Publication details

Functionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates

Authors

SOKOLOV Jan ŠTEFEK Adam ŠINDELÁŘ Vladimír

Year of publication 2020
Type Article in Periodical
Magazine / Source CHEMPLUSCHEM
MU Faculty or unit

Faculty of Science

Citation
Web https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cplu.202000261
Doi http://dx.doi.org/10.1002/cplu.202000261
Keywords anion receptors; enantioselective recognition; glycolurils; host-guest systems; macrocycles
Description 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.
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