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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
journal contribution
posted on 2016-06-22, 09:13 authored by Jiang-Lin Zhao, Chong Wu, Xi Zeng, Shofiur Rahman, P.E. Georghiou, Mark ElsegoodMark Elsegood, Thomas G. Warwick, Carl Redshaw, Simon J. Teat, Takehiko YamatoTwo 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 SelectVolume
1Pages
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-VCHVersion
- 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
2016Notes
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
2365-6549Publisher version
Language
- en