Abstract

High molecular weight poly(phthalazinone)s with high glass transition temperatures were prepared by a novel N−C coupling reaction. New bis(phthalazinone) monomers (5a−f), such as 7,7‘-oxobis[4-phenylphthalazin-1(2H)-one] (5c), were synthesized from the corresponding bis(phthalic anhydride)s (3a−f) in two steps. Other types of bis(phthalazinone) monomers (8, 9) were synthesized from phthalic anhydride and diphenyl sulfide or diphenyl ether. AB-type phthalazinone monomers (11a, 12−14) were also synthesized from phthalic anhydride. Poly(phthalazinone)s, having inherent viscosities of 0.3−0.4 dL/g, were prepared by the reaction of the bis(phthalazinone) monomers with an activated aryl halide such as bis(4-fluorophenyl) sulfone (22) in a dipolar aprotic solvent in the presence of potassium carbonate. AB-type phthalazinone monomers do not form high molecular weight polymers because of premature precipitation during the polymerization reaction. One of the AB-type phthalazinone monomers, 4-[4-((4-fluorophenyl)sul...

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