Copper(I) templated synthesis of a 2,2-bipyridine derived 2-catenane: synthetic, modelling, and X-ray studies

Price, Jason R., Clegg, Jack K., Fenton, Ronald R., Lindoy, Leonard F., McMurtrie, John C., Meehan, George V., Parkin, Andrew, Perkins, David and Turner, Peter (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: 1014-1019. doi:10.1071/CH09253


Author Price, Jason R.
Clegg, Jack K.
Fenton, Ronald R.
Lindoy, Leonard F.
McMurtrie, John C.
Meehan, George V.
Parkin, Andrew
Perkins, David
Turner, Peter
Title Copper(I) templated synthesis of a 2,2-bipyridine derived 2-catenane: synthetic, modelling, and X-ray studies
Journal name Australian Journal of Chemistry   Check publisher's open access policy
ISSN 0004-9425
1445-0038
Publication date 2009-01-01
Year available 2009
Sub-type Article (original research)
DOI 10.1071/CH09253
Open Access Status DOI
Volume 62
Issue 9
Start page 1014
End page 1019
Total pages 6
Place of publication Collingwood, VIC, Australia
Publisher C S I R O Publishing
Language eng
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.
Keyword Molecular machine prototypes
Transition metal complexes
Macrocyclic ligands
Derivatives
Catenane
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ
Additional Notes Published online: 17 September 2009. This special issue of the Australian Journal of Chemistry includes reviews and research papers from the University of Singapore joint symposium held on the 15th and 16th of December 2008.

Document type: Journal Article
Sub-type: Article (original research)
Collection: School of Chemistry and Molecular Biosciences
 
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