4.8 Article

Exploiting the Hydrogen Bond Donor/Acceptor Properties of PN-Heterocycles: Selective Anion Receptors for Hydrogen Sulfate

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 12, Pages 3934-3938

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201814431

Keywords

anion recognition; anion-pi interaction; host-guest systems; hydrogen bonding

Funding

  1. National Science Foundation [CHE-1607214]
  2. NSF [CHE-1625529]
  3. Bradshaw and Holzapfel Research Professorship in Transformational Science and Mathematics

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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.

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