Affinity of deep eutectic solvents with aromatic molecules and aromatic nanostructures in chemical transformations

Giofrè, Salvatore V.; Celesti, Consuelo; Mistretta, Giuseppe; Tiecco, Marcello

doi:10.1016/j.cogsc.2023.100779

Cited by 4 publications

(5 citation statements)

References 68 publications

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“…Also tyrosine revealed to be really soluble in the trimethylglycine-based DES, as observed also in GA/H2O DES. The phenol moiety present in tyrosine could increase its solubility thanks to the affinity of this portions in DESs' structures [74]. Surprisingly, the water dilution of the GA/TMG DES revealed inefficient for the solubilization of this aminoacid, showing an anti-synergic effect.…”

Section: Solubility Measuresmentioning

confidence: 99%

“…One of the most peculiar and relevant properties of DESs is their capability of solubilization of a wide number of differently structured molecules. In particular, they show a high affinity with aromatic structures and nanostructures thanks to the participation of the aromatic rings as HBAs in the Hbond network of the DES liquid [74]. In this work we investigated the solubilizing properties of the two novel aquo-DESs considering their peculiar structural properties.…”

Section: Solubility Measuresmentioning

confidence: 99%

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aquo-DESs: WATER-BASED BINARY NATURAL DEEP EUTECTIC SOLVENTS

Picciolini

Pastore

Giacco

et al. 2023

Preprint

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Deep Eutectic Solvents (DESs) are a class of solvents that are increasing their relevance in the research activity thanks to their environmental-friendly features as well as to their structural characteristics and catalytic properties. Formed by no-solvent mixing of two substances, namely a hydrogen bond donor and a hydrogen bond acceptor, DESs are finding fruitful applications in many different topics as alternatives to common organic compounds. In this work the realization, the characterization and the solubility applications of a novel water- based class of DESs are proposed. These innovative liquids, called aquo-DESs, are binary mixtures of water with glycolic acid (GA) and with trimethylglycine (TMG): GA/H2O (1/4 molar ratio) and TMG/H2O (1/5 molar ratio). The DES identity of these mixtures was demonstrated by: shifts both in terms of the molar fraction and of the melting points in the experimental melting point curves from the theoretical ones; amounts of components over their reported maximum solubility in water; thermogravimetric profiles compared to the pure substances. The aquo-DESs were characterized in their viscosity and ionic conductivity in the temperature range 20-55 C, showing really low viscosity and low ionic conductivity, with a peculiar behavior of the ionic conductivity of GA/H2O DES. The solubilizing properties of aminoacids, phenols and carboxylic acids showed peculiar really high values whenever the solute can participate to the DES as DES component itself.

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Section: Solubility Measuresmentioning

confidence: 99%

Section: Solubility Measuresmentioning

confidence: 99%

aquo-DESs: WATER-BASED BINARY NATURAL DEEP EUTECTIC SOLVENTS

Picciolini

Pastore

Giacco

et al. 2023

Preprint

View full text Add to dashboard Cite

show abstract

“…[19][20][21][22] Its unique intermolecular hydrogen bonded networks (HBN) and supramolecular dynamics characteristics have attracted widespread attention. [23][24][25] Several researchers have applied DES to enzyme-mediated radical polymerization, 26 photo-RAFT, 27 and Fe-ATRP, 28 all of which exhibit fast polymerization rates compared to conventional media. From the perspective of chemical process intensification technology, DES enabled polymerization acceleration is attractive but kinetic features have not been reported.…”

Section: Introductionmentioning

confidence: 99%

“…DES as an emerging material has the advantages of low volatility, low flammability, and thermal stability 19–22 . Its unique intermolecular hydrogen bonded networks (HBN) and supramolecular dynamics characteristics have attracted widespread attention 23–25 . Several researchers have applied DES to enzyme‐mediated radical polymerization, 26 photo‐RAFT, 27 and Fe‐ATRP, 28 all of which exhibit fast polymerization rates compared to conventional media.…”

Section: Introductionmentioning

confidence: 99%

Quantum chemical calculation driven insights into deep eutectic solvent‐accelerated photoinduced reversible complexation‐mediated polymerization

Li,

Fu,

Zhou

et al. 2024

AIChE Journal

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Deep eutectic solvent (DES) is used as both photocatalyst and solvent for photoinduced reversible complexation‐mediated polymerization (photo‐RCMP), which enables a rapid polymerization to produce polymers with predictable molar mass and low molar mass dispersity (Đ). This work illustrates a comprehensive understanding of DES‐accelerated RCMP's mechanism and kinetic features through quantum chemical calculations and kinetic modeling. According to the results, electrons transferring from hydrogen bond in DES to iodine atom in alkyl iodide (RI) initiator under light irradiation lowers the decomposition free energy of complex RI‐DES. This procedure facilitates the generation of primary radicals, thus contributing to the DES‐accelerated phenomenon. In the meantime, the reaction paths are identified by computation as (i) decomposition of RI‐DES under light irradiation generates active radicals and ·I‐DES complex and (ii) combination of two ·I‐DES releases iodine (I2) and regenerates DES. In addition, kinetic modeling based on the method of moments successfully identifies kinetic features of polymerization in the presence and absence of DES, respectively. Kinetic modeling shows a fast increase in primary radicals concentration and rapid build‐up of the photo‐RCMP activation‐deactivation equilibrium, demonstrating that DES is a beneficial photocatalyst and solvent to enable the rapid generation of primary radicals and accelerate the completion of catalytic cycle. This research provides an in‐depth understanding of DES‐involved photo‐RCMP and lays a theoretical foundation for expanding the application of DES to other polymerization systems.

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“…In organic synthesis, DESs can also have acid, basic, reductive, organocatalytic catalytic properties and in the extraction/preconcentration of valuable molecules from food or vegetal matrixes they show better results than VOCs (Duan, Dou, Guo, Li, & Liu, 2016;Rollo et al, 2023). In particular in the latter, DESs are finding excellent results because of their affinity with aromatic, in particular phenolic, molecules (Giofrè, Celesti, Mistretta, & Tiecco, 2023). Thanks to the richness of this class of valuable molecules in food and vegetal matrixes, to the effectiveness of this class of liquids far superior by far to the VOCs, and to their environmental friendly features, DESs can be clearly identified as a winning choice in this subject(Zainal-Abidin, Hayyan, Hayyan, & Jayakumar, 2017).…”

Section: Introductionmentioning

confidence: 99%

The Glycerol/Water Mixture Is an Effective Deep Eutectic Solvent for the Extractions From Food Waste Matrixes

Pompei,

Lepore,

Torregrosa-Chinillach

et al. 2024

Preprint

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Deep Eutectic Solvents (DESs) are a novel class of organic liquids that are becoming increasingly important in the literature for their green and catalytic properties and for their peculiar structural features. Because of these, they are finding fruitful applications in many different topics. One of the most explored one is their use as green effective extracting agents from food matrices and food waste matrices of valuable bioactive compounds, thanks to their affinity with aromatic and phenolic compounds. In this work, the mixture glycerol/water at 1/2.55 molar ratio is demonstrated to be a DES thanks to the comparison of the experimental melting points with the theoretical curves. This approach is used with both liquid starting components for the first time to our knowledge. This DES was then tested as extracting agent on different food waste matrixes: onion, tomato and apple peels; spent coffee grounds and grape pomace. The results were compared with those obtained with the water and glycerol only components, showing a superior capability of the DES in the extractions, as well as superior antioxidant properties of the extracts. This promotes the use of this mixture at the eutectic point as a DES and opens for a novel approach in which the extract could be directly used without further purification procedures considering the food grade of the DES components.

show abstract

Affinity of deep eutectic solvents with aromatic molecules and aromatic nanostructures in chemical transformations

Cited by 4 publications

References 68 publications

aquo-DESs: WATER-BASED BINARY NATURAL DEEP EUTECTIC SOLVENTS

aquo-DESs: WATER-BASED BINARY NATURAL DEEP EUTECTIC SOLVENTS

Quantum chemical calculation driven insights into deep eutectic solvent‐accelerated photoinduced reversible complexation‐mediated polymerization

The Glycerol/Water Mixture Is an Effective Deep Eutectic Solvent for the Extractions From Food Waste Matrixes

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