Synthesis of novel poly(dithienylpyridines)

G.M. Chapman, S.P. Stanforth, R. Berridge, C. Pozo-Gonzalo, P.J. Skabara

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7 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)2292-2298
Number of pages6
JournalJournal of Materials Chemistry
Volume12
Issue number8
DOIs
Publication statusPublished - Aug 2002

Keywords

  • electron-donating thiophene
  • electrochemical properties
  • accepting pyridine
  • units
  • copolymers
  • quinoxaline
  • betaines
  • polymers
  • bandgap

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  • Cite this

    Chapman, G. M., Stanforth, S. P., Berridge, R., Pozo-Gonzalo, C., & Skabara, P. J. (2002). Synthesis of novel poly(dithienylpyridines). Journal of Materials Chemistry, 12(8), 2292-2298. https://doi.org/10.1039/b201229d