Journal
TETRAHEDRON
Volume 68, Issue 27-28, Pages 5346-5355Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.04.114
Keywords
Aromatic amide; Molecular switch; Molecular device; External stimulus responsive; Oxidation; Reduction
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Funding
- Japan Society for the Promotion of Science
- Grants-in-Aid for Scientific Research [22590106, 24590137] Funding Source: KAKEN
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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. (c) 2012 Elsevier Ltd. All rights reserved.
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