Natural-based chiral task-specific deep eutectic solvents: A novel, effective tool for enantiodiscrimination in electroanalysis

Arnaboldi, Serena; Mezzetta, Andrea; Grecchi, Sara; Longhi, Mariangela; Emanuele, Elisa; Rizzo, Simona; Arduini, Fabiana; Micheli, Laura; Guazzelli, Lorenzo; Mussini, Patrizia R.

doi:10.1016/j.electacta.2021.138189

Cited by 34 publications

(21 citation statements)

References 60 publications

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“…6 The key favourable aspects of (Na)DESs are their ease of preparation, the possibility to tailor their physico-chemical properties by selecting suitable HBA-HBD combinations, and the reduced volatility and toxicity when compared to VOCs. 14 DESs have found application in several areas of research spanning from biomass treatment 15,16 to added value compounds for extraction, 17,18 and from electrochemistry 19,20 to biotechnology. 21 Furthermore, the exploitation of DESs as solvents and/or catalysts for organic reactions has been a recent and intense area of study.…”

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confidence: 99%

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Radical-mediated thiol–ene ‘click’ reactions in deep eutectic solvents for bioconjugation

et al. 2022

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“…Further investigation into the reaction scope included use of thioacetic acid in an Acyl Thiol-Ene (ATE) reaction. Again, a general study into a number of simple examples gave promising yields (17)(18)(19)(20). With these results in hand, the reaction was applied to synthesis of S-acetylated homocysteine 21.…”

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confidence: 99%

Radical-mediated thiol–ene ‘click’ reactions in deep eutectic solvents for bioconjugation

et al. 2022

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“…1 In principle, the properties of a DES depend upon the choice of HBA and HBD, which should make it possible to "tune" the properties of a DES. For example, incorporating a chiral HBA or HBD results in a chiral DES solvent which can be utilized in asymmetric synthesis, [33][34][35][36][37] chiral separations, 24,38 and circularly polarized light emitting materials. [39][40][41] The role of chirality in chemistry and biochemistry highlights the importance of developing new chiral DES solvents However, the large number of possible chiral HBA and HBDs and lack of predictive capability make finding new chiral DES a time-consuming process of trial and error.…”

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confidence: 99%

Chiral Solvent Discovery: Exploring Chiral Eutectic Mixtures and Deep Eutectic Solvents

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VandenElzen

Nelson

et al. 2022

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Deep eutectic solvents (DES) are mixtures that have a melting point much lower than either component. Because the properties of a DES, such as chiral discrimination, can be controlled through choice of components, DES have potential as solvents in many chemical and industrial applications. However, the large number of potential components makes high throughput methods of DES discovery critical for their development. In this study, mixtures of small quantities of HBAs and chiral HBDs were mixed at 55 C and cooled to 20 C to screen for potential liquid formation. Variable molar ratios of 10 HBAs were mixed with 93 chiral HBDs to measure a total of 1250 mixtures, and 356 mixtures were liquid at 20 C. All of the results are provided in a publicly available database. Several of the mixtures were prepared in larger quantities to characterize their physical properties, including melting points, densities, and viscosities. The results of this study can be used to guide the discovery and development of new chiral DES.

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“…The most important property of DES is the ability to control the physicochemical properties through the choice and molar ratio of HBA and HBD. Deep eutectic solvents have been touted as alternatives to molecular solvents in a list of potential applications that has grown too large to comprehensively enumerate [1,6–11] . Among these, there are several examples of applications of DES used as electrolytes in electroluminescent materials, batteries, and electrochromic devices [12–19] .…”

Section: Introductionmentioning

confidence: 99%

Chiral Eutectic Mixtures and Deep Eutectic Solvents for Induced Circularly Polarized Luminescence

et al. 2021

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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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Natural-based chiral task-specific deep eutectic solvents: A novel, effective tool for enantiodiscrimination in electroanalysis

Cited by 34 publications

References 60 publications

Radical-mediated thiol–ene ‘click’ reactions in deep eutectic solvents for bioconjugation

Radical-mediated thiol–ene ‘click’ reactions in deep eutectic solvents for bioconjugation

Chiral Solvent Discovery: Exploring Chiral Eutectic Mixtures and Deep Eutectic Solvents

Chiral Eutectic Mixtures and Deep Eutectic Solvents for Induced Circularly Polarized Luminescence

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