Cyrene: A Green Solvent for the Synthesis of Bioactive Molecules and Functional Biomaterials

Citarella, Andrea; Amenta, Arianna; Passarella, Daniele; Micale, Nicola

doi:10.3390/ijms232415960

Cited by 19 publications

(13 citation statements)

References 52 publications

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“…In the current study, we explored the potential of cyrene for the exfoliation of 2D-MoS 2 and 2D-WS 2 nanosheets under optimized sonication conditions [ 36 ]. So far, cyrene has only been used to exfoliate graphene for bio-inkjet and IoT applications, for which optimized fabrication conditions were utilized to obtain high-quality 2D graphene nanosheet dispersion [ 31 , 37 ].…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, we could observe the different textural and morphological features of the cyrene film with MoS 2 and WS 2 NSs, as below described. Visualizing the NSs in their solvent matrix context was important in view of the possible bioapplications of our liquid dispersion, mostly in the case of the cyrene solvent, which, though organic, is nevertheless biocompatible [36] and thus promising in this direction. The SEM analyses were carried out with the MoS2 and WS2 NS flakes absorbed in the cyrene solid solution drop-casted on regular (Figure 4A-F) and irregular (Figure 5A-D) glass supports.…”

Section: Morphological Characterization: Semmentioning

confidence: 99%

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The Effectiveness of Cyrene as a Solvent in Exfoliating 2D TMDs Nanosheets

Adam

Singh

Abduvakhidov

et al. 2023

IJMS

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The pursuit of environmentally friendly solvents has become an essential research topic in sustainable chemistry and nanomaterial science. With the need to substitute toxic solvents in nanofabrication processes becoming more pressing, the search for alternative solvents has taken on a crucial role in this field. Additionally, the use of toxic, non-economical organic solvents, such as N-methyl-2 pyrrolidone and dimethylformamide, is not suitable for all biomedical applications, even though these solvents are often considered as the best exfoliating agents for nanomaterial fabrication. In this context, the success of producing two-dimensional transition metal dichalcogenides (2D TMDs), such as MoS2 and WS2, with excellent captivating properties is due to the ease of synthesis based on environment-friendly, benign methods with fewer toxic chemicals involved. Herein, we report for the first time on the use of cyrene as an exfoliating agent to fabricate monolayer and few-layered 2D TMDs with a versatile, less time-consuming liquid-phase exfoliation technique. This bio-derived, aprotic, green and eco-friendly solvent produced a stable, surfactant-free, concentrated 2D TMD dispersion with very interesting features, as characterized by UV–visible and Raman spectroscopies. The surface charge and morphology of the fabricated nanoflakes were analyzed using ς-potential and scanning electron microscopy. The study demonstrates that cyrene is a promising green solvent for the exfoliation of 2D TMD nanosheets with potential advantages over traditional organic solvents. The ability to produce smaller-sized—especially in the case of WS2 as compared to MoS2—and mono/few-layered nanostructures with higher negative surface charge values makes cyrene a promising candidate for various biomedical and electronic applications. Overall, the study contributes to the development of sustainable and environmentally friendly methods for the production of 2D nanomaterials for various applications.

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Section: Resultsmentioning

confidence: 99%

Section: Morphological Characterization: Semmentioning

confidence: 99%

The Effectiveness of Cyrene as a Solvent in Exfoliating 2D TMDs Nanosheets

Adam

Singh

Abduvakhidov

et al. 2023

IJMS

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“…Cyrene is manufactured using wood waste and has proven to be non-toxic, non-persistent and biodegradable [39]. Cyrene has already been demonstrated as a suitable solvent for a multitude of applications, successfully replacing the traditional and more toxic polar aprotic solvents NMP, DMF and DMAc [40][41][42][43][44]. Herein we use a non-porous aluminium slide and a highly porous ceramic tile to study removing both acrylic and cellulose-based graffiti paints by Cyrene for the first time.…”

Section: Peer Reviewmentioning

confidence: 99%

Cyrene™, a Sustainable Solution for Graffiti Paint Removal

Milescu

Farmer

Sherwood

et al. 2023

Sustainable Chemistry

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Graffiti can create detrimental aesthetic and environmental damage to city infrastructure and cultural heritage and requires improved removal methods. Incumbent laser, mechanical and chemical removal techniques are often not effective, are expensive or damage the substrate. Solvents are generally hazardous and not always effective because of the insolubility of the graffiti paint. This study proposes a simple strategy for safe and effective graffiti removal, using the bio-based, non-toxic and biodegradable solvent dihydrolevoglucosenone (Cyrene™). The results showed that the type of substrate influenced the cleaning performance; in benchmark studies a non-porous substrate was easy to clean, while porous ceramic showed the presence of residual paint and yellowing when the conventional polar aprotic solvents were used. Cyrene, however, showed good removability of graffiti paint from both glazed and porous substrates, with little paint remaining in the pores of ceramic tiles. The paint suffered a reversible change in colour and a selective solubility of its components when using N-methyl-2-pyrrolidone; no changes occurred when Cyrene was used. While N-methyl-2-pyrrolidone and N,N′-dimethylformamide were only effective when neat, a Cyrene–water mixture showed some cleaning results. The performance of Cyrene was validated with Hansen solubility parameters and represents a greener and more sustainable solvent for paint removal.

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“…In recent times, dihydrolevoglucosenone (marketed as Cyrene TM ) has emerged as a green alternative to potentially hazardous aprotic dipolar solvents such as DMF, DMSO and NMP. [14] Therefore, it is essential nowadays to explore novel approaches to run SNAr reactions under more environmentally friendly conditions. [11h,15] Cyrene, sustainably derived from cellulose and biocompatible, can also be used at very high temperature (b.p.…”

Section: Introductionmentioning

confidence: 99%

“…An alternative solvent for S N Ar reactions is MeCN, but it has suffered from supply chain issues in the past. In recent times, dihydrolevoglucosenone (marketed as Cyrene TM ) has emerged as a green alternative to potentially hazardous aprotic dipolar solvents such as DMF, DMSO and NMP [14] . Therefore, it is essential nowadays to explore novel approaches to run SNAr reactions under more environmentally friendly conditions [11h,15] .…”

Section: Introductionmentioning

confidence: 99%

A Green Approach to Nucleophilic Aromatic Substitutions of Nicotinic Esters in Cyrene

Citarella,

Cavinato,

Amenta

et al. 2024

Eur J Org Chem

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The green solvent CyreneTM has emerged as a valuable substitute for conventional polar aprotic organic solvents such as DMF, DMSO and NMP (renowned for their toxicity and environmental concerns). However, in the presence of bases, Cyrene is prone to polymerization, thus potentially incompatible with reactions where a base is needed to generate reactive nucleophiles. In this study, we developed an efficient synthetic strategy for nucleophilic aromatic substitutions of nicotinic esters in Cyrene. The success of this protocol relies on a very short reaction time (only 15 minutes) which prevents polymerization from occurring. Indeed, Cyrene not only outperformed typical solvents such as DMF and DMSO, but also, being highly soluble in water, allowed an easy purification of the desired products by simple precipitation upon the addition of ice‐water.

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Cyrene: A Green Solvent for the Synthesis of Bioactive Molecules and Functional Biomaterials

Cited by 19 publications

References 52 publications

The Effectiveness of Cyrene as a Solvent in Exfoliating 2D TMDs Nanosheets

The Effectiveness of Cyrene as a Solvent in Exfoliating 2D TMDs Nanosheets

Cyrene™, a Sustainable Solution for Graffiti Paint Removal

A Green Approach to Nucleophilic Aromatic Substitutions of Nicotinic Esters in Cyrene

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