A new heteroditopic chiral uranyl-salen complex incorporating two pyrenyl groups was designed and synthesized for the recognition of ammonium salts, tetrabutylammonium (TBA) and tetramethylammonium (TMA) amino acids. UV/Vis measurements indicate the formation of 1:1 host-guest complexes with high association constants and an excellent enantiomeric discrimination between the two enantiomers of phenylalanine-TMA. T-ROESY NMR experiments confirm cation-pi and CH-pi interactions between the TBA and TMA cations and the two pyrenyl arms, leading to the strong stability of the complexes. This is the first report of a uranyl receptor able to recognize chiral carboxylate guests.

Heteroditopic chiral uranyl-salen receptor for molecular recognition of amino acid ammonium salts

BALLISTRERI, Francesco Paolo;PAPPALARDO, ANDREA;TOMASELLI, Gaetano;TOSCANO, Rosa Maria;TRUSSO SFRAZZETTO, GIUSEPPE
2010-01-01

Abstract

A new heteroditopic chiral uranyl-salen complex incorporating two pyrenyl groups was designed and synthesized for the recognition of ammonium salts, tetrabutylammonium (TBA) and tetramethylammonium (TMA) amino acids. UV/Vis measurements indicate the formation of 1:1 host-guest complexes with high association constants and an excellent enantiomeric discrimination between the two enantiomers of phenylalanine-TMA. T-ROESY NMR experiments confirm cation-pi and CH-pi interactions between the TBA and TMA cations and the two pyrenyl arms, leading to the strong stability of the complexes. This is the first report of a uranyl receptor able to recognize chiral carboxylate guests.
2010
Amino acids ; Enantioselectivity; Host–guest systems; Molecular recognition
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11769/6816
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