title: Synthesis, photophysical and photochemical properties of photoacid generators based on N-hydroxyanthracene-1,9-dicarboxyimide and their application toward modification of silicon surfaces.
abstract: We have introduced a series of nonionic photoacid generators (PAGs) for carboxylic and sulfonic acids based on N-hydroxyanthracene-1,9-dicarboxyimide (HADI). The newly synthesized PAGs exhibited positive solvachromatic emission (λ(max)(hexane) 461 nm, λ(max)(ethanol) 505 nm) as a function of solvent polarity. Irradiation of PAGs in acetonitrile (ACN) using UV light above 410 nm resulted in the cleavage of weak N-O bonds, leading to the generation of carboxylic and sulfonic acids in good quantum and chemical yields. Mechanism for the homolytic N-O bond cleavage for acid generation was supported by time-dependent density functional theory (TD-DFT) calculations. More importantly, using the PAG monomer N-(p-vinylbenzenesulfonyloxy)anthracene-1,9-dicarboxyimide (VBSADI), we have synthesized N-(p-vinylbenzenesulfonyloxy)anthracene-1,9-dicarboxyimide-methyl methacrylate (VBSADI-MMA) and N-(p-vinylbenzenesulfonyloxy)anthracene-1,9-dicarboxyimide-ethyl acrylate (VBSADI-EA) copolymer through atom transfer radical polymerization (ATRP). Finally, we have also developed photoresponsive organosilicon surfaces using the aforementioned polymers.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur-721302, India.
authors.forename: Mohammed
authors.initials: M
authors.lastname: Ikbal
authors.forename: Rakesh
authors.initials: R
authors.lastname: Banerjee
authors.forename: Sanghamitra
authors.initials: S
authors.lastname: Atta
authors.forename: Dibakar
authors.initials: D
authors.lastname: Dhara
authors.forename: Anakuthil
authors.initials: A
authors.lastname: Anoop
authors.forename: N D Pradeep
authors.initials: ND
authors.lastname: Singh