A study of anion binding behaviour of 1,3-alternate thiacalix[4]arene-based receptors bearing urea moieties

Rahman, Shofiur; Tomiyasu, Hirotsugu; Kawazoe, Hiroto; Zhao, Jiang-Lin; Cong, Hang; Ni, Xin-Long; Zeng, Xi; Elsegood, Mark R. J.; Warwick, Thomas G.; Teat, Simon J.; Redshaw, Carl; Georghiou, Paris E.; Yamato, Takehiko

doi:10.1039/c6nj00923a

A study of anion binding behaviour of 1,3-alternate thiacalix[4]arene-based receptors bearing urea moieties

Rahman, Shofiur; Tomiyasu, Hirotsugu; Kawazoe, Hiroto; Zhao, Jiang-Lin; Cong, Hang; Ni, Xin-Long; Zeng, Xi; Elsegood, Mark R. J.; Warwick, Thomas G.; Teat, Simon J.; Redshaw, Carl; Georghiou, Paris E.; Yamato, Takehiko

Authors

Shofiur Rahman

Hirotsugu Tomiyasu

Hiroto Kawazoe

Jiang-Lin Zhao

Hang Cong

Xin-Long Ni

Xi Zeng

Mark R. J. Elsegood

Thomas G. Warwick

Simon J. Teat

Emeritus Professor Carl Redshaw C.Redshaw@hull.ac.uk
Emeritus Professor

Paris E. Georghiou

Takehiko Yamato

Abstract

© 2016 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique. Three novel thiacalix[4]arene receptors 4 a-c each with a 1,3-alternate conformation and possessing two urea moieties linking various phenyl groups substituted with either para electron-donating or -withdrawing groups have been synthesized. The binding properties of these receptors were investigated by means of 1 H NMR spectroscopy and UV-vis absorption titration experiments using various anions. The structures and complexation energies were also studied by density functional theory (DFT) methods. The results suggested that receptor 4 c , which possesses two p-(trifluoromethyl)phenyl ureido moieties, can complex most efficiently in the urea cavity and exhibits high selectivity towards F - and AcO - ions.

Citation

Rahman, S., Tomiyasu, H., Kawazoe, H., Zhao, J.-L., Cong, H., Ni, X.-L., Zeng, X., Elsegood, M. R. J., Warwick, T. G., Teat, S. J., Redshaw, C., Georghiou, P. E., & Yamato, T. (2016). A study of anion binding behaviour of 1,3-alternate thiacalix[4]arene-based receptors bearing urea moieties. New journal of chemistry = Nouveau journal de chimie, 40(11), 9245-9251. https://doi.org/10.1039/c6nj00923a

Journal Article Type	Article
Acceptance Date	Sep 7, 2016
Online Publication Date	Sep 12, 2016
Publication Date	Sep 12, 2016
Deposit Date	Sep 16, 2016
Publicly Available Date	Sep 16, 2016
Journal	New journal of chemistry
Print ISSN	1144-0546
Publisher	Royal Society of Chemistry
Peer Reviewed	Peer Reviewed
Volume	40
Issue	11
Pages	9245-9251
DOI	https://doi.org/10.1039/c6nj00923a
Keywords	Thiacalix[4]arene receptors
Public URL	https://hull-repository.worktribe.com/output/443177
Publisher URL	http://pubs.rsc.org/en/content/articlelanding/2016/nj/c6nj00923a#!divAbstract
Additional Information	Authors' accepted manuscript of article published in: New journal of chemistry, 2016, issue 11
Contract Date	Sep 16, 2016