PEROXIDASE-CATALYZED POLYMERIZATION OF FLUORINE-CONTAINING PHENOLS

Abstract

Peroxidase-catalyzed oxidative polymerization of fluorine-containing phenols has been performed in a mixture of a water-miscible organic solvent and buffer at room temperature under air. The monomers used were 2,6-difluorophenol, 3- and 4-fluorophenols. In the polymerization of 2,6-diflurophenol catalyzed by horseradish peroxidase (HRP), effects of an organic solvent, buffer pH, and their mixed ratio have been systematically investigated with respect to the polymer yield and molecular weight. The resulting polymer was soluble in common polar organic solvents and showed good water repellent property. From NMR and IR data, it was supposed that the polymer was of mainly 2,6-difluoro-1,4-oxyphenylene unit. Elemental analysis showed that the elimination of a small amount of the fluorine atom took place during the polymerization. HRP catalysis induced the polymerization of 3- and 4-fluorophenols, yielding a new class of fluorine-containing polyphenols.