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

Authors
  • Nakashima, Takuya
  • Tsuchie, Kenta
  • Kanazawa, Rui
  • Li, Ruiji
  • Iijima, Shunsuke
  • Galangau, Olivier
  • Nakagawa, Hisako
  • Mutoh, Katsuya
  • Kobayashi, Yoichi
  • Abe, Jiro
  • Kawai, Tsuyoshi
Type
Published Article
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Publication Date
Jun 10, 2015
Volume
137
Issue
22
Pages
7023–7026
Identifiers
DOI: 10.1021/jacs.5b02826
PMID: 25992804
Source
Medline
License
Unknown

Abstract

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.

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