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.File | Dimensione | Formato | |
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Eur. J. Org. Chem. 2010, 3806–3810.pdf
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