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

Morshedi, Mahbod; Thomas, Michael; White, Nicholas; Boer, Stephanie

Description

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 CD3CN:D2O, showing a selectivity preference for sulfate....[Show more]

dc.contributor.authorMorshedi, Mahbod
dc.contributor.authorThomas, Michael
dc.contributor.authorWhite, Nicholas
dc.contributor.authorBoer, Stephanie
dc.date.accessioned2020-07-07T00:10:07Z
dc.identifier.issn1861-4728
dc.identifier.urihttp://hdl.handle.net/1885/205849
dc.description.abstractDespite 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 CD3CN:D2O, 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, 1H 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.
dc.description.sponsorshipWe thank Michael McTigue (Australian National University) for contributing to preliminary synthetic work, and the Australian Research Council for supporting this research (Discovery Early Career Research Award, DE170100200).
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherWiley-VCH Verlag GMBH
dc.rights© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
dc.sourceChemistry - An Asian Journal
dc.subjectalcohols
dc.subjectanions
dc.subjectmolecular dynamics
dc.subjectsimulations
dc.subjectsupramolecular chemistry
dc.subjectX-ray crystallography
dc.titleEasily-prepared Hydroxy-containing Receptors Recognize Anions in Aqueous Media
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume14
dc.date.issued2019-02-12
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.absfor030302 - Nanochemistry and Supramolecular Chemistry
local.identifier.absfor030505 - Physical Organic Chemistry
local.identifier.ariespublicationu3102795xPUB1414
local.publisher.urlhttps://onlinelibrary.wiley.com/
local.type.statusAccepted Version
local.contributor.affiliationMorshedi, Mahbod, College of Science, ANU
local.contributor.affiliationThomas, Michael, College of Science, ANU
local.contributor.affiliationWhite, Nicholas, College of Science, ANU
local.contributor.affiliationBoer, Stephanie, College of Science, ANU
dc.relationhttp://purl.org/au-research/grants/arc/DE170100200
local.bibliographicCitation.issue8
local.bibliographicCitation.startpage1271
local.bibliographicCitation.lastpage1277
local.identifier.doi10.1002/asia.201900033
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2020-06-23T00:53:53Z
local.identifier.scopusID2-s2.0-85061430828
dcterms.accessRightsOpen Access
dc.provenancehttp://v2.sherpa.ac.uk/id/publication/1526..."author accepted version can be made open access on non-commercial institutional repository after 12 month embargo" from SHERPA/RoMEO site (as at 10/7/20).
CollectionsANU Research Publications

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