POLY(P-PHENYLENE)S WITH POLAR SIDE-GROUPS .1. PD-CATALYZED SYNTHESIS,CHARACTERIZATION AND MODIFICATION OF POLY(P-PHENYLENE)S BEARING BUTOXYMETHYL SIDE-CHAINS

This is a description of the Pd-catalyzed synthesis of two poly(p-phen ylene) (PPP) derivatives which have butoxymethyl side groups on each, or every alternate, phenylene moiety. For the latter, details are give n of the quantitative transformation of the ether functionalities into bromomethyl pendant groups. Subsequent reaction of these bromo functi onalities with sodium 4-cyanophenolate or sodium acetate produced stru cturally homogeneous PPP's which had 4-cyanophenoxymethyl and acetoxym ethyl side groups, respectively. The PPP derivatives described here ar e soluble in common organic solvents and were characterized in detail by NMR spectroscopy, membrane osmometry and size exclusion chromatogra phy (SEC). The degrees of polycondensation of the butoxymethyl-substit uted polymers were found to be in the order of 30-65. No evidence for chain degradation during the following conversions was found on the ba sis of the NMR and SEC measurements.