Novel terthiophene and bis(thienyl)furan derivatives as precursors to highly electroactive polymers

P.J. Skabara, I.M. Serebryakov, D.M. Roberts, I.F. Perepichka, S.J. Coles, M.B. Hursthouse

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

The syntheses of a series of 1,3-dithiole-2-thione derivatives (3-6), bearing fused terthiophene or bis(2-thienyl)-2,5-furan units, are reported. These novel heterocycles are readily polymerized electrochemically to give stable electroactive materials. The target compounds were obtained in moderate to high yield via the cyclization of the corresponding diketones or hydroxyketones, using phosphorus pentasulfide or acidic conditions. The ketones 12 and 17 were prepared directly from their hydroxy precursors by treatment with MnO2. The trans configuration of diketone 20 was confirmed by X-ray crystallography.
LanguageEnglish
Pages6418-6424
Number of pages6
JournalJournal of Organic Chemistry
Volume64
Issue number17
DOIs
Publication statusPublished - 20 Aug 1999

Fingerprint

Bearings (structural)
Thiones
X ray crystallography
Cyclization
Ketones
Polymers
Derivatives
furan
alpha-terthienyl
phosphorus pentasulfide

Keywords

  • thiophene
  • tetrathiafulvalene
  • oligomers
  • pyrrole
  • crytsal
  • donors
  • furan

Cite this

Skabara, P. J., Serebryakov, I. M., Roberts, D. M., Perepichka, I. F., Coles, S. J., & Hursthouse, M. B. (1999). Novel terthiophene and bis(thienyl)furan derivatives as precursors to highly electroactive polymers. Journal of Organic Chemistry, 64(17), 6418-6424. https://doi.org/10.1021/jo990198+
Skabara, P.J. ; Serebryakov, I.M. ; Roberts, D.M. ; Perepichka, I.F. ; Coles, S.J. ; Hursthouse, M.B. / Novel terthiophene and bis(thienyl)furan derivatives as precursors to highly electroactive polymers. In: Journal of Organic Chemistry. 1999 ; Vol. 64, No. 17. pp. 6418-6424.
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Skabara, PJ, Serebryakov, IM, Roberts, DM, Perepichka, IF, Coles, SJ & Hursthouse, MB 1999, 'Novel terthiophene and bis(thienyl)furan derivatives as precursors to highly electroactive polymers' Journal of Organic Chemistry, vol. 64, no. 17, pp. 6418-6424. https://doi.org/10.1021/jo990198+

Novel terthiophene and bis(thienyl)furan derivatives as precursors to highly electroactive polymers. / Skabara, P.J.; Serebryakov, I.M.; Roberts, D.M.; Perepichka, I.F.; Coles, S.J.; Hursthouse, M.B.

In: Journal of Organic Chemistry, Vol. 64, No. 17, 20.08.1999, p. 6418-6424.

Research output: Contribution to journalArticle

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AU - Skabara, P.J.

AU - Serebryakov, I.M.

AU - Roberts, D.M.

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AB - The syntheses of a series of 1,3-dithiole-2-thione derivatives (3-6), bearing fused terthiophene or bis(2-thienyl)-2,5-furan units, are reported. These novel heterocycles are readily polymerized electrochemically to give stable electroactive materials. The target compounds were obtained in moderate to high yield via the cyclization of the corresponding diketones or hydroxyketones, using phosphorus pentasulfide or acidic conditions. The ketones 12 and 17 were prepared directly from their hydroxy precursors by treatment with MnO2. The trans configuration of diketone 20 was confirmed by X-ray crystallography.

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KW - tetrathiafulvalene

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Skabara PJ, Serebryakov IM, Roberts DM, Perepichka IF, Coles SJ, Hursthouse MB. Novel terthiophene and bis(thienyl)furan derivatives as precursors to highly electroactive polymers. Journal of Organic Chemistry. 1999 Aug 20;64(17):6418-6424. https://doi.org/10.1021/jo990198+