Highly effective and reversible control of the rocking rates of rotaxanes by changes to the size of stimulus-responsive ring components

Keiji Hirose*, Kazuaki Ishibashi, Yoshinobu Shiba, Yasuko Doi, Yoshito Tobe

*Corresponding author for this work

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

We have designed and synthesized rotaxanes whose rates of rocking motion (pendular motion) were switched reversibly through changes to the size of the ring component in response to external stimuli. The ring molecules of the rotaxanes incorporate a metaphenylene unit, which swings like a pendulum, and a dianthrylethane unit, which undergoes reversible isomerization in response to photo- and thermal stimuli and changes the size of the ring component. The rocking rates were estimated quantitatively by variable-temperature (VT) NMR spectroscopy and saturation transfer experiments, which revealed substantial changes in the rates between the open and closed forms, particularly in the case of rotaxanes with an isopropoxy group attached to a phenylene unit.

Original languageEnglish
Pages (from-to)5803-5811
Number of pages9
JournalChemistry - A European Journal
Volume14
Issue number19
DOIs
StatePublished - 27 Jun 2008

Keywords

  • Crown compounds
  • Molecular devices
  • Rotaxanes
  • Supramolecular chemistry

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