Macrocyclic squaramides: anion receptors with high sulfate binding affinity and selectivity in aqueous media

Chemical Science
Lei QinKatrina A Jolliffe

Abstract

A number of macrocyclic squaramide-containing receptors (MSQs) have been designed and synthesised and their interaction with a range of inorganic anions was studied in solution by 1H NMR spectroscopy and ESI-HRMS. The binding data revealed remarkable binding of sulfate in aqueous mixtures from 0.5 to 50% v/v H2O/DMSO-d6. The larger [3]-MSQs were found to better match the size and shape of the sulfate ion than the [2]-MSQs, providing high affinity and selectivity for sulfate while other tetrahedral divalent anions such as selenate, phosphate species and chromate have substantially lower binding affinities. In mixtures of anions mimicking the composition of either nuclear waste or plasma, the [3]-MSQs were still able to bind sulfate ions with high affinity.

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Citations

Jun 11, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Catarina V EstevesRita Delgado
Sep 29, 2019·Chemical Communications : Chem Comm·Lei QinKatrina A Jolliffe
Aug 20, 2020·Chemical Communications : Chem Comm·Giacomo PicciClaudia Caltagirone
Jul 5, 2017·Organic & Biomolecular Chemistry·Krzysztof M BąkMichał J Chmielewski
Apr 13, 2018·Chemical Communications : Chem Comm·Oleksandr ShyshovMax von Delius
Jun 30, 2019·Chemical Communications : Chem Comm·Ye LeiHao Li
Oct 26, 2016·Chemistry : a European Journal·Dawid LichosytJanusz Jurczak
Aug 3, 2017·Chemical Communications : Chem Comm·Yu-Dong YangHan-Yuan Gong
Feb 27, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Marta ZaleskayaJan Romański
Jun 15, 2021·Chemical Science·Charles L Perrin, Annadka Shrinidhi
Aug 6, 2021·ChemPlusChem·Lokesh K KumawatRobert B P Elmes
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Oct 24, 2021·Chemistry : a European Journal·Wenyao ZhangBiao Wu

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Methods Mentioned

BETA
amidation
X-ray
NMR
1

Software Mentioned

Hyperquad

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