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

Price, J. R., Clegg, J. K., Fenton, R. R., Lindoy, L. F., McMurtrie, J. C., Meehan, G. V., Parkin, A., Perkins, D. and Turner, P. (2009) Copper(I) Templated Synthesis of a 2,2 '-Bipyridine Derived 2-Catenane: Synthetic, Modelling, and X-ray Studies. Australian Journal of Chemistry, 62(9), pp. 1014-1019. (doi: 10.1071/CH09253)

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.

• Item Type: Articles
• Keywords: CATENANE COMPLEX COMPLEXES Copper(I) complex CORE DERIVATIVES DESIGN IN-SITU LIGAND MACROCYCLIC LIGANDS MOLECULAR MACHINE PROTOTYPES REDUCTION TEMPLATE TRANSITION-METAL-COMPLEXES X-RAY X-RAY-STRUCTURE
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Parkin, Dr Andrew
• Authors: Price, J. R., Clegg, J. K., Fenton, R. R., Lindoy, L. F., McMurtrie, J. C., Meehan, G. V., Parkin, A., Perkins, D., and Turner, P.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Australian Journal of Chemistry
• ISSN: 0004-9425