Abstract
A novel carbon−sulfur (C2S) analogue of polyacene has been synthesized and characterized. The polymer is composed of a nondegenerate trans−cisoid polyacetylene backbone in which all hydrogen atoms are replaced with sulfur atoms to form thiophene rings that are fused into a linear cross-conjugated ladder-type structure. The newly developed synthetic route of the ladder-type polymer is based on an intramolecular condensation of a prepolymer consisting of 3-(alkane-1-sulfinyl)thiophen-2,5-diyl units in triflic acid. The geometric and band electronic structure of the ladder-type polymer were calculated and analyzed at the PM5 level of theory. The fused ring structure imposes strong quinonoid-type character to the originally benzenoid polyene backbone, which destabilizes the HOMO and stabilizes the LUMO and thus reduces the band gap. The shift of absorption and emission maxima to longer wavelengths responding to lower π−π* transition energies than those of polythiophene and the smaller gap between electrochemi...
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