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 Stoddard; David J. Williams

doi:10.1055/s-1997-4467

Synthesis 1997; 1997(4): 480-488
DOI: 10.1055/s-1997-4467

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Towards a Molecular Anchor Chain. Synthesis and Catenations of Spiro Crown Ethers

Peter R. Ashton¹ , Thomas Horn¹ , Stephan Menzer² , Jon A. Preece¹ , Neil Spencer¹ , J. Fraser Stoddard³ , David J. Williams²

¹School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK
²Department of Chemistry, Imperial College, South Kensington, London SW7 2AY, UK
³School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK, Fax +44(121)4143531

Abstract

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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.

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

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