Photoswitching of the association of a permethylated α-cyclodextrin-azobenzene dyad forming a Janus [2]pseudorotaxane

Tatsuhiko Fujimoto, Asao Nakamura, Yoshihisa Inoue, Yoshiteru Sakata, Takahiro Kaneda

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Abstract

For achieving the on-off operation of the superstructure formation of hermaphrodite cyclodextrin derivatives, we synthesized azobenzene-modified permethylated α-cyclodextrins, 1 and 2. These compounds formed Janus [2]pseudorotaxanes in CD3OD-D2O mixtures. The E-Z photoisomerization of 1 by UV light irradiation resulted in the dissociation of the superstructure, but, by boiling the solution, the superstructure was recovered through the thermal isomerization of (Z)-1 to (E)-1. These processes could be repeated many times without any side reactions. This is the first example of the dynamic control of the [2]pseudorotaxane formation of modified cyclodextrins by external stimuli.

Original languageEnglish
Pages (from-to)7987-7989
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number45
DOIs
Publication statusPublished - 2001 Nov 5

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Keywords

  • Azo compounds
  • Cyclodextrins
  • Photochemistry
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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