Facile Synthesis of 2,6-Disubstituted Benzobisthiazoles: Functional Monomers for the Design of Organic Semiconductors

被引:35
作者
Mike, Jared F. [1 ]
Inteman, Jeremy J. [1 ]
Ellern, Arkady [1 ]
Jeffries-EL, Malika [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50010 USA
基金
美国国家科学基金会;
关键词
RIGID-ROD; OPTICAL-PROPERTIES; POLYMER; UNITS; POLYBENZOXAZOLES; TRANSPORT;
D O I
10.1021/jo9023864
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of several synthetically useful 2,6-disubstituted benzobisthiazoles is described. The method is based oil the Lewis acid-catalyzed ring-closing reaction between Substituted orthoesters and diamino benzene dithiol. The resulting benzobisthiazoles are obtained cleanly and in good yields, These materials are of interest for the development of new organic semiconductors.
引用
收藏
页码:495 / 497
页数:3
相关论文
共 23 条
[11]   Novel rigid-rod 2,6-diphenylbenzo[1,2-d:4,5-d]bisthiazole (DPBBT) derivatives for second-order nonlinear optical chromophorest [J].
Lee, SH ;
Otomo, A ;
Nakahama, T ;
Yamada, T ;
Kamikado, T ;
Yokoyama, S ;
Mashiko, S .
JOURNAL OF MATERIALS CHEMISTRY, 2002, 12 (08) :2187-2188
[12]   An Efficient Synthesis of 2,6-Disubstituted Benzobisoxazoles: New Building Blocks for Organic Semiconductors [J].
Mike, Jared F. ;
Makowski, Andrew J. ;
Jeffries-El, Malika .
ORGANIC LETTERS, 2008, 10 (21) :4915-4918
[13]   EFFECTS OF MOLECULAR-STRUCTURE ON THE ELECTROACTIVE AND OPTICAL-PROPERTIES OF CONJUGATED RIGID-ROD POLY(BENZOBISAZOLES) [J].
OSAHENI, JA ;
JENEKHE, SA .
CHEMISTRY OF MATERIALS, 1995, 7 (04) :672-682
[14]   NEW RED LIGHT-EMITTING CONJUGATED RIGID-ROD POLYMER - POLY(BENZOBISTHIAZOLE-1,4-PHENYLENEBISVINYLENE) [J].
OSAHENI, JA ;
JENEKHE, SA .
MACROMOLECULES, 1993, 26 (17) :4726-4728
[15]  
Osman A.M., 1971, U. A. R. J. Chem, V14, P475
[16]  
OSMAN AM, 1973, INDIAN J CHEM, V11, P868
[17]   Advantageous 3D ordering of π-conjugated systems:: A new approach towards efficient charge transport any direction [J].
Pang, Hao ;
Vilela, Filipe ;
Skabara, Peter J. ;
McDouall, Joseph J. W. ;
Crouch, David J. ;
Anthopoulos, Thomas D. ;
Bradley, Donal D. C. ;
De Leeuw, Dago M. ;
Horton, Peter N. ;
Hursthouse, Michael B. .
ADVANCED MATERIALS, 2007, 19 (24) :4438-+
[18]   3RD-ORDER OPTICAL NONLINEARITIES OF MODEL COMPOUNDS CONTAINING BENZOBISTHIAZOLE, BENZOBISOXAZOLE, AND BENZBISIMIDAZOLE UNITS [J].
REINHARDT, BA ;
UNROE, MR ;
EVERS, RC ;
ZHAO, MT ;
SAMOC, M ;
PRASAD, PN ;
SINSKY, M .
CHEMISTRY OF MATERIALS, 1991, 3 (05) :864-871
[19]   Progress in plastic electronics devices [J].
Singh, Th. Birendra ;
Sariciftci, Niyazi Serdar .
ANNUAL REVIEW OF MATERIALS RESEARCH, 2006, 36 (199-230) :199-230
[20]   POLYMERS WITH QUINOXALINE UNITS .4. POLYMERS WITH QUINOXALINE AND OXAZINE UNITS [J].
WOLF, R ;
OKADA, M ;
MARVEL, CS .
JOURNAL OF POLYMER SCIENCE PART A-1-POLYMER CHEMISTRY, 1968, 6 (6PA1) :1503-&