A modular procedure for the synthesis of functionalised β-substituted terthiophene monomers for conducting polymer applications

被引:13
作者
Collis, Gavin E. [1 ,2 ]
Burrell, Anthony K. [1 ]
Blandford, Esther J. [2 ]
Officer, David L. [2 ]
机构
[1] Los Alamos Natl Lab, Los Alamos, NM 87545 USA
[2] Massey Univ, Nanomat Res Ctr, MacDiarmid Inst Adv Mat & Nanotechnol, Palmerston North, New Zealand
关键词
D O I
10.1016/j.tet.2007.08.022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient modular strategy has been developed for the synthesis of beta-functionalised terthiophene monomers using Suzuki-Miyaura and Wittig/Horner-Emmons chemistries. This paper discusses the problems encountered with converting the beta-terthiophene aldehyde building block to the beta-terthiophene phosphonium salt and the use of this material in a Wittig condensation. An improved strategy using the beta-terthiophene phosphonate building block constructed via Suzuki-Miyaura coupling protocols was developed. We have synthesised and characterised a broad range of functionalised terthiophene materials that have been designed for specific end-use applications. The availability of these building blocks has dramatically increased access to a range of key monomers. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:11141 / 11152
页数:12
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[1]   STUDIES ON SYNTHETIC DRUGS .17. CHEMISTRY OF 4,5-DIHYDRO-10H-BENZO(5,6)CYCLOHEPTA(1.2-B)THIOPHENE [J].
BASTIAN, JM ;
EBNOTHER, A ;
JUCKER, E ;
RISSI, E ;
STOLL, AP .
HELVETICA CHIMICA ACTA, 1971, 54 (01) :277-&
[2]   SELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED OLIGOTHIOPHENES [J].
BAUERLE, P ;
WURTHNER, F ;
GOTZ, G ;
EFFENBERGER, F .
SYNTHESIS-STUTTGART, 1993, (11) :1099-1103
[3]   Preparation, characterisation and biosensor application of conducting polymers based on ferrocene substituted thiophene and terthiophene [J].
Chen, J ;
Burrell, AK ;
Collis, GE ;
Officer, DL ;
Swiegers, GF ;
Too, CO ;
Wallace, GG .
ELECTROCHIMICA ACTA, 2002, 47 (17) :2715-2724
[4]   Photoelectrochemical cells based on a novel porphyrin containing light harvesting conducting copolymer [J].
Chen, J ;
Burrell, AK ;
Campbell, WM ;
Officer, DL ;
Too, CO ;
Wallace, GG .
ELECTROCHIMICA ACTA, 2004, 49 (02) :329-337
[5]   Photovoltaic devices based on poly(bis-terthiophenes) and substituted poly(bisterthiophene) [J].
Chen, J ;
Too, CO ;
Burrell, AK ;
Collis, GE ;
Officer, DL ;
Wallace, GG .
SYNTHETIC METALS, 2003, 137 (1-3) :1373-1374
[6]   Synthesis and electrochemical properties of new star-shaped thiophene oligomers and their polymers [J].
Cherioux, F ;
Guyard, L ;
Audebert, P .
CHEMICAL COMMUNICATIONS, 1998, (20) :2225-2226
[7]  
Ciana L. D., 1989, J ORG CHEM, V54, P1731
[8]   Electropolymerization of Pd(II) complexes containing phosphinoterthiophene ligands [J].
Clot, O ;
Wolf, MO ;
Patrick, BO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (41) :9963-9973
[9]   The design and synthesis of porphyrin/oligiothiophene hybrid monomers [J].
Collis, GE ;
Campbell, WM ;
Officer, DL ;
Burrell, AK .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (11) :2075-2084
[10]   Toward functionalized conducting polymers:: synthesis and characterization of novel β-(Styryl)terthiophenes [J].
Collis, GE ;
Burrell, AK .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23) :8974-8983