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Issue 8, 2013
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A rotaxane host system containing integrated triazole C–H hydrogen bond donors for anion recognition

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Abstract

Two rotaxanes incorporating a 3,5-bis(triazole)-pyridinium axle component have been prepared using either an anion templated amide condensation or ring closing metathesis (RCM) clipping strategy. The respective yields of interlocked receptor were found to be significantly higher when the RCM clipping synthetic route was used. Proton NMR titration experiments in competitive 1 : 1 CDCl3–CD3OD solvent media reveal that the rotaxane prepared by the clipping procedure is selective for halide anions over larger, more basic oxoanions. Interestingly, the interlocked host displays an unusual preference for bromide over other halide anions.

Graphical abstract: A rotaxane host system containing integrated triazole C–H hydrogen bond donors for anion recognition

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Supplementary files

Article information


Submitted
16 Nov 2012
Accepted
18 Dec 2012
First published
11 Jan 2013

Org. Biomol. Chem., 2013,11, 1326-1333
Article type
Paper

A rotaxane host system containing integrated triazole C–H hydrogen bond donors for anion recognition

N. G. White and P. D. Beer, Org. Biomol. Chem., 2013, 11, 1326
DOI: 10.1039/C2OB27229F

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