Highly arylated bis-cyclopentadienones in the synthesis of aromatic condensation monomers and polymers

Abstract A great variety of condensation monomers—highly arylated bis-cyclopentadienones—have been prepared by the reaction of bis( α -diketones) with two-fold molar amounts of diarylacetones. Reaction of these monomers with bis-acetylenes and N,N ’-bis-maleimides under Diels-Alder reaction conditions led to the formation of highly arylated polyphenylenes and polyimides combining outstanding tractability with excellent thermal properties. Alternatively, these monomers were transformed into the corresponding highly arylated bis(phthalic anhydrides), bis(naphthalic anhydrides) and diamines, which were used for the preparation of organo-soluble polyimides, polynaphthylimides and polynaphthoylenebenzimidazoles.