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.
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.
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.
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.
Spectroscopic observation of the dimerization reactions of the 9-phenylcarbazole cation radical in acetonitrile
Oyama, Munetaka,Matsui, Jun
, p. 953 - 957 (2004)
The dimerization reaction processes of the 9-phenylcarbazole cation radical (PCZ>=+) in acetonitrile (AN) were observed using an electron-transfer stopped-flow method. Although the lifetime of PCZ >=+ in AN is less than a few hundred milliseconds, the dynamic transformation of the absorption spectra of PCZ>=+ was successfully observed in AN for the first time with the proposed method. By observing the changes in the absorption spectra in the visible region, the decrease in PCZ>=+ and the concurrent increase in the dimer cation radical were observed with isosbestic points. In addition, in the presence of neutral PCZ, the acceleration of the dimerization of PCZ >=+ was clearly confirmed. Consequently, in the presence of PCZ, the rate law was determined to be -d[PCZ>=+]/dt = 3Kk′[PCZ>=+]2 [PCZ], where 3Kk′ is 1.4 × 109 M-2 s-1. This means that the reaction mechanism involves a two-step interaction with the catalytic effect of neutral PCZ. Although the difference in the reactivity had already been known between PCZ>=+ and the triphenylamine cation radical, the reaction mechanism has been clarified to be different in both cases.
Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide
Xu, Shiyang,Huang, Baoliang,Qiao, Guanyu,Huang, Ziyue,Zhang, Zhen,Li, Zongyang,Wang, Peng,Zhang, Zhenhua
, p. 5578 - 5582 (2018)
A Rh(III)-catalyzed C-H activation of boronic acid with aryl azide to obtain unsymmetric carbazoles, 1H-indoles, or indolines has been developed. The reaction constructs dual distinct C-N bonds via sp2/sp3 C-H activation and rhodium nitrene insertion. Synthetically, this approach represents an access to widely used carbazole derivatives. The practical application to CBP and unsymmetric TCTA derivatives has also been performed. Mechanistic experiments and DFT calculations demonstrate that a five-membered rhodacycle species is the key intermediate.
A novel donor-acceptor polymeric electrochromic material containing carbazole and 1,8-naphtalimide as subunit
Koyuncu, Fatma Baycan,Koyuncu, Sermet,Ozdemir, Eyup
, p. 4935 - 4941 (2010)
We report here the synthesis of a novel polymeric electrochromic material containing carbazole (Cbz)-donor and 1,8-napthalimide-acceptor as subunit. The band gap Eg was measured using UV-vis spectroscopy and compared with that obtained by cyclic voltammetry (CV). Due to intramolecular electron transfer from Cbz-donor to 1,8-napthalimide-acceptor, the fluorescence quenching was observed. When the spectro-electrochemical and electrochromic properties of polymer film were investigated, various tones of green color were obtained on the polymeric film. In the positive regime, the polymer film obtained thereby is dark green resulting from the association of carbazolylium cation radicals at oxidized state and then it can be bleached by electrochemical reduction. Besides, in the negative regime, yellowish green color of film converted to blue attributed to reduction of the 1,8-napthalimide moiety. Finally, the polymeric electrochromic exhibits multi-electrochromic behavior, high redox stability, high coloration efficiency and reasonable response time.
Fluorinated tetraketone derivatives of N-substituted carbazoles and their Eu(III) complexes for fluorescence immunoassay
Pugachov, Dmitriy E.,Kostryukova, Tatiana S.,Zatonsky, Georgy V.,Vatsadze, Sergey Z.,Vasil’ev, Nikolai V.
, p. 528 - 534 (2018)
[Figure not available: see fulltext.] New fluorinated tetraketone derivatives of N-substituted carbazoles were synthesized and tested as ligands for fluorescence immunoassay. The spectral properties of the obtained heterocyclic tetraketones and their Eu(III) complexes were studied. The complexes showed longwave absorption at 360–380 nm, high extinction coefficient values, long lifetime of excited states, and intense luminescence, allowing to consider the use of such lanthanide complexes in immunofluorescence analysis.
Synthesis of novel star-shaped carbazole-functionalized triazatruxenes
Feng, Guo-Liang,Lai, Wen-Yong,Ji, Shun-Jun,Huang, Wei
, p. 7089 - 7092 (2006)
The syntheses of novel well-defined star-shaped carbazole-functionalized triazatruxenes, which consist of six carbazole arms linked with a central triazatruxene core consisting of three carbazoles with one phenyl, are presented. Both 9-hexylcarbazole and 9-phenylcarbazole as arms gave high yields. Their chemical formulas were confirmed by means of 1H NMR, MALDI-TOF mass spectroscopy, and elementary analysis. The fluorescent spectra showed that these compounds exhibit good blue fluorescence. The maximum fluorescence emission wavelengths were between 420 and 430 nm.
A facile one-step approach for the synthesis of uniform spherical Cu/Cu2O nano- and microparticles with high catalytic activity in the Buchwald-Hartwig amination reaction
Bhosale, Manohar A.,Bhanage, Bhalchandra M.
, p. 15122 - 15130 (2014)
In the present work, we have developed a rapid, one step, calcination-free protocol for the synthesis of uniform spherical Cu/Cu2O nano/microparticles (NMPs). The synthesis of Cu/Cu2O NMPs was achieved by microwave irradiation of copper acetate as a precursor and 1,4-butanediol as a solvent in a few minutes. The prepared Cu/Cu2O NMPs gave 100% yield of uniform spherical morphology. 1,4-Butanediol plays a crucial role in reactions such as a solvent, reactant, stabilizer and capping agent which control the crystal morphology. The resultant product was characterized with the help of different techniques such as XRD, FEG-SEM, EDS, TEM, FT-IR, TPR, DSC-TGA, XPS and BET surface area analysis. The results confirm that the Cu/Cu2O NMPs had good crystallinity and were essentially pure. This is a simple, faster, inexpensive and additive-free protocol for synthesis of nanocrystalline Cu/Cu2O compared to the conventional method. These Cu/Cu2O NMPs showed excellent catalytic activity in the Buchwald-Hartwig amination coupling reaction. Notably the reaction does not require any ligand source, and requires low catalyst loading, and low temperature with catalyst recyclability. the Partner Organisations 2014.
Touch-sensitive mechanoluminescence crystals comprising a simple purely organic molecule emit bright blue fluorescence regardless of crystallization methods
Zhang, Kai,Sun, Qikun,Zhang, Zhenzhen,Tang, Linagliang,Xie, Zongliang,Chi, Zhenguo,Xue, Shanfeng,Zhang, Haichang,Yang, Wenjun
, p. 5225 - 5228 (2018)
Simple N-phenylcarbazole (NPC) could readily form brightly mechanofluorescent crystals with mechanically touch-sensitive response, regardless of crystallization methods. NPC with roomerature photophosphorescence did not exhibit mechano-phosphorescence, signifying that the excitation modes could play an important role in affecting light-emitting processes.
Novel benzothiadiazine 1,1-dioxide based bipolar host materials for efficient red phosphorescent organic light emitting diodes
Lade, Jatin,Lee, Nian-Yun,Patil, Bhausaheb,Deshpande, Yogita Y.,Pownthurai,Hsieh, Chung-An,Pingale, Subhash S.,Chen, Li-Yin,Chaskar, Atul
, (2021/03/04)
In this work, three novel bipolar host materials TPA-SA, 3CBZ-SA and 4CBZ-SA have been designed and synthesized by incorporating triphenyl amine and carbazole as donor and benzothiadiazine 1,1-dioxide as an acceptor. These molecules exhibit moderately high triplet energies and bipolar carrier transport characteristics (ambipolarity) which is useful for the exothermic energy transfer to the dopants and also for the balanced carrier injection/transport in the emissive layers. These materials exhibited good performances in PhOLEDs and furnished external quantum efficiency in the range of 10.0–15.0%. Notably, a red phosphorescent device using TPA-SA as the host doped with Ir(pq)2(acac) exhibited a maximum EQE, power efficiency and current efficiency of 15.0%, 16.0 lm/W, and 25.3 cd A?1, respectively.
A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
Huang, Binbin,Guo, Lin,Xia, Wujiong
supporting information, p. 2095 - 2103 (2021/03/26)
A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
