Pseudorotaxanes formed between secondary dialkylammonium salts and crown ethers

Peter R. Ashton, Ewan J T Chrystal, Peter T. Glink, Stephan Menzer, Cesare Schiavo, Neil Spencer, J. Fraser Stoddart*, Peter A. Tasker, Andrew J P White, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

325 Scopus citations

Abstract

A very simple self-assembling system, which produces inclusion complexes with pseudorotaxane geometries, is described. The self-assembly of eight pseudorotaxanes with a range of stoichiometries - 1:1, 1:2, 2:1, and 2:2 (host: guest) - has been achieved. These pseudorotaxanes self-assemble from readily available components - well-known crown ethers, such as dibenzo[24]crown-8 and bis-p-phenylene[34]crown-10, and secondary dialkylammonium hexafluorophosphate salts, such as (PhCH2)2-NH2+ PF 6- and (MBu)2NH2+PF 6- - and have been characterized not only in the solid state, but also in solution and in the "gas phase". The pseudorotaxanes are stabilized largely by hydrogen-bonding interactions and, in some instances, by aryl-aryl interactions.

Original languageEnglish (US)
Pages (from-to)709-728
Number of pages20
JournalChemistry - A European Journal
Volume2
Issue number6
DOIs
StatePublished - 1996

Keywords

  • Crown ethers
  • Dialkylammonium salts
  • Hydrogen bonding
  • Molecular recognition
  • Pseudorotaxanes
  • Self-assembly

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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