A simple and highly effective ligand system for the copper(I)-mediated assembly of rotaxanes

Christopher J Campbell; David A Leigh; Inigo J Vitorica-Yrezabal; Steffen L Woltering

doi:10.1002/anie.201407817

A simple and highly effective ligand system for the copper(I)-mediated assembly of rotaxanes

Angew Chem Int Ed Engl. 2014 Dec 8;53(50):13771-4. doi: 10.1002/anie.201407817. Epub 2014 Oct 14.

Authors

Christopher J Campbell¹, David A Leigh, Inigo J Vitorica-Yrezabal, Steffen L Woltering

Affiliation

¹ School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ (UK).

Abstract

A [2]rotaxane was produced through the assembly of a picolinaldehyde, an amine, and a bipyridine macrocycle around a Cu(I) template by imine bond formation in close-to-quantitative yield. An analogous [3]rotaxane is obtained in excellent yield by replacing the amine with a diamine, thus showing the suitability of the system for the construction of higher order interlocked structures. The rotaxanes are formed within a few minutes simply through mixing the components in solution at room temperature and they can be isolated through removal of the solvent or precipitation.

Keywords: copper; imines; rotaxanes; self-assembly; supramolecular chemistry.