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

Kazuto Takaishi, Masuki Kawamoto

Research output: Contribution to journalReview article

15 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1603-1624
Number of pages22
JournalMolecules
Volume16
Issue number2
DOIs
Publication statusPublished - Feb 2011
Externally publishedYes

Keywords

  • Axial chirality
  • Binaphthyl, azobenzene
  • Chiroptical switch
  • Circular dichroism
  • DFT calculation
  • Helical chirality
  • Optical rotation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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