20440-95-3Relevant academic research and scientific papers
Copper(I)-anilide complex [Na(phen)3][Cu(NPh2) 2]: An intermediate in the copper-catalyzed N-Arylation of N-Phenylaniline
Tseng, Chia-Kai,Lee, Chi-Rung,Han, Chien-Chung,Shyu, Shin-Guang
, p. 2716 - 2723 (2011)
Complex [Na(phen)3][Cu(NPh2)2] (2), containing a linear bis(N-phenylanilide)copper(I) anion and a distorted octahedral tris(1,10-phenanthroline)sodium counter cation, has been isolated from the catalytic C-N cross-coupling reaction with the CuI/phen/tBuONa (phen=1,10-phenanthroline) catalytic system. Complex 2 can react with 4-iodotoluene to produce 4-methyl-N,N-diphenylaniline (3a) with 70.6% yield. In addition, 2 can work as an effective catalyst for Ci￡N coupling under the same reaction conditions, thus indicating that 2 is the intermediate of the catalytic system. Both [Cu(NPh2) 2]- and [Cu(NPh2)I]- have been observed by in situ electron ionization mass spectrometry (ESI-MS) under catalytic reaction conditions, thus confirming that they are intermediates in the reaction. A catalytic cycle has been proposed based on these observations. The molecular structure of 2 has been determined by single-crystal X-ray diffraction analysis.
Amination and amidation of aryl iodides catalyzed by copper(I)- phenanthroline complexes
Moriwaki, Kazuyuki,Satoh, Kazuyoshi,Takada, Masahiro,Ishino, Yoshio,Ohno, Toshinobu
, p. 7559 - 7562 (2005)
Four kinds of copper(I)-phenanthroline complexes ([CuI(phen) 2]Cl, [CuI(phen)Cl]2, [CuI(phen) 2]BF4, and CuI(phen)PPh3Cl) were prepared and used as catalysts for amination and amidation of aryl iodide to investigate the influence on the yields of products due to differences of the structures. These complexes were found to work as catalysts on these reactions and showed that the differences of structures of copper(I) complexes significantly influenced the yield of aryl-nitrogen bond forming processes.
Heterogeneously Catalyzed Selective Decarbonylation of Aldehydes by CeO2-Supported Highly Dispersed Non-Electron-Rich Ni(0) Nanospecies
Matsuyama, Takehiro,Yatabe, Takafumi,Yabe, Tomohiro,Yamaguchi, Kazuya
, p. 13745 - 13751 (2021/11/17)
Aldehyde decarbonylation has been extensively investigated, primarily using noble-metal catalysts; however, nonprecious-base-metal-catalyzed aldehyde decarbonylation has been hardly reported. We have established an efficient selective aldehyde decarbonylation reaction with a broad substrate scope and functional group tolerance utilizing a heterogeneous Ni(0) nanospecies catalyst supported on CeO2. The high catalytic performance is attributable to the highly dispersed and non-electron-rich Ni(0) nanospecies, which possibly suppress a side reaction producing esters and adsorbed CO-derived inhibition of the catalytic turnover, according to detailed catalyst characterization and kinetic evaluation.
Design and synthesis of efficient electrogenerated chemiluminescent emitters derived from pyrene
Cappellari, Maria V.,Mangione, María I.,Spanevello, Rolando A.,Marzari, Gabriela,Morales, Gustavo M.,Fungo, Fernando
, p. G163 - G170 (2019/05/21)
The design and synthesis of novel dendrimeric structures derived from a pyrene core with substituted triphenylamine and carbazole periphery demonstrated how molecular engineering allowed the fine tuning of the electrogenerated chemiluminiscence (ECL) properties. These two compound (Py-CBZ and Py-TPA) in comparison with the parent structures (Py and Py-Core) showed better chemical stability and anti-aggregation capability. At the same time, the photophysical (Absλmax, E00FLλmaxΦFL), photochemical (oxygen quenching), electrochemical (redox potentials) and optoelectronic (HOMO-LUMO gap and their energy position) properties were modulated, resulting in obtaining two highly ECL emitting molecular structures (Py-CBZ and Py-TPA). This study showed that functionalization of organic dyes with redox moieties (with the proper linker and position) improved the radical stability and also, modulated the optoelectronic properties with the concomitant enhancement of the ECL performance and their potential use in applications such as organic light-emitting devices.
Synthesis of Triarylamines via Sequential C-N Bond Formation
Modha, Sachin G.,Popescu, Mihai V.,Greaney, Michael F.
, p. 11933 - 11938 (2017/11/24)
A one-pot domino N-arylation protocol is described using diaryliodonium reagents under copper catalysis. The reaction uses both aryl groups of the diaryliodonium reagent to generate triarylamines starting from simple anilines, representing an atom-economical preparation of an important class of organic material building blocks.
Donor and acceptor substituted triphenylamines exhibiting bipolar charge-transporting and NLO properties
Gudeika, Dalius,Bundulis, Arturs,Mihailovs, Igors,Volyniuk, Dmytro,Rutkis, Martins,Grazulevicius, Juozas V.
, p. 431 - 440 (2017/02/10)
Donor-acceptor type triphenylamine-based malonodinitriles were synthesized and their thermal, optical, photophysical, electrochemical and nonlinear optical properties were studied. The synthesized compounds formed glasses with the glass transition temperatures ranging from 38 to 107 °C. The ionization potentials of the samples of the compounds established by cyclic voltammetry were found to be in the range of 5.50–5.57 eV, while those estimated by photoelectron emission spectrometry ranged from 5.36 to 5.74 eV. The electron affinity values of the compounds were found to be in the range of ?3.41–?3.05 eV. The ambipolar charge-transporting properties were observed for the layers of triphenylamine-based malonodinitriles. Hole mobilities of the layers of the compounds were in the range of 10?7–10?6 cm2/V·s, while electron mobilities were by ca. two orders of magnitude higher. All the synthesized compounds had positive sign for second order hyperpolarizability.
PdCl2(Ph3P)2/Salicylaldimine Catalyzed Diarylation of Anilines with Unactivated Aryl Chlorides
Tao, Xiaochun,Li, Lei,Zhou, Yu,Qian, Xuanying,Zhao, Min,Cai, Liangzhen,Xie, Xiaomin
, p. 1749 - 1754 (2017/10/06)
Triphenylphosphine and salicylaldimine could be used as a mixed ligand system to obtain a high catalytic activity for palladium catalyzed diarylation of primary anilines with unactivated aryl chlorides by the synergistic effect of ligands. The activity and selectivity of the catalytic system could be improved by modifying the structure of salicylaldimine. In refluxing o-xylene, PdCl2(Ph3P)2 with 2,5-ditrifluoromethyl N-phenylsalicylaldimine as a coligand shows high efficiency for the diarylation of various anilines. The catalytic system shows good toleration for the steric hindrance of the substrates. The facile catalytic system works as well on the multiple arylation of 1,1′-biphenyl- 4,4′-diamine with aryl chlorides to afford N,N,N′,N′-tetraaryl-1,1′-biphenyl-4,4′-diamines which are important intermediates of organic light emitting diode (OLED) hole transport materials.
N/O-doped carbon as a "solid ligand" for nano-Pd catalyzed biphenyl- and triphenylamine syntheses
Pang, Shaofeng,Zhang, Yujing,Huang, Yongji,Yuan, Hangkong,Shi, Feng
, p. 2170 - 2182 (2017/07/24)
A series of N/O-doped porous carbon supported nanopalladium catalysts have been successfully prepared, in which the N/O doped carbons were controllably produced via polypyrrole/furan synthesis followed by carbonization. These catalysts exhibit good performance in biphenylamine and triphenylamine syntheses with nitrobenzene and cyclohexanone as starting materials. Their catalytic activity can be tuned efficiently by the N/O functional groups on the carbon surface. TEM, XRD, XPS and laser Raman methods were applied to probe the structure of these catalysts. These results indicate that the Pd nanoparticles were supported on N/O-doped porous carbon via the "coordination" between Pd nanoparticles and N/O functional groups including O-CO, CN and tertiary nitrogen, and better catalytic performance was obtained if carbon with the highest N-species loading was used as the support. In addition, a mechanistic study proved that the reaction starts with the catalytic reduction of nitrobenzene with cyclohexanone as the hydrogen source. During this reaction, aniline was formed and the cyclohexanone was transformed into phenol. Then biphenylamine and triphenylamine were generated through the reaction of aniline and cyclohexanone. This work should facilitate the controllable preparation of carbon supported nanocatalysts with specific activity, and open up a promising pathway for the development of new methodologies for N-containing fine chemical synthesis.
Solvent-Free Buchwald-Hartwig (Hetero)arylation of Anilines, Diarylamines, and Dialkylamines Mediated by Expanded-Ring N-Heterocyclic Carbene Palladium Complexes
Topchiy, Maxim A.,Dzhevakov, Pavel B.,Rubina, Margarita S.,Morozov, Oleg S.,Asachenko, Andrey F.,Nechaev, Mikhail S.
supporting information, p. 1908 - 1914 (2016/04/20)
A highly efficient solvent-free protocol for the Buchwald-Hartwig (hetero)arylation of anilines, diarylamines, and dialkylamines mediated by the expanded-ring N-heterocyclic carbene palladium complex (THP-Dipp)Pd(cinn)Cl [THP-Dipp = 1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene; cinn = cinnamyl, 3-phenylallyl] was developed. The catalytic protocol was efficient for the coupling of amines and (hetero)aryl chlorides and bromides bearing donor, acceptor, and bulky substituents.
Polycarbazole compd., manufacturing method thereof, and use thereof
-
Paragraph 0075; 0078, (2016/11/14)
PROBLEM TO BE SOLVED: To provide a novel carbazole compound with a high T1, a production method thereof and a use thereof.SOLUTION: A carbazole compound represented by general formula (1) is used for any one or more layer of a light emitting layer, a hole transport layer and a hole injection layer of an organic EL element, where Arand Arindependently represent a 6-40C aryl group or a 3-40C heteroaryl group or the like.
