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.-L., Wu, C., Zeng, X., Rahman, S., Georghiou, P. E., Elsegood, M. R., Warwick, T. G., Redshaw, C., Teat, S. J., & 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.
• Contract Date: Jun 22, 2016