1150-62-5Relevant articles and documents
Easily oxidizable triarylamine materials with naphthalene and binaphthalene core: structure–properties relationship
Kerner, Luká?,Gmucová, Katarína,Ko?í?ek, Jozef,Pet?í?ek, Václav,Putala, Martin
, p. 7081 - 7092 (2016)
We devised and synthesized a series of electron-rich compounds featuring diphenylamine, carbazole or dibenzo[c,g]carbazole connected via phenylacetylene linkers to an aromatic central unit. The key synthetic step was a high yielding cross coupling reaction between halogenated (bi)naphthalene and organometallic reagents prepared in situ from terminal alkynes (side-arms). By masking one of the iodo functions with a diethyltriazenyl group in the side-arm precursors, we efficiently circumvented the formation of doubly aminated by-products. Although one step longer, this approach led to higher yields of terminal alkynes than the direct coupling route. Spectroscopic and electrochemical measurements supported by computational evidence revealed that conjugation in the 1,4-disubstituted naphthalene backbone is superior to the 1,5 or 2,6 substituted cores. The diphenylamine derivative gets oxidized more readily when compared to its carbazole analogs. Expanding the core to binaphthalene did not alter electronic properties, but influenced the physical characteristics significantly.
Multifunctional iridium complexes based on carbazole modules as highly efficient electrophosphors
Wong, Wai-Yeung,Ho, Cheuk-Lam,Gao, Zhi-Qiang,Mi, Bao-Xiu,Chen, Chin-Hsin,Cheah, Kok-Wai,Lin, Zhenyang
, p. 7800 - 7803 (2006)
(Figure Presented) Getting the green light: Highly efficient organic light-emitting diodes (OLEDs) have been synthesized from robust green-electrophosphorescent IrIII complexes based on carbazole derivatives (see picture, HT = hole transporting, EL = electroluminescence). The combination of short triplet lifetime, high emission efficiency, and improved charge-transporting properties allows these OLEDs to achieve peak efficiencies of 12% photons per electron and 38 cd A-1.
Synthesis of N-Arylcarbazoles by Palladium-Catalyzed Direct C–H Arylation of 2-(Diarylamino)phenyl Triflates
Uwa, Koji,Tseng, Ya-Yi,Kamikawa, Ken
, p. 892 - 895 (2017)
The palladium-catalyzed direct arylation of a series of 2-(diarylamino)phenyl triflates was examined. The triflates were first synthesized in moderate to good yields through the CuI-catalyzed aryl amination of aminophenol and aryl iodides, followed by triflation of the resulting triarylphenols. The thus-obtained 2-(diarylamino)phenyl triflates were subjected to direct C–H arylation under Pd catalysis to furnish the corresponding N-arylcarbazoles in excellent yields if Josiphos was used as the supporting ligand.
The interplay of photophysical properties in carbazole fluorescent oligomers
Hsu, Chung-Yi,Hsieh, Mu-Tao,Chen, Yen-Fu,Hsu, Chun-Chia,Hung, Tzu-Lin,Chen, Chun-Shuo,Whang, Thou-Jen
, p. 579 - 589 (2013)
The photophysical properties and the organic synthesis using effective palladium-catalyzed Suzuki coupling reactions from a series of carbazole derivatives are described and the relationships of the donor and acceptor groups are also investigated. The purification of the materials and its applications along with the corresponding photo-physical characterizations were presented. With the advantages gained from 2DCOSY spectra, which provide more correlated information between immediate atoms than 1H-NMR spectra and a series of further investigations were undertaken including powder X-ray diffraction analysis, Infrared and Raman spectroscopy, constructing the composition conformation and chemical structure of the materials is more easily to achieve. Additionally, the optimized structure of the minimized energy geometries and spatial distributions of carbazole derivatives was calculated using density functional theory (DFT), new materials can be developed and designed selectively based on the method proposed in this work.
A simple and versatile strategy for realizing bright multicolor mechanoluminescence
Sun, Qikun,Zhang, Kai,Zhang, Zhenzhen,Tang, Linagliang,Xie, Zongliang,Chi, Zhenguo,Xue, Shanfeng,Zhang, Haichang,Yang, Wenjun
, p. 8206 - 8209 (2018)
Multicolor mechanoluminescence (ML) was first realized by using the stable organic blue ML emitter N-phenylcarbazole as the host matrix. It is claimed that a good ML host should have a moderate melting point and be able to dissolve or disperse organic dyes but maintain high ML activity and crystallinity. This strategy is versatile and can avoid difficult molecular design and troublesome chemical synthesis.
The double N-arylation of primary amines: Toward multisubstituted carbazoles with unique optical properties
Nozaki, Kyoko,Takahashi, Keita,Nakano, Koji,Hiyama, Tamejiro,Tang, Hong-Zhi,Fujiki, Michiya,Yamaguchi, Shigehiro,Tamao, Kohei
, p. 2051 - 2053 (2003)
A powerful method: A variety of sterically crowded, substituted carbazoles have been prepared from anilines and biphenyl compounds (see scheme). The method enabled the preparation of 2,2′-dicarbazolyl-1,1′-biaryl compounds, which show excimer (or exciplex) emissions with significant solvent dependency.
Nickel-Catalyzed N-Arylation Using N -Trimethylsilyl-carbazole
Minami, Yasunori,Komiyama, Takeshi,Shimizu, Kenta,Uno, Shu-Ichi,Hiyama, Tamejiro,Goto, Osamu,Ikehira, Hideyuki
, p. 2407 - 2410 (2017)
Nickel-catalyzed N-arylation reaction of N -trimethylsilyl-carbazole using aryl bromides is found to proceed in the presence of sodium acetate, giving N -aryl-carbazoles in high yields. Under these conditions, N -trimethylsilyl-carbazole could react with aryl bromides selectively even in the presence of other N -trimethylsilyl-amines or N -H-amines. This arylation reaction was applied to the polymerization to provide a polycarbazole.
Metal-organic frameworks derived CuONPs@C nanocatalysts for synthesizing optoelectronic triarylamine molecules
Kundu, Anu,Kumar, Vadivel Vinod,Anthony, Savarimuthu Philip
, (2021)
Carbon encapsulated copper oxide nanoparticles (CuONPs@C) fabricated using copper metal organic frameworks (Cu-MOFs) used as reusable nanocatalysts in Ullmann C[sbnd]N coupling reactions for synthesizing optoelectronic triphenylamine (TPA) and carbazole (CBZ) derivatives. The formation of CuONPs in carbon matrix was confirmed by powder X-ray diffraction (PXRD), X-ray photoelectron spectroscopy (XPS) and high-resolution transmission electron microscopy (HR-TEM). The catalytic activity of CuONPs@C was performed with diphenylamine/carbazole with substituted aryl halides in presence of mild K2CO3 base that produced triarylamines with 63–83% yields. Carbazole triarylamines exhibited strong solid state fluorescence (Φf = 14.54–36.32%) with λmax between 370 and 420 nm.
Ternary donor-acceptor phosphine oxide hosts with peculiar high energy gap for efficient blue electroluminescence
Sun, Mingzhi,Zhu, Liping,Kan, Wenjing,Wei, Ying,Ma, Dongge,Fan, Xuefeng,Huang, Wei,Xu, Hui
, p. 9469 - 9478 (2015)
Ternary donor (D)-acceptor (A)-acceptor (A) molecules are commonly considered as low triplet (T1) energy systems for specific applications. In this work, exception to this behavior was observed in a triangle-shaped D-A-A molecule PCImbPO with unusually high triplet energy of 3.0 eV. Profiting from the enhanced D-A electronic coupling, electron injecting and transporting ability of PCImbPO was dramatically improved with negligible influences on its highest occupied molecular orbital (HOMO) characteristics. Its particular T1 configuration adjustment further gives rise to the separated frontier MO and T1 locations, beneficial to suppress quenching effects. By utilizing PCImbPO as host in blue phosphorescent organic light-emitting diodes (PHOLEDs) and thermally activated delayed fluorescence devices, impressively high external quantum efficiency of 22% and 12% were achieved, respectively. This work established a new understanding of high-energy-gap complicated D-A systems.
Transition Metal-Free Carbazole Synthesis from Arylureas and Cyclohexanones
Wu, Jun,Xie, Yanjun,Chen, Xiangui,Deng, Guo-Jun
, p. 3206 - 3211 (2016)
An efficient strategy for carbazole synthesis from arylureas and cyclohexanones under transition metal-free conditions has been developed. The combined use of potassium iodide and iodine could significantly improve the reaction efficiency to provide 2,6-disubstituted 9-arylcarbazoles in moderate to good yields. In this kind of transformation, the whole carbazole moiety (except the nitrogen atom) comes from two equivalents of cyclohexanones. (Figure presented.).
