The topological and chemical implications of introducing oriented rings to [3]catenanes

Ross S. Forgan, Anthea K. Blackburn, Megan M. Boyle, Severin T. Schneebeli, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations


We report the synthesis of three donor-acceptor azido-functionalised catenanes, wherein the asymmetric positioning of the azide group on one or two of the ring components renders its resident macrocycle constitutionally asymmetric, and so it acts as an oriented ring. As a consequence, the analyses of (i) a monoazido[2]catenane, (ii) a monoazido[3]catenane and (iii) a bisazido[3]catenane, which exists as a mixture of two conditional topological isomers, are significantly complicated. Accordingly, characterisation of the catenanes, which was achieved by a combination of dynamic 1H NMR spectroscopy, mass spectrometry and single crystal X-ray diffraction, is an arduous task. We expect that the difficulties in analysing these mechanically interlocked molecules will be encountered more frequently as chemists prepare entities with increasingly complex topologies.

Original languageEnglish (US)
Pages (from-to)192-201
Number of pages10
JournalSupramolecular Chemistry
Issue number3-4
StatePublished - 2014


  • NMR spectroscopy
  • X-ray crystallography
  • catenanes
  • chemical topology

ASJC Scopus subject areas

  • Chemistry(all)


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