Copper(I) Templated Synthesis of a 2,2´-Bipyridine Derived 2-Catenane: Synthetic, Modelling, and X-ray Studies

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Contents Vol 62(9)

doi:10.1071/CH09253

Copper(i) Templated Synthesis of a 2,2′-Bipyridine Derived 2-Catenane: Synthetic, Modelling, and X-ray Studies*

Jason R. Price ^A, Jack K. Clegg ^A, Ronald R. Fenton ^A, Leonard F. Lindoy ^A ^E ^F, John C. McMurtrie ^B, George V. Meehan ^C, Andrew Parkin ^D, David Perkins ^A, Peter Turner ^A

^A School of Chemistry, The University of Sydney, NSW 2006, Australia.
^B School of Physical and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Brisbane, Qld 4001, Australia.
^C School of Pharmacy and Molecular Sciences, James Cook University, Townsville, Qld 4811, Australia.
^D Department of Chemistry, University of Glasgow, G12 8QQ, UK.
^E Corresponding author. Email: lindoy@chem.usyd.edu.au
^F Visiting Professor, Department of Chemistry, National University of Singapore, 2008.





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Australian Journal of Chemistry 62(9) 1014–1019 http://dx.doi.org/10.1071/CH09253
Submitted: 28 April 2009 Accepted: 26 May 2009 Published online: 17 September 2009

Abstract

Following molecular modelling employing molecular mechanics and semi-empirical (PM3) calculations as an aid to ligand design, a new copper(i)-containing [2]-catenane has been prepared by the reaction of 6,6′-bis[(4″-formylphenoxy)methyl]-2,2′-bipyridyl with 1,6-hexanediamine in the presence of a copper(i) template, followed by in situ sodium borohydride reduction of the tetra-imine species generated. The corresponding [2]-catenane was obtained as a deep orange crystalline solid. The X-ray structure of this product along with that of the corresponding bis-dialdehyde precursor copper(i) complex have been determined. In the latter case, the structure is pre-organized for catenane formation. The new catenane appears to be the first example of a tetrahedral metal template product incorporating a bis-bipyridyl derivative core. Isolation of the metal-free [2]-catenane has also been achieved following treatment of the copper(i) catenane complex in dimethylsulfoxide with tetrabutylammonium cyanide.