Polyimidazopyrrolone model compounds

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Abstract
The model reactions between phthalic anhydride and o‐phenylenediamine were studied under conditions analogous to the polymerization and post cyclization of dianhydrides with bis(o‐diamines) to form polyimidazopyrrolones (Pyrrones). The route from the initial amide‐acid‐amine to the tetracyclic Pyrrone model when the reactions are conducted in aprotic solvents is highly competitive between isolatable benzimidazole‐acid and imide‐amine intermediates. Solid‐state thermal conversion of the amide‐acid‐amine affords a unique dimeric species containing amide, imide, and benzimidazole functions. It was confirmed that melt techniques lead to disproportionation products. The application of these findings to related polymer synthesis is discussed.

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