) offers an alternative for cancer treatment by using ultraviolet or visible light in the presence of a photosensitizer and molecular oxygen, which can produce highly reactive oxygen species that ultimately leading to the ablation of tumor cells by multifactorial mechanisms. However, this technique is limited by the penetration depth of incident light, the hypoxic environment of solid tumors, and the vulnerability of photobleaching reduces the efficiency of many imaging agents. In this work, we reported a cellular level dual-functional imaging and PDT nanosystem BMEPC-loaded DNA origami for photodynamic therapy with high efficiency and stable photoreactive property. The carbazole derivative BMEPC is a one- and two-photon imaging agent and photosensitizer with large two-photon absorption cross section, which can be fully excited by near-infrared light, and is also capable of destroying targets under anaerobic condition by generating reactive intermediates of Type I photodynamic reactions. However, the application of BMEPC was restricted by its poor solubility in aqueous environment and its aggregation caused quenching. We observed BMEPC-loaded DNA origami effectively reduced the photobleaching of BMEPC within cells. Upon binding to DNA origami, the intramolecular rotation of BMEPC became proper restricted, which intensify fluorescence emission and radicals production when being excited. After the BMEPC-loaded DNA origami are taken up by tumor cells, upon irradiation, BMEPC could generate free radicals and be released due to DNA photocleavage as well as the following partially degradation. Apoptosis was then induced by the generation of free radicals. This functional nanosystem provides an insight into the design of photosensitizer-loaded DNA origami for effective intracellular imaging and photodynamic therapy.

  6. Synthesis of Fluorescent Gelators and Direct Observation of Gelation with a Fluorescence Microscope. (United States)

    Hanabusa, Kenji; Ueda, Takuya; Takata, Shingo; Suzuki, Masahiro


    Fluorescein-, benzothiazole-, quinoline-, stilbene-, and carbazole-containing fluorescent gelators have been synthesized by connecting gelation-driving segments, including l-isoleucine, l-valine, l-phenylalanine, l-leucine residue, cyclo(l-asparaginyl-l-phenylalanyl), and trans-(1R,2R)-diaminocyclohexane. The emission behaviors of the gelators were investigated, and their gelation abilities studied against 15 solvents. The minimum gel concentration, variable-temperature spectroscopy, transmission electron microscopy, scanning electron microscopy, fluorescence microscopy (FM), and confocal laser scanning microscopy (CLSM) were used to characterize gelation. The intermolecular hydrogen bonding between the N-H and C=O of amide, van der Waals interactions and π-π stacking play important roles in gelation. The colors of emission are related to the fluorescence structures of gelators. Fibrous aggregates characterized by the color of their emission were observed by FM. 3D images are produced by the superposition of images captured by CLSM every 0.1 μm to a settled depth. The 3D images show that the large micrometer-sized aggregates spread out three dimensionally. FM observations of mixed gelators are studied. In the case of gelation, two structurally related gelators with the same gelation-driving segment lead to the gelators build up of the same aggregates through similar hydrogen-bonding patterns. When two gelators with structurally different gelation-driving segments induce gelation, the gelators build up each aggregate through individual hydrogen-bonding patterns. A fluorescent reagent that was incorporated into the aggregates of gels through van der Waals interactions was developed. The addition of this fluorescent reagent enables the successful observation of nonfluorescent gelators' aggregates by FM.

  7. Polarized photoluminescence from nematic and chiral- nematic liquid crystalline films (United States)

    Conger, Brooke Morgan

    Polarization control is key to optoelectronics in terms of the processing and display of optical information. In principle, photonic or electronic excitation of anisotropic films should result in polarized light emission. Because of spontaneous molecular self-assembly, liquid crystals are ideal for the exploration of polarized luminescence. Although most studies on polarized luminescence have been based on liquid crystalline fluid films, solid films are preferred in view of morphological stability. Therefore, the theme of my thesis is the study of polarized luminescence from various fluorescent liquid crystal systems. From the fundamental perspective, a theory modeling the process of polarized photoluminescence was validated using fluorophore doped fluid liquid crystal films. To provide the morphological stability crucial to practical application, polarized fluorescence using vitrifiable and polymeric liquid crystals functionalized with fluorescent moieties was investigated. In addition, liquid crystalline π- conjugated polymers were synthesized and characterized as a new class of optical polymers. The effect of the emission source on achievable polarization from pyrene and carbazole systems was also elucidated. The main observations are as follows: (1) The observed degrees of polarization for all fluorescent liquid crystal systems were found to agree with the theories governing polarized fluorescence. (2) Low molar mass vitrifiable and polymeric liquid crystalline cyanoterphenyl and cyanotolane derivatives were found to yield moderate polarized fluorescence. Monomer emission was established as the decay pathway for the precursors and cyclohexane and polymethacrylate derivatives. (3) Ordered solid films from thiophene and p-phenylene π-conjugated polymers were found to induce significant degrees of polarized fluorescence. (4) Emission from glass-forming pyrenyl derivatives exhibited excimer emission in dilute solution and neat film, whereas in solid hosts it was

  8. Efficient ternary organic photovoltaics incorporating a graphene-based porphyrin molecule as a universal electron cascade material. (United States)

    Stylianakis, M M; Konios, D; Kakavelakis, G; Charalambidis, G; Stratakis, E; Coutsolelos, A G; Kymakis, E; Anastasiadis, S H


    A graphene-based porphyrin molecule (GO-TPP) was synthesized by covalent linkage of graphene oxide (GO) with 5-(4-aminophenyl)-10,15,20-triphenyl porphyrin (TPP-NH2). The yielded graphene-based material is a donor-acceptor (D-A) molecule, exhibiting strong intermolecular interactions between the GO core (A) and the covalently anchored porphyrin molecule (D). To demonstrate the universal role of GO-TPP as an electron cascade material, ternary blend organic photovoltaics based on [6,6]-phenyl-C71-butyric-acid-methyl-ester (PC71BM) as an electron acceptor material and two different polymer donor materials, poly[N-9'-hepta-decanyl-2,7-carbazole-alt-5,5-(40,70-di-2-thienyl-20,10,30-benzothiadiazole)] (PCDTBT) and the highly efficient poly({4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']dithiophene-2,6-diyl}{3-fluoro-2-[(2-ethylhexyl)carbonyl]thieno[3,4-b]thiophenediyl}) (PTB7), were fabricated. The addition of GO-TPP into the active layer implies continuous percolation paths between the D-A interfaces, enhancing charge transport, reducing exciton recombination and thus improving the photovoltaic performance of the device. A simultaneous increase of short circuit current density (Jsc), open-circuit voltage (Voc) and fill factor (FF), compared to the PTB7:PC71BM reference cell, led to an improved power conversion efficiency (PCE) of 8.81% for the PTB7:GO-TPP:PC71BM-based device, owing mainly to the more efficient energy level offset between the active layer components.

  9. Fabricating thin-film photovoltaic devices using ultra-sonic spray-coating (Presentation Recording) (United States)

    Lidzey, David G.


    The scale-up of thin-film electronic devices requires a manufacture tool set that is capable of fabricating thin films at high speed over large areas. One such technique capable of such a task is ultra-sonic spray coating. Here, a target solution is fed onto a vibrating tip that breaks the solution up into very fine droplets, with such droplets being carried to a surface by a gas stream. Such ultra-sonic coating processes are already widely used in Electronics, Medical and Displays industries to create films having excellent smoothness and homogeneity. In this talk, I describe the use of ultra-sonic spray-coating to deposit a range of materials for thin-film optoelectronics. As our spray-coating system operates in air, it was first necessary to explore the relative sensitivity of various conjugated polymer / fullerene blends to an air-based process route. It is found that carbazole based co-polymers are particularly stable, and can be processed in air (by spin-coating) into organic photovoltaic devices (OPV) without any apparent loss in device efficiency. I then show that spray-coating can be used to deposit a range of semiconductor materials into smooth, thin-films, including PEDOT:PSS, MoOx (from a precursor) and a series of polymer:fullerene blends. Using such a technique, we are able to scale up an array of devices having an area of 7 cm2, and using a PBDTTT-EFT:PC70BM blend, obtain OPVs having a power conversion efficiency (PCE) of 8.7%. I then discuss spray-coating as a method to fabricate photovoltaic devices based on CH3NH3PbI(3-x)Clx perovskite films. Here, by optimization of deposition parameters, devices are created having a PCE of 11.1%.

  10. White Polymer Light-Emitting Diodes Based on Exciplex Electroluminescence from Polymer Blends and a Single Polymer. (United States)

    Liang, Junfei; Zhao, Sen; Jiang, Xiao-Fang; Guo, Ting; Yip, Hin-Lap; Ying, Lei; Huang, Fei; Yang, Wei; Cao, Yong


    In this Article, we designed and synthesized a series of polyfluorene derivatives, which consist of the electron-rich 4,4'-(9-alkyl-carbazole-3,6-diyl)bis(N,N-diphenylaniline) (TPA-Cz) in the side chain and the electron-deficient dibenzothiophene-5,5-dioxide (SO) unit in the main chain. The resulting copolymer PF-T25 that did not comprise the SO unit exhibited blue light-emission with the Commission Internationale de L'Eclairage coordinates of (0.16, 0.10). However, by physically blending PF-T25 with a blue light-emitting SO-based oligomer, a novel low-energy emission correlated to exciplex emerged due to the appropriate energy level alignment of TPA-Cz and the SO-based oligomers, which showed extended exciton lifetime as confirmed by time-resolved photoluminescent spectroscopy. The low-energy emission was also identified in copolymers consisting of SO unit in the main chain, which can effectively compensate for the high-energy emission to produce binary white light-emission. Polymer light-emitting diodes based on the exciplex-type single greenish-white polymer exhibit the peak luminous efficiency of 2.34 cd A(-1) and the maximum brightness of 12 410 cd m(-2), with Commission Internationale de L'Eclairage color coordinates (0.27, 0.39). The device based on such polymer showed much better electroluminescent stability than those based on blending films. These observations indicated that developing a single polymer with the generated exciplex emission can be a novel and effective molecular design strategy toward highly stable and efficient white polymer light-emitting diodes.

  11. Synthesis and characterization of hyaluronic acid/human-like collagen hydrogels

    Energy Technology Data Exchange (ETDEWEB)

    Zhang, Jingjing; Ma, Xiaoxuan, E-mail:; Fan, Daidi, E-mail:; Zhu, Chenhui; Deng, Jianjun; Hui, Junfeng; Ma, Pei


    Injectable hydrogel plays an important role in soft tissue filling and repair. We report an injectable hydrogel based on hyaluronic acid (HA) and human-like collagen (HLC), both with favorable biocompatibility and biodegradability. These two types of biomacromolecules were crosslinked with 1,4-butanediol diglycidyl ether to form a three-dimensional network. The redundant crosslinker was removed by dialysis and distillation. An HA-based hydrogel prepared by the same method was used as a control. The cytocompatibility was studied with a Cell Counting Kit-8 (CCK-8) test. Carbazole colorimetry was used to analyze the in vitro degradation rate. The histocompatibility was evaluated by hematoxylin and eosin (H and E) staining analysis and immunohistochemical analysis. The CCK-8 assay demonstrated that the HA/HLC hydrogel was less cytotoxic than the HA-based hydrogel and could promote baby hamster kidney cell (BHK) proliferation. The cell adhesion indicated that BHK could grow well on the surface of the materials and maintain good cell viability. The in vitro degradation test showed that the HA/HLC hydrogel had a longer degradation time and an excellent antienzyme ability. In vivo injection showed that there was little inflammatory response to HA/HLC after 1, 2, and 4 weeks. Therefore, the HA/HLC hydrogel is a promising biomaterial for soft tissue filling and repair. - Highlights: • Human-like collagen was used with hyaluronic acid to prepare soft tissue filling meterials. • 1,4-Butanediol diglycidyl ether (BDDE) was introduced to treat the hydrogels. • The addition of human-like collagen could improve the biological properties of hydrogels.

  12. CO{sub 2} capture using fly ash-derived activated carbons impregnated with low molecular mass amines

    Energy Technology Data Exchange (ETDEWEB)

    Smith, K.M.; Arenillas, A.; Drage, T.C.; Snape, C.E. [University of Nottingham, Nottingham (United Kingdom). Nottingham Fuel and Energy Centre


    Two different approaches to develop high capacity CO{sub 2} sorbents are presented. Firstly, the modification of the surface chemistry of low cost carbons by impregnation with a basic nitrogen-containing polymer (i.e.polyethylenimine) is described. Relatively low molecular mass (MM) amines, namely diethanolamine (DEA, MM 105) and tetraethylenepentaamineacrylonitrile (TEPAN, MM 311) are used to produce high capacity CO{sub 2} sorbents from activated carbons derived from unburned carbon in fly ash, which have low mesoporosities. The CO{sub 2} adsorption capacity and thermal stability of the prepared sorbents was measured as a function of temperature in a thermogravimetric analyser. The results indicate that TEPAN is more effective than DEA; at a temperature of 75{sup o}C, fly ash-derived activated carbons loaded with TEPAN achieved CO{sub 2} adsorption capacities in excess of 5 wt%, which compares fabvourably with the CO{sub 2} absorption capacity of 6.5 wt% achieved with a mesoporous silica loaded with TEPAN, and outperforms fly ash-derived activated carbons loaded with PEI. TEPAN has also been shown to have a higher thermal stability than DEA. The second approach involves the development of high nitrogen content carbon matrix adsorbents by carbonisation and subsequent thermal or chemical activation of a range of materials (polyacrylonitrile, glucose-amine mixtures, melamine and urea/melamine-formaldehyde resins). The results show that although the amount of nitrogen incorporated to the final adsorbent is important, the N-functionality seems to be more relevant for increasing CO{sub 2} uptake. However, the adsorbent obtained from carbazole-sugar co-pyrolysis, despite the lower amount of N incorporated, shows high CO{sub 2} uptake, up to 9 wt%, probably because the presence of more basic functionalities as determined by XPS analysis. 9 refs., 2 figs.

  13. Apoptosis Effect of Girinimbine Isolated from Murraya koenigii on Lung Cancer Cells In Vitro

    Directory of Open Access Journals (Sweden)

    Syam Mohan


    Full Text Available Murraya koenigii Spreng has been traditionally claimed as a remedy for cancer. The current study investigated the anticancer effects of girinimbine, a carbazole alkaloid isolated from Murraya koenigii Spreng, on A549 lung cancer cells in relation to apoptotic mechanistic pathway. Girinimbine was isolated from Murraya koenigii Spreng. The antiproliferative activity was assayed using MTT and the apoptosis detection was done by annexin V and lysosomal stability assays. Multiparameter cytotoxicity assays were performed to investigate the change in mitochondrial membrane potential and cytochrome c translocation. ROS, caspase, and human apoptosis proteome profiler assays were done to investigate the apoptotic mechanism of cell death. The MTT assay revealed that the girinimbine induces cell death with an IC50 of 19.01 μM. A significant induction of early phase of apoptosis was shown by annexin V and lysosomal stability assays. After 24 h treatment with 19.01 μM of girinimbine, decrease in the nuclear area and increase in mitochondrial membrane potential and plasma membrane permeability were readily visible. Moreover the translocation of cytochrome c also was observed. Girinimbine mediates its antiproliferative and apoptotic effects through up- and downregulation of apoptotic and antiapoptotic proteins. There was a significant involvement of both intrinsic and extrinsic pathways. Moreover, the upregulation of p53 as well as the cell proliferation repressor proteins, p27 and p21, and the significant role of insulin/IGF-1 signaling were also identified. Moreover the caspases 3 and 8 were found to be significantly activated. Our results taken together indicated that girinimbine may be a potential agent for anticancer drug development.

  14. Importance of UDP-glucuronosyltransferase 1A1 expression in skin and its induction by UVB in neonatal hyperbilirubinemia. (United States)

    Sumida, Kyohei; Kawana, Makiko; Kouno, Emi; Itoh, Tomoo; Takano, Shuhei; Narawa, Tomoya; Tukey, Robert H; Fujiwara, Ryoichi


    UDP-glucuronosyltransferase (UGT) 1A1 is the sole enzyme that can metabolize bilirubin. Human infants physiologically develop hyperbilirubinemia as the result of inadequate expression of UGT1A1 in the liver. Although phototherapy using blue light is effective in preventing jaundice, sunlight has also been suggested, but without conclusive evidence, to reduce serum bilirubin levels. We investigated the mRNA expression pattern of human UGT1A1 in human skin, human skin keratinocyte (HaCaT) cells, and skin of humanized UGT1 mice. The effects of UVB irradiation on the expression of UGT1A1 in the HaCaT cells were also examined. Multiple UGT1A isoforms, including UGT1A1, were expressed in human skin and HaCaT cells. When HaCaT cells were treated with UVB-exposed tryptophan, UGT1A1 mRNA and activity were significantly induced. Treatment of the HaCaT cells with 6-formylindolo[3,2-b]carbazole, which is one of the tryptophan derivatives formed by UVB, resulted in an induction of UGT1A1 mRNA and activity. In neonates, the expression of UGT1A1 was greater in the skin; in adults, UGT1A1 was expressed mainly in the liver. Treatment of humanized UGT1 mice with UVB resulted in a reduction of serum bilirubin levels, along with increased UGT1A1 expression and activity in the skin. Our data revealed a protective role of UGT1A1 expressed in the skin against neonatal hyperbilirubinemia. Sunlight, a natural and free source of light, makes it possible to treat neonatal jaundice while allowing mothers to breast-feed neonates.

  15. 3-(Dipropylamino)-5-hydroxybenzofuro[2,3-f]quinazolin-1(2H)-one (DPA-HBFQ-1) plays an inhibitory role on breast cancer cell growth and progression. (United States)

    Rizza, Pietro; Pellegrino, Michele; Caruso, Anna; Iacopetta, Domenico; Sinicropi, Maria Stefania; Rault, Sylvain; Lancelot, Jean Charles; El-Kashef, Hussein; Lesnard, Aurelien; Rochais, Christophe; Dallemagne, Patrick; Saturnino, Carmela; Giordano, Francesca; Catalano, Stefania; Andò, Sebastiano


    A series of unknown 3-(alkyl(dialkyl)amino)benzofuro[2,3-f]quinazolin-1(2H)-ones 4-17 has been synthesized as new ellipticine analogs, in which the carbazole moiety and the pyridine ring were replaced by a dibenzofuran residue and a pyrimidine ring, respectively. The synthesis of these benzofuroquinazolinones 4-17 was performed in a simple one-pot reaction using 3-aminodibenzofuran or its 2-methoxy derivative, as starting materials. From 3-(dipropylamino)-5-methoxybenzofuro[2,3-f] quinazolin-1(2H)-one (13), we prepared 3-(dipropylamino)-5-hydroxybenzofuro[2,3-f]quinazolin-1(2H)-one (18), referred to as DPA-HBFQ-1. The cytotoxic activities of all the synthesized compounds, tested in different human breast cancer cell lines, revealed that DPA-HBFQ-1 was the most active compound. In particular, the latter was able to inhibit anchorage-dependent and -independent cell growth and to induce apoptosis in estrogen receptor alpha (ERα)-positive and -negative breast cancer cells. It did not affect proliferation and apoptotic responses in MCF-10A normal breast epithelial cells. The observed effects have been ascribed to an enhanced p21(Cip1/WAF1) expression in a p53-dependent manner of tumor suppressor and to a selective inhibition of human topoisomerase II. In addition, DPA-HBFQ-1 exerted growth inhibitory effects also in other cancer cell lines, even though with a lower cytotoxic activity. Our results indicate DPA-HBFQ-1 as a good candidate to be useful as cancer therapeutic agent, particularly for breast cancer.

  16. Speciation of nitrogen-containing compounds in an unfractionated coal tar sample by comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry. (United States)

    da Silva, Juliana M; Machado, Maria Elisabete; Maciel, Gabriela P S; Dal Molin, Daniela; Caramão, Elina B


    Comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry (GC×GC/TOFMS) has shown great skill in analyzing complex mixtures such as fossil fuels, especially for compounds at low concentrations. The analysis of N-polyaromatic compounds (NPAC) in coal and crude oil is a great challenge for analytical chemistry due to its environmental and technological importance, and also its diversity of concentration in the matrix. This study is the first report in the applicability of GC×GC/TOFMS for detection of NPAC in a coal tar sample with no fractionation. Normally these compounds are analyzed after sample treatment, making the process expensive and time consuming. However, the higher separation power of GC×GC/TOFMS, compared to 1D-GC, produces cleaner mass spectra in complex samples, which helps in identification of analytes with no pre-fractionation. In this paper, the main objectives were to demonstrate the applicability of GC×GC/TOFMS in the speciation and separation between basic and neutral NPAC from coal tar sample derived from fast pyrolysis, without prior sample fractionation. The methodology used here consisted of chromatographic injection of the diluted sample using a conventional columns set and data analysis by ChromaTOF/Excel™ software. Some basic compounds (pyridines and quinolines) and neutral ones (carbazoles and indoles) were detected with good chromatographic separation and spectral similarity. Tools like spectral deconvolution, extracted ion chromatogram (EIC) and dispersion graphics allowed greater security on the identification and separation of NPAC in this complex sample of coal tar, with no pre-treatment.

  17. Combination effects of AHR agonists and Wnt/β-catenin modulators in zebrafish embryos: Implications for physiological and toxicological AHR functions

    Energy Technology Data Exchange (ETDEWEB)

    Wincent, Emma [Department of Environmental Toxicology, Uppsala University, 75236 Uppsala (Sweden); Institute of Environmental Medicine, Karolinska Institutet, 17177 Stockholm (Sweden); Stegeman, John J. [Biology Department, Woods Hole Oceanographic Institution, Woods Hole, MA 02543-1050 (United States); Jönsson, Maria E., E-mail: [Department of Environmental Toxicology, Uppsala University, 75236 Uppsala (Sweden)


    Wnt/β-catenin signaling regulates essential biological functions and acts in developmental toxicity of some chemicals. The aryl hydrocarbon receptor (AHR) is well-known to mediate developmental toxicity of persistent dioxin-like compounds (DLCs). Recent studies indicate a crosstalk between β-catenin and the AHR in some tissues. However the nature of this crosstalk in embryos is poorly known. We observed that zebrafish embryos exposed to the β-catenin inhibitor XAV939 display effects phenocopying those of the dioxin-like 3,3′,4,4′,5-pentachlorobiphenyl (PCB126). This led us to investigate the AHR interaction with β-catenin during development and ask whether developmental toxicity of DLCs involves antagonism of β-catenin signaling. We examined phenotypes and transcriptional responses in zebrafish embryos exposed to XAV939 or to a β-catenin activator, 1-azakenpaullone, alone or with AHR agonists, either PCB126 or 6-formylindolo[3,2-b]carbazole (FICZ). Alone 1-azakenpaullone and XAV939 both were embryo-toxic, and we found that in the presence of FICZ, the toxicity of 1-azakenpaullone decreased while the toxicity of XAV939 increased. This rescue of 1-azakenpaullone effects occurred in the time window of Ahr2-mediated toxicity and was reversed by morpholino-oligonucleotide knockdown of Ahr2. Regarding PCB126, addition of either 1-azakenpaullone or XAV939 led to lower mortality than with PCB126 alone but surviving embryos showed severe edemas. 1-Azakenpaullone induced transcription of β-catenin-associated genes, while PCB126 and FICZ blocked this induction. The data indicate a stage-dependent antagonism of β-catenin by Ahr2 in zebrafish embryos. We propose that the AHR has a physiological role in regulating β-catenin during development, and that this is one point of intersection linking toxicological and physiological AHR-governed processes.

  18. Electrochemical Polymerization of Carbazolyl Triphenyl Ethylene and Its Properties%咔唑基三苯乙烯衍生物的电化学聚合及其性能

    Institute of Scientific and Technical Information of China (English)

    刘聪; 杨嘉健; 罗海媛; 张崧; 石光; 池振国


    对具有明显聚集诱导发光性能(AIE)的化合物4,4′-双(2,2′-双(4-(6-(9H-咔唑基)己氧基)苯基)乙烯基)联苯( p2bc6)以电化学聚合法制备了聚合物发光薄膜。该聚合薄膜的结构、光学性能和表面形貌通过红外光谱、紫外光谱( UV)、荧光光谱和原子力显微镜表征。结果表明:聚合前体通过分子中咔唑基团聚合形成聚合物薄膜;薄膜具有良好的发光性质;制得的电化学聚合薄膜表面平整,表面粗糙度可达到3 nm以下,有望作为发光材料应用于PLED器件中。%A compound ( p2bc6) which shows a significant aggregation-induced emission phenomenon was used to make polymers by electrochemical polymerization.The structures, optical performance and surface morphology of the electrochemical polymerized films were characterized by means of infrared spectroscopy, near ultra violet( UV) , photoluminescence measurements and atomic force microscopy.The results showed that the electrochemical poly-merization proceeded from carbazole groups, the film emitted fluorescence and had flat surface which the root mean square ( rms) of surface roughnesses was less than 3 nm.It is suggested that they are potential materials for fabrica-tion in PLED devices.

  19. Rational Molecular Engineering of Indoline-Based D-A-π-A Organic Sensitizers for Long-Wavelength-Responsive Dye-Sensitized Solar Cells. (United States)

    Zhang, Weiwei; Wu, Yongzhen; Zhu, Haibo; Chai, Qipeng; Liu, Jingchuan; Li, Hui; Song, Xiongrong; Zhu, Wei-Hong


    Indoline-based D-A-π-A organic sensitizers are promising candidates for highly efficient and long-term stable dye-sensitized solar cells (DSSCs). In order to further broaden the spectral response of the known indoline dye WS-2, we rationally engineer the molecular structure through enhancing the electron donor and extending the π-bridge, resulting in two novel indoline-based D-A-π-A organic sensitizers WS-92 and WS-95. By replacing the 4-methylphenyl group on the indoline donor of WS-2 with a more electron-rich carbazole unit, the intramolecular charge transfer (ICT) absorption band of dye WS-92 is slightly red-shifted from 550 nm (WS-2) to 554 nm (WS-92). In comparison, the incorporation of a larger π-bridge of cyclopentadithiophene (CPDT) unit in dye WS-95 not only greatly bathochromatically tunes the absorption band to 574 nm but also largely enhances the molar extinction coefficients (ε), thus dramatically improving the light-harvesting capability. Under the standard global AM 1.5 solar light condition, the photovoltaic performances of both organic dyes have been evaluated in DSSCs on the basis of the iodide/triiodide electrolyte without any coadsorbent or cosensitizer. The DSSCs based on WS-95 display better device performance with power conversion efficiency (η) of 7.69%. The additional coadsorbent in the dye bath of WS-95 does not improve the photovoltaic performance, indicative of its negligible dye aggregation, which can be rationalized by the grafted dioctyl chains on the CPDT unit. The cosensitization of WS-95 with a short absorption wavelength dye S2 enhances the IPCE and improves the η to 9.18%. Our results indicate that extending the π-spacer is more rational than enhancing the electron donor in terms of broadening the spectral response of indoline-based D-A-π-A organic sensitizers.

  20. 高效窄带隙共轭聚合物太阳能电池材料设计及器件性能研究进展%Recent Progress of Design and Device of High Efficiency Low Band Gap Conjugated Polymer Materials for Application in Solar Cells

    Institute of Scientific and Technical Information of China (English)

    霍延平; 聂晓李; 方小明


    窄带隙聚合物材料因能与太阳光谱更好地匹配而备受重视,是聚合物太阳能电池的研究热点.按照窄带隙聚合物给体单元的结构分类,总结了含芴、硅芴、咔唑、环戊二烯并双噻吩、三苯胺和吩噻嗪给体单元的太阳能电池材料的设计以及器件性能,介绍了聚合物的HOMO和LUMO能隙值对其光谱和光电转换效率的影响,并指出了该研究领域目前存在的问题及今后的发展方向.%Low band gap conjugated polymer materials have attracted great interest in the research field of novel solar cells due to their spectrum matching the solar spectrum. Design and device of various types of low band gap polymer materials are summarized briefly, according to different donor units, such as fluorene, silafluorene carbazole, cy-clopenta[2,l-b:3, 4-b']dithiophene(CPDT) , triarylamine and phenothiazine-based polymers. The magnitude of the band gap and the energy positions of the HOMO and LUMO energy levels are the most important characteristics for determining the optical and electrical properties of a given conjugated polymer. These in turn greatly influence the ultimate power conversion efficiency. The existing problems and future prospect of this kind of materials are discussed.