Preparation of poly(p-phenylene vinylene) derivatives by a debromination–chain polymerization–debromination sequence

Abstract

A debromination-chain polymerization-debromination (DPD) route to poly(p-phenylene vinylene) (PPV) derivatives is reported. In contrast to existing chain polymerization routes for the preparation of PPV derivatives, this route takes advantage of a symmetric monomer to preclude head-to-head or tail-to-tail coupling that ultimately leads to alkyne or alkyl defects in the polymer chain. Mechanistic studies were performed and revealed that the DPD route can be carried out with the desirable intermediacy of a soluble, isolable polymer precursor. Unsubstituted PPV, poly(p-(2,5-dihexyloxyphenylene)vinylene) and a PPV derivative with a sterically encumbering side chain were all readily prepared by the new DPD route.