Synthesis of novel poly(dithienylpyridines)

Chapman, Glen, Stanforth, Stephen, Berridge, Rory, Pozo-Gonzalo, Cristina and Skabara, Peter (2002) Synthesis of novel poly(dithienylpyridines). Journal of Materials Chemistry, 12 (8). pp. 2292-2298. ISSN 0959-9428

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

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-d 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.

Item Type: Article
Subjects: F100 Chemistry
Department: Faculties > Health and Life Sciences > School of Life Sciences > Applied Sciences
Depositing User: Becky Skoyles
Date Deposited: 11 Feb 2015 15:57
Last Modified: 10 Aug 2015 11:51
URI: http://nrl.northumbria.ac.uk/id/eprint/19405

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