Design, synthesis and characterization of novel heterocyclic polymers

New classes of monomers containing heterocyclic groups have been prepared in good yield from readily available compounds. The heterocyclic groups were phthalazinone, quirnazolinone, benzopyrenequinone and acridone.;Bisphthalazinones, such as oxy-7-bis(1,2-dihydro-4-phenylphthalazinone) were reacted with a series of activated aryl halides to give high molecular weight novel poly(phthalazinone)s in a one-step reaction involving the formation of a N-C bond.;A series of novel quinazolinone containing monomers synthesized for nucleophilic aromatic displacement polymerization reactions, bisphenols and activated difluorides, were unstable under the polymerization conditions. Only low molecular weight oligomers were formed.;Two new quinazolinone diamines, oxy-bis(1,4-phenylene)-bis[3-(4-aminophenyl)-1-oxo-quinazolin-2-yl] and 2-(4-aminophenyl)-3-amino-4-quinazolinone were synthesized. They did not form high molecular weight polyimides because of low reactivity or instability of the monomers. A series of high molecular weight polyimides were synthesized from 2-(4-aminophenyl)-16-amino-4-quinazolinone either by one-step solution polymerization or two-step low temperature solution polymerization followed by thermal cyclodehydration.;The new monomer, 1,5-bis(4-fluorobenzoyl)naphthalene, was polymerized with a series of bisphenols to form high molecular weight poly(arylene ether)s containing the 1,5-dibenzoyl unit.;1,5-bis(4-fluorobenzoyl)naphthalene was converted to 2,3;7,8-bis(4-fluorobenzoyl)pyrene-1,6-quinone by a Scholl reaction using antimony pentafluoride. It was reacted with bisphenols, however because of side reactions only crosslinked insoluble material formed.;A series of novel acridone containing monomers, such as N-benzyl-3-chloro-6-fluoroacridone were synthesized for nucleophilic aromatic displacement polymerization reactions. High molecular weight poly(arylene ether)s containing the acridone, moiety could not be obtained because of instability or low reactivity of the monomers. Model reactions on acridone derivatives were carried out. The fluorine at the 3-position on acridone can be displaced by phenolate anion quantitatively. New acridone monomers which can be synthesized using this reaction were proposed.;All the high molecular weight novel polymers synthesized have very high glass transition temperatures and excellent thermal stabilities. Films made from the polymers had high moduli and maintained the high moduli to high temperatures.