- A short route to heteroarylcarbazoles: Synthesis of new pyrazolylcarbazoles and carbazolylquinolines
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A short synthesis of pyrazolylcarbazoles from 9-alkyl-carbazoles in three steps is reported. The acetylcarbazoles prepared by the acetylation of carbazoles with acetic anhydride catalyzed by BiCl3 were converted into chloroaldehydes with Vilsmeier reagent. Condensation of chloroaldehydes with hydrazine followed by cyclization yield the pyrazolylcarbazoles. Carbazolyl chalcones were prepared by the condensation of carbazole-3-aldehyde with o-aminoacetophenone and cyclized to carbazolylquinolone using several catalysts. Cyclization of carbazolyl chalcones with the Vilsmeier reagent yields a mixture of carbazolylquinoline carbaldehydes.
- Nagarajan, Rajagopal,Perumal, Paramasivan T.
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- Facile procedure for the synthesis of 3-acetyl-9-ethylcarbazole and corresponding functionalized bis-diketone compounds
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Acetylation-substituted N-ethylcarbazole at the 3-position was synthesized in 80% yield using ZnCl2 as catalyst, and its corresponding functionalized bis-diketone compounds 2a and 2b were prepared by Claisen condensation with acceptable yields.
- Tang, Rui-Ren,Zhang, Wei
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- A New and Facile Method for the Synthesis of Nitrocarbazoles by Urea Nitrate
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Urea nitrate in acetic acid is found to be an effective and mild nitrating agent for the preparation of mono nitrocarbazoles.
- Nagarajan, Rajagopal,Muralidharan,Perumal, Paramasivan T.
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- Pure Organic Room Temperature Phosphorescence from Excited Dimers in Self-Assembled Nanoparticles under Visible and Near-Infrared Irradiation in Water
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Pure organic room temperature phosphorescence (RTP) has unique advantages and various potential applications. However, it is challengeable to achieve organic RTP under visible and near-infrared (NIR)-light excitation, especially in aqueous solution. Herei
- Wang, Xiao-Fang,Xiao, Hongyan,Chen, Peng-Zhong,Yang, Qing-Zheng,Chen, Bin,Tung, Chen-Ho,Chen, Yu-Zhe,Wu, Li-Zhu
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- A facile method for the synthesis of acetylcarbazoles and carbazole aldehydes
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Acetylation of 9-alkylcarbazoles with acetic anhydride catalyzed by PPh3. HClO4 was reported to give acetylcarbazoles. Carbazole aldehydes were easily synthesized by the Vilsmeier reaction of 9-alkylcarbazoles under microwave condition in good yields.
- Nagarajan, Rajagopal,Perumal, Paramasivan T.
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- HS? facilitated sulfur pyran realizing hydrogen sulfide detection and imaging in HepG2 cells and chlorella
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The new carbazole-based fluorescent probe CA-1 was designed and synthesized for the high selective detection of H2S based on HS? facilitated sulfur pyran resulting in UV–Vis and fluorescent spectra changes. At the same time, the probe showed good sensitivity to the detection of H2S with a low detection limit of 0.16 μM. The detection process can be monitored by naked eye: with the addition of H2S, the probe system changed from yellow to pink. Importantly, the probe could be applied in monitoring H2S in HepG2 cells and Chlorella. These results indicate that CA-1 can be used as a promising fluorescent probe for the detection of H2S in situ.
- Chao, Jianbin,Xu, Miao,Zhang, Yongbin,Huo, Fangjun,Liu, Yaoming,Wang, Xiaolu,Yin, Caixia
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- Influence of thiophene spacer and auxiliary acceptor on the optical properties of 4-(Diethylamino)-2-hydroxybenzaldehyde based D-π-A-π-D Colorants with N-alkyl donors: Experimental, DFT and Z-scan study
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We report here design and synthesis of four new D-π-A-π-D type dyes (4 and 5) with triphenylamine/N-ethyl carbazole as fixed rotor/donor and N, N-diethyl amine as a secondary donor having dicyanovinylene as a common acceptor. The Influence of π-linker (thiophene) along with an auxillary cyano group on the nonlinear and linear optical properties is investigated. Molecules with thiophene spacer (4b and 5b) exhibit progressive variation in their absorption and emission profiles reflecting the effect of π-linker, compared to those devoid of thiophene spacer (4a and 5a). The dyes display solvent dependent emission [e.g. 4b (toluene = 689 nm) and 5b (DMSO = 795 nm)] suggesting a more polarized photo-excited state arising as a result of enhanced intramolecular charge transfer in the excited state. The solvatochromic nature is supportive of a general solvent effect, which is confirmed by solvent polarity plots (Weller's and Rettig's plot). The trends in the optical properties were also validated by time dependent density functional theory computations which further reveals charge transfer (from secondary donor to acceptor) for the long wavelength absorption. Dye with the highest charge transfer dipole moment relatively has the maximum two-photon absorption cross-section area (4b = 246–399 GM) which was established using theoretical two-level model. Non-linear optical properties were investigated using solvatochromic two-level model and computationally using global and range separated hybrid functionals. The dyes show high first-order hyperpolarizability (β0) in the range of 191–1162 × 10?30 e.s.u. and second-order hyperpolarizability (γ0) in the range of 491–6,704 × 10?36 e.s.u. Z-scan results show 4a (3.79 × 10?13 e.s.u.) possesses a higher value of third order nonlinear susceptibility in DMSO. Thus, the dyes can be considered as promising candidates for NLO application in material science.
- Raikwar, Manish M.,Patil, Dinesh S.,Mathew, Elizabeth,Varghese, Manu,Joe, Issac H.,Sekar, Nagaiyan
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- A Solid-State Fluorescent Material Based on Carbazole-Containing Difluoroboron β-Diketonate: Multiple Chromisms, the Self-Assembly Behavior, and Optical Waveguides
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A carbazole-containing difluoroboron β-diketonate complex (BCZ), which shows strong fluorescence in both the solid state and in organic solutions, is reported. The crystalline materials of BCZ obtained from different solvents display different emission colors. Single-crystal analysis reveals that the enhanced overlap between adjacent molecules induces increased excited-state delocalization and is responsible for the variation of the emission colors from yellow to red. The emission colors of the materials are effectively tuned by external stimuli such as grinding, heating, and solvent vapor. The powder X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, and 1H NMR studies on materials of BCZ reveal that the thermochromic properties of BCZ are closely related to the removal of solvent molecules from the crystalline powders upon heating. Moreover, uniform 1D microstructures of BCZ obtained by solvent exchange in solution exhibit optical waveguide property with low optical loss.
- Chen, Peng-Zhong,Zhang, Han,Niu, Li-Ya,Zhang, Yi,Chen, Yu-Zhe,Fu, Hong-Bing,Yang, Qing-Zheng
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- Fluorescent probe of reversible sulfur dioxide/sulphurous acid (hydrogen) salt
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The invention provides a fluorescent probe of reversible sulfur dioxide/sulphurous acid (hydrogen) salt, with the chemical name of 7-diethylin-2-(9-ethyl-9H-carbazole-3) benzo iso-pyran oxonium ion. The fluorescent probe can detect sulfur dioxide/sulphurous acid (hydrogen) salt in a solution, cells, tissues or a living body, wherein the living body includes fish, mice, rat, guinea pig and rabbit;and reversibility is realized by formaldehyde. The fluorescent probe is simple in synthesis steps, easily available in material, high in yield and suitable for industrial application.
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- Synthesis and application of colorimetric carbazole fluorescent probe for detecting hydrogen sulfide
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The invention belongs to the technical field of a fluorescent probe, and provides synthesis and application of a colorimetric carbazole fluorescent probe for detecting hydrogen sulfide. The fluorescent probe is 5-chlorine-2-cyano-5-[3-(9-ethyl carbazole)] penta-2,4-ethyl dienoate. 3-acetyl-N-ethyl carbazole is synthesized by using N-ethyl carbazole as a raw material; 3-chlorine-3-[3-(9-ethyl carbazole)] acraldehyde is synthesized; and the 3-chlorine-3-[3-(9-ethyl carbazole)] acraldehyde and ethyl cyanoacetate are dissolved into absolute ethyl alcohol, a catalyst piperidine is added to performa reaction and obtain a crude product, and the crude product is dried to recrystallize the absolute ethyl alcohol, thereby obtaining the fluorescent probe. The probe reacts with the hydrogen sulfide to cause changes of a fluorescence signal and a solution color, and naked eye detection on the hydrogen sulfide can be implemented. The probe has excellent selectivity, is high in detection sensitivity, has a detection limit of 0.16 muM, and can be used for detecting the hydrogen sulfide in cells and chlorella by combining a laser confocal scanning microscopical technique.
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Paragraph 0015
(2018/12/13)
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- Beta-dicarbonyl fluoroboron compound, preparation method and application thereof
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The invention discloses a Beta-dicarbonyl fluoroboron compound, a preparation method and an application thereof. The Beta-dicarbonyl fluoroboron compound is a 2,2-difluoro-(N-ethyl carbazole-3)-1-(6-bromonaphthalene-2)-2H-1,3,2-dioxin borane compound and has a structural formula shown as formula (I). The invention firstly realizes the synthesis and preparation of the compound 2,2-difluoro-(N-ethylcarbazole-3)-1-(6-bromonaphthalene-2)-2H-1,3,2-dioxin borane, utilizes the property of the compound capable of assembling into nanoballs and nanorods in an aqueous solution under the effect of a weakinteraction force to prepare a corresponding organic nanometer material with a special appearance, and meanwhile, constructs a pure organic room temperature phosphorescence system basing on the 2,2-difluoro-(N-ethyl carbazole-3)-1-(6-bromonaphthalene-2)-2H-1,3,2-dioxin borane nanoballs and nanorods and establishes a basis for searching the application of such materials in the fields of bioimagingand photoelectric materials.
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Paragraph 0051; 0052
(2019/01/07)
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- A Green Synthesis of 2-Amino-4-(9H-carbazole-3-yl)thiophene-3-carbonitriles by a Step-wise and One-pot Three-component Gewald Reaction
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An eco-friendly method has been developed for the synthesis of 2-amino-4-(9H-carbazole-3-yl)thiophene-3-carbonitriles from preliminary carbazole (1) through an intermediate of 2-(1-(9H-carbazole-3-yl)ethylidene)malononitriles using the Knoevenagel condensation followed by the Gewald reaction. On the other hand, the target compounds could also be prepared in a one-pot three-component manner by treating equimolar quantities of 1-(9H-carbazole-3-yl)ethanone (3), malononitrile, and elemental sulfur. The merits of this preparation are mild reaction conditions. The Gewald reaction is executed with inorganic base NaHCO3 (H2O) in tetrahydrofuran, easy work-up procedure with good yields.
- Avula, Vijay Kumar Reddy,Vallela, Swetha,Anireddy, Jaya Shree,Chamarthi, Naga Raju
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p. 2471 - 2482
(2017/07/25)
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- 2. 2 - difluoro - 4, 6 - b (N - ethyl carbazole - 3) - 2H - 1, 3, 2 - dioxin borane compound and its preparation method and application
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The invention discloses a 2,2-fluoro-4,6-bis(N-ethylcarbazole-3)-2H-1,3,2-dioxin borane compound as well as a preparation method and application thereof. The compound has the structural formula represented by the formula (I) as shown in the description. A corresponding organic nano-material with special morphology is prepared by using the characteristic that the compound is assembled into nanometer spheres, nanometer rods or nanotubes in an aqueous solution through weak interaction and the compound is important significance of more deeply understanding the photophysical properties of fluorine boride diaromatic formyl methane compounds at the nanometer scale and exploring an application of the nanometer material in the field of biological imaging and optoelectronic materials and meanwhile, the receptor molecules can be doped in nanorods at different proportions, the luminescent behavior of the nanorods is regulated as desired so that the nanorods also have good application value in artificially simulating a light capture system.
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Paragraph 0066; 0067; 0068; 0087; 0088; 0089
(2017/08/25)
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- Carbazole-containing difluoroboron β-diketonate dyes: Two-photon excited fluorescence in solution and grinding-induced blue-shifted emission in the solid state
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Mechanochromic luminescent (MCL) materials have attracted considerable attention in recent years because of their potential applications in various fields and the fundamental importance of understanding the mechanism of mechanochromic luminescence. The most reported MCL materials show a bathochromic shift after external mechanical stimulus. Here we report new MCL materials with hypochromic shift of the emission after grinding. These materials are based on carbazole-containing difluoroboron β-diketonate complexes. These complexes show strong fluorescence in both the solid state and organic solutions. Our study reveals that the emission of structural symmetrical complexes is less influenced by the polarity of the solvent than those of unsymmetrical complexes and they retain strong fluorescence in highly polar solvents. In addition, the good planarity of the carbazole group and the ICT character of the complexes make them exhibit obvious two-photon excited fluorescence. In the solid state, their emission colours can be tuned reversibly by external stimuli, and they exhibit an unusual hypochromic shift after grinding. Single crystal X-ray analysis of the complexes reveals that the initial close molecular packing is responsible for the blue-shifted emission. Interestingly, both hypsochromic and bathochromic shifts of the emission are realized by different treatments of the samples. Our work provides information on the mechanism of the mechanochromic luminescent properties of organic luminescent materials and expands the potential applications of MCL materials.
- Chen, Peng-Zhong,Wang, Jian-Xin,Niu, Li-Ya,Chen, Yu-Zhe,Yang, Qing-Zheng
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supporting information
p. 12538 - 12546
(2017/12/26)
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- Light-Harvesting Systems Based on Organic Nanocrystals To Mimic Chlorosomes
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We report the first highly efficient artificial light-harvesting systems based on nanocrystals of difluoroboron chromophores to mimic the chlorosomes, one of the most efficient light-harvesting systems found in green photosynthetic bacteria. Uniform nanocrystals with controlled donor/acceptor ratios were prepared by simple coassembly of the donors and acceptors in water. The light-harvesting system funneled the excitation energy collected by a thousand donor chromophores to a single acceptor. The well-defined spatial organization of individual chromophores in the nanocrystals enabled an energy transfer efficiency of 95%, even at a donor/acceptor ratio as high as 1000:1, and a significant fluorescence of the acceptor was observed up to donor/acceptor ratios of 200 000:1.
- Chen, Peng-Zhong,Weng, Yu-Xiang,Niu, Li-Ya,Chen, Yu-Zhe,Wu, Li-Zhu,Tung, Chen-Ho,Yang, Qing-Zheng
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supporting information
p. 2759 - 2763
(2016/02/26)
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- Synthesis and theoretical calculations of carbazole substituted chalcone urea derivatives and studies their polyphenol oxidase enzyme activity
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Synthesis of carbazole substituted chalcone urea derivatives and their polyphenol oxidase enzyme activity effects on the diphenolase activity of banana tyrosinase were evaluated. Tyrosinase has been purified from banana on an affinity gel comprised of Sep
- Nixha, Arleta Rifati,Arslan, Mustafa,Atalay, Yusuf,Gencer, Nahit,Erguen, Adem,Arslan, Oktay
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p. 808 - 815
(2013/07/26)
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- Bipolar luminescent materials containing pyrimidine terminals: Synthesis, photophysical properties and a theoretical study
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A new series of 4-monosubstituted pyrimidine bipolar materials containing a carbazole (PM1-PM2) or a triphenylamine (PM3-PM5) moiety as the electron donor have been synthesized by a ZnCl2-catalyzed three-component coupling reaction. These 4-monosubstituted pyrimidine compounds were characterized by UV-vis and fluorescence spectroscopy, cyclic voltammetry, as well as density functional theory (DFT) calculations. It was intriguing to find that these 4-monosubstituted pyrimidine compounds exhibited bright fluorescence with excellent quantum yields (~0.53-0.93) in the blue region. PM1 and PM2 had a lower LUMO than that of CBP (4,4-di(9H-carbazol-9-yl)biphenyl), meaning that both of them had better electron injection and transfer abilities. The variation tendencies of energy levels and absorption spectra obtained from DFT calculations agreed well with those from experiment. Other electronic properties including ionization potentials (IP), electronic affinities (EA), and reorganization energies (λhole and λ electron) have been theoretically studied as well. These electronic properties could be tuned by introducing a different number of pyrimdin-4-yl moieties onto to the donor fragments. The incorporation of pyrimdin-4-yl can significantly decrease the λelectron and then improve the electron-accepting and hole-electron charge balance abilities. The combined theoretical and experimental studies offer insights into the nature of bipolar molecules containing 4-monosubstituted pyrimidine moieties, and provided a fertile ground for the design of appropriate ambipolar materials for optoelectronic applications. The Royal Society of Chemistry 2013.
- Weng, Jiena,Mei, Qunbo,Fan, Quli,Ling, Qidan,Tong, Bihai,Huang, Wei
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p. 21877 - 21887
(2013/11/06)
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- Studies on pyrrolidinones. Reaction of pyroglutamic acid and vinylogues with aromatics in Eaton's reagent
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The optimization of the synthesis of 5-aryl-2-pyrrolidinones through decarbonylation of pyroglutamic acid in Eaton's reagent, in presence of aromatic derivatives, is described. The utilization of these reaction conditions in the arylation of enaminoester vinylogues (17, 24) of pyroglutamic acid was also realized, confirming that these derivatives are subject to decarbonylation? in the same way as the parent acid. Depending on the nature of the aromatic derivative (15, 21, 28, and 32), two different families of compounds were obtained. Many by-products were also formed, suggesting a utilization of this reaction for compounds more stable than the enaminoesters and enaminonitriles used in this study. The possibility of enaminoesters reacting with aromatics in bimolecular reactions to give enaminoketones should also be noted. Five synthesized compounds were evaluated for their antiproliferative activity on the NCI-60 cancer cell lines panel.
- Ghinet, Alina,Van Hijfte, Nathalie,Gautret, Philippe,Rigo, Beno?t,Oulyadi, Hassan,Rousseau, Jolanta
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experimental part
p. 1109 - 1116
(2012/02/15)
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- New carbazole-containing chalcones and pyrimidines based thereon: Synthesis and electrochemical study
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Condensations of aromatic carbo- and heterocyclic ketones and aldehydes in methanol gave new chalcones containing carbazole fragments, 1,3-diaryl(9-R-9H- carbazol-3-yl)prop-2-en-1-ones. Some of the synthesized chalcones reacted with guanidine sulfate to produce 2-amino-4,6-diarylpyrimidines that are promising materials for the design of light emitting diodes. Study on electrochemical polymerization of both chalcones and pyrimidines derived therefrom showed that almost all the examined substrates give rise to stable colored conjugated polymer films on the surface of working electrode under conditions of cyclic voltammetry. Pleiades Publishing, Ltd., 2011.
- Syutkin,Abashev,Shklyaeva,Kudryavtsev
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p. 530 - 536
(2011/07/29)
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- The synthesis, crystal structures and photophysical properties of a series of novel 4,6-diphenyl-1,9-anthrazolines
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The synthesis and properties of a series of nine new 4,6-diphenyl-1,9- anthrazolines molecules 1a-1i are reported. Compounds 1a-1i were synthesized by Friedl?nder condensation of 4,6-dibenzoyl-1,3-phenylenediamines and acetyl-functionalized compounds in the presence of polyphosphoric acid as catalyst, in yields ranging from 60% to 94%. The 4,6-diphenyl-1,9-anthrazolines are thermally robust with high decomposition temperatures (>371.0 °C) and high melt transitions (215.1-322.8 °C). Compounds 1a and 1f crystallized in the triclinic system with the space groups P-1. All of them show the lowest energy absorption bands (λmaxAbs: 397-454 nm), revealing low optical band gaps (2.55-3.00 eV). The compounds emit blue fluorescence with λmaxEm ranging from 432 to 493 nm in dilute toluene solution. 4,6-Diphenyl-1,9-anthrazolines 1a-1i have a formal reduction potential in the range -1.02 to -1.19 V (versus SCE) and estimated electron affinities (LUMO levels) of 3.21-3.38 eV. These results demonstrate that the new 4,6-diphenyl-1,9-anthrazolines are promising thermally stable n-type semiconductors for organic electronics.
- Zhang, Qin,Jiang, Peng,Wang, Kunyan,Song, Guangliang,Zhu, Hongjun
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- Synthesis of a novel β-diketone containing carbazole and 2,5-diphenyl-1,3,4-oxadiazole fragments
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A novel β-diketone containing carbazole and 2,5-diphenyl-1,3,4- oxadiazole fragments as hole- and electron-transporting functional groups, respectively, was synthesized via efficient and convenient procedure. The product attracts interest from the viewpoint of its potential applications as optoelectronic material.
- Tang, Huaijun,Zhang, Zhiguo,Cong, Changjie,Zhang, Keli
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experimental part
p. 559 - 563
(2009/09/06)
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- Study on the fluorescence properties of a new intramolecular charge transfer compound 1,5-diphenyl-3-(N-ethylcarbazole-3-yl)-2-pyrazoline
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The fluorescence properties of a newly synthesized compound, 1,5-diphenyl-3-(N-ethylcarbazole-3-yl)-2-pyrazoline (DEP) have been studied. On excitation at 352 nm, the fluorescence spectrum exhibits a large red shift with an increase in the polarity of solvents. The intensity of the band is different in different solvents as well. The change in the dipole moment in various solvents at room temperature has been characterized by the absorption and steady state fluorescence techniques and calculated based on the Lippert-Mataga equation. DEP has an increase of dipole moment of 2.83 D units on excitation to the lowest singlet state. It is concluded that photo-induced charge transfer from N (1) to C (3) actually exists in the excited state of the pyrazoline moiety. Its fluorescence property is relative to viscosity and temperature of solvents. The φ{symbol}f of DEP in neutral medium or basic medium is higher than acidic medium. In addition, when the concentration of DEP is higher than 10-3 M, its fluorescence is quenched by the collision of each molecule. The red shift of the maximum emission of DEP attributes to the formation of aggregates and the conjugate system is strengthened.
- Li,Guan,Li,Dong
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p. 404 - 408
(2008/02/13)
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