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Title: 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

Abstract

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 (CDCl 3/CD 3CN; 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.

Authors:
 [1];  [1];  [2];  [3];  [3];  [4];  [4];  [5];  [6];  [1]
  1. Saga Univ. (Japan)
  2. Guizhou Univ. (China)
  3. Memorial Univ. of Newfoundland (Canada)
  4. Loughborough Univ., Leicestershire (United Kingdom)
  5. Univ. of Hull, Yorkshire (United Kingdom)
  6. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Advanced Light Source (ALS)
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1530222
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
Chemistry Select
Additional Journal Information:
Journal Volume: 1; Journal Issue: 8; Journal ID: ISSN 2365-6549
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Zhao, Jiang-Lin, Wu, Chong, Zeng, Xi, Rahman, Shofiur, Georghiou, Paris E., Elsegood, Mark R. J., Warwick, Mr. Thomas G., Redshaw, Carl, Teat, Simon J., and Yamato, Takehiko. 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. United States: N. p., 2016. Web. doi:10.1002/slct.201600245.
Zhao, Jiang-Lin, Wu, Chong, Zeng, Xi, Rahman, Shofiur, Georghiou, Paris E., Elsegood, Mark R. J., Warwick, Mr. Thomas G., Redshaw, Carl, Teat, Simon J., & Yamato, Takehiko. 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. United States. doi:10.1002/slct.201600245.
Zhao, Jiang-Lin, Wu, Chong, Zeng, Xi, Rahman, Shofiur, Georghiou, Paris E., Elsegood, Mark R. J., Warwick, Mr. Thomas G., Redshaw, Carl, Teat, Simon J., and Yamato, Takehiko. Mon . "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". United States. doi:10.1002/slct.201600245. https://www.osti.gov/servlets/purl/1530222.
@article{osti_1530222,
title = {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},
author = {Zhao, Jiang-Lin and Wu, Chong and Zeng, Xi and Rahman, Shofiur and Georghiou, Paris E. and Elsegood, Mark R. J. and Warwick, Mr. Thomas G. and Redshaw, Carl and Teat, Simon J. and Yamato, Takehiko},
abstractNote = {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.},
doi = {10.1002/slct.201600245},
journal = {Chemistry Select},
number = 8,
volume = 1,
place = {United States},
year = {2016},
month = {6}
}

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Works referenced in this record:

Thiacalixarenes
journal, December 2006

  • Morohashi, Naoya; Narumi, Fumitaka; Iki, Nobuhiko
  • Chemical Reviews, Vol. 106, Issue 12, p. 5291-5316
  • DOI: 10.1021/cr050565j