Halide selective anion recognition by an amide-triazolium axle containing [2]rotaxane.

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...

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Main Authors: White, N, Colaço, A, Marques, I, Félix, V, Beer, P
Format: Journal article
Language:English
Published: 2014
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author White, N
Colaço, A
Marques, I
Félix, V
Beer, P
author_facet White, N
Colaço, A
Marques, I
Félix, V
Beer, P
author_sort White, N
collection OXFORD
description 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.
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spelling oxford-uuid:203c5bf3-dc07-4b15-8026-e40cf8bd52b72022-03-26T11:26:21ZHalide selective anion recognition by an amide-triazolium axle containing [2]rotaxane.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:203c5bf3-dc07-4b15-8026-e40cf8bd52b7EnglishSymplectic Elements at Oxford2014White, NColaço, AMarques, IFélix, VBeer, PA 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.
spellingShingle White, N
Colaço, A
Marques, I
Félix, V
Beer, P
Halide selective anion recognition by an amide-triazolium axle containing [2]rotaxane.
title Halide selective anion recognition by an amide-triazolium axle containing [2]rotaxane.
title_full Halide selective anion recognition by an amide-triazolium axle containing [2]rotaxane.
title_fullStr Halide selective anion recognition by an amide-triazolium axle containing [2]rotaxane.
title_full_unstemmed Halide selective anion recognition by an amide-triazolium axle containing [2]rotaxane.
title_short Halide selective anion recognition by an amide-triazolium axle containing [2]rotaxane.
title_sort halide selective anion recognition by an amide triazolium axle containing 2 rotaxane
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AT colacoa halideselectiveanionrecognitionbyanamidetriazoliumaxlecontaining2rotaxane
AT marquesi halideselectiveanionrecognitionbyanamidetriazoliumaxlecontaining2rotaxane
AT felixv halideselectiveanionrecognitionbyanamidetriazoliumaxlecontaining2rotaxane
AT beerp halideselectiveanionrecognitionbyanamidetriazoliumaxlecontaining2rotaxane