synthesis and conformation of substituted chiral binaphthyl-azobenzene cyclic dyads with chiroptical switching capabilities合成和构象的取代手性binaphthyl-azobenzene循环双chiroptical切换功能.pdfVIP

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synthesis and conformation of substituted chiral binaphthyl-azobenzene cyclic dyads with chiroptical switching capabilities合成和构象的取代手性binaphthyl-azobenzene循环双chiroptical切换功能.pdf

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synthesis and conformation of substituted chiral binaphthyl-azobenzene cyclic dyads with chiroptical switching capabilities合成和构象的取代手性binaphthyl-azobenzene循环双chiroptical切换功能

Molecules 2011, 16, 1603-1624; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Review Synthesis and Conformation of Substituted Chiral Binaphthyl- Azobenzene Cyclic Dyads with Chiroptical Switching Capabilities Kazuto Takaishi * and Masuki Kawamoto Supramolecular Science Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan * Author to whom correspondence should be addressed; E-Mail: ktakaishi@riken.jp. Received: 10 January 2011; in revised form: 2 February 2011 / Accepted: 11 February 2011 / Published: 14 February 2011 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