Photoinversion of cisoid/transoid binaphthyls

Kazuto Takaishi, Atsuya Muranaka, Masuki Kawamoto, Masanobu Uchiyama

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

Axially chiral binaphthyl-azobenzene cyclic dyads in which the two moieties are connected by two linkers of different lengths were synthesized. In the case of benzylated-binaphthyl analogue 2b, photoirradiation resulted in a dramatic change of the CD spectrum and optical rotation. Experimental and theoretical analyses indicated that the dihedral angle of the two naphthalene rings is strongly coupled to the azobenzene photoisomerization; cis-azobenzene induces a transoid-binaphthyl structure, while trans-azobenzene induces a cisoid-binaphthyl structure.

Original languageEnglish
Pages (from-to)276-279
Number of pages4
JournalOrganic Letters
Volume14
Issue number1
DOIs
Publication statusPublished - Jan 6 2012
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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