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

Research output: Contribution to journalArticle

47 Citations (Scopus)

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
Externally publishedYes

Fingerprint

Rotaxanes
Cyclodextrins
Association reactions
Photoisomerization
Isomerization
Ultraviolet radiation
Boiling liquids
Irradiation
azobenzene

Keywords

  • Azo compounds
  • Cyclodextrins
  • Photochemistry
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Photoswitching of the association of a permethylated α-cyclodextrin-azobenzene dyad forming a Janus [2]pseudorotaxane. / Fujimoto, Tatsuhiko; Nakamura, Asao; Inoue, Yoshihisa; Sakata, Yoshiteru; Kaneda, Takahiro.

In: Tetrahedron Letters, Vol. 42, No. 45, 05.11.2001, p. 7987-7989.

Research output: Contribution to journalArticle

Fujimoto, Tatsuhiko ; Nakamura, Asao ; Inoue, Yoshihisa ; Sakata, Yoshiteru ; Kaneda, Takahiro. / Photoswitching of the association of a permethylated α-cyclodextrin-azobenzene dyad forming a Janus [2]pseudorotaxane. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 45. pp. 7987-7989.
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