Synthesis and Properties of Symmetric and Unsymmetric Dibenzothienopyrroles

被引：38

作者：

Balaji, Ganapathy ^{[1
]}

Valiyaveettil, Suresh ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117546, Singapore

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 15期

关键词：

THIN-FILM TRANSISTORS; FIELD-EFFECT TRANSISTORS; STACKED ORGANIC SEMICONDUCTOR; HIGH-PERFORMANCE; FUNCTIONALIZED ACENES; GENERAL-SYNTHESIS; THIOPHENE; HETEROACENES; PENTACENE; DERIVATIVES;

D O I：

10.1021/ol901133m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Symmetrical and unsymmetrical heteroacenes containing thiophene and pyrrole rings were synthesized. The unsymmetrical heteroacene was synthesized In two steps involving an unexpected palladium catalyzed amination of alkyl or aryl amines with benzo[b]thiophene followed by a copper catalyzed coupling. The symmetrical heteroacene was obtained by a palladium catalyzed amination reaction and also by a copper catalyzed amidation reaction. The crystal structure, photophysical and electrochemical properties of symmetrical and unsymmetrical heteroacenes are described.

引用

页码：3358 / 3361

页数：4

共 43 条

[1] Functionalized acenes and heteroacenes for organic electronics [J].

Anthony, John E. .

CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048

[2] Synthesis, characterization, and application of indolo[3,2-b]carbazole semiconductors [J].

Boudreault, Pierre-Luc T. ;

Wakim, Salem ;

Blouin, Nicolas ;

Simard, Michel ;

Tessier, Christian ;

Tao, Ye ;

Leclerc, Mario .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (29) :9125-9136

[3] Charge-transfer and energy-transfer processes in π-conjugated oligomers and polymers:: A molecular picture [J].

Brédas, JL ;

Beljonne, D ;

Coropceanu, V ;

Cornil, J .

CHEMICAL REVIEWS, 2004, 104 (11) :4971-5003

[4] Shining light on a pentacene derivative: The role of photoinduced cycloadditions [J].

Coppo, P ;

Yeates, SG .

ADVANCED MATERIALS, 2005, 17 (24) :3001-+

[5] Thiophene-linked polyphenylquinoxaline: A new electron transport conjugated polymer for electroluminescent devices [J].

Cui, YT ;

Zhang, XJ ;

Jenekhe, SA .

MACROMOLECULES, 1999, 32 (11) :3824-3826

[6] The diyne reaction of 3,3'-bis(phenylethynyl)-2,2'-bithiophene derivatives via rhodium complexes: A novel approach to condensed benzo[2,1-b:3,4-b']dithiophenes [J].

Dahlmann, U ;

Neidlein, R .

HELVETICA CHIMICA ACTA, 1997, 80 (01) :111-120

[7] Highly soluble [1]benzothieno[3,2-b]benzothiophene (BTBT) derivatives for high-performance, solution-processed organic field-effect transistors [J].

Ebata, Hideaki ;

Izawa, Takafumi ;

Miyazaki, Eigo ;

Takimiya, Kazuo ;

Ikeda, Masaaki ;

Kuwabara, Hirokazu ;

Yui, Tatsuto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (51) :15732-+

[8] High-performance field-effect transistor based on dibenzo[d,d′]thieno[3,2-b;4,5-b′]dithiophene, an easily synthesized semiconductor with high ionization potential [J].

Gao, Jianhua ;

Li, Rongjin ;

Li, Liqiang ;

Meng, Qing ;

Jiang, Hui ;

Li, Hongxiang ;

Hu, Wenping .

ADVANCED MATERIALS, 2007, 19 (19) :3008-+

[9] ON THE REACTION BETWEEN 3-BROMO-2-NITROBENZO[B]THIOPHENE AND SOME AMINES - A NOVEL AROMATIC NUCLEOPHILIC-SUBSTITUTION WITH REARRANGEMENT [J].

GUERRERA, F ;

SALERNO, L ;

LAMARTINA, L ;

SPINELLI, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (10) :1243-1246

[10] Thin-film transistors based on well-ordered thermally evaporated naphthacene films [J].

Gundlach, DJ ;

Nichols, JA ;

Zhou, L ;

Jackson, TN .

APPLIED PHYSICS LETTERS, 2002, 80 (16) :2925-2927

← 1 2 3 4 5 →