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

Skabara, P.J. and Serebryakov, I.M. and Roberts, D.M. and Perepichka, I.F. and Coles, S.J. and Hursthouse, M.B. (1999) Novel terthiophene and bis(thienyl)furan derivatives as precursors to highly electroactive polymers. Journal of Organic Chemistry, 64 (17). pp. 6418-6424. ISSN 0022-3263

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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.