Functionalized [2]rotaxanes

Masumi Asakawa, Peter R. Ashton, Sayeedha Iqbal, Andrew Quick, J. Fraser Stoddart*, Nigel D. Tinker, Andrew J P White, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

The synthesis of a series of dumbbell-shaped compounds, which can act as a host (e.g., toward alkali metal cations) and as a guest (e.g., toward cyclobis(paraquat-p-phenylene)) in a supramolecular context is described. The self-assembly of [2]pseudorotaxanes and [2]rotaxanes, in which cyclobis(paraquat-p-phenylene) encircles polyether chains intercepted in their middles by a hydroquinone ring and terminated at each end by 12-crown-4, 15-crown-5, monoaza-18-crown-6, 18-crown-6, or adamantyl groups, is achieved using either threading, clipping, or slipping procedures. All the [2]pseudorotaxanes and [2]rotaxanes are characterized in solution by spectroscopic means and, in the case of two of the [2]rotaxanes, by X-ray crystal structures in the solid state. In the presence of metal ions, [2]pseudorotaxanes carrying 12-crown-4 or 15-crown-5 stoppers can be disassembled in solution. The research shows how one kind of complexation can affect another kind of complexation - manifesting itself in a physical change in the system and so acting as a prototype of a potential molecular device.

Original languageEnglish (US)
Pages (from-to)329-340
Number of pages12
JournalIsrael Journal of Chemistry
Volume36
Issue number4
DOIs
StatePublished - Jan 1 1996

ASJC Scopus subject areas

  • Chemistry(all)

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