Synthesis of new photoresponsive polyesters containing norbornadiene moieties by the ring‐opening copolymerization of donor–acceptor norbornadiene dicarboxylic acid anhydride with donor–acceptor norbornadiene dicarboxylic acid monoglycidyl ester derivatives

Abstract

AbstractThe ring‐opening copolymerization of donor–acceptor norbornadiene (D–A NBD) dicarboxylic acid monoglycidyl ester derivatives with D–A NBD dicarboxylic acid anhydride was performed with tetraphenylphosphonium bromide as a catalyst in toluene to produce new norbornadiene (NBD) polyesters containing D–A NBD moieties in the main chain and in the side chain in one step in good yields. The photoisomerization of the D–A NBD moieties in these polyesters proceeded very smoothly to give the corresponding quadricyclane groups. Because these NBD polyesters contained many NBD moieties in the polymer chain, they had the highest capacity for heat storage in the D–A NBD polymers reported so far. The stored thermal energy of the irradiated polyesters was evaluated by differential scanning calorimetry analysis to be approximately 150–190 J/g. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 4412–4421, 2005