Development of 1-Hydroxy-2(1H)-quinolone-Based Photoacid Generators and Photoresponsive Polymer Surfaces

A new class of carboxylate and sulfonate esters of 1-hydroxy-2(1H)-quinolone has been demonstrated as nonionic photoacid generators (PAGs). Irradiation of carboxylates and sulfonates of 1-hydroxy-2(1H)-quinolone by UV light (?=310 nm) resulted in homolysis of weak N?O bond leading to efficient generation of carboxylic and sulfonic acids, respectively. The mechanism for the homolytic N?O bond cleavage was supported by time-dependent DFT calculations. Photoresponsive 1-(p-styrenesulfonyloxy)-2-quinolonemethyl methacrylate (SSQL-MMA) and 1-(p-styrenesulfonyloxy)-2-quinolonelauryl acrylate (SSQL-LA) copolymers were synthesized from PAG monomer 1-(p-styrenesulfonyloxy)-2-quinolone, and subsequently controlled surface wettability was demonstrated for the above-mentioned photoresponsive polymers.