Development of 1-hydroxy-2(1H)-quinolone-based photoacid generators and photoresponsive polymer surfaces

Mohammed Ikbal; Rakesh Banerjee; Sanghamitra Atta; Avijit Jana; Dibakar Dhara; Anakuthil Anoop; N D Pradeep Singh

doi:10.1002/chem.201104065

Development of 1-hydroxy-2(1H)-quinolone-based photoacid generators and photoresponsive polymer surfaces

Chemistry. 2012 Sep 17;18(38):11968-75. doi: 10.1002/chem.201104065. Epub 2012 Aug 7.

Authors

Mohammed Ikbal¹, Rakesh Banerjee, Sanghamitra Atta, Avijit Jana, Dibakar Dhara, Anakuthil Anoop, N D Pradeep Singh

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur-721302, India.

PMID: 22887636
DOI: 10.1002/chem.201104065

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.