Abstract
We report on the mechanism of direct oxidation of 3-alkylthiophenes using ferric chloride (FeCl 3) as the polymerization oxidant/catalyst to produce high molecular weight poly(3-alkylthiophenes) (P3ATs), conjugated polymers that have potential as electrically and optically active polymers. This study shows that the FeCl 3 must exist in the solid state in the reaction mixture to be active as an oxidant in the polymerization of P3AT. A feasible polymerization mechanism for 3-alkylthiophene was developed on the basis of the crystal structure of FeCl 3 and quantum chemical computations of thiophene derivatives. The polymerization is hypothesized to proceed through a radical mechanism rather than a radical cation mechanism.
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