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Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media

Evans, N.H., Allinson, E.S.H., Lankshear, M.D., Ng, K.-Y., Cowley, A.R., Serpell, C.J., Santos, S.M., Costa, P.J., Félix, V., Beer, P.D. and others. (2011) Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media. RSC Advances, 1 (6). pp. 995-1003. ISSN 20462069 (ISSN). (doi:10.1039/c1ra00394a) (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

An anion templated double cyclization strategy to synthesize [2]catenanes in which two identical acyclic pyridinium receptor motifs interweave around a chloride anion template is described. Ring closing metathesis (RCM) of the preorganized orthogonal precursor chloride complex facilitates the isolation of [2]catenanes in very high yields. X-ray crystal structures provide an insight of the supramolecular forces responsible for chloride anion templated efficacy and recognition. Removal of the chloride anion template generates topologically unique interlocked binding cavities for anions. 1H NMR anion binding investigations demonstrate the catenanes to be highly selective hosts for chloride in preference to more basic monocharged oxoanions. In aqueous solvent media containing 30% water, such catenanes exclusively bind chloride, under which conditions no binding of acetate or dihydrogen phosphate is observed. Molecular dynamic simulations in the solution phase are used to account for the catenanes' anion recognition properties. This journal is © The Royal Society of Chemistry 2011.

Item Type: Article
DOI/Identification number: 10.1039/c1ra00394a
Additional information: Unmapped bibliographic data: LA - English [Field not mapped to EPrints] J2 - RSC Adv. [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 - Departamento de Química, CICECO and 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: [2]catenanes, Anion binding, Anion recognition, Aqueous solvents, Binding cavity, Catenanes, Chloride anions, Chloride complexes, Dihydrogen phosphate, High yield, NO binding, Oxoanions, Pyridinium, Ring closing metathesis, Solution phase, Templated, X ray crystal structures, Chlorine compounds, Computer simulation, 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 15:16 UTC
Last Modified: 23 Jan 2020 04:10 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/49490 (The current URI for this page, for reference purposes)
Serpell, C.J.: https://orcid.org/0000-0002-2848-9077
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