Issue 9, 2015

Contrasting anion recognition behaviour exhibited by halogen and hydrogen bonding rotaxane hosts

Abstract

A rotaxane host system containing a novel halogen bonding (XB) 5-iodo-1,2,3-triazole functionalised pyridinium motif, within its axle component, has been prepared via a ring closing metathesis reaction, using chloride as a template. Proton NMR titration experiments, in competitive 1 : 1 CDCl3–CD3OD solvent media, showed the XB rotaxane selectively bound halides over larger, more basic oxoanions. An all hydrogen bonding proto-triazole containing rotaxane analogue was also prepared, which in stark contrast demonstrated a reversal in the anion selectivity trend, with a preference for dihydrogen phosphate over the halides which is unprecedented for an interlocked host system.

Graphical abstract: Contrasting anion recognition behaviour exhibited by halogen and hydrogen bonding rotaxane hosts

Supplementary files

Article information

Article type
Paper
Submitted
05 Des 2014
Accepted
24 Des 2014
First published
24 Des 2014

Org. Biomol. Chem., 2015,13, 2582-2587

Contrasting anion recognition behaviour exhibited by halogen and hydrogen bonding rotaxane hosts

S. P. Cornes, C. H. Davies, D. Blyghton, M. R. Sambrook and P. D. Beer, Org. Biomol. Chem., 2015, 13, 2582 DOI: 10.1039/C4OB02547D

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