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Synthesis 1994; 1994(12): 1344-1352
DOI: 10.1055/s-1994-25692
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The Self-Assembly and Dynamic Properties of Thiophene-Containing [2]Catenanes

Peter R. Ashton* , Jon A. Preece, J. Fraser Stoddart, Malcolm S. Tolley, Andrew J. P. White, David J. Williams
  • *School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK
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Publication Date:
25 April 2002 (online)

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The template-directed syntheses of two novel [2]catenanes, incorporating bisparaphenylene-34-crown-10 interlocked with tetracationic cyclophanes, containing either one or two 2,5-disubstituted thiophene residues in addition to two bipyridinium units, are reported. The X-ray crystal structures of one of these [2]catenanes and of its component tetracationic cyclophane are reported. The former exhibits short [S · · · O] contacts in addition to the expected π-π and [C-H · · · O] stabilising interactions. Dynamic 1H NMR spectroscopy has revealed that there is a substantial degree of order which characterises the molecular structures of both these [2]catenanes in solution at a noncovalent bonding level. Identifying and understanding these noncovalent bonding interactions between the molecular components are crucial to the design of catenanes that will self-assemble in a highly efficient manner.