M. Chahma, A. Myles, R. Hicks
Apr 21, 2005
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0
Influential Citations
18
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Journal
Chemistry of Materials
Abstract
The synthesis and electrochemical properties of a series of bis(thiophene) sulfides is presented. The molecules were synthesized via either thiophenethiol substitution reactions with thienyl bromides or treatment of lithiated thiophenes with bis(phenylsulfonyl) sulfide. Bis(oligothienyl) sulfides based on thiophene, 3-hexylthiophene, and 3,4-ethylenedioxythiophene were similarly prepared. Investigation of the electrochemical properties reveal that, despite the presence of α,ω-CH positions on the two thiophene termini, not all derivatives formed polymers upon electro-oxidation. In some cases the inherent stability of the radical cation precluded coupling reactions; in others, radical cation solubility prevented electrodeposition of the putative polymer. Five of the monomers could be electropolymerized to afford poly(oligothienyl sulfides) which were characterized by electronic spectroscopy and electrochemical studies. Good correlations were found between the polymer redox properties and corresponding bis(a...