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Synthesis and conformation of substituted chiral binaphthyl-azobenzene cyclic dyads with chiroptical switching capabilities.

Authors
  • Takaishi, Kazuto1
  • Kawamoto, Masuki
  • 1 Supramolecular Science Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. [email protected] , (Japan)
Type
Published Article
Journal
Molecules
Publisher
MDPI AG
Publication Date
Feb 14, 2011
Volume
16
Issue
2
Pages
1603–1624
Identifiers
DOI: 10.3390/molecules16021603
PMID: 21321531
Source
Medline
Language
English
License
Unknown

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.

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