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Investigating the Influence of Steric Hindrance on Selective Anion Transport

1
School of Chemistry (F11), The University of Sydney, Sydney, NSW 2006, Australia
2
Chemistry, University of Southampton, Southampton SO17 1BJ, UK
3
Department of Pure and Applied Sciences, Chemistry Section, Universita Degli Studi Di Urbino “Carlo Bo”, via della Stazione 4, 61029 Urbino PU, Italia
*
Author to whom correspondence should be addressed.
Academic Editor: Jennifer R Hiscock
Molecules 2019, 24(7), 1278; https://doi.org/10.3390/molecules24071278
Received: 21 March 2019 / Revised: 1 April 2019 / Accepted: 1 April 2019 / Published: 2 April 2019
(This article belongs to the Special Issue Noncovalent Interactions and Supramolecular Complex Formation)
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Abstract

A series of symmetrical and unsymmetrical alkyl tren based tris-thiourea anion transporters were synthesised and their anion binding and transport properties studied. Overall, increasing the steric bulk of the substituents resulted in improved chloride binding and transport abilities. Including a macrocycle in the scaffold enhanced the selectivity of chloride transport in the presence of fatty acids, by reducing the undesired H+ flux facilitated by fatty acid flip-flop. This study demonstrates the benefit of including enforced steric hindrance and encapsulation in the design of more selective anion receptors. View Full-Text
Keywords: anion transport; thioureas; lipid bilayer anion transport; thioureas; lipid bilayer
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Jowett, L.A.; Ricci, A.; Wu, X.; Howe, E.N.W.; Gale, P.A. Investigating the Influence of Steric Hindrance on Selective Anion Transport. Molecules 2019, 24, 1278.

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