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Calix[4]arene-based rotaxane host systems for anion recognition

McConnell, A.J., Serpell, C.J., Thompson, A.L., Allan, D.R., Beer, P.D. (2010) Calix[4]arene-based rotaxane host systems for anion recognition. Chemistry - A European Journal, 16 (4). pp. 1256-1264. ISSN 09476539 (ISSN). (doi:10.1002/chem.200902659) (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

The synthesis, structure and anion binding properties of the first calix[4]arene-based [2]rotaxane anion host systems are described. Rotaxanes 9·Cl and 12·Cl, consisting of a calix[4]-arene functionalised macrocycle wheel and different pyridinium axle components, are prepared via adaption of an anion templated synthetic strategy to investigate the effect of preorganisation of the interlocked host's binding cavity on anion binding. Rotaxane 12·Cl contains a conformationally flexible pyridinium axle, whereas rotaxane 9·Cl incorporates a more preorganised pyridinium axle component. The X-ray crystal structure of 9·Cl and solution phase 1H NMR spectroscopy demonstrate the successful interlocking of the calix[4]arene macrocycle and pyridinium axle components in the rotaxane structures. Following removal of the chloride anion template, anion binding studies on the resulting rotaxanes 9·PF6 and 12·PF 6 reveal the importance of preorganisation of the host binding cavity on anion binding. The more preorganised rotaxane 9·PF6 is the superior anion host system. The interlocked host cavity is selective for chloride in 1:1 CDCl3/CD3OD and remains selective for chloride and bromide in 10% aqueous media over the more basic oxoanions. Rotaxane 12·PF6 with a relatively conformationally flexible binding cavity is a less effective and discriminating anion host system although the rotaxane still binds halide anions in preference to oxoanions. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

Item Type: Article
DOI/Identification number: 10.1002/chem.200902659
Additional information: Unmapped bibliographic data: LA - English [Field not mapped to EPrints] J2 - Chem. Eur. J. [Field not mapped to EPrints] AD - Inorganic Chemistry Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, OX1 3QR, United Kingdom [Field not mapped to EPrints] AD - Diamond Light Source, Harwell Science and Innovation Campus, Didcot, OX11 0QX, United Kingdom [Field not mapped to EPrints] DB - Scopus [Field not mapped to EPrints]
Uncontrolled keywords: Anions, Calixarenes rotaxanes, Supramolecular chemistry, Templation, Anion binding, Anion recognition, Aqueous media, Binding cavity, Calix[4]arenes, Calixarenes, Calixarenes rotaxanes, Chloride anions, H NMR spectroscopy, Halide anions, Macrocycles, Oxoanions, Pyridinium, Rotaxanes, Solution phase, Synthetic strategies, Templated, Templation, X ray crystal structures, Axles, Binding energy, Chlorine compounds, Crystal structure, Macromolecules, Nuclear magnetic resonance spectroscopy, Phenols, Supramolecular chemistry, Synthesis (chemical), Wheels, Negative ions
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Sciences > School of Physical Sciences > Functional Materials Group
Depositing User: Giles Tarver
Date Deposited: 10 Jul 2015 15:14 UTC
Last Modified: 23 Jan 2020 04:10 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/49504 (The current URI for this page, for reference purposes)
Serpell, C.J.: https://orcid.org/0000-0002-2848-9077
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