In this study, amino acid based chiral ionic liquids were prepared and their chiral recognition ability probed using a model system.  Potential applications of amino acid based chiral ionic liquids include enatioselective catalysis and chiral resolution.  The chiral ionic liquids under study were prepared from amino acid methyl ester cations and bis(trifluoromethane)sulfonamide  (TF2N) anions, specifically l-alanine methyl ester , d-alanine methyl ester, l-leucine methyl ester, l-proline methyl ester, l-serine methyl ester, and d-serine methyl ester.  The model system used to quantify chiral recognition of each chiral ionic liquid consisted of dissolving a chiral luminescent probe, racemic Eu(2,6,-pyridine dicarboxylate)33-, in the ionic liquid and measuring the ratios of left versus right-handed circularly polarized luminescence emitted from the sample.  The role of intermolecular interactions and stereochemistry of the amino acids in chiral recognition of the luminescent probe will be discussed.

Study of chiral recognition in amino acid based chiral ionic liquid solvents

243rd National Meeting (2012)

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