Towards a molecular anchor chain. Synthesis and catenations of spiro crown ethers

Peter R. Ashton, Thomas Horn, Stephan Menzer, Jon A. Preece, Neil Spencer, J. Fraser Stoddart, David J. Williams

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

Two new crown ethers (1 and 2) featuring a spiro linked assembly of two to three individual macrorings have been synthesised. The syntheses were achieved by means of high dilution techniques and blocking/deblocking procedures, beginning with pentaerythritol as the basic building block. The spiro and dispiro crown ethers 1 and 2 participate in template-directed self-assembly reactions with 1,1'[1,4-phenylenebis(methylene)]bis-4,4'-bipyridinium bis(hexafluorophosphate) and 1,4-bis(bromomethyl)benzene at either one or both recognition sites. The resulting new [2]catenanes (12·4PF6 and 14·4PF6) and bis[2]catenanes (13·8PF6 and 15·8PF6), incorporating interlocked cyclobis(paraquat-p-phenylene) tetracations, were characterised by (dynamic) NMR spectroscopy and high resolution FAB mass spectrometry. The X-ray crystal structure of one of these spiro-linked bis[2]catenanes, namely 13·8PF6, is reported.

Original languageEnglish (US)
Pages (from-to)480-488
Number of pages9
JournalSynthesis
Issue number4
StatePublished - Jan 1 1997

Keywords

  • [2]catenanes
  • bis[2]catenanes
  • poly[2]catenanes
  • self-assembly
  • spiro crown ethers

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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