Chiral discrimination by ionic liquids: impact of ionic solutes

Chirality
Christopher J Brown, Todd A Hopkins

Abstract

Chiral ionic liquids hold promise in many asymmetric applications. This study explores the impact of ionic solutes on the chiral discrimination of five amino acid methyl ester-based ionic liquids, including L- and D-alanine methyl ester, L-proline methyl ester, L-leucine methyl ester, and L-valine methyl ester cations combined with bis(trifluoromethanesulfonimide) anion. Circularly polarized luminescence spectroscopy was used to study the chiral discrimination by measuring the racemization equilibrium of a dissymmetric europium complex, Eu(dpa)3(3-) (where dpa = 2,6-pyridinedicarboxylate). The chiral discrimination measured was dependent on the concentration of Eu(dpa)3(3-) and this concentration-dependence was different in each of the ionic liquids. Ionic liquids with L-leucine methyl ester and L-valine methyl ester even switched enantiomeric preference based on the solute concentration. Changing the cation of the Eu(dpa)3(3-) salt from tetrabutylammonium to tetramethylammonium ion also affected the chiral discrimination demonstrated by the ionic liquids.

References

Jul 13, 2005·Chemical Communications : Chem Comm·Guo-hong TaoYuan Kou
Jun 17, 2006·Chemical Communications : Chem Comm·Alberto ArceKenneth R Seddon
Feb 10, 2010·Pharmaceutical Research·Jelena StoimenovskiRobin D Rogers
Dec 3, 2010·Chirality·Sergio L de RooyIsiah M Warner
Apr 8, 2011·Chemical Reviews·Jason P Hallett, Tom Welton
Dec 7, 2011·Chirality·Tharanga Payagala, Daniel W Armstrong
Mar 7, 2012·Chemical Communications : Chem Comm·Ana B PereiroLuís P N Rebelo
Apr 3, 2012·The Journal of Physical Chemistry. B·Daniel M KroupaTodd A Hopkins
Aug 15, 2012·Chemical Society Reviews·Heiko NiedermeyerTom Welton
Apr 20, 2013·Physical Chemistry Chemical Physics : PCCP·Burcu E GurkanJoan F Brennecke
Sep 26, 2013·Physical Chemistry Chemical Physics : PCCP·Filipe S OliveiraIsabel M Marrucho

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Citations

Aug 28, 2018·The Journal of Physical Chemistry. B·Cameron R WrightTodd A Hopkins

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