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Issue 43, 2016
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Chelated charge assisted halogen bonding enhanced halide recognition by a pyridinium-iodotriazolium axle containing [2]rotaxane

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Abstract

Four halogen and hydrogen bonding rotaxane host systems featuring pyridinium bis-amide-iodotriazole/prototriazole and pyridinium bis-amide-iodotriazolium/prototriazolium axle components have been synthesized by CuAAC-mediated mono-stoppering chloride anion templation and post-rotaxanation methylation reactions. In competitive 45 : 45 : 10 CDCl3–CD3OD–D2O aqueous solvent media, the dicationic halogen bonding rotaxane displayed a notable enhanced binding affinity and marked selectivity for Br over other halides and nitrate and dihydrogen phosphate oxoanions in contrast to an all hydrogen bonding counterpart which is attributed to chelated charge assisted halogen bonding interactions.

Graphical abstract: Chelated charge assisted halogen bonding enhanced halide recognition by a pyridinium-iodotriazolium axle containing [2]rotaxane

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Publication details

The article was received on 23 Aug 2016, accepted on 29 Sep 2016 and first published on 30 Sep 2016


Article type: Paper
DOI: 10.1039/C6OB01851C
Citation: Org. Biomol. Chem., 2016,14, 10193-10200
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    Chelated charge assisted halogen bonding enhanced halide recognition by a pyridinium-iodotriazolium axle containing [2]rotaxane

    A. E. Hess and P. D. Beer, Org. Biomol. Chem., 2016, 14, 10193
    DOI: 10.1039/C6OB01851C

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