Redox-responsive conformational alteration of aromatic amides bearing N-quinonyl system

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• 作者：Iwao Okamoto^a ; ^{iokamoto@ac.shoyaku.ac.jp} ; Yusuke Takahashi^a ; Mika Sawamura^a ; Mio Matsumura^b ; Hyuma Masu^c ; Kosuke Katagiri^d ; Isao Azumaya^d ; Masanori Nishino^a ; Yukari Kohama^a ; Nobuyoshi Morita^a ; Osamu Tamura^a ; Hiroyuki Kagechika^e ; Aya Tanatani^b ; ^{tanatani.aya@ocha.ac.jp}
• 关键词：Aromatic amide ; Molecular switch ; Molecular device ; External stimulus responsive ; Oxidation ; Reduction
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：8 July, 2012
• 卷：68
• 期：27-28
• 页码：5346-5355
• 文件大小：1132 K

摘要

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.