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Molecules 2011, 16(2), 1603-1624; doi:10.3390/molecules16021603

Synthesis and Conformation of Substituted Chiral Binaphthyl-Azobenzene Cyclic Dyads with Chiroptical Switching Capabilities

Supramolecular Science Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
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Received: 10 January 2011 / Revised: 2 February 2011 / Accepted: 11 February 2011 / Published: 14 February 2011
(This article belongs to the Special Issue Chiroptical Techniques)
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Abstract

Optically active binaphthyl-azobenezene cyclic dyads were synthesized to develop a photochromic switching molecule. Azobenezene moieties were cis-trans isomerized by photoirradiation. As a reflection of the structural change, the specific optical rotation and circular dichroism underwent significant shifts. Under certain conditions, the positive-negative and zero-positive (or zero-negative) signals were reversed. Optical rotation may potentially be applied in noise-cancelling nondestructive photoswiches. The conformations were studied by experimental and theoretical methods. The results revealed that the helical chirality, (P) or (M), of the cis-azobenzene moiety was induced by intramolecular axial chirality. The twist direction depended on the axial chirality as well as the azobenzene linkage position to the binaphthyls, but was independent of the identity of substituted groups. 2,2’-Linked-(R)-binaphthyl was found to induce cis-(P)-azobenzene, whereas symmetrically 7,7’-linked-(R)-binaphthyl was found to induce cis-(M)-azobenzene.
Keywords: optical rotation; circular dichroism; axial chirality; helical chirality; binaphthyl; azobenzene; DFT calculation; chiroptical switch optical rotation; circular dichroism; axial chirality; helical chirality; binaphthyl; azobenzene; DFT calculation; chiroptical switch
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Takaishi, K.; Kawamoto, M. Synthesis and Conformation of Substituted Chiral Binaphthyl-Azobenzene Cyclic Dyads with Chiroptical Switching Capabilities. Molecules 2011, 16, 1603-1624.

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