Issue 10, 2022

Macrocyclic versus open-chain carbazole receptors for carboxylate binding

Abstract

The anion recognition properties of six synthetic acyclic and macrocyclic carbazole-based receptors have been studied by 1H-NMR as well as with COSMO-RS calculations towards acetate, benzoate, lactate, sorbate and formate. The receptors differed by the number and geometry of hydrogen-bond donor (HBD) sites, the nature and length of the linker(s) between the HBD sites and the cyclic or non-cyclic nature. The binding ability of the receptors is strongly influenced by the structure and steric variables of the receptors and anions. It was found that when urea was replaced with the flexible diglycolyl as the connecting linker between carbazole subunits, the carboxylate binding affinity of the receptor decreased significantly. The effects of the receptors’ structure on anion binding have been investigated and several intriguing cases have been identified and analysed. The current findings shed light on carboxylate anion binding and contribute to the systematic synthesis of receptors with beneficial functional selectivity for carboxylate anions.

Graphical abstract: Macrocyclic versus open-chain carbazole receptors for carboxylate binding

Supplementary files

Article information

Article type
Paper
Submitted
08 dec 2021
Accepted
18 feb 2022
First published
18 feb 2022

Org. Biomol. Chem., 2022,20, 2121-2130

Macrocyclic versus open-chain carbazole receptors for carboxylate binding

S. Kheirjou, A. Rüütel, A. Darnell, T. Haljasorg and I. Leito, Org. Biomol. Chem., 2022, 20, 2121 DOI: 10.1039/D1OB02398E

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