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Rotaxanes capable of recognising chloride in aqueous media

Hancock, L.M., Gilday, L.C., Carvalho, S., Costa, P.J., Félix, V., Serpell, C.J., Kilah, N.L., Beer, P.D. (2010) Rotaxanes capable of recognising chloride in aqueous media. Chemistry - A European Journal, 16 (44). pp. 13082-13094. ISSN 09476539 (ISSN). (doi:10.1002/chem.201002076) (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided)

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Abstract

A new, versatile chloride-anion-templating synthetic pathway is exploited for the preparation of a series of eight new [2]rotaxane host molecules, including the first sulfonamide interlocked system. 1H 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. Chloride wins: A new, versatile chloride-anion-templating synthetic pathway is exploited in the preparation of a series of eight new [2]rotaxane host molecules (see image), including the first sulfonamide interlocked system. 1H NMR spectroscopic titration investigations demonstrate the rotaxanes' capability to recognise chloride anions in competitive aqueous solvent media, including a dicationic rotaxane that binds chloride in 35 % water. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Item Type: Article
DOI/Identification number: 10.1002/chem.201002076
Additional information: Unmapped bibliographic data: LA - English [Field not mapped to EPrints] J2 - Chem. Eur. J. [Field not mapped to EPrints] C2 - 21031371 [Field not mapped to EPrints] AD - Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, United Kingdom [Field not mapped to EPrints] AD - Departamento de Química, Secção Autónoma de Ciências da Saúde, Universidade de Aveiro, 3810-193 Aveiro, Portugal [Field not mapped to EPrints] DB - Scopus [Field not mapped to EPrints]
Uncontrolled keywords: anions, molecular recognition, rotaxanes, supramolecular chemistry, template synthesis, Anion binding, anions, Aqueous media, Aqueous solvents, Chloride anions, Electron-withdrawing substituents, Halide binding, Host molecules, Molecular dynamics simulations, NMR spectroscopy, Positive charges, Rotaxanes, Synthetic pathways, Template synthesis, Templating, X ray structural analysis, Binding energy, Electron affinity, Macromolecules, Molecular biology, Molecular dynamics, Molecular recognition, Negative ions, Nuclear magnetic resonance spectroscopy, Structural analysis, Sulfur compounds, Titration, Chlorine compounds, anion, chloride, rotaxane, sulfonamide, water, article, binding site, chemical structure, chemistry, conformation, nuclear magnetic resonance spectroscopy, synthesis, X ray crystallography, Anions, Binding Sites, Chlorides, Crystallography, X-Ray, Magnetic Resonance Spectroscopy, Models, Molecular, Molecular Conformation, Molecular Structure, Rotaxanes, Sulfonamides, Water
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Sciences > School of Physical Sciences > Functional Materials Group
Depositing User: Giles Tarver
Date Deposited: 10 Jul 2015 15:24 UTC
Last Modified: 23 Jan 2020 04:10 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/49500 (The current URI for this page, for reference purposes)
Serpell, C.J.: https://orcid.org/0000-0002-2848-9077
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