期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 20, 期 24, 页码 7309-7316出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201304849
关键词
arenes; electron transfer; photochemistry; photomechanical effect; radical ions
资金
- MEXT, Japan
- G-COE program, Science for Future Molecular Systems, Kyushu University, Japan
- Grants-in-Aid for Scientific Research [26410053, 21106015] Funding Source: KAKEN
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.
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