Evidence for the contribution of sulfur-bromine intramolecular interactions to the self-rigidification of thiophene-based π-conjugated systems

被引:27
作者
Hergue, Noemie [1 ]
Leriche, Philippe [1 ]
Blanchard, Philippe [1 ]
Allain, Magali [1 ]
Gallego-Planas, Nuria [1 ]
Frere, Pierre [1 ]
Roncali, Jean [1 ]
机构
[1] Univ Angers, CNRS, Lab Chim & Ingn Mol Angers, CIMA,UMR 6200,Grp SCL, F-49045 Angers, France
关键词
D O I
10.1039/b802313a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Bithiophene associating 3,4-ethylenedioxythiophene and 3-bromothiophene, and the corresponding polymer exhibit self-rigidified structures of the conjugated backbones resulting from the association of S-Br and S-O non-bonded intramolecular interactions.
引用
收藏
页码:932 / 936
页数:5
相关论文
共 23 条
[1]   Theoretical investigation of the 3,4-ethylenedioxythiophene dimer and unsubstituted heterocyclic derivatives [J].
Alemán, C ;
Casanovas, J .
JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (08) :1440-1447
[2]   SIR92 - a program for automatic solution of crystal structures by direct methods [J].
ALTOMARE, A ;
CASCARANO, G ;
GIACOVAZZO, G ;
GUAGLIARDI, A ;
BURLA, MC ;
POLIDORI, G ;
CAMALLI, M .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435
[3]   Synthesis of 3,4'-dibromo-2,2'-bithiophene: A useful intermediate for 3,4'-disubstituted 2,2'-bithiophenes. X-ray molecular structure of 3,4'-dibromo-2,2'-bithiophene [J].
Antolini, L ;
Goldoni, F ;
Iarossi, D ;
Mucci, A ;
Schenetti, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (13) :1957-1961
[4]  
Antolini L, 1998, ACTA POLYM, V49, P248, DOI 10.1002/(SICI)1521-4044(199805)49:5<248::AID-APOL248>3.0.CO
[5]  
2-U
[6]   THE DEFORMABILITY OF THE THIOPHENE RING - A KEY TO THE UNDERSTANDING OF THE CONFORMATIONAL PROPERTIES OF OLIGOPHENES AND POLYTHIOPHENES [J].
BARBARELLA, G ;
ZAMBIANCHI, M ;
BONGINI, A ;
ANTOLINI, L .
ADVANCED MATERIALS, 1993, 5 (11) :834-838
[7]   Electrochemical synthesis of poly(3-bromo-4-methoxythiophene) and its device application [J].
Cihaner, Atilla ;
Onal, Ahmet M. .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2007, 601 (1-2) :68-76
[8]   Thiophene and selenophene copolymers incorporating fluorinated phenylene units in the main chain: Synthesis, characterization, and application in organic field-effect transistors [J].
Crouch, DJ ;
Skabara, PJ ;
Lohr, JE ;
McDouall, JJW ;
Heeney, M ;
McCulloch, I ;
Sparrowe, D ;
Shkunov, M ;
Coles, SJ ;
Horton, PN ;
Hursthouse, MB .
CHEMISTRY OF MATERIALS, 2005, 17 (26) :6567-6578
[9]   Hexyl-substituted oligothiophenes with a central tetrafluorophenylene unit: crystal engineering of planar structures for p-type organic semiconductors [J].
Crouch, DJ ;
Skabara, PJ ;
Heeney, M ;
McCulloch, I ;
Coles, SJ ;
Hursthouse, MB .
CHEMICAL COMMUNICATIONS, 2005, (11) :1465-1467
[10]   Building blocks for n-type organic electronics: Regiochemically modulated inversion of majority carrier sign in perfluoroarene-modified polythiophene semiconductors [J].
Facchetti, A ;
Yoon, MH ;
Stern, CL ;
Katz, HE ;
Marks, TJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) :3900-3903