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, 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: an international journal for chemical science, 62 (9). pp. 1014-1019.

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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 ID: 10130
Item Type: Article (Research - C1)
ISSN: 1445-0038
Funders: ARC
Date Deposited: 28 May 2010 03:09
FoR Codes: 03 CHEMICAL SCIENCES > 0302 Inorganic Chemistry > 030207 Transition Metal Chemistry @ 100%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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