期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 20, 页码 9669-9677出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo501800g
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资金
- JSPS KAKENHI [26410034]
- Grants-in-Aid for Scientific Research [26102007, 26410034, 23245027] Funding Source: KAKEN
Molecular structures of dicyanomethylenated quinacridone (1) as a solid and in solution were examined on the basis of single-crystal X-ray structural analysis, temperature-dependent H-1 NMR in CD2Cl2, and theoretical calculations. Crystal 1 had a curved, butterfly-shaped molecular structure. Thermally activated flipping between the curved, butterfly-shaped structure and an armchair structure occurred in solution. Electrochemical reduction triggered a dynamic change from the curved, butterfly-shaped conformation in the neutral state to a planar conformation in the dianion state, which represented electrochromic behavior with electrochemical bistability. A large two-photon absorption cross section of compound 1 was observed in the resonance-enhancement region of 423 GM (1 GM = 1 X 10(-5) cm(4) s photon(-1) molecule(-1)) at 710 nm. Multiple donor acceptor charge-transfer pathways of molecule 1 enhanced two-photon absorption.
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