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Issue 6, 2011
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Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media

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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.

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

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Supplementary files

Article information


Submitted
30 Jun 2011
Accepted
03 Aug 2011
First published
28 Sep 2011

RSC Adv., 2011,1, 995-1003
Article type
Paper

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

N. H. Evans, E. S. H. Allinson, M. D. Lankshear, K. Ng, A. R. Cowley, C. J. Serpell, S. M. Santos, P. J. Costa, V. Félix and P. D. Beer, RSC Adv., 2011, 1, 995
DOI: 10.1039/C1RA00394A

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