Issue 77, 2022

Proton transfer mediated recognition of amines by ionizable macrocyclic receptors

Abstract

Ammonium ion/carboxylate ion pairing is a key interaction ubiquitous in biological systems, but amine recognition by ionizable molecular receptors, mediated by host-to-guest proton transfer, has too often been overlooked as a design element for molecular recognition. This survey will show that proton transfer mediated recognition is a powerful and versatile tool that can be made to work with different amines and diverse macrocyclic scaffolds, such as crown ethers, calixarenes or pillararenes. We will trace the history of this recognition motif since Cram's first report half a century ago down to the latest applications in supramolecular sensing, drug-delivery and materials science, highlighting along the way the impact of host-to-guest proton transfer on self-assembly and molecular recognition.

Graphical abstract: Proton transfer mediated recognition of amines by ionizable macrocyclic receptors

Article information

Article type
Feature Article
Submitted
20 Jul 2022
Accepted
22 Aug 2022
First published
22 Aug 2022
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2022,58, 10743-10756

Proton transfer mediated recognition of amines by ionizable macrocyclic receptors

G. Gattuso, D. Crisafulli, M. Milone, F. Mancuso, I. Pisagatti, A. Notti and M. F. Parisi, Chem. Commun., 2022, 58, 10743 DOI: 10.1039/D2CC04047F

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