Helical chirality of azobenzenes induced by an intramolecular chiral axis and potential as chiroptical switches

Kazuto Takaishi, Masuki Kawamoto, Kazunori Tsubaki, Taniyuki Furuyama, Atsuya Muranaka, Masanobu Uchiyama

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

The cis and trans forms of the azobenzene skeleton differ significantly in length and therefore are frequently used as photochromic parts for changing absorption and fluorescence properties, in addition to association constants when they are hosts.Although optically active compounds with azobenzene adducts have been reported,few studies have examined the asymmetry of the azobenzene moiety itself. Haberhauer and Kallweit have investigated the twisting direction of the cis-azobenzene moiety by studying the helical chirality linked to a chiral cyclic imidazole tetrapeptide, possessing four asymmetric centers.The axially chiral binaphthyl is rigid in the rod direction, but around the axis has a wide and flexible asymmetric field. Thus, binaphthyl skeletons have been employed in asymmetric organocatalysis,molecular recognition,and chiral doping of liquid crystals.

Original languageEnglish
Pages (from-to)1778-1782
Number of pages5
JournalChemistry - A European Journal
Volume17
Issue number6
DOIs
Publication statusPublished - Dec 7 2011
Externally publishedYes

Keywords

  • azo compounds
  • binaphthyl
  • chirality
  • isomerization
  • photochromism

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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