Photoinduced color change and photomechanical effect of naphthalene diimides bearing alkylamine moieties in the solid state

Yuki Matsunaga, Kenta Goto, Koji Kubono, Katsuya Sako, Teruo Shinmyozu

研究成果: ジャーナルへの寄稿学術誌査読

75 被引用数 (Scopus)

抄録

Photoinduced color change of naphthalene diimides (NDIs) bearing alkylamine moieties has been observed in the solid state. The color change is attributed to the generation of a NDI radical-anion species, which may be formed through a photoinduced electron-transfer process from the alkylamine moiety to the NDI. The photosensitivity of NDIs is highly dependent on the structures of the alkylamine moieties. Crystallographic analysis, kinetic analysis, UV/Vis/NIR spectroscopic measurements, and analysis of the photoproduct suggested that a radical anion was formed through an irreversible process initiated by proton abstraction between an amine radical cation and the neutral amine moiety. The radical anions formed stacks including mixed-valence stacks and radical-anion stacks, as shown by the broad absorption bands in near-IR spectra. These photosensitive NDIs also showed crystal bending upon photoirradiation, which may be associated with a change in the intermolecular distance of the NDI stacks by the formation of monomeric radical anions, mixed-valence stacks, and radical-anion stacks.

本文言語英語
ページ(範囲)7309-7316
ページ数8
ジャーナルChemistry - A European Journal
20
24
DOI
出版ステータス出版済み - 6月 10 2014

!!!All Science Journal Classification (ASJC) codes

  • 触媒
  • 有機化学

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