Issue 6, 2023

Construction of methylene-bridged electron-deficient corona[n]arenes and selective fluoride recognition through anion–π interactions

Abstract

Despite significant development of the nascent anion–π interactions in recent years, the noncovalent interactions between fluoride ion, a unique species that plays important roles in chemistry, biological and environmental sciences, and electron-neutral aromatic rings remain rare and even controversial. We disclose herein the construction of highly electron-deficient corona[n]arenes from the reaction of p-phenylenediacetonitrile and hydrazine, and show an unprecedented example of very selective fluoride recognition by a box-like corona[2]arene[2]tetrazine. We also report the formation of tetrazine radical anion from the interaction of tetrazine with hydroxide, with a warning on the influence of deprotonation of water by fluoride in the study of fluoride recognition by tetrazine-containing hosts.

Graphical abstract: Construction of methylene-bridged electron-deficient corona[n]arenes and selective fluoride recognition through anion–π interactions

Supplementary files

Article information

Article type
Research Article
Submitted
09 Jän 2023
Accepted
20 Jän 2023
First published
24 Jän 2023

Org. Chem. Front., 2023,10, 1405-1411

Construction of methylene-bridged electron-deficient corona[n]arenes and selective fluoride recognition through anion–π interactions

S. Guo, S. Tong, Q. Guo and M. Wang, Org. Chem. Front., 2023, 10, 1405 DOI: 10.1039/D3QO00024A

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