The Influence of Binding Site Geometry on Anion-Binding Selectivity: A Case Study of Macrocyclic Receptors Built on the Azulene Skeleton

Chemistry : a European Journal
Dawid LichosytJanusz Jurczak

Abstract

An understanding of host-guest noncovalent interactions lies at the very heart of supramolecular chemistry. Often a minute change to the structure of a host molecule's binding site can have a dramatic impact on a prospective host-guest binding event, changing the relative selectivity for potential guest molecules. With the overall goal of aiding the rational design of selective and effective receptors for anions, we have studied the influence of small perturbations in binding site geometry for a series of five closely related 20-membered macrocyclic tetra-amide receptors, constructed from two building blocks from a pool of azulene-5,7-bisamide, azulene-1,3-bisamide, and dipicolinic bisamide units. The solid-state structures revealed that the conformational preferences of the free receptors are driven by the inherent preferences of the building blocks, yet in some cases the macrocyclic topology is able to over-ride these to promote pre-organized conformations favorable for anion binding. The solid-state structures of the chloride complexes of these receptors revealed that although all the receptors can adapt to binding to the challenging small Cl- guest with all the NH groups, only receptors containing azulene-5,7-bisamide units...Continue Reading

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Citations

Jan 16, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lloyd C Murfin, Simon E Lewis
Mar 5, 2021·Organic & Biomolecular Chemistry·Georgia E WilliamsSimon E Lewis
Mar 5, 2019·The Journal of Organic Chemistry·Wenqi LiuBradley D Smith
Oct 22, 2020·The Journal of Organic Chemistry·Petter DunåsNina Kann
Nov 28, 2019·Journal of the American Chemical Society·Lloyd C MurfinSimon E Lewis
Sep 28, 2021·Chemical Communications : Chem Comm·Carlos M López-AlledSimon E Lewis

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