Deep Eutectic Solvents (DESs) offer advantages similar to ionic liquid (IL) ones, with easier and more sustainable synthesis; moreover, bio-based DESs often include chiral components, surprisingly underexploited. A proof of concept is now offered of the impressive potential of enantiopure chiral DESs as chiral media for enantioselective electroanalysis. Three chiral DESs, consisting of a molecular salt with bio-based chiral cation [NopolMIm](+) combined with three natural and/or low-cost partners (levulinic acid, glycerol and urea), are introduced and investigated as chiral voltammetry media. Significant potential differences are observed for the enantiomers of a model chiral probe, with a dramatic tuning depending on the achiral DES component, reaching an impressive similar to 0.5 V in the levulinic acid case (while less efficient appears [NopolMIm](+) as chiral additive in IL). With the same medium good enantiodiscrimination is also observed for aminoacid tryptophan, a quite different probe and of applicative interest. These findings can be considered as a remarkable step further in chiral electroanalysis as well as in the development of task-specific enantioselective media.

Arnaboldi, S., Mezzetta, A., Grecchi, S., Longhi, M., Emanuele, E., Rizzo, S., et al. (2021). Natural-based chiral task-specific deep eutectic solvents: a novel, effective tool for enantiodiscrimination in electroanalysis. ELECTROCHIMICA ACTA, 380 [10.1016/j.electacta.2021.138189].

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

Longhi M.;Arduini F.;Micheli L.;
2021-01-01

Abstract

Deep Eutectic Solvents (DESs) offer advantages similar to ionic liquid (IL) ones, with easier and more sustainable synthesis; moreover, bio-based DESs often include chiral components, surprisingly underexploited. A proof of concept is now offered of the impressive potential of enantiopure chiral DESs as chiral media for enantioselective electroanalysis. Three chiral DESs, consisting of a molecular salt with bio-based chiral cation [NopolMIm](+) combined with three natural and/or low-cost partners (levulinic acid, glycerol and urea), are introduced and investigated as chiral voltammetry media. Significant potential differences are observed for the enantiomers of a model chiral probe, with a dramatic tuning depending on the achiral DES component, reaching an impressive similar to 0.5 V in the levulinic acid case (while less efficient appears [NopolMIm](+) as chiral additive in IL). With the same medium good enantiodiscrimination is also observed for aminoacid tryptophan, a quite different probe and of applicative interest. These findings can be considered as a remarkable step further in chiral electroanalysis as well as in the development of task-specific enantioselective media.
2021
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore CHIM/01 - CHIMICA ANALITICA
English
Chiral bio-based deep eutectic solvents
Chiral electroanalysis
Enantiodiscrimination of electroactive probe enantiomers
Chiral voltammetry on SPEs
Task-specific enantioselective media
The paper is dedicated to Professor Cinzia Chiappe, Founder and Mentor of the Ionic Liquids Group at Università degli Studi di Pisa. Support of Fondazione Cariplo and Regione Lombardia (2016- 0923 RST−Avvisocongiunto FC-RL Sottomisura B) rafforzamento (Enhancing VINCE (Versatile INherently Chiral Electrochemistry)) are gratefully acknowledged, as well as advanced facilities avail- able at SmartMatLab at Department of Chemistry, Università degli Studi di Milano, operated by Dr. Serena Cappelli. Davide Grecchi is also acknowledged for the TOC photograph. Supplementary materials Supplementary material associated with this article can be found, in the online version, at doi:10.1016/j.electacta.2021.138189.
Arnaboldi, S., Mezzetta, A., Grecchi, S., Longhi, M., Emanuele, E., Rizzo, S., et al. (2021). Natural-based chiral task-specific deep eutectic solvents: a novel, effective tool for enantiodiscrimination in electroanalysis. ELECTROCHIMICA ACTA, 380 [10.1016/j.electacta.2021.138189].
Arnaboldi, S; Mezzetta, A; Grecchi, S; Longhi, M; Emanuele, E; Rizzo, S; Arduini, F; Micheli, L; Guazzelli, L; Mussini, Pr
Articolo su rivista
File in questo prodotto:
File Dimensione Formato  
proofs jan6_FF_SG_LM.pdf

accesso aperto

Descrizione: articolo su rivista
Tipologia: Documento in Pre-print
Licenza: Non specificato
Dimensione 917.94 kB
Formato Adobe PDF
917.94 kB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/292155
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 31
  • ???jsp.display-item.citation.isi??? 31
social impact