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Synthesis and evaluation of a novel ionophore based on a thiacalix[4]arene derivative bearing imidazole units

Zhao, Jiang Lin; Tomiyasu, Hirotsugu; Ni, Xin-Long; Zeng, Xi; Elsegood, Mark R. J.; Redshaw, Carl; Rahman, Shofiur; Georghiou, Paris E.; Yamato, Takehiko

Authors

Jiang Lin Zhao

Hirotsugu Tomiyasu

Xin-Long Ni

Xi Zeng

Mark R. J. Elsegood

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Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Shofiur Rahman

Paris E. Georghiou

Takehiko Yamato



Abstract

O-Alkylation of the flexible thiacalix[4]arene 1 with 2-chloromethyl-1-methyl-1H-imidazole 2 in the presence of Na₂CO₃ or K₂CO₃ afforded mono-O-alkylation product 3 in 29–51% yield, along with recovery of the starting compound. In contrast, the same reaction in the presence of Cs₂CO₃ gave only one pure stereoisomer, namely 1,3-alternate-4; other possible isomers were not observed. Alkali metal salts such as Na₂CO₃ and Cs₂CO₃ can play an important role in the conformer distribution via a template effect. The conformations of the receptors, mono-O-alkylation product 3 and that of 1,3-alternate-4, have been confirmed by X-ray crystallography. Furthermore, the complexation properties of the receptor 1,3-alternate-4 toward selected alkali/transition metal cations are reported. The two-phase solvent extraction data indicated that 1,3-alternate-4 exhibited a stronger extraction efficiency for transition metals over alkali metals. The dichromate anion extraction ability of 1,3-alternate-4 showed that it could serve as an efficient extractor of HCr₂O₇⁻/Cr₂O₇²⁻ anions at low pH.

Citation

Zhao, J. L., Tomiyasu, H., Ni, X., Zeng, X., Elsegood, M. R. J., Redshaw, C., …Yamato, T. (2014). Synthesis and evaluation of a novel ionophore based on a thiacalix[4]arene derivative bearing imidazole units. New journal of chemistry = Nouveau journal de chimie, 38(12), 6041-6049. doi:10.1039/c4nj01099j

Journal Article Type Article
Acceptance Date Sep 25, 2014
Online Publication Date Sep 29, 2014
Publication Date Dec 1, 2014
Deposit Date Jul 8, 2015
Publicly Available Date Jul 8, 2015
Journal New journal of chemistry
Print ISSN 1144-0546
Electronic ISSN 1369-9261
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 38
Issue 12
Pages 6041-6049
DOI https://doi.org/10.1039/c4nj01099j
Keywords Novel ionophore; Thiacalix[4]arene derivative; Na₂CO₃; Cs₂CO₃; Calixarene family
Public URL https://hull-repository.worktribe.com/output/376118
Publisher URL http://pubs.rsc.org/en/Content/ArticleLanding/2014/NJ/C4NJ01099J#!divAbstract
Copyright Statement ©2015 University of Hull
Additional Information Author's accepted manuscript of article published in: New journal of chemistry, 2014, v.38, issue 12 at http://pubs.rsc.org/en/...C4NJ01099J#!divAbstract

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