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.
| 元の言語 | 英語 |
|---|---|
| ページ（範囲） | 7309-7316 |
| ページ数 | 8 |
| ジャーナル | Chemistry - A European Journal |
| 巻 | 20 |
| 発行部数 | 24 |
| DOI | |
| 出版物ステータス | 出版済み - 6 10 2014 |
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All Science Journal Classification (ASJC) codes
- Catalysis
- Organic Chemistry
これを引用
Photoinduced color change and photomechanical effect of naphthalene diimides bearing alkylamine moieties in the solid state. / Matsunaga, Yuki; Goto, Kenta; Kubono, Koji; Sako, Katsuya; Shinmyozu, Teruo.
：: Chemistry - A European Journal, 巻 20, 番号 24, 10.06.2014, p. 7309-7316.研究成果: ジャーナルへの寄稿 › 記事
}
TY - JOUR
T1 - Photoinduced color change and photomechanical effect of naphthalene diimides bearing alkylamine moieties in the solid state
AU - Matsunaga, Yuki
AU - Goto, Kenta
AU - Kubono, Koji
AU - Sako, Katsuya
AU - Shinmyozu, Teruo
PY - 2014/6/10
Y1 - 2014/6/10
N2 - 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.
AB - 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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UR - http://www.scopus.com/inward/citedby.url?scp=84902106704&partnerID=8YFLogxK
U2 - 10.1002/chem.201304849
DO - 10.1002/chem.201304849
M3 - Article
AN - SCOPUS:84902106704
VL - 20
SP - 7309
EP - 7316
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 24
ER -