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

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.