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...
Gespeichert in:
Veröffentlicht in: | New journal of chemistry 2021-10, Vol.45 (41), p.19235-19243 |
---|---|
Hauptverfasser: | , , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
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 |