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Synlett 1994; 1994(12): 1063-1066
DOI: 10.1055/s-1994-34979
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The Design and Self-Assembly of a Pyridine-Containing [2]Catenane

Peter R. Ashton* , Mark A. Blower, Colin H. McLean, J. Fraser Stoddart, Malcolm S. Tolley
  • *School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK
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Publication Date:
22 March 2002 (online)

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A bispyridine-containing crown ether (6) has been incorporated, along with bis(paraquat-p-phenylene), into a [2]catenane 3.4PF6 using a self-assembly approach. The incorporation of pyridine units allows one of the noncovalent interactions - hydrogen bonding - that determines (i) the efficiency of the template-directed synthesis and (ii) the dynamic properties of the [2]catenane, to be assessed for its relative importance as a recognition feature during and after the formation of 3.4PF6. The pyridine-containing [2]catenane has also been used, for the first time, to determine the activation barrier to a previously predicted, yet unobserved, site-exchange process - 'rocking' - within the [2]catenane structures in the solution state.

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