A new slippage synthesis

Peter R. Ashton, Matthew C T Fyfe, Cesare Schiavo, J. Fraser Stoddart*, Andrew J P White, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

At elevated temperatures, the crown ether dibenzo[30]crown-10 (DB30C10) slips over the (relatively) bulky 3,5-(t-Bu)2C6H3CH2 termini of a bisammonium dication-bearing two secondary ammonium centers separated through a p-xylylene spacer-to form primarily a three-component rotaxane-like entity- stabilized by, inter alia, [N+-H···O] and [C-H···O] hydrogen bonds- that has been characterized by liquid secondary ion (LSI) mass spectrometry (in the 'gas phase'), 1H NMR spectroscopy (in solution) and X-ray crystallography (in the solid state). However, this species equilibrates, in solution, with the free DB30C10 macrocycle and its two-component rotaxane- like congener, a result that demonstrates that the products obtained from the slippage synthesis are pseudorotaxanes.

Original languageEnglish (US)
Pages (from-to)5455-5458
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number31
DOIs
StatePublished - Jul 30 1998

Keywords

  • Crown Ethers
  • Pseudorotaxanes
  • Self-assembly
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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