Palladium-Catalyzed Dehydrohalogenative Polycondensation of 2-Bromo-3-hexylthiophene: An Efficient Approach to Head-to-Tail Poly(3-hexylthiophene)

被引:314
作者
Wang, Qifeng [1 ]
Takita, Ryo [1 ]
Kikuzaki, Yuuta [1 ]
Ozawa, Fumiyuki [1 ]
机构
[1] Kyoto Univ, Inst Chem Res, Int Res Ctr Elements Sci IRCELS, Kyoto 6110011, Japan
关键词
DIRECT ARYLATION; CONJUGATED POLYMERS; POLYMERIZATION; POLYTHIOPHENES; POLY(3-ALKYLTHIOPHENES); REGIOREGULARITY;
D O I
10.1021/ja105767z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Dehydrohalogenative polycondensation of 2-bromo-3-hexylthiophene was successful with Herrmann's catalyst and tris(2-dimethylaminophenyl)phosphine as catalyst precursors, giving head-to-tail poly(3-hexylthiophene) (HT-P3HT) with high molecular weight (M-n = 30 600, M-w/M-n = 1.60) and high regioregularity (98%) in almost quantitative yield (99%).
引用
收藏
页码:11420 / 11421
页数:2
相关论文
共 24 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[3]   Materials and Applications for Large Area Electronics: Solution-Based Approaches [J].
Arias, Ana Claudia ;
MacKenzie, J. Devin ;
McCulloch, Iain ;
Rivnay, Jonathan ;
Salleo, Alberto .
CHEMICAL REVIEWS, 2010, 110 (01) :3-24
[4]   Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C-H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates [J].
Bellina, Fabio ;
Rossi, Renzo .
TETRAHEDRON, 2009, 65 (50) :10269-10310
[5]   THE 1ST REGIOREGULAR HEAD-TO-TAIL POLY(3-HEXYLTHIOPHENE-2,5-DIYL) AND A REGIORANDOM ISOPOLYMER - NI VS PD CATALYSIS OF 2(5)-BROMO-5(2)-(BROMOZINCIO)-3-HEXYLTHIOPHENE POLYMERIZATION [J].
CHEN, TA ;
RIEKE, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (25) :10087-10088
[6]   REGIOCONTROLLED SYNTHESIS OF POLY(3-ALKYLTHIOPHENES) MEDIATED BY RIEKE ZINC - THEIR CHARACTERIZATION AND SOLID-STATE PROPERTIES [J].
CHEN, TA ;
WU, XM ;
RIEKE, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :233-244
[7]   Synthesis of Conjugated Polymers for Organic Solar Cell Applications [J].
Cheng, Yen-Ju ;
Yang, Sheng-Hsiung ;
Hsu, Chain-Shu .
CHEMICAL REVIEWS, 2009, 109 (11) :5868-5923
[8]   Synthesis of Light-Emitting Conjugated Polymers for Applications in Electroluminescent Devices [J].
Grimsdale, Andrew C. ;
Chan, Khai Leok ;
Martin, Rainer E. ;
Jokisz, Pawel G. ;
Holmes, Andrew B. .
CHEMICAL REVIEWS, 2009, 109 (03) :897-1091
[9]   Palladium-catalyzed synthesis of oligo(alkylthiophenes) [J].
Hassan, J ;
Schulz, E ;
Gozzi, C ;
Lemaire, M .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 195 (1-2) :125-131
[10]   Palladacycles: Efficient new catalysts for the Heck vinylation of aryl halides [J].
Herrmann, WA ;
Brossmer, C ;
Reisinger, CP ;
Riermeier, TH ;
Ofele, K ;
Beller, M .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (08) :1357-1364