Easily-prepared Hydroxy-containing Receptors Recognize Anions in Aqueous Media

Mahbod Morshedi, Stephanie A. Boer, Michael Thomas, Nicholas G. White*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    6 Citations (Scopus)


    Despite their ready availability, O−H groups have received relatively little attention as anion recognition motifs. Here, we report two simple hydroxy-containing anion receptors that are prepared in two facile steps followed by anion exchange, without the need for chromatographic purification at any stage. These receptors contain a pyridinium bis(amide) motif as well as hydroxyphenyl groups, and bind mono- and divalent anions in 9:1 CD 3 CN:D 2 O, showing a selectivity preference for sulfate. Notably, a “model” receptor that does not contain hydroxy groups shows only very weak sulfate binding in this competitive solvent mixture. In the solid state, X-ray crystallographic studies show that the receptors tend to form extended assemblies with anions; however, 1 H and DOSY NMR studies as well as molecular dynamics simulations show that only 1:1 complexes are present in solution. Molecular dynamics simulations suggest that one of the receptors suffers from competing intramolecular hydrogen bonding, while another binds partially-hydrated anions, with the receptor's O−H groups forming hydrogen bonds to water molecules within the anion's coordination sphere.

    Original languageEnglish
    Pages (from-to)1271-1277
    Number of pages7
    JournalChemistry - An Asian Journal
    Issue number8
    Publication statusPublished - 15 Apr 2019


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