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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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Publication details

The article was received on 30 Jun 2011, accepted on 03 Aug 2011 and first published on 28 Sep 2011


Article type: Paper
DOI: 10.1039/C1RA00394A
Citation: RSC Adv., 2011,1, 995-1003
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    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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