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Positive and negative allosteric effects of thiacalix[4]arene-based receptors having urea and crown-ether moieties

Teate, Simon J.; Elsegood, Mark R. J.; Tomiyasu, Hirotsugu; Zhao, Jiang-Lin; Ni, Xin-Long; Ni, Xin Long; Zeng, Xi; Elsegood, Mark R. J.; Jones, Beth; Redshaw, Carl; Teat, Simon J.; Yamato, Takehiko; Zhao, Jiang Lin

Authors

Simon J. Teate

Mark R. J. Elsegood

Hirotsugu Tomiyasu

Jiang-Lin Zhao

Xin-Long Ni

Xin Long Ni

Xi Zeng

Mark R. J. Elsegood

Beth Jones

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

Simon J. Teat

Takehiko Yamato

Jiang Lin Zhao



Abstract

Heteroditopic receptors (4ₐ₋ₑ) based on a thiacalix[4]arene in the 1,3-alternate conformation, which have two urea moieties linking various phenyl groups substituted with either electron-donating or -withdrawing groups at their m-, or p-positions with a crown-ether moiety at the opposite side of the thiacalix[4]arene cavity, have been synthesized. The two examples with p-CH₃– (4b) and p-NO₂-substituted (4ₑ) phenyl groups have been characterized by X-ray crystallography. The binding properties of receptor 4ₑ were investigated by means of ¹H NMR spectroscopic and absorption titration experiments in CHCl₃–DMSO (10:1, v/v) solution in the presence of K⁺ ions and various anions. Interestingly, it was found that receptor 4ₑ, which possesses two p-nitrophenyl ureido moieties, can complex most efficiently in the urea cavity or the crown-ether moiety; and the plausible allosteric effect of receptor 4ₑ was also studied.

Citation

Tomiyasu, H., Zhao, J., Ni, X., Zeng, X., Elsegood, M. R. J., Jones, B., …Yamato, T. (2015). Positive and negative allosteric effects of thiacalix[4]arene-based receptors having urea and crown-ether moieties. RSC advances, 5(19), 14747-14755. doi:10.1039/c4ra15905e

Journal Article Type Article
Acceptance Date Jan 22, 2015
Online Publication Date Jan 22, 2015
Publication Date Jan 1, 2015
Deposit Date Jul 8, 2015
Publicly Available Date Jul 16, 2018
Journal RSC advances
Print ISSN 2046-2069
Electronic ISSN 2046-2069
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 5
Issue 19
Pages 14747-14755
DOI https://doi.org/10.1039/c4ra15905e
Keywords Allosteric effects; Thiacalix[4]arene-based receptors; Urea moieties
Public URL https://hull-repository.worktribe.com/output/376091
Publisher URL http://pubs.rsc.org/en/Content/ArticleLanding/2015/RA/C4RA15905E#!divAbstract
Additional Information This is a description of an article which has been published in: RSC advances, 2015, v.5 at http://pubs.rsc.org/en/Content/ArticleLanding/2015/RA/C4RA15905E#!divAbstract

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