Synthesis and polymerization of 3,3′-dialkyl-2,2′-bithiophenes

被引:39
作者
Hoffmann, KJ
Bakken, E
Samuelsen, EJ
Carlsen, PHJ [1 ]
机构
[1] Norwegian Univ Sci & Technol, Dept Chem, Trondheim, Norway
[2] Norwegian Univ Sci & Technol, Dept Phys, N-7491 Trondheim, Norway
关键词
conjugated polymers; heterocycle synthesis; polythiophene and derivatives;
D O I
10.1016/S0379-6779(00)00183-1
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
A series of 3,3'-dialkyl-2,2'-bithiophenes (DAT2s) has been synthesized by the nickel-catalyzed Kumada coupling of 2-bromo-3-alkylthiophene with 2-(3-alkylthienyl) magnesium bromide. These monomers were analyzed by NMR and UV-Vis spectroscopies. The monomers were oxidatively polymerized with iron(III) chloride to yield the respective pi-conjugated poly(3,3'-dialkyl-2,2'-bithiophene)s. The new polymers were characterized with H-1 NMR and UV-Vis spectroscopies. Conductivity was in the order of 10-10(2) S/cm, depending upon the length of the alkyl chain. (C) 2000 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:39 / 44
页数:6
相关论文
共 23 条
[1]  
AASMUNDTVEIT KE, UNPUB SYNTH MET
[2]   REGIOSELECTIVE POLYMERIZATION OF 3-(4-OCTYLPHENYL)THIOPHENE WITH FECL3 [J].
ANDERSSON, MR ;
SELSE, D ;
BERGGREN, M ;
JARVINEN, H ;
HJERTBERG, T ;
INGANAS, O ;
WENNERSTROM, O ;
OSTERHOLM, JE .
MACROMOLECULES, 1994, 27 (22) :6503-6506
[3]   ELECTROCHEMICAL AND OPTICAL-PROPERTIES OF POLY(3-METHYLTHIOPHENES) ELECTROSYNTHESIZED BY 3,3'-4,4'-DIMETHYL-2,2'-BITHIOPHENES, 3,4'-4,4'-DIMETHYL-2,2'-BITHIOPHENES AND 4,4'-DIMETHYL-2,2'-BITHIOPHENES [J].
ARBIZZANI, C ;
BARBARELLA, G ;
BONGINI, A ;
MASTRAGOSTINO, M ;
ZAMBIANCHI, M .
SYNTHETIC METALS, 1992, 52 (03) :329-339
[4]   CONFORMATION AND OPTICAL-ABSORPTION PROPERTIES OF THIOPHENE OLIGOMERS - C-13-NMR, UV, AND MMP2 CALCULATIONS OF DI-QUATERTHIOPHENES AND TETRAMETHYL-QUATERTHIOPHENES [J].
BARBARELLA, G ;
BONGINI, A ;
ZAMBIANCHI, M .
ADVANCED MATERIALS, 1991, 3 (10) :494-496
[5]   SYNTHESIS, C-13 NMR, LAMBDA-MAX AND MMP2 CALCULATIONS OF 2 TAILOR-MADE ALPHA-CONJUGATED HEXAMETHYLSEXITHIOPHENES [J].
BARBARELLA, G ;
BONGINI, A ;
ZAMBIANCHI, M .
TETRAHEDRON, 1992, 48 (32) :6701-6708
[6]   OLIGOTHIOPHENES - YET LONGER - SYNTHESIS, CHARACTERIZATION, AND SCANNING-TUNNELING-MICROSCOPY IMAGES OF HOMOLOGOUS, ISOMERICALLY PURE OLIGO(ALKYLTHIOPHENE)S [J].
BAUERLE, P ;
FISCHER, T ;
BIDLINGMEIER, B ;
STABEL, A ;
RABE, JP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (03) :303-307
[7]  
Bauerle P, 1998, ELECTRONIC MATERIALS: THE OLIGOMER APPROACH, P105
[8]   SYNTHESIS OF OLIGOMERIC 2,5-THIENYLENES - THEIR UV SPECTRA AND OXIDATION POTENTIALS [J].
CUNNINGHAM, DD ;
LAGURENDAVIDSON, L ;
MARK, HB ;
VANPHAM, C ;
ZIMMER, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (13) :1021-1023
[9]   DESIGN OF NOVEL ELECTROACTIVE POLYBITHIOPHENE DERIVATIVES [J].
FAID, K ;
CLOUTIER, R ;
LECLERC, M .
MACROMOLECULES, 1993, 26 (10) :2501-2507
[10]   THE EFFECT OF STEREOREGULARITY ON THE STRUCTURE OF POLY(OCTYLTHIOPHENE) - AN X-RAY-DIFFRACTION STUDY [J].
FELL, HJ ;
SAMUELSEN, EJ ;
MARDALEN, J ;
BAKKEN, E ;
CARLSEN, PHJ .
SYNTHETIC METALS, 1995, 69 (1-3) :301-302