Reversible Stereoselective Folding/Unfolding Fueled by the Interplay of Photoisomerism and Hydrogen Bonding

Christopher R. Opie, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

A linear molecular architecture equipped with complementary three-fold hydrogen-bonding units embedded with a photoswitchable trans-tetrafluoroazobenzene moiety was synthesized. The transto cis photoisomerism of the azobenzene unit induced drastic changes in the molecular architecture as a result of intramolecular hydrogen bonding as evidenced by NMR spectroscopy and size exclusion chromatography. A minute stereogenic element in the linear trans state enabled stereoselective folding into the cis state, thus producing a globular architecture with enhanced chiroptical property.

Original languageEnglish
Pages (from-to)3349-3353
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number12
DOIs
Publication statusPublished - 2017 Mar 13
Externally publishedYes

Keywords

  • azo compounds
  • foldamers
  • helical structures
  • hydrogen bonds
  • photochromism

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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