Halide selective anion recognition by an amide-triazolium axle containing [2]rotaxane
authors White, NG; Colaco, AR; Marques, I; Felix, V; Beer, PD
nationality International
journal ORGANIC & BIOMOLECULAR CHEMISTRY
keywords SURFACE-ELECTROSTATIC POTENTIALS; MACROCYCLIC RECEPTOR; CHLORIDE BINDING; DONOR GROUPS; ROTAXANE; CH; TRIAZOLOPHANES; COMPLEXATION; PROGRAM; SULFATE
abstract A new rotaxane containing the 3-amido-phenyl-triazolium group incorporated into the interlocked structure's axle component has been prepared by a chloride anion templated clipping strategy. Proton NMR titration experiments reveal that the interlocked host displays a high degree of halide anion recognition in competitive 1:1 CDCl3-CD3OD solvent mixture. Chloride and bromide anions are bound strongly and selectively, with negligible complexation of the larger, more basic oxoanions, acetate and dihydrogen phosphate being observed. Density functional theory calculations on the related axle motifs 3-amido-phenyl-triazolium, pyridinium bis-triazole and pyridinium bis-amide were performed, and indicate that the new rotaxane axle motif displays much weaker oxoanion binding than the pyridinium based systems.
publisher ROYAL SOC CHEMISTRY
issn 1477-0520
year published 2014
volume 12
issue 27
beginning page 4924
ending page 4931
digital object identifier (doi) 10.1039/c4ob00801d
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000338118400018
link 24876069
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