Design and Synthesis of Photoactive Polymer Systems Based on Amine-Catalyzed Intramolecular Imidization of Polymer Side Chains

A novel family of functionalized polystyrenes that can undergo base-catalyzed intramolecular side-chain imidization is reported. The thermal behaviors of poly(4-vinylphenyl succinamate), poly(4-vinylphenyl glutaramate), poly(4-vinylphenyl 3,3-dimethylglutaramate), and poly(4-vinylphenyl phthalamate), as well as their optical properties and chemical reactivities in the presence of an added amine have been studied. With the exception of poly(4-vinylphenyl phthalamate), the polymers are thermally stable up to 200 °C and have a relatively low optical density below 300 nm. A general trend for the ease of imidization of the polymers is summarized as follows: poly(4-vinylphenyl phthalamate) > poly(4-vinylphenyl succinamate) > poly(4-vinylphenyl 3,3-dimethylglutaramate) > poly(4-vinylphenyl glutaramate). Photoactive polymer systems were obtained by mixing either poly(4-vinylphenyl succinamate) or poly(4-vinylphenyl 3,3-dimethylglutaramate) with some bis((2,6-dinitrobenzyl)oxycarbonyl)hexane-1,6-diamine used as an amine photogenerator. Imaging of films of the polymers, as well as the effect of structure on their reactivity is discussed.