Issue 19, 2017

Tripodal halogen bonding iodo-azolium receptors for anion recognition

Abstract

The synthesis, characterization and anion binding properties of 1,3,5-tri-substituted benzene platform-based tripodal receptors containing halogen bonding (XB) iodo-imidazolium and iodo-triazolium motifs, and hydrogen bonding (HB) analogues are described. Proton NMR anion binding investigations reveal the XB receptors are superior halide complexants compared to hydrogen bonding (HB) receptor analogues, with the iodo-imidazolium tripodal receptor exhibiting notably higher association constant values in comparison to the iodo-triazolium host system. In contrast, the HB tripod receptors, display higher affinities for dihydrogen phosphate than the XB receptors. Computational DFT and molecular dynamics were used to corroborate the experimental observations, and to give a clearer insight into the intimate nature of halide binding. The studies reveal a fundamental different binding behavior for the imidazolium-based and the iodo-imidazolium-based receptors.

Graphical abstract: Tripodal halogen bonding iodo-azolium receptors for anion recognition

Supplementary files

Article information

Article type
Paper
Submitted
12 12 2016
Accepted
21 1 2017
First published
13 2 2017
This article is Open Access
Creative Commons BY license

RSC Adv., 2017,7, 11253-11258

Tripodal halogen bonding iodo-azolium receptors for anion recognition

S. Ruiz-Botella, P. Vidossich, G. Ujaque, E. Peris and P. D. Beer, RSC Adv., 2017, 7, 11253 DOI: 10.1039/C6RA28082J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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