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Issue 46, 2014
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Neutral redox-active hydrogen- and halogen-bonding [2]rotaxanes for the electrochemical sensing of chloride

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Abstract

The first examples of redox-active ferrocene-functionalised neutral [2]rotaxanes have been synthesised via chloride anion templation. 1H NMR spectroscopic titrations reveal that these [2]rotaxane host systems recognize chloride selectively over other halides and oxoanions in highly-competitive aqueous media. By replacing the hydrogen bonding prototriazole units of the rotaxane axle component with iodotriazole halogen bond-donor groups, the degree of chloride selectivity of the [2]rotaxanes is modulated. Electrochemical voltammetric experiments demonstrate that the rotaxanes can sense chloride via cathodic perturbations of the respective rotaxanes' ferrocene–ferrocenium redox-couple upon anion addition.

Graphical abstract: Neutral redox-active hydrogen- and halogen-bonding [2]rotaxanes for the electrochemical sensing of chloride

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Supplementary files

Article information


Submitted
26 Aug 2014
Accepted
02 Oct 2014
First published
14 Oct 2014

Dalton Trans., 2014,43, 17274-17282
Article type
Paper

Neutral redox-active hydrogen- and halogen-bonding [2]rotaxanes for the electrochemical sensing of chloride

J. Y. C. Lim, M. J. Cunningham, J. J. Davis and P. D. Beer, Dalton Trans., 2014, 43, 17274
DOI: 10.1039/C4DT02591A

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