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Rotaxanes capable of recognising chloride in aqueous media

Citation

Hancock, LM and Gilday, LC and Carvalho, S and Costa, PJ and Felix, V and Serpell, CJ and Kilah, NL and Beer, PD, Rotaxanes capable of recognising chloride in aqueous media, Chemistry: A European Journal, 16, (44) pp. 13082-13094. ISSN 0947-6539 (2010) [Refereed Article]

Copyright Statement

Copyright 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

DOI: doi:10.1002/chem.201002076

Abstract

A new, versatile chlorideanion-templating synthetic pathway is exploited for the preparation of a series of eight new [2]rotaxane host molecules, including the first sulfonamide interlocked system. 1 H NMR spectroscopic titration investigations demonstrate the rotaxanes capability to selectively recognise the chloride anion in competitive aqueous solvent media. The interlocked hosts halide binding affinity can be further enhanced and tuned through the attachment of electron-withdrawing substituents and by increasing its positive charge. A dicationic rotaxane selectively binds chloride in 35% water, wherein no evidence of oxoanion binding is observed. NMR spectroscopy, X-ray structural analysis and computational molecular dynamics simulations are used to account for rotaxane formation yields, anion binding strengths and selectivity trends.

Item Details

Item Type:Refereed Article
Keywords:Anions; Molecular recognition; Rotaxanes; Supramolecular chemistry; Template synthesis
Research Division:Chemical Sciences
Research Group:Macromolecular and Materials Chemistry
Research Field:Nanochemistry and Supramolecular Chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Kilah, NL (Dr Nathan Kilah)
ID Code:84251
Year Published:2010
Web of Science® Times Cited:45
Deposited By:Chemistry
Deposited On:2013-05-01
Last Modified:2013-05-02
Downloads:0

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