SYNTHESIS OF POLYMERS BEARING PENDANT NORBORNADIENE MOIETIES BY ADDITION-REACTION OF POLY (GLYCIDLY METHACRYLATE-CO-METHYL METHACRYLATE)S WITH 2,5-NORBORNADIENE-2-CARBOXYLIC ACIDS

Polymers bearing photoresponsive norbornadiene (NBD) moieties were synthesized by the addition reaction of poly (glycidyl methacrylate-co-methyl methacrylate) s containing pendant epoxide groups with 3-phenyl-2,5-norbornadiene-2-carboxylic acid (PNBC), 3-[(phenyl)carbamoyl]-2,5-norbornadiene-2-carboxylic acid 3-[(4-acetylphenyl)carbamoyl]-2,5-norbornadiene-2-carboxylic acid (APCND), and 3-[(4-methoxyphenyl)carbamoyl]-2,5-norbornadiene-2-carboxylic acid using tetrabutylammonium bromide as a catalyst in DMF. The polymers bearing pendant PNBC or APCND moieties have higher photochemical reactivity in the film state than the polymers bearing pendant PCND or MPCND moieties. Although the pendant quadricyclane (QC) group produced by the photoirradiation of the PNBC moiety in these polymers has excellent storage stability in the film state, without catalyst at room temperature, the QC group in the polymer film with the catalyst reverts gradually to the NBD moiety at room temperature.