654676-12-7Relevant articles and documents
A New Conducting Copolymer Bearing Electro-Active Nitroxide Groups as Organic Electrode Materials for Batteries
Assumma, L.,Dubois, L.,Gutel, T.,Kervella, Y.,Maurel, V.,Mendez, M.,Mouesca, J.-M.,Sadki, S.
, p. 2419 - 2427 (2020)
To reduce the amount of conducting additives generally required for polynitroxide-based electrodes, a stable radical (TEMPO) is combined with a conductive copolymer backbone consisting of 2,7-bisthiophene carbazole (2,7-BTC), which is characterized by a high intrinsic electronic conductivity. This work deals with the synthesis of this new polymer functionalized by a redox nitroxide. Fine structural characterization using electron paramagnetic resonance (EPR) techniques established that: 1) the nitroxide radicals are properly attached to the radical chain (continuous wave EPR) and 2) the polymer chain has very rigid conformations leading to a set of well-defined distances between first neighboring pairs of nitroxides (pulsed EPR). The redox group combined with the electroactive polymer showed not only a very high electrochemical reversibility but also a perfect match of redox potentials between the de-/doping reaction of the bisthiophene carbazole backbone and the redox activity of the nitroxide radical. This new organic electrode shows a stable capacity (about 60 mAh g?1) and enables a strong reduction in the amount of carbon additive due to the conducting-polymer skeleton.
Cyclo- N-alkyl-2,7-carbazoles: Influence of the Alkyl Chain Length on the Structural, Electronic, and Charge Transport Properties
Cornil, Jér?me,Donnio, Bertrand,Heinrich, Beno?t,Jacques, Emmanuel,Jeannin, Olivier,Lebreton, Christophe,Lucas, Fabien,McIntosh, Nemo,Poriel, Cyril,Quinton, Cassandre,Rault-Berthelot, Jo?lle
, p. 8804 - 8820 (2021)
Macrocycles possessing radially oriented π-orbitals have experienced a fantastic development. However, their incorporation in organic electronic devices remains very scarce. In this work, we aim at bridging the gap between organic electronics and nanorings by reporting the first detailed structure-properties-device performance relationship study of organic functional materials based on a nanoring system. Three [4]cyclo-N-alkyl-2,7-carbazoles bearing different alkyl chains on their nitrogen atoms have been synthesized and characterized by combined experimental and theoretical approaches. This study includes electrochemical, photophysical, thermal, and structural solid-state measurements and charge transport properties investigations. An optimized protocol of the Pt approach has been developed to synthesize the [4]cyclocarbazoles in high yield (52-64%), of great interest for further development of nanorings, especially in materials science. The charge transport properties of [4]cyclocarbazoles and model compound [8]cycloparaphenylene ([8]CPP) have been studied. Although no field effect (FE) mobility was recorded for the benchmark [8]CPP, FE mobility values of ca. 10-5 cm2·V-1·s-1 were recorded for the [4]cyclocarbazoles. The characteristics (threshold voltage VTH, subthreshold swing SS, trapping energy ΔE) recorded for the three [4]cyclocarbazoles appear to be modulated by the alkyl chain length borne by the nitrogen atoms. Remarkably, the space-charge-limited current mobilities measured for the [4]cyclocarbazoles are about 3 orders of magnitude higher than that of [8]CPP (1.37/2.78 × 10-4 cm2·V-1·s-1 for the [4]cyclocarbazoles vs 1.21 × 10-7 cm2·V-1·s-1 for [8]CPP), highlighting the strong effect of nitrogen bridges on the charge transport properties. The whole study opens the way to the use of nanorings in electronics, which is now the next step of their development.
Multi-photon properties in various condensed phases of dendritic chromophores derived from carbazole and indenoquioxaline units: Synthesis and characterization
Lin, Tzu-Chau,Chien, Wei,Dai, Shu-Wen,Lin, Hao-Wu,Liu, Yueh-Ching
, p. 140 - 150 (2019/05/01)
We have used functionalized carbazoles and indenoquonoxalines as the main building units and enthynyl groups as the π-linkages to construct two novel dendritic fluorophores and studied their degenerate multi-photon absorption properties in both the solution phase and the neat-film state within femtosecond and nanosecond regions. In our experiments, these model compounds are found to manifest strong and widely dispersed two-photon absorption as well as effective power-limiting properties against ultra-short laser pulses in the near-IR region. In addition, both chromophores exhibit medium to strong three-photon-induced fluorescence, indicating such scaffold may serve as a reference structural motif for the development of three-photon materials.
Conjugated polymers with carbazole, fluorene, and ethylene dioxythiophene in the main chain and a pendant cyano group: Synthesis, photophysical, and electrochemical studies
Anand, Vivek,Ramachandran, Elumalai,Dhamodharan, Raghavachari
, p. 2774 - 2784 (2016/07/28)
Six new conjugated polymers comprising of carbazole, fluorene, and ethylene dioxythiophene (EDOT) moieties along the backbone with a pendant cyano group attached to the ethylene moiety have been designed and synthesized via Sonogashira coupling polymerization reaction. Optical and electrochemical characterizations have shown that the energy band gaps lie within the range of 2.35–2.44 eV. Additionally, the presence of carbazole and EDOT makes these polymers better hole transporting materials, which is reflected from their low oxidation potential peaks (0.55–1.11 V) in cyclic voltammograms. Furthermore, the aggregation enhanced emission (AEE) phenomenon resulted in a 2.6-fold increase in fluorescence intensity in a 90:10 THF/water mixture in comparison to pristine THF. The AEE properties were further verified by DLS (dynamic light scattering) experiment and SEM (scanning electron microscopy) studies. Polymers in solution as well as in polystyrene matrix emit in the green region (quantum yield in solution state Φf =41–43%) with CIE values (0.25–0.36, 0.52–0.57). Excellent thermal stability is observed for the new polymers.
Heterocyclic heptacene analogs - 8H-16,17-epoxydinaphto[2,3-c:2′,3′-g]carbazoles as charge transport materials
Rimkus, Renaldas,Tumkevi?ius, Sigitas,Serevi?ius, Tomas,Komskis, Regimantas,Adomenas, Povilas,Gruodis, Alytis,Jankauskas, Vygintas,Kazlauskas, Karolis,Jur?enas, Saulius
, p. 133 - 144 (2015/10/12)
Owing to extended π-electron system higher polyacenes are promising materials for organic electronics, however realization of higher conjugation of acenes results in their instability under ambient conditions. We now report on synthesis, optical and electrical characterization of nitrogen heteroatom containing heptacene analogs - 8H-16,17-epoxydinaphto[2,3-c:2′,3′-g]carbazoles - decorated with various alkyl and aryl side-groups. V-shape geometry, incorporation of nitrogen heteroatom and introduced epoxy bridge ensure higher oxidative stability of the compounds as compared to analogous polyacenes. Additionally, the alteration of the molecular structure with various side-groups, either conjugated or non-conjugated, enabled the tuning of ionization potential from 4.7 eV to 5.5 eV with further gain in compound stability. This ensures of hole drift mobility up to 8 × 10-4 cm2/(V s) at 1 MV/cm for thick wet-casted films under ambient conditions. Peculiarities of forbidden lowest excited states in the V-shaped N-heptacenes are revealed based on detailed optical characterization and density functional modeling.
N,N'-diphenyl-N,N'-di(9,9-dimethyl fluorene-2-yl)-N-hexyl-(4,4'-diamine phenyl) carbazole and synthetic method thereof
-
Paragraph 0009; 0025; 0026; 0027, (2016/10/08)
The invention discloses N,N'-diphenyl-N,N'-di(9,9-dimethyl fluorene-2-yl)-N-hexyl-(4,4'-diamine phenyl) carbazole and a synthetic method thereof and belongs to the field of organic synthesis. According to the synthetic method, 2,7-dibromo-carbazole is used as a raw material and subjected to N-alkylation and a Suzuki coupled reaction to synthesize 2,7-di(4-bromophenyl)-N-hexyl carbazole; 2-bromo-9,9-dimethyl fluorene and aniline are used as raw materials and subjected to a Buchwald-Hartwig coupled reaction to synthesize 9,9-dimethyl-N-phenyl fluorine-2-amine; lastly, 2,7-di(4-bromophenyl)-N-hexyl carbazole and the 9,9-dimethyl-N-phenyl fluorine-2-amine are used as raw materials and subjected to a Buchwald-Hartwig coupled reaction to synthesize a target compound. The target compound has good heat stability and glass transition temperature and is suitable for hole transport materials of organic light-emitting devices.
Synthesis and molecular properties of methoxy-substituted diindolo[3,2-: B:2′,3′- h] carbazoles for organic electronics obtained by a consecutive twofold Suzuki and twofold Cadogan reaction
Srour, Hassan,Doan, Thu-Hong,Silva, Elisabeth Da,Whitby, Richard J.,Witulski, Bernhard
supporting information, p. 6270 - 6279 (2016/07/12)
A set of methoxy-substituted diindolo[3,2-b:2′,3′-h]carbazoles has been synthesized by twofold Suzuki-Miyaura, Cadogan and N-alkylation reactions starting from N-hexyl-2,7-dibromo-3,6-dinitro carbazole. Microwave accelerated reactions ensure a rapid strai
Dynamically controllable emission of polymer nanofibers: Electrofluorescence chromism and polarized emission of polycarbazole derivatives
Kawabata, Kohsuke,Goto, Hiromasa
, p. 15065 - 15072 (2013/01/15)
Electrochemical polymerization of a series of N-alkyl-2,7-di(2-thienyl) carbazoles in acetonitrile was performed to obtain conjugated polymers with fluorescence. Scanning electron and atomic force microscopies revealed that the surface morphology of the polymer films significantly depends on the alkyl chain lengths of the polymers. Particularly, a homopolymer bearing hexyl groups and copolymers with an average alkyl chain length of six carbon atoms show nanofiber morphology. The polymer nanofibers were stacked on a substrate electrode. The fluorescence of the polymer nanofiber film was tunable with application of voltage, with good repeatability. The X-ray diffraction pattern of the fibers showed the structural order. The polymer nanofibers thus prepared showed an electrochemically driven change in polarized photoluminescence.
Carbazole-linked porphyrin dimers for organic light emitting diodes: Synthesis and initial photophysical studies
Ryan, Aoife,Tuffy, Brian,Horn, Sabine,Blau, Werner J.,Senge, Mathias O.
, p. 8248 - 8254 (2011/11/12)
Carbazole linked porphyrin dimers were synthesized in good yields via stepwise Suzuki coupling reactions using bromoporphyrins and borylated carbazoles as the precursors, the latter of which were synthesized via known procedures from biphenyl derivatives. For comparative purposes porphyrin-carbazole monomers were synthesized. Single layer organic light emitting diodes (OLEDs) were created to demonstrate the optical properties of these materials. Light emission from these carbazole substituted porphyrins showed better results compared to previously examined bromo substituted porphyrins with better electroluminescence and lower turn-on voltages. Dimers exhibited turn-on voltages of 3 V compared to 6 V for monomeric porphyrin-carbazoles.
A novel approach to diindenocarbazoles via palladium-catalyzed intramolecular arylation
Rong, Lingling,Liu, Qiancai,Tang, Jie,Chi, Zhenguo
experimental part, p. 977 - 984 (2010/10/02)
The diindenocarbazole derivatives are synthesized by the reaction of 2,7-dibromo-9-hexylcarbazole with benzoyl chloride under Friedel-Crafts conditions, followed by Wolff-Kishner-Huang reduction to produce 3,6-dibenzyl-2,7-dibromo-9-hexylcarbazole, which was cyclized to form bis(indeno)-9-hexylcarbazole by palladium-catalyzed double intramolecular arylation. The diindeno-carbazole was further converted into fully alkylated compounds.
