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Amino Acid Based Chiral Ionic Liquids as Potential GC Stationary Phases
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In the poster 'Amino Acid Based Chiral Ionic Liquids as Potential GC Stationary Phases' Irene Kimaru et al. present the synthesis and characterization of both enantiomeric forms of amino acid based chiral ionic liquids (CILs).
D - and L -alanine- and D - and L -leucine t-butyl ester bis(perfluoroethyl)sulfonylimide were synthesized using a simple anion metathesis reaction between amino acid ester chlorides and a halide salt. Characterization was carried out using nuclear magnetic resonance (NMR), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC) and spectrofluorometry. The ionic liquids (ILs) were obtained as liquids at room temperature and found to be pure.
The thermal decomposition temperature of the leucine based ILs was 246 oC and for the alanine based ionic liquids, 288 oC. The chiral recognition ability and enantioselectivity of the chiral ionic liquids was determined using 2,2,2-trifluoroanthrylethanol as a model chiral analyte by fluorescence spectroscopy. The emission intensity of S-2,2,2-trifluoroanthrylethanol obtained in the presence of L-alanine t-butyl ester bis(perfluoroethyl)sulfonylimide was established to be higher than that of R-2,2,2-trifluoroanthrylethanol.
The observed difference in the emission intensity of S- and R-2,2,2-trifluoroanthrylethanol in the presence of the L-alanine based ionic liquid was attributed to differences in diastereomeric interactions between both enantiomers and the ionic liquid. The alanine based ionic liquids show promise as future GC stationary phases due to their chiral recognition ability and high thermal stability.
Authors:
Irene Kimaru, Brendan Clifford and Shannon Peterson
Please click here to read the poster as a PDF
This poster was presented at Pittcon 2011, 13 - 18 March in Atlanta, GA, USA.
Contact:
Irene Kimaru, PhD
Assistant Professor of Chemistry
St.
John Fisher College
Rochester, NY
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Keywords : Brendan Clifford Chemistry Chiral Ionic Liquids CILS Differential Scanning Calorimetry DSC ILs Ionic Liquids Irene Kimaru NMR Nuclear Magnetic Resonance Pittcon Pittcon 2011 Pittcon Poster Pittcon Poster 2011 Poster Shannon Peterson Spectrofluorometry St. John Fisher College TGA Thermal Gravimetric Analysis
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