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

Research output: Contribution to journalArticlepeer-review

60 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)7309-7316
Number of pages8
JournalChemistry - A European Journal
Volume20
Issue number24
DOIs
Publication statusPublished - Jun 10 2014

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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