Date of Award
In this study, amino acid and peptide based chiral ionic liquids (ILs) were prepared and their chiral recognition ability probed using circularly polarized luminescence (CPL) spectroscopy. Potential applications of amino acid and peptide based chiral ILs include asymmetric synthesis and chiral resolution. The amino acid based chiral ILs under study were prepared from amino acid methyl ester cations and bis(trifluoromethane)sulfonamide ([TF2ND anions, specifically L-alanine methyl ester, D-alanine methyl ester, L-Ieucine methyl ester, and L-proline methyl ester. Cationic peptide ILs were prepared from L-alanyl glycine methyl ester cations and [TF2Nr anions and anionic peptide based ILs were prepared from tetrabutylammonium ([TBAt) cations and DL-alanyl glycine and DL-Ieucyl DL-alanine anions. Chiral recognition was quantified for each chiral IL by dissolving a racemic chiralluminescent probe, A and ~ europium(2,6,-pyridine dicarboxylate)33-([Eu(dpa)3]3-), in the IL and measuring the ratios of left versus right-handed polarized light emitted from the sample using a custom-built CPL spectrometer. The role of amino acid stereochemistry and structural identity ofIL components are discussed in terms of thermodynamically controlled chiral recognition in chiral IL solvents.
Kroupa, Daniel McCray, "Chiral Recognition in Amino Acid and Peptide Based Chiral Ionic Liquids" (2012). Undergraduate Honors Thesis Collection. 178.