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

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