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

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• 作者：Takuya Nakashima ; Kenta Tsuchie ; Rui Kanazawa ; Ruiji Li ; Shunsuke Iijima ; Olivier Galangau ; Hisako Nakagawa ; Katsuya Mutoh ; Yoichi Kobayashi ; Jiro Abe ; Tsuyoshi Kawai
• 刊名：Journal of the American Chemical Society
• 出版年：2015
• 出版时间：June 10, 2015
• 年：2015
• 卷：137
• 期：22
• 页码：7023-7026
• 全文大小：294K
• ISSN：1520-5126

文摘

We herein propose a new type of efficient neutral photoacid generator. A photoinduced 6蟺-electrocyclization reaction of photochromic triangle terarylenes triggers subsequent release of a Br酶nsted acid, which took place from the photocyclized form. A H-atom and its conjugate base were introduced at both sides of a 6蟺-system to form the self-contained photoacid generator. UV irradiation to the 6蟺-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.