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

Fingerprint

naphthalene
dihedral angle
analogs
rings
Optical rotation
Optical Rotation
Photoisomerization
Dihedral angle
azobenzene

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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

Photoinversion of cisoid/transoid binaphthyls. / Takaishi, Kazuto; Muranaka, Atsuya; Kawamoto, Masuki; Uchiyama, Masanobu.

In: Organic Letters, Vol. 14, No. 1, 06.01.2012, p. 276-279.

Research output: Contribution to journalArticle

Takaishi, K, Muranaka, A, Kawamoto, M & Uchiyama, M 2012, 'Photoinversion of cisoid/transoid binaphthyls', Organic Letters, vol. 14, no. 1, pp. 276-279. https://doi.org/10.1021/ol203053q
Takaishi, Kazuto ; Muranaka, Atsuya ; Kawamoto, Masuki ; Uchiyama, Masanobu. / Photoinversion of cisoid/transoid binaphthyls. In: Organic Letters. 2012 ; Vol. 14, No. 1. pp. 276-279.
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