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The Strathprints institutional repository is a digital archive of University of Strathclyde's Open Access research outputs. Strathprints provides access to thousands of Open Access research papers by University of Strathclyde researchers, including by researchers from the Department of Computer & Information Sciences involved in mathematically structured programming, similarity and metric search, computer security, software systems, combinatronics and digital health.

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Synthesis of novel poly(dithienylpyridines)

Chapman, G.M. and Stanforth, S.P. and Berridge, R. and Pozo-Gonzalo, C. and Skabara, P.J. (2002) Synthesis of novel poly(dithienylpyridines). Journal of Materials Chemistry, 12 (8). pp. 2292-2298. ISSN 0959-9428

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Abstract

This paper describes the chemical and electrochemical synthesis of novel copolymers of thiophene and pyridine. Di-iodination of 3-hydroxypyridine 12 followed by O-substitution gave a series of ethers 14b-d and esters/carbamates 15a-d which were reacted with the stannylated bithiophene derivative 17 in a Stille cross-coupling reaction yielding poly (1b-d) and poly (2a-d) respectively. These chemical polymerisation reactions generally resulted in highly insoluble materials which were difficult to characterise. Ethers 14b-d and esters/carbamates 15a-d gave O-substituted 3-hydroxy-2,6-di(2-thienyl)pyridines 1b-d and 2a-4 respectively in Stille cross-coupling reactions with the stannylated thiophene 16. Ethers 1b-d underwent electrochemical polymerisation allowing the synthesis of O-alkylated polymers, poly (1b-d), with electrochemical band-gaps of 1.4 to 1.6 eV. In contrast, the esters/carbamates 2a-d could not be electropolymerised.