Visual chiral recognition of aromatic amino acids with (S)-mandelic acid-based ionic liquids via complexation

Abstract

Recently, chiral ionic liquids have attracted increasing attention in analytical chemistry. However, only a few papers focus on the application of them in visual chiral recognition. Herein, two functionalized chiral ionic liquids derived from (S)-mandelic acid (1-butyl-3-methylimidazolium mandelate, CIL1 and N-butyl-N-methylpyrrolidinium mandelate, CIL2) were prepared for visual chiral recognition of aromatic amino acids for the first time. In the presence of Cu(II) and appropriate solvents, visual enantiomeric responses of phenylalanine, tryptophane, tyrosine and phenylglycine were observed. Relying on solubility or color differences, all chiral recognition could be finished within 5 min. The potential mechanism was investigated by means of infrared spectroscopy, ultraviolet spectroscopy, thermal gravity analysis, elemental analysis and scanning electron microscope. Results revealed that CuSO4 interacted with CIL1 and D-tryptophane in the ratio of 1:1.96:0.43 in relevant precipitate, and the different stability of complex was responsible for the chiral recognition. In addition, resolution of racemic tryptophane was performed, which offered excellent enantiomeric excess values (94.2% for CIL1 and 95.1% for CIL2 in solid phase). The proposed ionic liquids had strong enantioselectivity for aromatic amino acids and great potential in visual chiral recognition.