Allosteric binding properties of a 1,3-alternate thiacalix[4]arene-based receptor having phenylthiourea and 2-pyridylmethyl moieties on opposite faces

Rahman, Shofiur; Tomiyasu, Hirotsugu; Wang, Chuan Zeng; Georghiou, Paris Elias; Alodhayb, Abdullah; Carpenter-Warren, Cameron L.; Elsegood, Mark Robert James; Teat, Simon; Redshaw, Carl; Yamato, Takehiko

doi:10.1039/d1nj02991f

Allosteric binding properties of a 1,3-alternate thiacalix[4]arene-based receptor having phenylthiourea and 2-pyridylmethyl moieties on opposite faces

Rahman, Shofiur; Tomiyasu, Hirotsugu; Wang, Chuan Zeng; Georghiou, Paris Elias; Alodhayb, Abdullah; Carpenter-Warren, Cameron L.; Elsegood, Mark Robert James; Teat, Simon; Redshaw, Carl; Yamato, Takehiko

Authors

Shofiur Rahman

Hirotsugu Tomiyasu

Chuan Zeng Wang

Paris Elias Georghiou

Abdullah Alodhayb

Cameron L. Carpenter-Warren

Mark Robert James Elsegood

Simon Teat

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

Takehiko Yamato

Abstract

The synthesis of three new heteroditopic receptors (5a-c) which are based on thiacalix[4]arenes in the 1,3-alternate conformation is reported herein. These new receptors each have two thiourea moieties linking phenyl groups, two of which are substituted with electron-withdrawing groups at their para-positions, and at the opposite side of the thiacalix[4]arene cavity, with two 2-pyridylmethyl groups. One example (5a) was also characterized by X-ray crystallography. A limited 1H-NMR and UV-vis anion complexation study was conducted. DFT computational determinations indicated that 5c, which has strongly electron-withdrawing NO2 groups, had the most effective recognition ability towards the selected anions. The binding of Ag+ at the 2-pyridyl moieties, and the binding of the anions at the two thiourea NH groups of the p-substituted phenylthioureido moieties, respectively, was also investigated. The appearance of a positive allosteric effect with receptor 5b was also found using 1H-NMR titration experiments.

Citation

Rahman, S., Tomiyasu, H., Wang, C. Z., Georghiou, P. E., Alodhayb, A., Carpenter-Warren, C. L., Elsegood, M. R. J., Teat, S., Redshaw, C., & Yamato, T. (2021). Allosteric binding properties of a 1,3-alternate thiacalix[4]arene-based receptor having phenylthiourea and 2-pyridylmethyl moieties on opposite faces. New journal of chemistry = Nouveau journal de chimie, 45(41), 19235-19243. https://doi.org/10.1039/d1nj02991f

Journal Article Type	Article
Acceptance Date	Aug 23, 2021
Online Publication Date	Aug 23, 2021
Publication Date	Nov 7, 2021
Deposit Date	Aug 24, 2021
Publicly Available Date	Aug 24, 2022
Journal	New Journal of Chemistry
Print ISSN	1144-0546
Electronic ISSN	1369-9261
Publisher	Royal Society of Chemistry
Peer Reviewed	Peer Reviewed
Volume	45
Issue	41
Pages	19235-19243
DOI	https://doi.org/10.1039/d1nj02991f
Keywords	Materials Chemistry; General Chemistry; Catalysis
Public URL	https://hull-repository.worktribe.com/output/3826189