Novel synthesis of poly(arylene thioether)s via one-pot polymerization of bis(N,N′-dimethyl-S-carbamate)s with activated dihalo aromatic compounds

Abstract

A novel and convenient method to prepare poly(arylene thioether)s by a one-pot polymerization of N,N′-dimethyl-S-carbamate masked bisthiols was developed. The polymerization reactions were carried out in diphenyl sulfone in the presence of a cesium carbonate and calcium carbonate mixture at 200 – 240 °C. N,N′-Dimethyl-S-carbamate masked bisthiols can be conveniently prepared from the corresponding dihydroxy compounds by the Newman-Kwart rearrangement reaction. A series of novel poly(arylene thioether)s were prepared from 9,9′-bis(4-hydroxyphenyl)fluorene and 2,2′-bis(hydroxyphenyl)hexafluoropropane, respectively. High molecular weight polymers were obtained in 3 – 4 hours.