Self-assembling [2]- And [3]rotaxanes from secondary dialkylammonium salts and crown ethers

Peter R. Ashton, Peter T. Glink, J. Fraser Stoddart*, Peter A. Tasker, Andrew J P White, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

173 Scopus citations

Abstract

The self-assembly of three new rotaxanes - two [2]rotaxanes and a [3]rotaxane - formed by a "threading followed by stoppering" approach is described. These template-directed syntheses rely on the formation of pseudorotaxane intermediates, which self-assemble in solution from functionalized secondary dialkylammonium hexafluorophosphate threads and macrocyclic polyether rings (either dibenzo[24]crown-8 or its asymmetric constitutional isomer). The stoppers - substituted 1,2,3-triazoles - were created by thermally allowed 1,3-dipolar cycloadditions between azido groups, which terminate the threads, and di-tert-butyl acetylenedicarboxylate.

Original languageEnglish (US)
Pages (from-to)729-736
Number of pages8
JournalChemistry - A European Journal
Volume2
Issue number6
DOIs
StatePublished - 1996

Keywords

  • Merlocking molecules
  • Molecular recognition
  • Pseudorotaxanes
  • Rotaxanes
  • Template syntheses

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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