Premium
Functionalized Chiral Bambusurils: Synthesis and Host‐Guest Interactions with Chiral Carboxylates
Author(s) -
Sokolov Jan,
Štefek Adam,
Šindelář Vladimír
Publication year - 2020
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202000261
Subject(s) - chemistry , steric effects , supramolecular chemistry , affinities , enantioselective synthesis , carboxylate , binding affinities , stereochemistry , selectivity , combinatorial chemistry , molecule , organic chemistry , catalysis , receptor , biochemistry
Bambusurils are a class of macrocyclic anion receptors that exhibit notable anion recognition properties, able to bind various inorganic anions as well the carboxylates or sulfonates. Recently, we reported enantioselective recognition of chiral carboxylates using non‐functionalized chiral bambusuril derivatives. Herein, we report the synthesis and host‐guest properties of two new representatives of chiral bambusuril macrocycles bearing ester functional groups, differing by the substituents attached to their portals. Their supramolecular properties in terms of carboxylate binding were studied by means of NMR in DMSO‐ d 6 . The reported bambusurils bind selected chiral carboxylates with enantioselectivity factors up to 3.1. The results indicated that the selectivity towards different carboxylates is governed by the steric constraint of the substituents surrounding bambusuril portals. No clear trend in the binding affinities and their enantioselectivities was found.