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

Research paper by Takuya T Nakashima, Kenta K Tsuchie, Rui R Kanazawa, Ruiji R Li, Shunsuke S Iijima, Olivier O Galangau, Hisako H Nakagawa, Katsuya K Mutoh, Yoichi Y Kobayashi, Jiro J Abe, Tsuyoshi T Kawai

Indexed on: 21 May '15Published on: 21 May '15Published in: Journal of the American Chemical Society


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 sp(3) 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.