- Diazadioxa[8]circulenes: Planar antiaromatic cyclooctatetraenes
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In this paper we describe a new class of antiaromatic planar cyclooctatetraenes: the diazadioxa[8]circulenes. The synthesis was achieved by means of a new acid-mediated oxidative dimerization of 3,6-dihydroxycarbazoles to yield the diazadioxa[8]circulenes
- Hensel, Thomas,Trpcevski, Denis,Lind, Christopher,Grosjean, Remi,Hammershoj, Peter,Nielsen, Christian B.,Brock-Nannestad, Theis,Nielsen, Bjarne E.,Schau-Magnussen, Magnus,Minaev, Boris,Baryshnikov, Gleb V.,Pittelkow, Michael
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- Stereoselective synthesis and luminescence properties of novel trans-regular N-alkylcarbazolylene-silylene-vinylene polymers
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Novel trans-stereoregular silylene-carbazolylene-vinylene derivatives (13-15) were synthesized via silylative coupling reaction of 3,6-bis(dimethylvinylsilyl)-N-alkylcarbazole (7-9) catalyzed by ruthenium-hydride complex RuHCl(CO)(PCy3)2 (1). All products were isolated, fully characterized by spectroscopic methods and GPC analyses and their absorption and fluorescence properties were determined.
- Ludwiczak, Monika,Majchrzak, Mariusz,Bayda, Ma?gorzata,Marciniak, Bronis?aw,Kubicki, Maciej,Marciniec, Bogdan
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- Branched Methoxydiphenylamine-Substituted Carbazole Derivatives for Efficient Perovskite Solar Cells: Bigger Is Not Always Better
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A set of novel branched molecules bearing a different number of 3,6-bis(4,4′-dimethoxydiphenylamino)carbazole-based (Cz-OMeDPA) periphery arms linked together by aliphatic chains have been developed, and their performance has been tested in perovskite sol
- Luizys, Povilas,Xia, Jianxing,Daskeviciene, Maryte,Kantminiene, Kristina,Kasparavicius, Ernestas,Kanda, Hiroyuki,Zhang, Yi,Jankauskas, Vygintas,Rakstys, Kasparas,Getautis, Vytautas,Nazeeruddin, Mohammad Khaja
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- A blue emission polymer: Synthesis, photophysical and electrochemical properties
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(Figure Presented) A novel π-conjugated polymer (PCPyrene) containing N-benzylcarbazole and pyrene units has been synthesized and characterized. The polymer possesses high thermal stability with the decomposition temperature of 440°C. It shows higher fluorescence quantum yields of in solution and solid state, respectively. PCPyrene can emit bright blue-lights both in different organic solutions (440-460 nm) and in the solid state (492 nm). Compared the emission spectra of PCPyrene in solutions with in solid state, the solid state emission of PCPyrene is significantly red-shifted. Additionally, it is not obvious changes of the solid emission spectra even after being annealed at 150°C under nitrogen for 24 h. The electrochemical properties and energy levels of PCPyrene were also investigated by cyclic voltammetry. Furthermore, in order to provide a basis forecasting the structure-physical property relationships, the photophysical properties of PCPyrene have been carefully investigated by fluorescence emission and UV-vis absorption spectra.
- Zhang, Caihong,Li, Feng,Wang, Yue,Feng, Liheng
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- Polymer-Supported Cation Radicals
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Reaction of chloromethylated polystyrene (3.90 mequiv/g) beads with triphenylamine and diethylchloroalane resulted in a higly cross-linked polymer.The chloromethylated polystyrene was modified by reaction with 2,6-dibromocarbazole (4) and K2CO3 in DMF at 100 deg C to give an excellent yield of polymer-supported 2,6-dibromocarbazole (5) without concomitant cross-linking.The polymer-bound 2,6-dibromocarbazole was nonreactive toward SbCl5, whereas the homogeneous counterpart 9-N-benzyl-2,6-dibromocarbazole (6) was found to readily generate the aminium cation radical upon reaction with SbCl5.Attachment of phenothiazine to a polystyrene support yielded a reagent that would react very rapidly with SbCl5 in dichloromethane.The polymer-bound phenothiazine cation radical was found to readily oxidize the metal-metal bond in 2 and undergo anion exchange with Bu4NPF6 to afford a more synthetically useful reagent.
- Wright, Michael E.,Jin, Myung-Jong
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- Organic fluorescent dendrimer thin film material and preparation method thereof
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The invention discloses an organic fluorescent dendritic molecular film material and a preparation method thereof, and relates to the technical field of fluorescence sensing. A dendritic molecular main chain skeleton is formed by a central core unit A and
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- Carbazole-nitrogen heterocyclic A-D-A type room-temperature organic phosphorescent white light material
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The invention belongs to the field of organic luminescent materials, and particularly relates to a carbazole-nitrogen heterocyclic A-D-A type room-temperature organic phosphorescent white light material. The room-temperature organic phosphorescent white l
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Paragraph 0026-0030
(2021/02/10)
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- 9-Aryl-3-aminocarbazole as an Environment- and Stimuli-Sensitive Fluorogen and Applications in Lipid Droplet Imaging
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Environment-sensitive luminophoric molecules have played an important role in the fields of smart materials, sensing, and bioimaging. In this study, it was demonstrated that depending on the substituents, 9-aryl-3-aminocarbazoles can display aggregation-induced emission and solvatofluorochromism, and the operating mechanism was clarified. The application of these compounds to lipid droplet imaging and fluorescent probes for cysteamine was demonstrated.
- Matsubara, Ryosuke,Kaiba, Tomoaki,Nakata, Akito,Yabuta, Tatsushi,Hayashi, Masahiko,Tsubaki, Motonari,Uchino, Takashi,Chatani, Eri
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p. 5535 - 5547
(2019/05/10)
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- Diversity of metal-organic macrocycles assembled from carbazole based ligands with different lengths
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A series of carbazole based ligands with different lengths were assembled with nickel ions to construct metal-organic macrocycles. High-resolution mass spectrometry and ion mobility-mass spectrometry have been used to analyse the resulting MnLn assembly coexisting in solution. Combining with the structural analysis of their solid confirmation, it was revealed that the diversity of the metal-organic macrocycles was increased with the flexibility of the ligands.
- Yu, Hao,Wang, Jing,Guo, Xiangyang,Zhang, Rong,He, Cheng,Duan, Chunying
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p. 4040 - 4044
(2018/03/26)
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- A benzhydryl radical based on the room temperature of the organic light-emitting material and using the material preparation of organic electroluminescent device
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A benzhydryl radical based on the stability of the organic light-emitting material at room temperature and using the material preparation of the organic electroluminescent device, which belongs to the field of organic light-emitting technology. The present invention in the preparation of the organic light-emitting material, the center of the common characteristic is the carbon free radical, is composed of two C - C covalent bond and a C - N to form a covalent bond. Stability is the light-emitting free radical material in the application of the key nature, connected to the electronic group conducive to stable free radical, in this invention through the nitrogen-containing heterocyclic carbazole, indole, dimethyl acridine and the like in the electronic group to the nitrogen atom is connected directly to the benzyl group, to obtain a stable benzhydryl radical, its stability and PTM, compared with the TTM is greatly improved, and has a room temperature fluorescent. The preparation of the material of the organic electroluminescent device using double thread condition exciton light-emitting, can avoid the traditional organic electroluminescent device in the use of the triplet state exciton, the maximum external quantum efficiency of the device is 0.66%.
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Paragraph 0063; 0074; 0075
(2018/07/30)
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- A new carbazole-based hole-transporting material with low dopant content for perovskite solar cells
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A new carbazole-based hole-transporting material incorporating a 3,3′-biphenyl central core has been synthesized via a facile route. A reference compound without carbazole moiety was also prepared. Their geometric structures, thermal stability and photovoltaic properties were investigated. This new carbazole-based material exhibits a high glass transition temperature (167.8 °C) and a suitable highest occupied molecular orbital level well-matched with CH3NH3PbI3 perovskite. A low doping content of 4-tert-butylpyridine (120 mM) is observed for the best performance of perovskite solar cell in conjunction with a carbon counter electrode. The device achieves a power conversion efficiency of 4.53% under illumination of 100 mW cm-2. The performance is much better than that of the reference compound (0.19%), and comparable to that of spiro-OMeTAD at the same dopant level (5.10%). The results indicate the carbazole-based material is a promising class of hole-transporting materials for perovskite solar cells.
- Wang, Jiang,Chen, Yu,Li, Fusheng,Zong, Xueping,Guo, Jinlin,Sun, Zhe,Xue, Song
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p. 673 - 680
(2016/07/06)
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- HOST MATERIAL FOR LIGHT-EMITTING DIODES
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The present invention relates to a host material comprising a compound having two carbazole moieties which is suitable for blue-emitting OLEDs. Surprisingly, it has been found that when appropriate substituents are present in the carbazole structure, the solubility of the compounds can be improved without any adverse effect on the OLED performance. The present invention further relates to the use of the host materials and to an organic light emitting device comprising the host material.
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Page/Page column 14; 15
(2010/04/30)
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- Design of high efficiency for two-photon polymerization initiator: Combination of radical stabilization and large two-photon cross-section achieved by N-benzyl 3,6-bis(phenylethynyl)carbazole derivatives
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Novel A-π-D-π-A V-shaped 3,6-bis(phenylethynyl)carbazole based chromophores were designed and synthesized as two-photon polymerization (TPP) initiators combining a large two-photon absorption cross-section with facilitated radical formation. 9-Benzyl-3,6-
- Xing, Jin-Feng,Chen, Wei-Qiang,Gu, Jie,Dong, Xian-Zi,Takeyasu, Nobuyuki,Tanaka, Takuo,Duan, Xuan-Ming,Kawata, Satoshi
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p. 1433 - 1438
(2008/02/07)
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- Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system
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The preparation, isolation and characterization by elemental analysis and 1H-NMR, 13C-NMR, and MS data of the bromo derivatives of N-substituted carbazoles, i.e., of 9-methyl-9H-carbazole (1), 9-phenyl-9H-carbazole (2), 9-benzyl-9H-carbazole (3), 2-methoxy-9-methyl-9H- carbazole (4), and of C-substituted carbazoles, i.e., of 2-(acetyloxy)-9H- carbazole (5) and 3-nitro-9H-carbazole (6), are reported, in part for the first time. As brominating reagents, N-bromosuccinimide (NBS) or NBS/silica gel in CH2Cl2, NBS in AcOH, KBrO3/KBr in EtOH doped with a catalytic amount of H2SO4, or KBrO3/KBr in AcOH were employed, and their uses were compared. Semi-empirical PM3 calculations were performed to predict the reactivity of the N-substituted and C-substituted carbazoles and of their bromo derivatives and found to verify the experimental results. The UV-absorption and fluorescence and phosphorescence emission spectra of the bromocarbazole derivatives in MeCN solution at 298 K and in a solid matrix at 77 K were compared with those of the corresponding carbazoles 1-6. The dynamic properties of the lowest excited singlet and triplet states (τf, τp, φf, and φp) were measured under the same experimental conditions. The intramolecular spin-orbital-coupling effect of the Br-atom and NO2 group on the spectroscopic data, photophysical parameters, and on the photo reactivity were also briefly analyzed.
- Ponce, Maria B.,Cabrerizo, Franco M.,Bonesi, Sergio M.,Erra-Balsells, Rosa
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p. 1123 - 1139
(2007/10/03)
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- Carbazole derivative, organic semiconductor element, light emitting element, and electronic device
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The problem of the present invention is to provide a carbazole derivative which has an excellent heat resistance and can be formed into a film without crystallization. Also, a problem is to produce an organic semiconductor element, a light emitting element and an electronic device by employing the carbazole derivative. For the purpose, a novel carbazole derivative represented by following general formula (1) is provided: (in the formula, I represents a core carbazole (G0) illustrated by general formula (2), Z represents an internally branched carbazole (G1 to Gn-1) illustrated by general formula (3), E represents an end carbazole (Gn) illustrated by general formula (4), n represents an integer showing generation number of dendrimer, X1 represents hydrogen, halogen, a cynano group, an alkyl group, an aryl group, a heterocyclic residue or the like, X2 and X3 in (G(n-m)-1) (provided, n-m≧1) make a covalent bond with X4 in (G(n-m)), and each of R1 to R8 represents independently hydrogen, halogen, a cynano group, an alkyl group, a dialkylamino group, a diarylamino group, a heterocyclic residue or the like).
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Page/Page column 18-19
(2008/06/13)
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- N-Alkylation of 1H-indoles and 9H-carbazoles with alcohols
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A comparative study of N-alkylation of 1H-indole and 9H-carbazole derivatives with alcohol derivatives was performed using classic Mitsunobu reaction conditions, i.e. DEAD/PPh3, azodicarboxamide derivatives such as TMAD in the presence of PBus
- Bombrun, Agnes,Casi, Giulio
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p. 2187 - 2190
(2007/10/03)
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- SN2 Reactions of Nitranions with Benzyl Chlorides
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The rates of SN2 reactions of 19 nitranions with PhCH2Cl and 9 nitranions with m-CF3C6H4CH2Cl were measured in Me2SO at 25 deg C.Bronsted plots of log k vs. pKHA for reactions of anion families derived from carbazoles, phenothiazines, and diphenylamines with PhCH2Cl are linear with slopes of 0.32-0.33.Extension of the carbazole and phenothiazine family lines, which are collinear, provided a reference line by which nucleophilicities of other nitranions could be assessed at constant basicity.Nitranions of varied structural types were found to have remarkably similar nucleophilicities when compared at the same basicities.Steric effects caused rates of reactions of ArAr'N(1-) ions and acetanilide ion to be retarded slightly and that of benzanilide ion to be retarded appreciably.Evidence is presented to show that nitranions, like carbanions, utilize the electron pair in a p orbital for bonding to an electrophile whereas pyridines utilize a nonbonded electron pair.Comparisons with literature data for neutral nitrigen nucleophiles, such as n-BuNH2 and PhNH2, indicate that they are 10-100 times more reactive than nitranion nucleophiles of comparable basicity.The order of nucleophilicities toward PhCH2Cl of anion families with different donor atoms when compared at the same basicity was found to be the following: 9-methylfluoredine ion family (25) > 2-naphthoxide ion family (3) > carbazole ion family (1.0).The results show that basicity is the primary factor in controlling nucleophilicities of nitranions, carbanions, and oxanions of diverse structural types in SN2 reactions.Donor atom, solvation, and steric effects generally play a secondary role.
- Bordwell, Frederick G.,Hughes, David L.
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p. 3234 - 3240
(2007/10/02)
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