M. Miyasaka, T. Yamazaki, E. Tsuchida
Oct 14, 2000
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0
Influential Citations
37
Citations
Journal
Macromolecules
Abstract
Poly[3-(3‘,5‘-di-tert-butyl-4‘-acetoxyphenyl)thiophene] (1a) was regioselectively synthesized via simple oxidative polymerization of 3-(3‘,5‘-di-tert-butyl-4‘-acetoxyphenyl)thiophene (2a) with ferric chloride. Head-to-tail content of 1a with a molecular weight of >104 reached 96% by modulating both the polymerization conditions and the purification procedure of the polymer. Visible absorption and fluorescence maxima were bathochromically shifted for both 1a and poly[3-(3‘,5‘-di-tert-butyl-4‘-hydroxyphenyl)thiophene] (1b), which suggests an extended π-conjugation, i.e., a regioregular structure. Redox of the phenolate and of the thiophene residue of 1b was observed reversibly and independently under alkaline conditions. The polyphenoxyl 1 derived from the oxidation of 1b showed an electrical conductivity of 10-5 S cm-1. The polyradical 1 satisfies both an alternant but non-Kekule-type π-conjugation and ferromagnetic connectivity of the unpaired electrons of the pendant phenoxyls. 1 with a spin concentratio...