Poly(3,4-ethylenedioxyselenophene (original) (raw)

2008, Journal of The American Chemical Society

Since the discovery of highly conductive iodine-doped polyacetylene, 1 conducting polymers 2 have become a rapidly growing field in chemistry. However, despite significant efforts, the types of conducting polymers are limited to polythiophenes, polypyrroles, polyacetylenes, polyphenylenes, poly(p-phenylene vinylene)s, and a few others. Given the similarity between thiophene and selenophene rings, and considering that selenium analogues of tetrathiafulvalene (TTF), such as tetramethyltetraselenafulvalene (TMTSF) and bis(ethylenedithio)tetraselenafulvalene (BETS), have been shown 3 to be even better organic superconductors than TTF derivatives, it is surprising that very little is known about polyselenophenes and no highly conductive polyselenophene was reported. 4,5 Theoretical studies 6 indicate that polyselenophenes should have a lower band gap than polythiophenes. Polyselenophenes are also expected to have some advantages over polythiophenes, such as having lower oxidation and reduction potentials, 6 being easier to polarize (since the selenium atom is more easily polarized than sulfur), and being more suited to interchain charge transfer (which should be facilitated by intermolecular Se · · · Se contacts).