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Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media

DOI: 10.1039/c1ra00394a DOI Help

Authors: Nicholas H. Evans (University of Oxford) , Emma S. H. Allinson (University of Oxford) , Michael D. Lankshear (University of Oxford) , Ka-yuen Ng (University of Oxford) , Andrew R. Cowley (University of Oxford) , Chris Serpell (University of Oxford) , SĂ©rgio M. Santos (Universidade de Aveiro) , Paulo J. Costa (Universidade de Aveiro) , Vitor Felix (Universidade de Aveiro) , Paul D. Beer (University of Oxford)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Rsc Advances , VOL 1 (6) , PAGES 995-1003

State: Published (Approved)
Published: September 2011
Diamond Proposal Number(s): 1858

Abstract: An anion templated double cyclization strategy to synthesize [2]catenanes in which two identical acyclic pyridinium receptor motifs interweave around a chloride anion template is described. Ring closing metathesis (RCM) of the preorganized orthogonal precursor chloride complex facilitates the isolation of [2]catenanes in very high yields. X-ray crystal structures provide an insight of the supramolecular forces responsible for chloride anion templated efficacy and recognition. Removal of the chloride anion template generates topologically unique interlocked binding cavities for anions. 1H NMR anion binding investigations demonstrate the catenanes to be highly selective hosts for chloride in preference to more basic monocharged oxoanions. In aqueous solvent media containing 30% water, such catenanes exclusively bind chloride, under which conditions no binding of acetate or dihydrogen phosphate is observed. Molecular dynamic simulations in the solution phase are used to account for the catenanes’ anion recognition properties.

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction

Added On: 26/10/2011 11:05

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