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

Jason R. Price; Jack K. Clegg; Ronald R. Fenton; Leonard F. Lindoy; John C. McMurtrie; George V. Meehan; Andrew Parkin; David Perkins; Peter Turner

doi:10.1071/CH09253

RESEARCH FRONT

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 and Peter Turner ^A

+ Author Affiliations

- Author Affiliations

^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.

Australian Journal of Chemistry 62(9) 1014-1019 https://doi.org/10.1071/CH09253
Submitted: 28 April 2009 Accepted: 26 May 2009 Published: 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.

^* Dedicated to the memory of our co-author, the late Dr Andrew Parkin, a fine young chemist whose untimely passing is a great loss to us all.

Acknowledgement

We thank the Australian Research Council for support.

References

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

Abstract

Acknowledgement

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