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

• Published in: Chemistry : a European journal Vol. 18; no. 38; pp. 11968 - 11975
• Main Authors: Ikbal, Mohammed, Banerjee, Rakesh, Atta, Sanghamitra, Jana, Avijit, Dhara, Dibakar, Anoop, Anakuthil, Singh, N. D. Pradeep
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 17-09-2012; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Carboxylates; Chemistry; Cleavage; copolymerization; Copolymers; Esters; Generators; hydroxyquinolones; Monomers; photoacid generators; photochemistry; Sulfonates; Sulfonic acid; thin films
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201104065

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.
Facile NO cleavage of carboxylate and sulfonate esters of 1‐hydroxy‐2(1H)‐quinolone by UV light (λ≥310 nm) has been exploited for use as nonionic photoacid generators (PAGs) for efficient generation of carboxylic and sulfonic acids, respectively. Furthermore, photoresponsive copolymers were constructed from a styryl‐substituted PAG monomer and acrylate co‐monomers, and their light‐controlled surface wettability was demonstrated (see figure).