American Chemical Society
ja5b02826_si_003.cif (29.41 kB)

Self-Contained Photoacid Generator Triggered by Photocyclization of Triangle Terarylene Backbone

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posted on 2015-06-10, 00:00 authored by Takuya Nakashima, Kenta Tsuchie, Rui Kanazawa, Ruiji Li, Shunsuke Iijima, Olivier Galangau, Hisako Nakagawa, Katsuya Mutoh, Yoichi Kobayashi, Jiro Abe, Tsuyoshi Kawai
We herein propose a new type of efficient neutral photoacid generator. A photoinduced 6π-electrocyclization reaction of photochromic triangle terarylenes triggers subsequent release of a Brønsted acid, which took place from the photocyclized form. A H-atom and its conjugate base were introduced at both sides of a 6π-system to form the self-contained photoacid generator. UV irradiation to the 6π-system produces a cyclohexa-1,3-diene part with a H-atom and a conjugate base on the sp3 C-atoms at 5- and 6-positions, respectively, which spontaneously release an acid molecule quantitatively forming a polyaromatic compound. A net quantum yield of photoacid generation as high as 0.52 under ambient conditions and a photoinitiated cationic polymerization of an epoxy monomer are demonstrated.