Proton transfer mediated recognition of amines by ionizable macrocyclic receptors. Issue 77 (14th September 2022)

• Record Type: Journal Article
• Authors: Gattuso, Giuseppe; Crisafulli, Daniele; Milone, Marco; Mancuso, Francesca; Pisagatti, Ilenia; Notti, Anna; Parisi, Melchiorre F.
• Is Part Of: Chemical communications. Volume 58:Issue 77(2022)
• Page Start: 10743
• Page End: 10756
• Publication Date: 2022-09-14
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d2cc04047f
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Host-to-guest proton transfer triggers the recognition between ionizable macrocyclic receptors and amines, providing overall-neutral, internally ion-paired alkylammonium complexes with ionized macrocycles as counterions. 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.