Template-directed synthesis of a [2]rotaxane by the clipping under thermodynamic control of a crown ether like macrocycle around a dialkylammonium ion

Peter T. Glink, Ana I. Oliva, J. Fraser Stoddart, Andrew J P White, David J. Williams

Research output: Contribution to journalArticlepeer-review

146 Scopus citations

Abstract

A dumbbell-shaped dialkylammonium ion (see scheme) templates the formation, about its NH2+ center, of a crown ether like macrocycle under thermodynamic control from dialdehyde and diamine precursors. The imine-containing [2]rotaxane that ensues was converted by reduction into a kinetically stable interlocked molecule, which has been characterized in the solid state by X-ray crystallography in both free vase and salt forms.

Original languageEnglish (US)
Pages (from-to)1870-1875
Number of pages6
JournalAngewandte Chemie - International Edition
Volume40
Issue number10
DOIs
StatePublished - May 18 2001

Keywords

  • Macrocycles
  • Rotaxanes
  • Self-assembly
  • Template synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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