Preorganized Homochiral Pyrrole-Based Receptors That Display Enantioselective Anion Binding.

ABSTRACT: Herein, a new scaffold for anion recognition based on a tripodal tris(pyrrolamide) motif is presented. The receptors were able to bind to a variety of anions with high affinity. Using density functional theory methods, the three-dimensional geometry of the receptor-anion complex was calculated. These calculations show that the receptors bind anions via a preorganized cavity of amide and pyrrole hydrogen bond donor groups. Based on these findings, homochiral tris(pyrrolamide) receptors were prepared, which produced as much as a 1.6-fold greater affinity for (S)-(+)-mandelate over (R)-(-)-mandelate, demonstrating the ability to differentiate between these enantiomeric anions. The interaction of (S)-(+)-mandelate and (R)-(-)-mandelate within the homochiral receptor

SUBMITTER: Karges J 

PROVIDER: S-EPMC9912926 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature