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

Evans, Nicholas H. and Allinson, Emma S. H. and Lankshear, Michael D. and Ng, Ka-Yuen and Cowley, Andrew R. and Serpell, Christopher J. and Santos, Sergio M. and Costa, Paulo J. and Felix, Vitor and Beer, Paul D. (2011) Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media. RSC Advances, 1 (6). pp. 995-1003. ISSN 2046-2069

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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. H-1 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.

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Journal Article
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RSC Advances
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07 Aug 2013 10:35
Last Modified:
18 Sep 2023 00:43