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Positive allosteric binding behavior of pyrene-appended triazole-modified thiacalix[4]arene-based fluorescent receptors

Tomiyasu, Hirotsugu; Shigyo, Naoki; Ni, Xin-Long; Zeng, Xi; Redshaw, Carl; Yamato, Takehiko

Authors

Hirotsugu Tomiyasu

Naoki Shigyo

Xin-Long Ni

Xi Zeng

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

Takehiko Yamato



Abstract

The novel heteroditopic receptors 5a∼c have been synthesized, which bear a thiacalix[4]arene in the 1,3-alternate conformation. Two urea moieties possessing various aryl groups with either electron-donating or -withdrawing groups at their p-positions function as anion-binding sites. At the opposite side of the cavity are two pyrene-appended triazole rings, which act as cation-binding sites. The binding property of receptor 5c was investigated by means of 1H NMR and UV–vis spectroscopy and by fluorescence titration experiments in the presence of various transition metal cations and anions in CH2Cl2–DMSO (10:1, v/v) solution. Interestingly, it was found that receptor 5c possessing two p-nitrophenyl ureido moieties, most efficiently complexes in the urea cavity or bistriazoles; the plausible allosteric effect of receptor 5c was also investigated.

Journal Article Type Article
Publication Date Oct 28, 2014
Journal Tetrahedron
Print ISSN 0040-4020
Electronic ISSN 1464-5416
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 70
Issue 43
Pages 7893-7899
APA6 Citation Tomiyasu, H., Shigyo, N., Ni, X., Zeng, X., Redshaw, C., & Yamato, T. (2014). Positive allosteric binding behavior of pyrene-appended triazole-modified thiacalix[4]arene-based fluorescent receptors. Tetrahedron, 70(43), (7893-7899). doi:10.1016/j.tet.2014.08.068. ISSN 0040-4020
DOI https://doi.org/10.1016/j.tet.2014.08.068
Keywords Thiacalix[4]arene, 1,3-alternate conformation, Pyrenyl-appended triazole, Urea, Allosteric effect
Publisher URL http://www.sciencedirect.com/science/article/pii/S0040402014012745
Copyright Statement © 2014. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
Additional Information This is a description of an article which has been published in: Tetrahedron, 2014, v.70, issue 43

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Copyright Statement
© 2014. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/



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