Datong Wu,Qiuhong Yin,Pengfei Cai,Xiaoyong Zhao,Yuanjiang Pan
Novel task-specific ionic liquids derived from (S)-phenyl amino acid were prepared as a chiral sensor for the first time. It was found that the ionic liquids exhibited different chiral visual responses to the enantiomers . When (S)-tryptophan was treated with the sensor and Cu(II) in water, the clear solution would change to a sapphire suspension. Differently, another enantiomer could not produce the precipitate. Furthermore, the enantiomers could generate different colors in DMSO under the same conditions. The substantial difference contributes to the easy discrimination with visual determination. Four racemates were successfully tested with this strategy. The precipitation was isolated in the range of 90–94% yields after complete formation of the coordinative bonds, which could be as a simple way for enantioseparation. The responsive mechanism of the sensor was studied by NMR spectroscopy , FTIR and SEM . UV-vis spectrophotometer was used to monitor the colorimetric signal of the racemate with different e.e. values.
The colorimetric enantiodiscrimination between mandelic acid and l -proline-Cu (II) is exploited to develop enantioselective indicator displacement assays. The sensitivity of the assay could be tuned by using a colorimetric indicator. The chromophoric ligand, pyrocatechol violet, effectively competes with the mandelic acid guest for open coordination sites on l -proline-Cu (II). The Δ A could be increased to 0.12 by changing the ratio of (+)- and (−)-mandelic acid concentrations that were found to be optimal from the displacement experiments. The resultant enantiomer excess versus Δ A relationship is linear. From the calibration curves, the absorbance values of the unknowns may be calculated for the enantiomeric excess value and the colorimetric enantiodiscrimination of mandelic acid can thus be obtained.
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