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

Forgan, R. S. , Blackburn, A. K., Boyle, M. M., Schneebeli, S. T. and Stoddart, J. F. (2014) The topological and chemical implications of introducing oriented rings to [3]catenanes. Supramolecular Chemistry, 26(3-4), pp. 192-201. (doi: 10.1080/10610278.2013.844812)

Abstract

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.

• Item Type: Articles
• Additional Information: Special Issue: Eighth International Symposium of Macrocyclic and Supramolecular Chemistry (ISMSC-8)
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Forgan, Professor Ross
• Authors: Forgan, R. S., Blackburn, A. K., Boyle, M. M., Schneebeli, S. T., and Stoddart, J. F.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Supramolecular Chemistry
• Publisher: Taylor and Francis
• ISSN: 1061-0278
• ISSN (Online): 1029-0478