- Easily oxidizable triarylamine materials with naphthalene and binaphthalene core: structure–properties relationship
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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.
- Kerner, Luká?,Gmucová, Katarína,Ko?í?ek, Jozef,Pet?í?ek, Václav,Putala, Martin
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- Multifunctional iridium complexes based on carbazole modules as highly efficient electrophosphors
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(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.
- Wong, Wai-Yeung,Ho, Cheuk-Lam,Gao, Zhi-Qiang,Mi, Bao-Xiu,Chen, Chin-Hsin,Cheah, Kok-Wai,Lin, Zhenyang
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- Synthesis of N-Arylcarbazoles by Palladium-Catalyzed Direct C–H Arylation of 2-(Diarylamino)phenyl Triflates
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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.
- Uwa, Koji,Tseng, Ya-Yi,Kamikawa, Ken
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- The interplay of photophysical properties in carbazole fluorescent oligomers
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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.
- Hsu, Chung-Yi,Hsieh, Mu-Tao,Chen, Yen-Fu,Hsu, Chun-Chia,Hung, Tzu-Lin,Chen, Chun-Shuo,Whang, Thou-Jen
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- A simple and versatile strategy for realizing bright multicolor mechanoluminescence
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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.
- Sun, Qikun,Zhang, Kai,Zhang, Zhenzhen,Tang, Linagliang,Xie, Zongliang,Chi, Zhenguo,Xue, Shanfeng,Zhang, Haichang,Yang, Wenjun
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- The double N-arylation of primary amines: Toward multisubstituted carbazoles with unique optical properties
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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.
- Nozaki, Kyoko,Takahashi, Keita,Nakano, Koji,Hiyama, Tamejiro,Tang, Hong-Zhi,Fujiki, Michiya,Yamaguchi, Shigehiro,Tamao, Kohei
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- Nickel-Catalyzed N-Arylation Using N -Trimethylsilyl-carbazole
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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.
- Minami, Yasunori,Komiyama, Takeshi,Shimizu, Kenta,Uno, Shu-Ichi,Hiyama, Tamejiro,Goto, Osamu,Ikehira, Hideyuki
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- Metal-organic frameworks derived CuONPs@C nanocatalysts for synthesizing optoelectronic triarylamine molecules
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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.
- Kundu, Anu,Kumar, Vadivel Vinod,Anthony, Savarimuthu Philip
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- Ternary donor-acceptor phosphine oxide hosts with peculiar high energy gap for efficient blue electroluminescence
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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.
- Sun, Mingzhi,Zhu, Liping,Kan, Wenjing,Wei, Ying,Ma, Dongge,Fan, Xuefeng,Huang, Wei,Xu, Hui
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- Transition Metal-Free Carbazole Synthesis from Arylureas and Cyclohexanones
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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.).
- Wu, Jun,Xie, Yanjun,Chen, Xiangui,Deng, Guo-Jun
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- Spectroscopic observation of the dimerization reactions of the 9-phenylcarbazole cation radical in acetonitrile
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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.
- Oyama, Munetaka,Matsui, Jun
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- Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide
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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.
- Xu, Shiyang,Huang, Baoliang,Qiao, Guanyu,Huang, Ziyue,Zhang, Zhen,Li, Zongyang,Wang, Peng,Zhang, Zhenhua
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- Scope, Kinetics, and Mechanism of “On Water” Cu Catalysis in the C–N Cross-Coupling Reactions of Indole Derivatives
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A simple and cost-effective protocol for the C–N cross coupling of indole derivatives with aryl iodides using CuI/phenanthroline catalytic system in aqueous and DME/H2O solvent mixture is described. The reactions were performed in the absence of phase-transfer catalyst, and afforded N-arylated products in moderate to excellent yields under mild reaction conditions. A systematic tuning of reaction conditions using DME as a co-solvent enables to improve product yields of N-arylation reactions. The broad substrate scope, easy performance, and low loading of catalyst as well as ligand render this approach appropriate for large scale processes. The mechanism of “on water” Cu-catalyzed N-arylation reaction is investigated using kinetic and computational studies, which reveal interesting mechanistic aspects of the reaction. A series of kinetic experiments showed significant rate enhancement for “on water” Cu-catalyzed N-arylation over the reaction performed in the organic solvent (DME). Computational studies corroborated “on water” rate acceleration by delineating the role of water in the reaction. The water induces rate acceleration by stabilizing the transition state of oxidative addition through hydrogen bonding interactions, presumably at the oil-water interface, and thus helps to reduce the free energy of activation of oxidative addition of iodobenzene to the Cu complex, which is identified as the rate-limiting step of reaction.
- Malavade, Vrunda,Patil, Manish,Patil, Mahendra
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- A novel donor-acceptor polymeric electrochromic material containing carbazole and 1,8-naphtalimide as subunit
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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.
- Koyuncu, Fatma Baycan,Koyuncu, Sermet,Ozdemir, Eyup
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- Phenothiazine dioxide-containing derivatives as efficient hosts for blue, green and yellow thermally activated delayed fluorescence OLEDs
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By conjugating 10-phenyl-10H-phenothiazine-5,5-dioxide (2PTO) with aromatic amine substituents (PhCz and DMACMN), three novel host materials namely 10-(9-phenyl-9H-carbazol-3-yl)-10H-phenothiazine 5,5-dioxide (3CzNPTO), (10-(4-(9H-carbazol-9-yl)phenyl)-10H-phenothiazine 5,5-dioxide (9CzNPTO) and 10-(4-(9,9-dimethylacridin-10(9H)-yl)-2,5-dimethylphenyl)-10H-phenothiazine 5,5-dioxide (DMACMNPTO) were designed and synthesized. DMACMNPTO with thermally activated delayed fluorescence (TADF) properties exhibited bipolar characteristics resulting from the completely separated HOMO/LUMO distribution. Using DMACMNPTO as a host for TADF emitters, devices showed a maximum external quantum efficiency (EQEmax), current efficiency (CEmax) and power efficiency (PEmax) of 18.3%, 33.3 cd A-1 and 37.4 lm W-1 in blue-emitting diodes, 18.6%, 49.1 cd A-1 and 47.2 lm W-1 in green-emitting diodes, and 19.1%, 59.2 cd A-1 and 66.0 lm W-1 in yellow-emitting diodes, respectively. These results corroborated the potential of phenothiazine dioxide-containing derivatives as host materials in a sequence of color TADF-OLEDs.
- Guo, Runda,Huang, Zhi,Liu, Wei,Wang, Lei,Wang, Yaxiong,Xiang, Songpo,Ye, Shaofeng,Zhang, Qing
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- Fluorinated tetraketone derivatives of N-substituted carbazoles and their Eu(III) complexes for fluorescence immunoassay
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[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.
- Pugachov, Dmitriy E.,Kostryukova, Tatiana S.,Zatonsky, Georgy V.,Vatsadze, Sergey Z.,Vasil’ev, Nikolai V.
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- Carbazole based nanoprobe for selective recognition of Fe3?+ ion in aqueous medium: Spectroscopic insight
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A simple carbazole based nanoprobe prepared by reprecipitation method shows selective sensing behavior for Fe3?+ ion in aqueous medium. The prepared SDS capped 9-phenyl carbazole nanoparticles (9-PCzNPs) has narrower particle size distribution with an average diameter 35?nm and zeta potential of ??34.3?mV predicted a good stability with negative surface charge over the nanoparticles. The Field Emission Scanning Electron Microscopy (FE-SEM) image showed cubic shape morphology of nanoparticles. The aqueous suspension of SDS capped 9-phenyl carbazole nanoparticles exhibited aggregation induced enhanced red shifted intense emission in comparison with the emission arising from dilute solution of 9-phenyl carbazole in DCM. The cation recognition test based on fluorescence change shows Fe3?+ ion induce significant fluorescence quenching, however remaining cations responds negligibly. The obtained quenching data fit into Stern–Volmer relation in the concentration range of 0.0–1.0?μg·mL??1 of Fe3?+ ion solution and the detection limit is 0.0811?μg·mL??1. The probable mechanism of fluorescence quenching of SDS capped 9-PCzNPs is because of adsorption of Fe3?+ ion over the negatively charged surface of NPs through electrostatic interaction. Thus the proposed method was successfully applied for the detection of Fe3?+ ion in environmental water sample.
- Suryawanshi, Sonali B.,Mahajan, Prasad G.,Bodake, Anita J.,Kolekar, Govind B.,Patil, Shivajirao R.
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- Synthesis of novel star-shaped carbazole-functionalized triazatruxenes
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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.
- Feng, Guo-Liang,Lai, Wen-Yong,Ji, Shun-Jun,Huang, Wei
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- Synthesis of a carprofen analogue using a continuous flow UV-reactor
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A continuous flow UV light reactor has been constructed using commercially available equipment, and its efficiency was demonstrated by performing a photocyclodehydrogenation reaction to prepare carbazole derivatives of the drug carprofen.
- Caron, Antoine,Hernandez-Perez, Augusto C.,Collins, Shawn K.
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- 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
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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.
- Bhosale, Manohar A.,Bhanage, Bhalchandra M.
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- Facile Assembly of Carbazolyl-Derived Phosphine Ligands and Their Applications in Palladium-Catalyzed Sterically Hindered Arylation Processes
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Phosphine ligands embodying a carbazolyl motif have been found to be successful in many palladium-catalyzed biaryl syntheses and direct C-H bond arylation processes. Here, a practical scaled-up synthesis of a series of carbazolyl-derived phosphine ligands, the PhenCarPhos series, is described. The original protocol for accessing the target ligand skeleton via aromatic C-N bond formation is limited by the use of a substoichiometric amount of copper salt and diamine catalysts, which both add cost and generate purification problems (significant amounts of side products and copper residues). In order to develop a more attractive and scalable synthetic pathway, a simple nucleophilic substitution method was attempted involving simple heating of 1-bromo-2-fluorobenzene, a carbazole derivative, and KOH in DMF without inert atmosphere protection. This route enables the large-scale synthesis of the desired ligand skeletons and minimizes the association of inseparable reduction side products. Particular examples of the use of these ligands in Pd-catalyzed sterically hindered arylation processes are also shown.
- Leung, Man Pan,Choy, Pui Ying,Lai, Wing In,Gan, Kin Boon,Kwong, Fuk Yee
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- Touch-sensitive mechanoluminescence crystals comprising a simple purely organic molecule emit bright blue fluorescence regardless of crystallization methods
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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.
- Zhang, Kai,Sun, Qikun,Zhang, Zhenzhen,Tang, Linagliang,Xie, Zongliang,Chi, Zhenguo,Xue, Shanfeng,Zhang, Haichang,Yang, Wenjun
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- Synthesis and characterization of nano-cellulose immobilized phenanthroline-copper (I) complex as a recyclable and efficient catalyst for preparation of diaryl ethers, N-aryl amides and N-aryl heterocycles
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Functionalized nanocellulose was prepared and employed for immobilization of phenanthroline-copper(I) complex to afford cellulose nanofibril grafted heterogeneous copper catalyst [CNF-phen-Cu(I)]. This nanocatalyst was well characterized using FT-IR, NMR, XRD, CHNS, AAS, TGA, EDX and SEM. The activities of the synthesized catalyst were examined in the synthesis of diaryl ethers via C-O cross-coupling of phenols and aryl iodides, as well as, the preparation of N-aryl amides and N-aryl heterocycles through C-N cross-coupling of amides and N-H heterocycle compounds with aryl halides. In this trend, various substrates containing electron-donating and electron-withdrawing groups were exploited to evaluate the generality of this catalytic protocol. Accordingly, the catalyst demonstrated remarkable catalytic efficiency for both C-N and C-O cross-coupling reactions, thereby resulting in good to excellent yields of the desired products. Furthermore, the recoverability experiments of the catalyst showed that it can be readily retrieved by simple filtration and successfully reused several times with negligible loss of its catalytic activity.
- Aghili, Nora,Hosseinzadeh, Rahman,Mavvaji, Mohammad
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- Photochemistry of triphenylamine (TPA) in homogeneous solution and the role of transient N -phenyl-4 a,4 b -dihydrocarbazole. A steady-state and time-resolved investigation
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The photoreactivity of triphenylamine in homogeneous media has been investigated by means of laser flash photolysis spectroscopy and preparative experiments. The goal of this study consists in the evaluation of the photophysical and photochemical behavior of transient N-phenyl-4a,4b-dihydrocarbazole (DHC0) under polar and non-polar solvents which was not performed yet. The kinetic parameters of such a key intermediate including lifetime (τd, τR and τox) and rate constants (kd, kR and kox) have been measured and the intermediacy of DHC0 in the co-oxidation of nucleophilic substrates such as sulfides and phosphines was investigated by a combined time-resolved and steady-state approach. Two distinctly oxidizing intermediates, a hydroperoxy radical and a hydroperoxide derivative were formed from transient DHC0 in the presence of molecular oxygen. Radical I oxidizes triarylphosphines, whereas intermediate II converts sulfides into the corresponding sulfoxides.
- Bonesi, Sergio M.,Mella, Mariella,Protti, Stefano
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p. 16581 - 16593
(2021/10/01)
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- Preparation method of N-arylcarbazole-3-boric acid
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The invention discloses a preparation method of N-arylcarbazole-3-boric acid, and belongs to the field of liquid crystal intermediates. The preparation method comprises the following steps: coupling carbazole with aryl halide in the presence of alkali to generate N-arylcarbazole, enabling the N-arylcarbazole to react with a bromination reagent to generate Naryl-3, 6-dibromo carbazole, enabling theNaryl-3, 6-dibromo carbazole to react with borate and butyl lithium by a one-pot method, and carrying out hydrolyzing to obtain N-arylcarbazole-3-boric acid. According to the method, dibromides whichare easy to purify are generated during bromination, monosubstituted products are generated by controlling the using amount of the lithiation reagent and the boric acid ester during lithiation, the method is verified on the scale of dozens of kilograms, and the method has the prospect of industrial methods.
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Paragraph 0026-0028; 0040-0042
(2021/02/06)
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- Amine-based compound and organic light emitting diode comprising the same
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Disclosed are an amine-based compound and an organic light emitting device including the same. The amine-based compound is represented by chemical formula 1A.
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Paragraph 0223; 0227-0228
(2021/03/16)
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- Novel benzothiadiazine 1,1-dioxide based bipolar host materials for efficient red phosphorescent organic light emitting diodes
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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.
- Lade, Jatin,Lee, Nian-Yun,Patil, Bhausaheb,Deshpande, Yogita Y.,Pownthurai,Hsieh, Chung-An,Pingale, Subhash S.,Chen, Li-Yin,Chaskar, Atul
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- Transition-metal free synthesis of: N -aryl carbazoles and their extended analogs
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Herein, we describe a facile synthesis of N-arylated carbazoles via ladderization of fluorinated oligophenylenes. The reaction consists of two subsequent nucleophilic substitutions triggered by an electronic transfer from dimsyl anions. The reaction allows the effective one-pot formation of at least six C-N bonds with pronounced selectivity to the C-F bond placement.
- Akhmetov, Vladimir,Amsharov, Konstantin,Feofanov, Mikhail,Takayama, Ryo
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supporting information
p. 7172 - 7175
(2021/08/30)
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- A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
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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.
- Huang, Binbin,Guo, Lin,Xia, Wujiong
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supporting information
p. 2095 - 2103
(2021/03/26)
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- Method for synthesizing carbazole derivative
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The invention aims to provide a method for synthesizing a carbazole derivative. The method is characterized in that palladium chloride is used as a catalyst, 2, 2' - dibromobiphenyl is used as an electrophilic reagent, primary amine is taken as a nucleophile, and the carbazole derivative is directly cross-coupled under the conditions of toluene as a solvent and an air atmosphere. The method has the advantages of high yield, high selectivity, simplicity and convenience in operation and the like.
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Paragraph 0013; 0016-0017
(2021/10/05)
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- Efficient Copper-Catalysed Synthesis of Carbazoles by Double N -Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air
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An efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C-N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.
- Do, Ha Nam,Quan, Nguyen Minh,Van Phuc, Ban,Van Tinh, Dinh,Tien, Nguyen Quyet,Nga, Truong Thi Thanh,Nguyen, Van Tuyen,Hung, Tran Quang,Dang, Tuan Thanh,Langer, Peter
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supporting information
p. 611 - 615
(2021/01/21)
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- Redox-neutral decarboxylative photocyclization of anthranilic acids
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A mild metal-, catalyst-, and oxidant-free photoredox neutral system has been found to efficiently enable intramolecular decarboxylative cyclization of anthranilic acids. This facile protocol provides an alternative method for the synthesis of carbazoles. Mechanistic studies reveal a key photoinduced 6π-electrocyclization process and formic acid was released as the sole byproduct.
- Huang, Huawen,Deng, Kun,Deng, Guo-Jun
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supporting information
p. 8243 - 8247
(2020/12/29)
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- Method for preparing N-phenyl carbazole by coupling bromobenzene and carbazole C-N under catalysis of copper
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The invention relates to the field of chemical intermediate preparation, and specifically relates to a method for preparing N-phenyl carbazole by coupling bromobenzene and carbazole C-N under the catalysis of copper. The method is characterized in that under the protection of nitrogen, bromobenzene and carbazole react under the action of a copper catalyst, alkali and a mixed solvent to generate N-phenyl carbazole, compared with reported methods, cheap copper salt is used as a catalyst, a ligand does not need to be added in the reaction, the reaction conditions are mild, the operation is convenient, the production cost is low, the yield is high, and the method is more suitable for industrial large-scale production.
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Paragraph 0026; 0030-0051
(2021/03/06)
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- COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, COMPOSITION FOR ORGANIC OPTOELECTRONIC DEVICE AND ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY DEVICE
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The present invention relates to: a compound for an organic optoelectronic device, which is represented by chemical formula 1; a composition for an organic optoelectronic device; and an organic optoelectronic device and a display device to which the compound and composition are applied. The details of the chemical formula 1 are as defined in the specification. One embodiment provides the compound for the organic optoelectronic device, which can realize the organic optoelectronic device having high efficiency and long lifetime.
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Paragraph 0270-0272
(2020/09/12)
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- Preparation method for synthesizing N-phenylcarbazole and recovery method of catalyst
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The invention discloses a preparation method for synthesizing N-phenylcarbazole and a recovery method of a catalyst, which belong to the technical field of chemistry. The preparation method comprisesthe steps of carrying out coupling reaction on halogen benzene and carbazole under the catalytic action of bivalent copper salt to generate N-phenylcarbazole , the bivalent copper salt catalyst beingcopper 8-hydroxyquinoline, and the reaction being carried out in the presence of an organic solvent and alkali; and after the reaction is finished, carrying out reduced pressure distillation on the reaction system, dissolving, carrying out suction filtration, washing with water, extracting, carrying out reduced pressure distillation, and recrystallizing to obtain a N-phenylcarbazole pure product.The recovery method of the catalyst comprises the following steps: carrying out water washing, alcohol washing and vacuum drying on a filter cake obtained by suction filtration, recovering the bivalent copper salt, and putting the recovered bivalent copper salt into a new catalytic reaction to realize repeated use of the catalyst. According to the method, the bivalent copper salt is used as the catalyst in the carbazole C-N coupling reaction, no ligand needs to be added, recovery and repeated use of the bivalent copper salt are achieved, and the high-purity N-phenylcarbazole product is obtained.
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Paragraph 0035-0048
(2020/12/30)
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- ORGANIC LIGHT-EMITTING DEVICE AND LIGHT-EMITTING APPARATUS INCLUDING THE SAME
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Provided are an organic light-emitting device including a capping layer including an amine-based compound represented by a set or predetermined formula and a radical scavenger, and a light-emitting apparatus including the organic light-emitting device. The organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode and including an emission layer a capping layer on the second electrode, wherein the capping layer includes the amine-based compound.
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Paragraph 0436-0440
(2020/08/30)
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- Method for preparing N-phenyl carbazole by oxidative coupling of benzene and carbazole
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The invention relates to the field of chemical intermediate preparation, and specifically relates to a method for preparing N-phenyl carbazole through oxidative coupling of benzene and carbazole. Themethod comprises the following steps: taking benzene and carbazole as raw materials; and preparing N-phenyl carbazole under the action of a catalyst, a ligand, and an oxidant. Compared with a reportedmethod, the method has the advantages that benzene, which is low in price and easy to obtain, is used as a raw material, benzene does not need to be converted into halogenated benzene, benzene and carbazole are directly subjected to oxidative coupling to prepare N-phenyl carbazole, benzene serves as a reactant and a solvent in the reaction process, the reaction condition is mild, and operation isconvenient. The method is good in raw material economy, low in cost, remarkable in economic benefit and good in product quality, and a new method is provided for synthesis of N-phenyl carbazole.
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Paragraph 0012; 0023; 0027-0028; 0029-0030; 0031-0032; 0033
(2021/03/06)
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- Method for synthesizing N-aryl carbazole compound by catalyzing reaction of carbazole with aryl hydrazine by using transition metal
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The invention relates to a method for synthesizing an N-aryl carbazole compound by catalyzing reaction of carbazole with aryl hydrazine through transition metal. According to the method, a transitionmetal salt is used as a catalyst, a carbazole compound and an aryl hydrazine compound are used as reaction substrates, the reaction substrates and an alkali compound are added into a solvent for a reaction for a certain period of time to obtain a reaction solution, and the reaction solution is separated and purified to obtain the N-aryl carbazole compound. According to the method, low-boiling-point acetonitrile is used as a reaction solvent, so post-reaction treatment is easy to carry out; oxygen in the air serves as an oxidizing agent, so reaction conditions are environmentally friendly and safe, cost is low, and excessive oxidation is avoided; an aryl hydrazine compound is used as an arylation reagent, and reaction byproducts only comprise water and nitrogen, so the method is environment-friendly and pollution-free; the transition metal salt is used as the catalyst, the activity of the transition metal salt is high, the use of equivalent noble metals is avoided, and synthesis cost isreduced; and generally speaking, the synthesis method is friendly to environment, simple in process, good in reaction selectivity and high in yield, and has a relatively strong industrial applicationprospect.
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Paragraph 0045-0048; 0099
(2020/12/14)
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- Palladium-catalyzed C-H bond activation for the assembly of: N -aryl carbazoles with aromatic amines as nitrogen sources
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A convenient and efficient palladium-catalyzed C-H bond activation for the assembly of N-aryl carbazole is reported, in which two C-N bonds were formed under one set of conditions. The desired carbazoles were achieved in decent yields with a wide substrate scope by utilizing readily available 2-iodo biphenyls and aromatic amines as starting materials.
- Liu, Xiaobing,Sheng, Heyun,Zhou, Yao,Song, Qiuling
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p. 1665 - 1668
(2020/02/18)
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- Method for preparing carbazole compound
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The invention discloses a method for synthesizing a carbazole compound by utilizing N,N-di-substituted o-aminobenzoate compound. The synthesis method comprises the following steps of adopting a palladium salt as a catalyst, mixing the palladium salt, the N,N-di-substituted o-aminobenzoate compound, an oxidant and an organic solvent, and carrying out heating reaction to obtain the carbazole compound. The method disclosed by the invention has the advantages that the preparation route is short, the universality of a substrate is good, the synthesis yield is high, the used catalyst is simple and easy to obtain and the like.
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Paragraph 0098; 0099; 0100; 0101; 0102; 0103
(2019/04/13)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF
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The present invention relates to a compound for an organic electric device including a cyclopenta phenanthrene, which improves low driving voltage, color purity, and lifetime characteristics of a device, and to an organic electric device including the same, and an electronic device thereof. The compound for an organic electric device is represented by chemical formula 1. In the chemical formula 1, Ar_1 and Ar_2 are each independently deuterium and a C_6 to C_30 aryl group which is substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group having C_1 to C_20, and an aryl group having C_6 to C_30, or a heterocyclic group having C_4 to C_24, which is substituted or unsubstituted with an aryl group having C_6 to C_30 and includes at least one heteroatom of O, N, S and Si.COPYRIGHT KIPO 2019
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Paragraph 0065-0069
(2019/05/28)
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- ORGANIC COMPOUND, ORGANIC LIGHT EMITTING DIODE AND ORGANIC LIGHT EMITING DEVICE HAVING THE COMPOUND
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The present invention refers to the highest level is calculated by calculating a smallest track occupied molecules track molecules containing molecules path energy level and high energy, low energy corresponds to the energy level path track function is an electron donor moiety containing molecules in both molecules distributed subbands cells with an organic compound, an organic compound applied to the organic light-emitting diodes and organic light-emitting device of the whole structure are disclosed. They are out of charge-transporting organic compounds of the present invention, distributed in charge injection delay caused a rise in drive voltage can be prevent, with an adjacent layer interface region in emission since before al but capable, can be semiconductor layer on the organic layer. (by machine translation)
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Paragraph 0162-0166
(2019/05/11)
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- New Insights into the Reaction Capabilities of Ionic Organic Bases in Cu-Catalyzed Amination
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The application of ionic organic bases in the copper-catalyzed amination reaction (Ullmann reaction) has been studied at room temperature, with sub-mol-% catalyst loadings, and with more challenging amines at elevated temperatures. The cation present in the base has been shown to have little effect on the reaction at standard catalyst and ancillary ligand loadings, whereas the choice of anion is crucial for good reactivity. A substrate scope carried out at room temperature with the best performing bases, TBAM and TBPM, showed both bases to be highly effective under these mild reaction conditions. Moreover, under sub-mol % catalyst loadings and room temperature conditions, TBPM gave good to excellent yields for a number of different amines and functionalized aryl iodides (14 examples). However, reactions involving more challenging amines gave little or no yield. By using more forceful conditions (120 °C) moderate to excellent yields of cross-coupled products containing more challenging amines was achievable using TBPM and to a lesser extent with TBAM. As part of this work a study on the stability of the organic bases at 120 °C was undertaken. TBAM is shown to decompose to give nBu3N and mono-butylmalonate at higher temperatures, and this can be correlated to a decrease in performance in the coupling reaction. The phosphonium cations in TBPM did not undergo analogous reactivity but were shown instead to experience some degree of deprotonation at the α-CH2 to generate phosphonium ylides. This however did not lead to a significantly degradation in the activity of the TBPM in the cross-coupling reaction.
- Lo, Quintin A.,Sale, David,Braddock, D. Christopher,Davies, Robert P.
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p. 1944 - 1951
(2019/02/19)
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- C?N Cross-Coupling Reactions Under Mild Conditions Using Singlet Di-Radical Nickel(II)-Complexes as Catalyst: N-Arylation and Quinazoline Synthesis
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Herein we report a cost-effective synthetic approach for C?N cross-coupling reactions of a broad array of nitrogen nucleophiles and aryl halides under mild conditions. These reactions are catalyzed by an inexpensive, air-stable, earth-abundant and easy-to-prepare singlet di-radical nickel(II)-catalyst containing two antiferromagnetically coupled single-electron oxidized diiminosemiquinonato type ligands. This protocol provides an alternative method for C?N cross-coupling reactions avoiding nickel(0)/nickel(II) or nickel(I)/nickel(III) redox processes via cooperative participation of metal and ligand-centered redox events. Besides a wide range of N-arylation reactions, by judicious choice of aryl halides and nitrogen nucleophiles the synthesis of a variety of polysubstituted quinazolines has been achieved in moderate to good yields under relatively mild reaction conditions. Our catalyst has been found to be almost equally effective in quinazoline synthesis via C?N cross-coupling of (i) 2-bromobenzylamine with benzamide, and (ii) 2-bromobenzylbromide with amidine. Control experiments and DFT studies were performed to improve the understanding of the cooperative participation of ligand and metal (nickel)-centered redox events during oxidative addition/reductive elimination processes of the catalytic cycle and to shed light on the plausible mechanistic pathway of the C?N cross-coupling reactions. (Figure presented.).
- Sikari, Rina,Sinha, Suman,Chakraborty, Gargi,Das, Siuli,van Leest, Nicolaas Petrus,Paul, Nanda D.
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supporting information
p. 4342 - 4353
(2019/08/21)
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- Iron-Catalyzed/Mediated C-N Bond Formation: Competition between Substrate Amination and Ligand Amination
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Iron catalyzed carbon-nitrogen bond formation reactions of a wide variety of nucleophiles and aryl halides using well-defined iron-complexes featuring redox noninnocent 2-(arylazo)-1,10-phenanthroline (L1) ligands are reported. Besides substrate centered C-N coupling, C-N bond formation reactions were also observed at the ortho- and para-positions of the phenyl ring of the coordinated azo-aromatic scaffolds affording new tetradentate ligands, 2-N-aryl-(2-arylazo)-1,10-phenanthroline (L2), and tridentate ligands, 4-N-aryl-(2-arylazo)-1,10-phenanthroline (L3), respectively. Control experiments and mechanistic studies reveal that the complex [FeL1Cl2] (1) undergoes in situ reduction during the catalytic reaction to produce the monoanionic complex [1]-, which then acts as the active catalyst. The metal (iron) and the coordinated ligand were found to work in a cooperative manner during the transfer processes involved in the fundamental steps of the catalytic cycle. Detailed experimental and theoretical (DFT) studies were performed to get insight into the competitive substrate versus ligand centered amination reactions.
- Sinha, Suman,Sikari, Rina,Sinha, Vivek,Jash, Upasona,Das, Siuli,Brand?o, Paula,Demeshko, Serhiy,Meyer, Franc,De Bruin, Bas,Paul, Nanda D.
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p. 1935 - 1948
(2019/01/25)
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- Mixed er-NHC/phosphine Pd(ii) complexes and their catalytic activity in the Buchwald-Hartwig reaction under solvent-free conditions
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A series of novel (NHC)PdCl2-PR3 complexes were synthesized and fully characterized by 1H, 13C, 31P NMR and FT-IR spectroscopy. These complexes showed high catalytic activity toward solvent-free Buchwald-Hartwig amination. Both primary and secondary amines were efficiently utilized under the same reaction conditions. The solvent-free synthesis of valuable N-aryl carbazoles and similar N-heterocyclic systems was described.
- Ageshina, Alexandra A.,Sterligov, Grigorii K.,Rzhevskiy, Sergey A.,Topchiy, Maxim A.,Chesnokov, Gleb A.,Gribanov, Pavel S.,Nechaev, Mikhail S.,Asachenko, Andrey F.,Bermeshev, Maxim V.,Melnikova, Elizaveta K.
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p. 3447 - 3452
(2019/04/30)
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- Base-promoted SNAR reactions of fluoro- And chloroarenes as a route to N-aryl indoles and carbazoles
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KOH/DMSO-promoted C-N bond formation via nucleophilic aromatic substitution (SNAr) between chloroarenes or fluoroarenes with indoles and carbazole under transition metal-free conditions affording the corresponding N-arylated indoles and carbazoles has been developed.
- Iqbal, Muhammad Asif,Mehmood, Hina,Lv, Jiaying,Hua, Ruimao
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- Buchwald-Hartwig amination reaction of aryl halides using heterogeneous catalyst based on Pd nanoparticles decorated on chitosan functionalized graphene oxide
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In this work, graphene oxide was functionalized with chitosan (GO-Chit) followed by a simple approach for immobilization of palladium nanoparticles onto a chitosan grafted graphene oxide surface. The Pd-nanocomposite (GO-Chit-Pd) was characterized using Transmission Electron Microscopy (TEM), Fourier transforms infrared spectroscopy (FT-IR), and X-ray diffraction (XRD) measurements. The catalytic activity of the prepared heterogeneous graphene oxide functionalized chitosan-palladium (GO-Chit-Pd) was investigated in term of C-N coupling reaction (Buchwald-Hartwig amination reaction of aryl halides) yielding products of N-arylamines. The easy purification, convenient operation, and environmental friendliness, combined with a high yield, render this method viable for use in both laboratory research and larger industrial scales. Studying the reusability of the catalyst in this work showed that it could be reused for five times without obvious loss in catalytic activity.
- Sarvestani, Mosayeb,Azadi, Roya
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- Ultrafine hybrid Cu2O-Fe2O3 nanoparticles stabilized by hexaphenylbenzene-based supramolecular assemblies: A photocatalytic system for the Ullmann-Goldberg coupling reaction
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Ultrafine hybrid Cu2O-Fe2O3 NPs have been prepared using the supramolecular assemblies of hexaphenylbenzene (HPB) derivative 3 as nanoreactors and stabilizers. The as-prepared hybrid Cu2O-Fe2O3 NPs serve as an efficient and recyclable photocatalytic system for carrying out C-N coupling between aryl halides and various amines (aliphatic, aromatic and N-heterocyclic) at room temperature in mixed aqueous media under visible light irradiation. Amazingly, Cu2O-Fe2O3 NPs also exhibited high efficiency in the reactions involving the synthesis of biologically important N-substituted carbazole derivatives. The work being presented in this article demonstrates the preparation of a 'dip strip' coated with the as-prepared catalytic system and utilization of this paper strip as a recyclable and portable heterocatalytic system for carrying out the Ullmann-Goldberg coupling.
- Singh, Gurpreet,Kumar, Manoj,Bhalla, Vandana
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p. 5346 - 5357
(2018/12/05)
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- A waste-minimized protocol for copper-catalyzed Ullmann-type reaction in a biomass derived furfuryl alcohol/water azeotrope
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We report the use of biomass-derived furfuryl alcohol as an effective bidentate ligand able to promote the Ullmann-type copper-catalyzed coupling of aryl halides with heteroaromatic or aliphatic amines. Furfuryl alcohol (FA) can be mixed with water to form the corresponding azeotrope (20 wt% of FA) and therefore can be easily recovered and reused. This protocol is efficiently applied to substrates with various electronic nature and affords the expected products (27 examples) in generally good to excellent yields. It has also been demonstrated that the protocol is both chemically and environmentally effective as the azeotropic mixture can be easily and almost quantitatively recovered at the end of the process.
- Ferlin, Francesco,Trombettoni, Valeria,Luciani, Lorenzo,Fusi, Soliver,Piermatti, Oriana,Santoro, Stefano,Vaccaro, Luigi
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supporting information
p. 1634 - 1639
(2018/04/12)
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- Blue light emission of new anthracene derivatives produced using optimized side group link positions
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Using an anthracene chromophore as a core group and a phenyl carbazole chromophore as a side group, three new emitters of blue light, 2-DCPA, 3-DCPA and 4-DCPA, were synthesized. The three compounds differed with regard to the position of the carbazole linked to the core, with 2-DCPA and 4-DCPA using carbazole nodes and 3-DCPA using the lobe position. Density functional theory calculations were performed to determine which positions of the carbazole moiety had node characteristics and which had lobe characteristics. The PLmax values of 2-DCPA, 3-DCPA and 4-DCPA in the film state were in the blue region, at 453, 457, and 452 nm, respectively. Of these materials, 3-DCPA, i.e., that with the linkage to the lobe position, showed the highest efficiency, with a value of 2.91 cd/A, and EQE, with a value of 2.65%. In a doped device using CBP as a host material and 3-DCPA as a dopant, the ELmax emission was observed to be in the deep blue region, at 433 nm, and with a CIE value of (0.150, 0.068).
- Kang, Seokwoo,Jung, Hyocheol,Lee, Hayoon,Lee, Suji,Jung, Mina,Lee, Jaehyun,Chul Kim, Young,Park, Jongwook
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p. 369 - 378
(2018/05/09)
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- Transition-Metal-Free N-Arylation of Amines by Triarylsulfonium Triflates
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A simple and efficient method for transition-metal-free N-arylation of various amines by triarylsulfonium triflates is described. Both aliphatic and aromatic amines were smoothly converted at 80 °C in the presence of tBuOK or KOH to give the corresponding mono N-arylated products in good to high yields. The molar ratios of the reactants and the choice of bases had a big effect on the reaction. When a large excess of [Ph3S][OTf] and tBuOK were employed for primary amines under the standard conditions, the bis(N-phenyl) products were predominantly formed. This method was also applicable to the synthesis of bioactive N-phenyl amino acid derivatives. The control experiments, the deuterium labelling study, and the presence of regioisomers of N-arylated products when using 4-substituted triarylsulfonium triflates suggested that the reaction might proceed through an aryne intermediate. The present protocol demonstrated that triarylsulfonium salts are versatile arylation reagents in the construction of CAr?N bonds.
- Tian, Ze-Yu,Ming, Xiao-Xia,Teng, Han-Bing,Hu, Yu-Tian,Zhang, Cheng-Pan
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supporting information
p. 13744 - 13748
(2018/09/14)
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- Reductive Denitration of Nitroarenes
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The Pd-catalyzed reductive denitration of nitroarenes has been achieved via a direct cleavage of the C-NO2 bonds. The catalytic conditions reported exhibit a broad substrate scope and good functional-group compatibility. Notably, the use of inexpensive propan-2-ol as a mild reductant suppresses the competitive formation of anilines, which are normally formed by other conventional reductions. Mechanistic studies have revealed that alcohols serve as efficient hydride donors in this reaction, possibly through β-hydride elimination from palladium alkoxides.
- Kashihara, Myuto,Yadav, M. Ramu,Nakao, Yoshiaki
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supporting information
p. 1655 - 1658
(2018/03/23)
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- Design, synthesis and biological evaluation of: N -arylsulfonyl carbazoles as novel anticancer agents
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In this work, a set of structurally diverse synthetic carbazoles was screened for their anticancer activities. According to structure-activity relationship studies, carbazoles with an N-substituted sulfonyl group exhibited better anticancer activity. Moreover, compound 8h was discovered to show the most potent anticancer effects on Capan-2 cells by inducing apoptosis and cell cycle arrest in G2/M phase. Finally, the in vivo study demonstrated that 8h prevented the tumor growth in PANC-1 and Capan-2 xenograft models without apparent toxicity.
- You, Xin,Zhu, Daqian,Lu, Wenhua,Sun, Yichen,Qiao, Shuang,Luo, Bingling,Du, Yongliang,Pi, Rongbiao,Hu, Yumin,Huang, Peng,Wen, Shijun
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p. 17183 - 17190
(2018/05/28)
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- Organic compound with long afterglow effect as well as preparation method and application of organic compound
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The invention discloses an organic compound with a long afterglow effect as well as a preparation method and application of the organic compound. The organic compound has a structural formula as follows: the formula is shown in the description; 9-phenylcarbazole with n-pi* is used as a basic unit, and a meta-position and a para-position of phenyl are modified; after modification, different 9-phenylcarbazole derivatives are obtained; a test shows that the fluorescence lifetime of the compound can reach 100ms or more. The compound provided by the invention has the characteristics of simple synthesis method, easiness of being purified, adjustable luminescent spectrum, flexibility, no need of doping inorganic rare-earth materials, cheap price, low toxicity and the like, and can be widely to various fields including biological imaging, disease diagnosis, optical counterfeiting prevention and the like.
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Paragraph 0024; 0025; 0026
(2017/07/21)
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- Immobilized Pd nanoparticles on silica-starch substrate (PNP-SSS): Efficient heterogeneous catalyst in Buchwald–Hartwig C–N cross coupling reaction
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An immobilized Pd nanoparticle on silica-starch substrate (PNP-SSS) is introduced as an efficient heterogeneous catalyst in Pd-catalyzed Buchwald–Hartwig C–N cross coupling reaction. A range of aryl amines were synthesized using reaction of aryl halides (chloride, bromide and iodide) and amines using PNP-SSS catalyst in good to excellent yields. The PNP-SSS catalyst shows high catalytic activity in C-N bond formation reaction and it is reusable in this reaction at least for five times without significant decreasing in its catalytic activity.
- Panahi, Farhad,Daneshgar, Fatemeh,Haghighi, Fatemeh,Khalafi-Nezhad, Ali
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p. 210 - 217
(2017/10/09)
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- Organic light-emitting device, and flat panel display device including the same
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Provided are an organic light emitting device and a flat panel display device including the same. The organic light emitting device comprises: a first electrode, a second electrode facing the first electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises an emission layer; and the organic layer comprises a compound represented by Formula 1 (As shown in the description).
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Paragraph 0317; 0318; 0319; 0320; 0321
(2017/08/02)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND ELECTRONIC DEVICE THEREOF
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Disclosed is an organic electronic element including the compound or the composition as a material for a hole injection layer or a hole transport layer. By using a material including deuterium, with a high driving characteristic and a long life span, it is possible to reduce a driving voltage, and increase a luminous efficiency and a device life span in an organic electro-luminescence element.
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Page/Page column 38
(2017/09/02)
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- Organic Dye and Dye-Sensitized Solar Cell
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PURPOSE: An organic dye, photoelectric diode including the same and dye-sensitized solar battery are provided to have an absorbing band in long wavelength. CONSTITUTION: An organic dye is represented by chemical formula 1. A photoelectric diode includes porous oxide semiconductor membrane which includes the organic dye. A dye-sensitized solar cell comprises a first electrode, a second electrode which is formed on one side of the first electrode and includes a light absorptive layer, and electrolyte buried in a space between the first and second electrodes.
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Paragraph 0116-0122
(2018/02/10)
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- Stereoelectronic control of oxidation potentials of 3,7-bis(diarylamino)phenothiazines
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The influence of diarylamino (Ar2N-) substituents on the oxidation potential of 3,7-bis(diarylamino)phenothiazines (Ar2N)2-PTZ (1a-f, a: carbazolyl; b: dihydrodibenzoazepinyl; c: dibenzoazepinyl; d: diphenylamino; e: phenothiazinyl; and f: phenoxazinyl) is investigated, where the Ar2N-substituent sequence a→f is aligned in the increasing order of their electron-donating ability. Interestingly, a different sequence of electron-donating ability for Ar2N-substituents was observed for the oxidation potentials of (Ar2N)2-PTZ: 1a (Eox1 = +0.35 V vs. Fc/Fc+) > 1f (+0.30 V) > 1e (+0.15 V) > 1d (-0.05 V) > 1c (-0.19 V) > 1b (-0.22 V). The observed sequence can be explained by the stereoelectronic effect of the Ar2N-substituents to stabilize (Ar2N)2-PTZ+. Clear-cut examples are observed in the crystal structure of 1c+ and 1e+, for which coplanar conformation is observed between the PTZ+-plane and the planes of the sp2-hybridized nitrogen atoms in Ar2N-substituents through a large conformational change during the oxidation process of (Ar2N)2-PTZ.
- Karimata, Ayumu,Suzuki, Shuichi,Kozaki, Masatoshi,Okada, Keiji
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p. 56144 - 56152
(2017/12/26)
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- METHOD FOR PRODUCING π-CONJUGATED COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for producing a π-conjugated compound, which uses an aromatic condensed ring amine containing a group 14 element or a derivative thereof to enable N-aryl derivatives of them to be obtained in high yield. SOLUTION: There is provided the method for producing a π-conjugated compound represented by general formula (2) by using an amide compound having a structure represented by general formula (1). [X1 is a group 14 element; Ra and Rb are each independently H or a substituent; Y1 is an alkali metal bonded to N; Z1 and Z2 are each independently a substituted or unsubstituted aromatic hydrocarbon ring or a heteroaromatic ring; one of Z1 and Z2 may be omitted; and Ar1 is a substituted or unsubstituted aromatic hydrocarbon ring or a heteroaromatic ring.] SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0053; 0054
(2017/09/23)
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- Highly reusable support-free copper(II) complex of para-hydroxy-substituted salen: Novel, efficient and versatile catalyst for C─N bond forming reactions
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An air-stable, highly active and versatile method for C─N bond forming reactions is reported. Under mild conditions using a highly reusable support-free Cu(II)–salen complex, structurally diverse N-aryl-substituted compounds were obtained via direct C─N bond forming reaction of HN-heterocycles with aryl iodides or three-component C─N bond forming reaction of 2-bromobenzaldehyde, aniline derivatives and sodium azide in good to excellent yields. C─N bond forming reaction for benzimidazole derivatives was also performed in the presence of the catalyst under ambient conditions. A series of hybrid benzimidazoles bearing morpholine, tetrazole and quinoxaline backbones were produced using this method. All reactions were performed in short times under air. The Cu(II) catalyst could be reused up to eight times in the direct cross-coupling reaction of 9H–carbazole with iodobenzene without any decrease in its catalytic activity.
- Sharghi, Hashem,Aberi, Mahdi,Shiri, Pezhman
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- An electronic transmission material and its preparation and device
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The invention provides carbazole-imidazole electron transport materials. Based on triphenyl imidazole and carbazole, a kind of classic compounds is formed by connecting triphenyl imidazole and carbazole with benzene of different substituent groups. A preparation method is based on improvement of existing methods. Through repeated verification, the preparation method is simple in synthesis and purification processes and low in cost and can meet the industrial development requirements. A device prepared by using the substances has high light emitting efficiency.
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Paragraph 0035; 0037
(2017/10/14)
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