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Thiacalix[4]arene derivatives bearing imidazole units: a ditopic hard/soft receptor for Na+ and K+/Ag+ with an allosteric effect and a reusable extractant for dichromate anions

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posted on 22.06.2016, 09:13 by Jiang-Lin Zhao, Chong Wu, Xi Zeng, Shofiur Rahman, P.E. Georghiou, Mark Elsegood, Thomas G. Warwick, Carl Redshaw, Simon J. Teat, Takehiko Yamato
Two novel receptors 5,11,17,23-tetra-tert-butyl-25,27-bis[(ethoxycarbonyl)methoxy]-26,28-bis-[1-methyl-(imidazole)meth-oxy]-2,8,14,20-tetra-thiacalix[4]arene (L1) and 5,11,17,23-tetra-tert-butyl-25,27-bis-[(benzyl)methoxy]-26,28-bis-[1-methyl-(imidazole)-methoxy]-2,8,14,20-tetrathiacalix[4]arene (L2) possessing imidazole moieties based on thiacalix[4]arene in the 1,3-alternate conformation have been synthesized and characterized. The crystal structures of L1 and L2 have been determined. The binding behaviour towards Li+, Na+, K+ and Ag+ ions has been examined by 1H NMR titration experiments in (CDCl3/CD3CN; 10:1, v/v) solution. The exclusive formation of mononuclear complexes of L1 with metal cations is of particular interest revealing a negative allosteric effect in the thiacalix[4]arene family. Liquid-liquid extraction experiments indicate that synthesized L2 can be utilized as an efficient reusable extractant for dichromate anion by controlling the pH of the aqueous solution.

Funding

We would like to thank the OTEC at SagaUniversity and the International Cooperation Projects of Guiz-hou P rovince (N o. 20137005) for financial support. The EPSRC isthanked for a travel grant (to CR).

History

School

  • Science

Department

  • Chemistry

Published in

Chemistry Select

Volume

1

Pages

1541 - 1547 (7)

Citation

ZHAO, J.-L. ... et al., 2016. Thiacalix[4]arene derivatives bearing imidazole units: a ditopic hard/soft receptor for Na+ and K+/Ag+ with an allosteric effect and a reusable extractant for dichromate anions. Chemistry Select, 1 (8), pp.1541-1547.

Publisher

© Wiley-VCH

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2016

Notes

This is the peer reviewed version of the following article: ZHAO, J.-L. ... et al., 2016. Thiacalix[4]arene derivatives bearing imidazole units: a ditopic hard/soft receptor for Na+ and K+/Ag+ with an allosteric effect and a reusable extractant for dichromate anions. Chemistry Select, 1 (8), pp.1541-1547., which has been published in final form at http://dx.doi.org/10.1002/slct.201600245. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

ISSN

2365-6549

Language

en

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