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Rotaxanes capable of recognising chloride in aqueous media
journal contribution
posted on 2023-05-17, 17:16 authored by Hancock, LM, Gilday, LC, Carvalho, S, Costa, PJ, Felix, V, Serpell, CJ, Nathan KilahNathan Kilah, Beer, PDA 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 host's 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.
History
Publication title
Chemistry: A European JournalVolume
16Issue
44Pagination
13082-13094ISSN
0947-6539Department/School
School of Natural SciencesPublisher
Wiley-V C H Verlag GmbhPlace of publication
Po Box 10 11 61, Weinheim, Germany, D-69451Rights statement
Copyright 2010 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimRepository Status
- Restricted