Natural eutectogels: sustainable catalytic systems for C–C bond formation reactions

Saavedra, Beatriz; Meli, Alessandro; Rizzo, Carla; Ramón, Diego J.; D’Anna, Francesca

doi:10.1039/d1gc01647d

Cited by 19 publications

(25 citation statements)

References 64 publications

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“…Compound 1 was earlier reported to gelate the ionic liquid of 1-butyl-3methylimidazolium (BMIM) and 1-butylpyridinium (BPy) salts in the presence and absence of 10% water. 22 Ionic liquid gelation was also cumbersome as most of the reported ILs are solid at room temperature. Interestingly, the DES of choline chloride/phenylacetic acid (1:2 mol ratio) is liquid at room temperature and compound 1 has shown excellent gelation ability in this DES with a minimum gelation concentration (MGC) of 2.0%, w/v (Table 1).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Amino Acid- and Dipeptide Amphiphile-Based Supramolecular Eutectogels: Soft Materials for Drug Entrapment–Release and Wastewater Treatment

Khan

Pal

Ghosh

et al. 2023

ACS Appl. Eng. Mater.

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Supramolecular gels prepared in solvents of extreme polarities have received widespread importance across scientific disciplines. In this regard, soft materials based on deep eutectic solvents (DESs) have been receiving notable attention owing to their low toxicity, low volatility, and ability to solubilize hydrophobic drugs and natural products. A DES is a mixture of two or more compounds having a melting point lower than that of the individual components. Reports on supramolecular eutectogels derived from small molecules are very few and serendipitous. Therefore, designing a low-molecular-weight eutectogelator (LMWEG) remains challenging and demands comprehensive structure−property correlation. To this end, we have developed amino acid-and dipeptide amphiphile-based LMWEGs that immobilized choline chloride/phenylacetic acid-based DES with a minimum gelation concentration (MGC) of 0.5−10.0%, w/v. Variation of amino acids, protecting groups at the N-terminal, and hydrophobic chain length of the gelator delineated the crucial influence of the hydropathy index of amino acids and thereby the hydrophilic−lipophilic balance in eutectogelation. Replacement of the aromatic moiety in the gelator and/or in the DES with an aliphatic one ascertained the optimal necessity of aromaticity for efficient eutectogelation. Eutectogels were thermoreversible and showed considerable thermal stability (T gel ∼ 50−70 °C). Spectroscopic and microscopic studies confirmed the fiber-like morphology of the eutectogels and the participation of hydrogen bonding in eutectogelation. Newly derived eutectogels exhibited considerably good mechanical strength (γ c ∼ 7.5−16.5%) and interesting injectable as well as thixotropic properties. The ability to adsorb cationic and anionic dyes by the eutectogels ensured their potential in wastewater treatment. Importantly, these supramolecular eutectogels can be used in drug delivery owing to their ability to entrap the hydrophobic drug curcumin and subsequently its pH-dependent sustained release.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Amino Acid- and Dipeptide Amphiphile-Based Supramolecular Eutectogels: Soft Materials for Drug Entrapment–Release and Wastewater Treatment

Khan

Pal

Ghosh

et al. 2023

ACS Appl. Eng. Mater.

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“…Considering that ChCl-PGA and ChCl-VA NADES presented the lowest viscosities of the studied series, both liquids were combined with gelatin to prepare fully green soft ionic materials or gels. The use of DES in the preparation of ionic soft materials are a relatively recent research topic that has been attracting much attention in different applications. − ChCl-PGA showed an excellent capacity to dissolve gelatin at room temperature. However, the mixture remained a viscous liquid after heating at 90 °C and cooling at 4 °C for 24 h, indicating that the gelatin’s triple helix formation was hindered in this NADES.…”

Section: Results and Discussionmentioning

confidence: 99%

Natural Deep Eutectic Solvents Based on Choline Chloride and Phenolic Compounds as Efficient Bioadhesives and Corrosion Protectors

Picchio

Minudri

Mantione³

et al. 2022

ACS Sustainable Chem. Eng.

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Natural deep eutectics solvents (NADES), owing to their high solvation capacity and nontoxicity, are actively being sought for many technological applications. Herein, we report a series of novel NADES based on choline chloride and plant-derived polyphenols. Most of the obtained phenolic NADES have a wide liquid range and high thermal stability above 150 °C. Among them, small-sized polyphenols, like pyrogallol, vanillyl alcohol, or gentisic acid, lead to low-viscosity liquids with ionic conductivities in the order of 10 –3 S cm –1 at room temperature. Interestingly, polyphenols possess valuable properties as therapeutic agents, antioxidants, adhesives, or redox-active compounds, among others. Thus, we evaluated the potential of these novel NADES for two applications: bioadhesives and corrosion protection. The mixture of choline chloride-vanillyl alcohol (2:3 mol ratio) and gelatin resulted in a highly adhesive viscoelastic liquid (adhesive stress ≈ 135 kPa), affording shear thinning behavior. Furthermore, choline chloride-tannic acid (20:1) showed an extraordinary ability to coordinate iron ions, reaching excellent corrosion inhibitive efficiencies in mild steel protection.

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“…These soft materials were used as catalytic reaction media to promote C–C bond formation reaction such as the enantioselective aldol reaction. 216 Among the tested materials, the l -proline/ChCl/Urea eutectogel was the one exhibiting the best catalytic performance with excellent yield and good enantiomeric excess. From the environmental point-of-view, the method presented various advantages such as a simple and recyclable method, renewable components, and lower reagent loadings.…”

Section: Applications Of Hydrophilic Dess In Various Organic Reactionsmentioning

confidence: 98%

“…215 Saavedra et al prepared natural eutectogels by combining the properties of amino acids with that of DES. 216 Various DESs were used and among these, the amino acids used were able to gel with DES composed of ChCl and urea (1 : 2). The soft materials obtained were characterized to determine their thermal stability, rheological properties, and morphological features.…”

Section: Applications Of Hydrophilic Dess In Various Organic Reactionsmentioning

confidence: 99%

Neoteric deep eutectic solvents: history, recent developments, and catalytic applications

Shaibuna

Theresa

2022

Soft Matter

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Natural eutectogels: sustainable catalytic systems for C–C bond formation reactions

Abstract: Natural eutecto gels were prepared combining properties of amino acids with the ones of deep eutectic solvents. Soft materials obtained were fully characterised determining the gel-sol transition temperatures and analysing...

Cited by 19 publications

References 64 publications

Amino Acid- and Dipeptide Amphiphile-Based Supramolecular Eutectogels: Soft Materials for Drug Entrapment–Release and Wastewater Treatment

Amino Acid- and Dipeptide Amphiphile-Based Supramolecular Eutectogels: Soft Materials for Drug Entrapment–Release and Wastewater Treatment

Natural Deep Eutectic Solvents Based on Choline Chloride and Phenolic Compounds as Efficient Bioadhesives and Corrosion Protectors

Neoteric deep eutectic solvents: history, recent developments, and catalytic applications

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