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Synthesis of novel poly(dithienylpyridines)

Lookup NU author(s): Glen Chapman

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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.

Publication metadata

Author(s): Chapman GM, Stanforth SP, Berridge R, Pozo-Gonzalo C, Skabara PJ

Publication type: Article

Publication status: Published

Journal: Journal of Materials Chemistry

Year: 2002

Volume: 12

Issue: 8

Pages: 2292-2298

ISSN (print): 0959-9428

ISSN (electronic): 1364-5501

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/b201229d

DOI: 10.1039/b201229d

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