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Redox-responsive conformational alteration of aromatic amides bearing N-quinonyl system |
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| Authors: | Iwao Okamoto Yusuke Takahashi Mika Sawamura Mio Matsumura Hyuma Masu Kosuke Katagiri Isao Azumaya Masanori Nishino Yukari Kohama Nobuyoshi Morita Osamu Tamura Hiroyuki Kagechika Aya Tanatani |
| Affiliation: | 1. Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan;2. Department of Chemistry, Faculty of Science, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan;3. Chemical Analysis Center, Chiba University, Japan;4. Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, Kagawa, Japan;5. Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Tokyo, Japan |
| Abstract: | Redox-induced conformational alteration of N-aryl-N-phenylamides, in which the N-aryl group consists of a hydroquinone–p-quinone system, was examined. The reduced form bearing a dihydroxyphenyl or dimethoxyphenyl group exists mainly in the E-form, whereas the oxidized form bearing a N-benzoquinone moiety takes the Z-form both in the crystal and in solution. This redox-induced conformational alteration is associated with a marked change in optical properties. This system appears to have suitable properties for use in external redox stimulus-responsive functional switching. |
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