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Exploiting the Hydrogen Bond Donor/Acceptor Properties of PN‐Heterocycles: Selective Anion Receptors for Hydrogen Sulfate
Author(s) -
Deng ChunLin,
Bard Jeremy P.,
Lohrman Jessica A.,
Barker Joshua E.,
Zakharov Lev N.,
Johnson Darren W.,
Haley Michael M.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201814431
Subject(s) - hydrogen bond , chemistry , aqueous solution , acceptor , ion , urea , hydrogen , sulfate , receptor , molecule , combinatorial chemistry , organic chemistry , biochemistry , condensed matter physics , physics
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 (HSO 4 − ) 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 HSO 4 − anion from an aqueous, biphasic system.