Development of 1‐Hydroxy‐2(1<i>H</i>)‐quinolone‐Based Photoacid Generators and Photoresponsive Polymer Surfaces

Abstract

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 (λ≥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-quinolone-methyl methacrylate (SSQL-MMA) and 1-(p-styrenesulfonyloxy)-2-quinolone-lauryl 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.