Poly(imidoaryl ether)s with bulky highly fluorescent pendent groups

Three novel aromatic imidoaryl bisphenols 6a-c with bulky groups of varying size on the pendent phenyl ring have been synthesized from 3,8-bis(4-hydroxyphenyl)-N-phenyl-1,2-naphthalimide 1a. Poly(imidoaryl ether)s were synthesized in dipolar aprotic solvents by reacting the monomers with activated difluoro compounds. Glass transition temperatures (T-g) for the polymers are in the range 265.9-315.0 degreesC, and they exhibit a range of colors from yellow to red. The highest T-g and 5% weight loss temperature of these polymers were 315 and 496 degreesC, respectively. Most of the polymers are soluble in chloroform at room temperature. The UV-vis absorption spectra of polymers 11ae, 11be and 16 were recorded in chloroform. Polymer 16 has the most intense absorption peaks (above 300 nm) at 492 and 528 nm, respectively, while the fluorescent spectrum of polymer 16 shows several peaks at 428, 539, 577 and 625 nm, respectively, when excited at 350 nm. Copyright (C) 2001 John Wiley & Sons, Ltd.