Issue 43, 2016

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

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

Supplementary files

Article information

Article type
Paper
Submitted
23 aug 2016
Accepted
29 sep 2016
First published
30 sep 2016

Org. Biomol. Chem., 2016,14, 10193-10200

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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