Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media
authors Evans, NH; Allinson, ESH; Lankshear, MD; Ng, KY; Cowley, AR; Serpell, CJ; Santos, SM; Costa, PJ; Felix, V; Beer, PD
nationality International
journal RSC ADVANCES
keywords OLEFIN METATHESIS CATALYSTS; STABILITY-CONSTANTS; ROTAXANE SYNTHESIS; CATENANES; INTERLOCKING; PSEUDOROTAXANES; MACROCYCLE; MACHINES; RING
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. 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.
publisher ROYAL SOC CHEMISTRY
issn 2046-2069
year published 2011
volume 1
issue 6
beginning page 995
ending page 1003
digital object identifier (doi) 10.1039/c1ra00394a
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000295920900011
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