Synthesis, biocompatibility, and antimicrobial properties of glucose-based ionic liquids

Jopp, Stefan; Fleischhammer, Tabea; Lavrentieva, Antonina; Kara, Selin; Meyer, Johanna

doi:10.1039/d3su00191a

Cited by 10 publications

(13 citation statements)

References 45 publications

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“…The first step of this work was to produce the envisioned starting material 3 needed for the hydrogel synthesis. We adopted the reaction conditions from our previous works on glucosyl imidazolium salts bearing different alkyl chain lengths on the imidazole, , this time however focusing on vinyl imidazole (Scheme ). Here, the vinyl group is crucial for the three-dimensional cross-linking of the resulting monomer.…”

Section: Resultsmentioning

confidence: 99%

“…Our group works in the field of carbohydrate-based ionic liquids. − We previously found that glucosyl imidazolium-based ionic liquids can be produced in high total yields up to 90% and that they exhibit a remarkably high biocompatibility in comparison to commercial imidazolium ILs . In this work, we synthesized a series of novel glucosyl vinyl imidazolium salts and used these as monomers to produce novel glucose-based ionic hydrogels, cross-linked by several commercially available cross-linkers (Figure ).…”

Section: Introductionmentioning

confidence: 99%

“… 19 − 21 We previously found that glucosyl imidazolium-based ionic liquids can be produced in high total yields up to 90% 22 and that they exhibit a remarkably high biocompatibility in comparison to commercial imidazolium ILs. 23 In this work, we synthesized a series of novel glucosyl vinyl imidazolium salts and used these as monomers to produce novel glucose-based ionic hydrogels, cross-linked by several commercially available cross-linkers ( Figure 1 ). These hydrogels combine several properties and techniques previously not found in this combination: They are semisynthetic hydrogels (produced from a synthetically modified natural carbohydrate source) bearing a unique cationic charge not found in natural carbohydrate hydrogels and are synthesized directly from a monomer–cross-linker mixture.…”

Section: Introductionmentioning

confidence: 99%

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Swelling Behavior of Novel Hydrogels Produced from Glucose-Based Ionic Monomers with Varying Cross-Linkers

Lambrecht,

Schröter,

Pohle

et al. 2024

ACS Omega

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This work presents the synthesis of glucose-based vinyl imidazolium monomers and the hydrogels produced thereof. These novel semisynthetic, cationic hydrogels were prepared by radical polymerization with different types of commercial cross-linkers such as N,N′-methylenebis(acrylamide) or poly(ethylene glycol) diacrylate. Both the type and the amount of cross-linker were investigated as influencing factors with respect to the swelling degree. It was found that the cross-linker type majorly influences the swelling degree and long-term stability of the hydrogels. Last, the influence of different anions (e.g., halogens, acetate, and triflate) in the monomer molecule on the swelling properties of the hydrogels was investigated.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Swelling Behavior of Novel Hydrogels Produced from Glucose-Based Ionic Monomers with Varying Cross-Linkers

Lambrecht,

Schröter,

Pohle

et al. 2024

ACS Omega

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“…The synthesis was carried out as previously reported in our group. [12] In short, methyl-α-D-glucopyranoside was converted into Methyl-6-iodo-α-D-glucopyranoside via a selective Appel-type iodination, followed by the quarternisation with N-methylimidazole in the second step.…”

Section: Synthesis Of 1-(methyl-α-d-glucopyranosid-6-yl)-3methylimida...mentioning

confidence: 99%

“…GMIMÀ I itself can easily be prepared in a two-step synthesis in a total yield of 90 % and has been proven to exhibit a considerably higher biocompatibility than commercially available ILs. [12] Carbohydrate based ILs are not limited to glucose-based compounds. This vast area is covered by extensive reviews recommended to interested readers.…”

Section: Introductionmentioning

confidence: 99%

Excellence in Acrylation – Scope and Limitation of Glucosyl Imidazolium‐coated Novozym 435 Catalyzed (Meth)acryl Ester Synthesis

Lehmann,

Jopp

2023

Chemistry An Asian Journal

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The incorporation of carbohydrate based ionic liquids as a support for Novozym 435 was previously studied by the authors for the acrylation of n‐butanol as the target substrate, which was used as the foundation for the design of experiments. The combination of carbohydrate based ionic liquids and Novozym 435 remains a key aspect of this work. Building upon this, the reaction parameters were optimized for the Novozym catalyst. Substrate screening was performed to explore the scope and limitations of room temperature acrylation reactions. Herein, different alcohols and reaction conditions were screened extensively for the different acrylate products with yields of up to 99.9 % determined via gas chromatography (GC). Standard straight chain alcohols, 2‐functionalized ethanol derivatives with electron donating and withdrawing groups, and more sterically challenging substrates were investigated over a broad concentration region. To further underline the applicability of the modified biocatalyst, two alcohols were converted with methacrylic acid. The presented method offers a greener pathway for acrylate synthesis, which eliminates the need for high reaction temperatures, strongly acidic catalysts and/or polymerization inhibitors as used in non‐biocatalytic acrylate synthesis.

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Unexpected Energy Applications of Ionic Liquids

Matuszek,

Piper,

Brzęczek‐Szafran

et al. 2024

Advanced Materials

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Ionic liquids and their various analogues are without doubt the scientific sensation of the last few decades, paving the yellow brick road to a worldly version of Oz's green “Emerald city” – a more sustainable society. Their versatile suite of properties, originating from an almost inconceivably large number of possible cation and anion combinations, allows tuning of the structure to serve a desired purpose. Ionic liquids hence offer a myriad of useful applications from solvents to catalysts, through to lubricants, gas absorbers and azeotrope breakers. The purpose of this review is to explore the more unexpected of these applications, particularly in the energy space. It guides the reader through the application of ionic liquids and their analogues as i) phase change materials (PCMs) for thermal energy storage, ii) organic ionic plastic crystals (OIPCs), which have been studied as battery electrolytes and in gas separation, iii) key components in the nitrogen reduction reaction (NRR) for sustainable ammonia generation, iv) as electrolytes in aluminum ion batteries, and v) in other emerging technologies. We conclude that there is tremendous scope for further optimizing and tuning of the ionic liquid in its task, subject to sustainability imperatives in line with current global priorities, assisted by artificial intelligence.This article is protected by copyright. All rights reserved

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Synthesis, biocompatibility, and antimicrobial properties of glucose-based ionic liquids

Abstract: New carbohydrate-based ionic liquids are characterized, towards their thermal stability, biocompatibility and antimicrobial behavior. The results led to structure–property relationships and higher cell viabilities than most commercial ionic liquids.

Cited by 10 publications

References 45 publications

Swelling Behavior of Novel Hydrogels Produced from Glucose-Based Ionic Monomers with Varying Cross-Linkers

Swelling Behavior of Novel Hydrogels Produced from Glucose-Based Ionic Monomers with Varying Cross-Linkers

Excellence in Acrylation – Scope and Limitation of Glucosyl Imidazolium‐coated Novozym 435 Catalyzed (Meth)acryl Ester Synthesis

Unexpected Energy Applications of Ionic Liquids

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