Photoinversion of cisoid/transoid binaphthyls

Kazuto Takaishi, Atsuya Muranaka, Masuki Kawamoto, Masanobu Uchiyama

Research output: Contribution to journalArticle

21 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

Fingerprint Dive into the research topics of 'Photoinversion of cisoid/transoid binaphthyls'. Together they form a unique fingerprint.

  • Cite this

    Takaishi, K., Muranaka, A., Kawamoto, M., & Uchiyama, M. (2012). Photoinversion of cisoid/transoid binaphthyls. Organic Letters, 14(1), 276-279. https://doi.org/10.1021/ol203053q