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Electropolymerization Studies on a Series of Thiophene-Substituted 1,3-Dithiole-2-ones: Solid-State Preparation of a Novel TTF-Derivatized Polythiophene

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journal contribution
posted on 14.04.2009, 00:00 by Tania Anjos, Adam Charlton, Simon J. Coles, Anna K. Croft, Michael B. Hursthouse, Maher Kalaji, Patrick J. Murphy, Susan J. Roberts-Bleming
The synthesis, electrochemical and spectroscopic properties of a series of thiophene-substituted 1,3-dithiole-2-ones is described. The derivatives Th-3,3, Th-2,2, Th-2,3, Th-3,3(2,2′-Me), and Th3,3-(2,5,2′,5′-Me), have been successfully polymerized by cyclic voltammetry. From the UV−visible spectra of the neutral films, it was determined that PTh-3,3, PTh-2,2 and PTh-2,3 have a bandgap of 2.04, 2.30, and 2.18 eV, respectively. The voltammetric response of Th-3,3(2,2′-Me) was noticeably different from the other polymers. The SNIFTIRS data suggested that Th-3,3(2,2′-Me) was formed by bonding via the β-positions of the thiophene ring, resulting in a poorly conductive polymer. The in situ solid-state modification of PTh-3,3 to produce a new TTF-derivatized polythiophene was carried out. The cyclic voltammetry of the modified polymer confirmed the inclusion of TTF into the backbone of the film.