Poly(Aryl ether‐phenylquinoxaline)s: Self‐polymerization of an A—B monomer via quinoxaline‐activated ether synthesis

A new A—B monomer, 2‐(4‐hydroxyphenyl)‐3‐phenyl‐6‐fluoroquinoxaline (1), which contains both a quinoxaline‐activated fluoro group and a phenol group was prepared and it's self‐polymerization studied. Compound 1 was prepared either by condensation of 3,4‐diaminofluorobenzene with 4‐hydroxybenzil, or condensation/demethylation with 4‐methoxybenzil in a one pot procedure. The polymerization of 1 was carried out in NMP in the presence of potassium carbonate at 180–190°C, analogous to previous examples of quinoxaline‐activated polyether synthesis. A new poly(aryl ether‐phenylquinoxaline) (2) was synthesized by this procedure, which was processable from N‐methylpyrrolidone, displayed a Tg of 255°C and a polymer decomposition temperature of 450°C. The mechanistic implications of quinoxaline activated fluoro‐displacement using an A—B monomer are discussed. Copyright © 1992 John Wiley & Sons, Inc.