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Title: Chiral Solvent Discovery: Exploring Chiral Eutectic Mixtures and Deep Eutectic Solvents
Award ID(s):
1800269
NSF-PAR ID:
10474704
Author(s) / Creator(s):
; ; ; ; ; ; ; ; ; ;
Publisher / Repository:
American Chemical Society
Date Published:
Journal Name:
Industrial & Engineering Chemistry Research
Volume:
62
Issue:
3
ISSN:
0888-5885
Page Range / eLocation ID:
1606 to 1613
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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  1. Abstract

    Deep eutectic solvents (DES) or eutectic mixtures prepared with a chiral component can lead to new chiral solvents with applications that include asymmetric synthesis and chiral light emitting materials. DES have low melting points, because of strong interactions, such as hydrogen bonding, between components of the mixture. Mixtures are prepared with ammonium salts, tetrabutylammonium chloride ([TBA]Cl) and choline chloride ([Ch]Cl), as hydrogen bond acceptor (HBA) and L‐lactic acid, L‐leucic acid, L‐ascorbic acid, R/S‐acetoxypropionic acid, and methyl‐(S)‐lactate as chiral hydrogen bond donors (HBD). Eight combinations of the HBAs and HBDs were prepared, and a racemic mixture of dissymmetric chiral europium complexes was dissolved in the mixtures. The circularly polarized luminescence (CPL) spectra were measured to determine the chiral discrimination by these chiral solvents. The CPL spectra show that the handedness of the chiral HBD is important to the chiral discrimination exhibited. However, the inversion of the sign of the CPL spectra in 1 : 3 [TBA]Cl:L‐lactic acid vs. 1 : 3 [Ch]Cl:L‐lactic acid, and 1 : 1.5 [Ch]Cl:L‐leucic acid vs. 1 : 1 [TBA]Cl:L‐leucic acid shows that the achiral HBA also plays a critical role in the handedness of the chiral discrimination by the chiral solvent.

     
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  2. null (Ed.)