Exploiting the Hydrogen Bond Donor/Acceptor Properties of PN‐Heterocycles: Selective Anion Receptors for Hydrogen Sulfate. Issue 12 (13th March 2019)

• Record Type: Journal Article
• Authors: Deng, Chun‐Lin; Bard, Jeremy P.; Lohrman, Jessica A.; Barker, Joshua E.; Zakharov, Lev N.; Johnson, Darren W.; Haley, Michael M.
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 12(2019)
• Page Start: 3934
• Page End: 3938
• Publication Date: 2019-03-13
• Subjects: anion recognition -- anion-π interaction -- host-guest systems -- hydrogen bonding; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201814431
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: We describe two novel hybrid receptors combining a phosphorus‐/nitrogen‐containing (PN) phosphonamidate heterocycle with urea recognition units in an arylethynyl backbone. Structural, spectroscopic and computational studies reveal that the origin of superior binding for hydrogen sulfate (HSO4 − ) anion is correlated with the formation of strong hetero‐complementary hydrogen bonds with the phosphonamidate motif. We further demonstrate that the hybrid host system is capable of capturing/transporting the HSO4 − anion from an aqueous, biphasic system. Abstract : Choosy host : The unprecedented integration of a unique rigid and cis ‐configured phosphonamidate motif into the bis‐arylethynyl monourea framework can significantly enhance hydrogen sulfate anion selectivity and affinity. The hybrid host system is capable of capturing/transporting the HSO4 − anion from an aqueous source under liquid‐liquid extraction conditions.