Synthesis of novel poly(thioether-naphthalimide)s that utilize hydrazine as the diamine

A series of bis(4-thio-1,8-naphthalic anhydride)s and the corresponding bis (N-amino naphthalimide) derivatives were synthesized from readily available compounds in high yield. A series of novel poly(thioether-naphthalimide)s, which utilized hydrazine as the diamine, were synthesized by a one-step po lymerization reaction in m-cresol. Poly(thioether-naphthalimide)s with inhe rent viscosities of 0.57-1.73 dL/g were obtained. The polymers were soluble in CHCl3 and were determined to have high molecular weights by means of ge l permeation chromatographic analysis. They were soluble in m-cresol and co uld be cast into tough films from m-cresol solution. The glass-transition t emperature (T-g) values of the polyimides ranged from 320 to 353 degreesC. Polyimides from the bisphenol dianhydride, derived from 9,9-bis(4-hydroxyph enyl)fluorene, did not show a clear transition in the DSC analysis. Degrada tion temperatures for 5% weight loss all occurred above 430 degreesC in nit rogen. The series of monomers were successfully copolymerized with each oth er. Monomers 6a and 7a, containing the bisphenol A moiety, could also be co polymerized with perylenetetracarboxylic dianhydride. These copolymers had high T-g's and were thermally stable. The UV-vis absorption properties of t he polymers were also examined. (C) 2001 John Wiley & Sons, Inc.