Photoswitching of dextro/levo rotation with axially chiral binaphthyls linked to an azobenzene

Kazuto Takaishi, Masuki Kawamoto, Kazunori Tsubaki, Tatsuo Wada

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

(Figure Presented) To examine the reversible photoisomerization and subsequent change of asymmetric field, we synthesized optically active 3,3′-disubstituted-1,1′-binaphthyls with an azobenzene moiety. Reflecting the structural change, the specific rotation and circular dichroism underwent significant variations. Under certain conditions, the positive-negative signals were reversible. Furthermore, the magnitude of these changes showed a 3,3′-substituent dependency. Dibenzyloxy or bis(diphenylmethyloxy) derivatives were better suited for sign interconversion of the optical properties. In contrast, the hydroxy group(s) lacked both optical signals and durability.

Original languageEnglish
Pages (from-to)5723-5726
Number of pages4
JournalJournal of Organic Chemistry
Volume74
Issue number15
DOIs
Publication statusPublished - Aug 7 2009
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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