Synthesis and Electropolymerization of 2-(3-Thienylethyl)-3-thiopheneacetate

Nicholas Leventis, Missouri University of Science and Technology
Lia Sotiriou-Leventis, Missouri University of Science and Technology
Sudhir Mulik
Amala Dass

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Conducting polymers offer great promise in the development of electronic devices, displays and sensors. In that regard, biomolecules can be attached to these polymers via functional groups, but the presence of such groups oftentimes hinders polymerization.1-3 One strategy is to polymerize a functionalized monomer precursor of a conducting polymer, followed by reaction of the dangling functional groups of the polymer with appropriately functionalized labels. An attractive functionalized thiophene for that purpose is 3-thienylethanol. Unfortunately, however, this monomer is not polymerizable.1,2 Thus, 3-thienylethanol has been esterified, followed by co-polymerization with 3-methylthiophene (3-MT), and subsequent hydrolysis of the ester to the free alcohol.1,2 Here, we present a viable alternative, whereas we have synthesized monomer 1 from commercially available 3-thiopheneacetic acid and 2-(3-thienylethanol). Monomer 1 was electropolymerized both by itself and as a copolymer with 3- methylthiophene (3-MT). The ester linkage was reduced with LiAlH4, and the resulting hydroxyl groups were re-esterified by reaction with acetyl chloride. The functional group transformations were followed by FT-IR.