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

Zhao, Jiang-Lin; Wu, Chong; Zeng, Xi; Rahman, Shofiur; Georghiou, Paris E.; Elsegood, Mark R.J.; Warwick, Thomas G.; Redshaw, Carl; Teat, Simon J.; Yamato, Takehiko

Abstract

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim 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 1 H NMR titration experiments in (CDCl 3 /CD 3 CN; 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.

Citation

Zhao, J., Wu, C., Zeng, X., Rahman, S., Georghiou, P. E., Elsegood, M. R., …Yamato, T. (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. ChemistrySelect, 1(8), 1541-1547. https://doi.org/10.1002/slct.201600245

• Journal Article Type: Article
• Acceptance Date: May 11, 2016
• Online Publication Date: Jun 6, 2016
• Publication Date: Jun 6, 2016
• Deposit Date: Jun 22, 2016
• Publicly Available Date: Jun 22, 2016
• Journal: ChemistrySelect
• Electronic ISSN: 2365-6549
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 1
• Issue: 8
• Pages: 1541-1547
• DOI: https://doi.org/10.1002/slct.201600245
• Keywords: Thiacalix[4]arene, Imidazole, Allosteric effect, Dichromate
• Public URL: https://hull-repository.worktribe.com/output/440023
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/slct.201600245/abstract
• Additional Information: Authors' accepted manuscript of article published in: ChemistrySelect, 2016, v.1 issue 8.