General synthesis of thiophene and selenophene-based heteroacenes

被引:151
作者
Okamoto, T
Kudoh, K
Wakamiya, A
Yamaguchi, S [1 ]
机构
[1] Nagoya Univ, Grad Sch Sci, Dept Chem, Nagoya, Aichi 4648602, Japan
[2] Japan Sci & Technol Agcy, SORST, Nagoya, Aichi 4648602, Japan
关键词
D O I
10.1021/ol0523650
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new intramolecular triple cyclization of bis(o-haloaryl)diacetylenes, via dilithiation followed by reaction with chalcogen elements, produces pi-conjugated compounds containing heterole-1,2-dichalcogenin-heterole fused tricyclic skeletons. The subsequent dechalcogenation with copper metal affords a series of thiophene- and selenophene-based heteroacenes.
引用
收藏
页码:5301 / 5304
页数:4
相关论文
共 32 条
[1]   Functionalized pentacene: Improved electronic properties from control of solid-state order [J].
Anthony, JE ;
Brooks, JS ;
Eaton, DL ;
Parkin, SR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9482-9483
[2]   Oligoacenes: Theoretical prediction of open-shell singlet diradical ground states [J].
Bendikov, M ;
Duong, HM ;
Starkey, K ;
Houk, KN ;
Carter, EA ;
Wudl, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7416-7417
[3]   Organic semiconductors:: A theoretical characterization of the basic parameters governing charge transport [J].
Brédas, JL ;
Calbert, JP ;
da Silva, DA ;
Cornil, J .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (09) :5804-5809
[4]   A soluble pentacene: synthesis, EPR and electrochemical studies of 2,3,9,10-tetrakis(trimethylsilyl)pentacene [J].
Chan, SH ;
Lee, HK ;
Wang, YM ;
Fu, NY ;
Chen, XM ;
Cai, ZW ;
Wong, HNC .
CHEMICAL COMMUNICATIONS, 2005, (01) :66-68
[5]   Solid-state packing of conjugated oligomers:: from π-stacks to the herringbone structure [J].
Curtis, MD ;
Cao, J ;
Kampf, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4318-4328
[6]  
Dimitrakopoulos CD, 2002, ADV MATER, V14, P99, DOI 10.1002/1521-4095(20020116)14:2<99::AID-ADMA99>3.0.CO
[7]  
2-9
[8]  
Harvery R. G., 1997, POLYCYCLIC AROMATIC
[9]  
Holmes D, 1999, CHEM-EUR J, V5, P3399, DOI 10.1002/(SICI)1521-3765(19991105)5:11<3399::AID-CHEM3399>3.0.CO
[10]  
2-V