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

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 pa...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:New journal of chemistry 2021-10, Vol.45 (41), p.19235-19243
Hauptverfasser: Rahman, Shofiur, Tomiyasu, Hirotsugu, Wang, Chuan-Zeng, Georghiou, Paris E, Alodhayb, Abdullah, Carpenter-Warren, Cameron L, Elsegood, Mark R. J, Teat, Simon J, Redshaw, Carl, Yamato, Takehiko
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung: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 1 H-NMR and UV-vis anion complexation study was conducted. DFT computational determinations indicated that 5c , which has strongly electron-withdrawing NO 2 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 1 H-NMR titration experiments. Thiacalix[4]arene receptors with two thiourea moieties and two 2-pyridyl moieties exhibited a heteroditopic dinuclear receptor with F − and Ag + ions by a positive allosteric effect.
ISSN:1144-0546
1369-9261
DOI:10.1039/d1nj02991f