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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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Publication details

The article was received on 16 Nov 2012, accepted on 18 Dec 2012 and first published on 11 Jan 2013


Article type: Paper
DOI: 10.1039/C2OB27229F
Citation: Org. Biomol. Chem., 2013,11, 1326-1333
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    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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