Issue 46, 2014

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

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

Supplementary files

Article information

Article type
Paper
Submitted
26 Aug 2014
Accepted
02 Oct 2014
First published
14 Oct 2014

Dalton Trans., 2014,43, 17274-17282

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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