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Issue 9, 2015
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Contrasting anion recognition behaviour exhibited by halogen and hydrogen bonding rotaxane hosts

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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

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Publication details

The article was received on 05 Dec 2014, accepted on 24 Dec 2014 and first published on 24 Dec 2014


Article type: Paper
DOI: 10.1039/C4OB02547D
Org. Biomol. Chem., 2015,13, 2582-2587

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    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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