Construction of Nitrogen-containing Polycyclic Aromatic Compounds by Intramolecular Oxidative C-H/C-H Coupling of Bis(9H-carbazol-9-yl)benzenes and Their Properties

被引:15
作者
Taniguchi, Taisei [1 ]
Itai, Yuhei [1 ]
Nishii, Yuji [2 ]
Tohnai, Norimitsu [3 ]
Miura, Masahiro [1 ]
机构
[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] Osaka Univ, Grad Sch Engn, Frontier Res Base Global Young Researchers, Suita, Osaka 5650871, Japan
[3] Osaka Univ, Grad Sch Engn, Dept Mat & Life Sci, Suita, Osaka 5650871, Japan
关键词
C-H/C-H coupling; Carbazole; Polycyclic aromatic compounds; DERIVATIVES; CARBAZOLES; DONOR;
D O I
10.1246/cl.190494
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of 1,3- and 1,4-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)benzenes with an oxidizing system of Pd(II)/Ag(I) has been found to induce double intramolecular C-H/C-H coupling to give the corresponding highly p-extended polycyclic compounds. In contrast, a singly cyclized product in a different manner has been isolated from the reaction of 1,2-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)benzene. Cardinal optoelectronic properties of the products have also been estimated.
引用
收藏
页码:1160 / 1163
页数:4
相关论文
共 33 条
[1]   New D-π-A organic dyes containing a tert-butyl-capped indolo[3,2,1-jk] carbazole donor with bithiophene unit as π-linker for dye-sensitized solar cells [J].
Cao, Wei ;
Fang, Manman ;
Chai, Zhaofei ;
Xu, Han ;
Duan, Tainan ;
Li, Zhen ;
Chen, Xingguo ;
Qin, Jingui ;
Han, Hongwei .
RSC ADVANCES, 2015, 5 (42) :32967-32975
[2]   Thermal ring contraction of dibenz[b,f]azepin-5-yl radicals:: New routes to pyrrolo[3,2,1-jk]carbazoles [J].
Crawford, Lynne A. ;
McNab, Hamish ;
Mount, Andrew R. ;
Wharton, Stuart I. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6642-6646
[3]  
Hagelin H, 1999, CHEM-EUR J, V5, P2413, DOI 10.1002/(SICI)1521-3765(19990802)5:8<2413::AID-CHEM2413>3.0.CO
[4]  
2-3
[5]   Specific Indolo[3,2,1-jk]carbazole Conducting Thin-Film Materials Production by Selective Substitution [J].
Henry, John B. ;
Wharton, Stuart I. ;
Wood, Elanor R. ;
McNab, Hamish ;
Mount, Andrew R. .
JOURNAL OF PHYSICAL CHEMISTRY A, 2011, 115 (21) :5435-5442
[6]   Syntheses of Diverse Donor-Substituted Bisbenzofuro[2,3-b:3′,2′-e]pyridines (BBZFPys) via Pd Catalysis, and Their Photophysical Properties [J].
Itai, Yuhei ;
Nishii, Yuji ;
Stachelek, Patrycja ;
Data, Przemyslaw ;
Takeda, Youhei ;
Minakata, Satoshi ;
Miura, Masahiro .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (17) :10289-10302
[7]   Benzene-Fused Azacorannulene Bearing an Internal Nitrogen Atom [J].
Ito, Shingo ;
Tokimaru, Yuki ;
Nozaki, Kyoko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (25) :7256-7260
[8]   Strained Dehydrogenative Ring Closure of Phenylcarbazoles [J].
Jones, Alexander W. ;
Louillat-Habermeyer, Marie-Laure ;
Patureau, Frederic W. .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (05) :945-949
[9]   Construction of Bisbenzofuro[2,3-b:3',2'-e]pyridines by Palladium-Catalyzed Double Intramolecular Oxidative C-H/C-H Coupling [J].
Kaida, Hiroyuki ;
Goya, Tsuyoshi ;
Nishi, Yuji ;
Hirano, Koji ;
Satoh, Tetsuya ;
Miura, Masahiro .
ORGANIC LETTERS, 2017, 19 (05) :1236-1239
[10]   Synthesis of Benzobis- and Benzotrisbenzofurans by Palladium-Catalyzed Multiple Intramolecular C-H/C-H Coupling [J].
Kaida, Hiroyuki ;
Satoh, Tetsuya ;
Nishii, Yuji ;
Hirano, Koji ;
Miura, Masahiro .
CHEMISTRY LETTERS, 2016, 45 (09) :1069-1071