Chemoselective oxidative polymerization of m-ethynylphenol by peroxidase catalyst to a new reactive polyphenol

Enzymatic oxidative polymerization of m-ethynylphenol possessing two reacti ve groups, phenol and acetylene moieties, was carried out in aqueous methan ol under air. Horseradish peroxidase and hydrogen peroxide were used as cat alyst and oxidizing agent, respectively. H-1 NMR and IR analysis showed tha t only the phenolic moiety was polymerized to produce the polymer having th e ethynyl group in the side chain. The reaction of the monomer using a copp er/amine catalyst, a conventional catalyst for oxidative coupling, exclusiv ely produced a diacetylene derivative. From these data, it was found that t he peroxidase catalysis induced the chemoselective polymerization of the mo nomer. The resulting polymer was converted to carbonized polymer in a much higher yield than enzymatically synthesized poly(m-cresol) and is expected to have potential applications as a reactive starting polymer.