Sustainable synthesis of cyclodextrin-based polymers by exploiting natural deep eutectic solvents

Cecone, Claudio; Hoti, Gjylije; Krabicová, Ilona; Appleton, Silvia Lucia; Caldera, Fabrizio; Bracco, Pierangiola; Zanetti, Marco; Trotta, Francesco

doi:10.1039/d0gc02247k

Cited by 30 publications

(23 citation statements)

References 57 publications

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“…Significant advances on the synthesis of CD-NSs [39], and their applications ranging from the environment [40] to other fields such as pharmacy, chemistry, agriculture, gene delivery, biomedicine and biotechnology, food, cosmetics, biocatalysis, etc., [6][7][8][9][10]22] have emerged over years. As judged from the historical development of CD-NSs [39], they have been the subject of numerous surveys, heading towards greener processes such as the CD-NSs synthesis in natural deep eutectic solvents (NADES) [41] and solvent-free CD-NSs synthesis [42]. Studies performed on the polymeric structure of ester-bridged βCD-NSs based on PMDA [27,[43][44][45] showed that the crosslinking degree is strongly dependent on the PMDA:β-CD molar ratio used during the CD-NSs synthesis, related to the swelling capacity as an important parameter.…”

Section: Introductionmentioning

confidence: 99%

Effect of the Cross-Linking Density on the Swelling and Rheological Behavior of Ester-Bridged β-Cyclodextrin Nanosponges

et al. 2021

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The cross-linking density influences the physicochemical properties of cyclodextrin-based nanosponges (CD-NSs). Although the effect of the cross-linker type and content on the NSs performance has been investigated, a detailed study of the cross-linking density has never been performed. In this contribution, nine ester-bridged NSs based on β-cyclodextrin (β-CD) and different quantities of pyromellitic dianhydride (PMDA), used as a cross-linking agent in stoichiometric proportions of 2, 3, 4, 5, 6, 7, 8, 9, and 10 moles of PMDA for each mole of CD, were synthesized and characterized in terms of swelling and rheological properties. The results, from the swelling experiments, exploiting Flory–Rehner theory, and rheology, strongly showed a cross-linker content-dependent behavior. The study of cross-linking density allowed to shed light on the efficiency of the synthesis reaction methods. Overall, our study demonstrates that by varying the amount of cross-linking agent, the cross-linked structure of the NSs matrix can be controlled effectively. As PMDA βCD-NSs have emerged over the years as a highly versatile class of materials with potential applications in various fields, this study represents the first step towards a full understanding of the correlation between their structure and properties, which is a key requirement to effectively tune their synthesis reaction in view of any specific future application or industrial scale-up.

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Section: Introductionmentioning

confidence: 99%

Effect of the Cross-Linking Density on the Swelling and Rheological Behavior of Ester-Bridged β-Cyclodextrin Nanosponges

et al. 2021

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“…The peak at around 3287–3306 cm −1 , which corresponds to hydroxyl groups, is present in all spectra [ 30 , 31 ]. The peak at 2894 cm −1 corresponds to the aliphatic C–H vibration in cellulose [ 33 , 34 , 35 , 36 ]. The peaks observed at around 1368 cm −1 and 1064 cm −1 are attributed to C–O and C–H groups present in the cellulose polysaccharide ring and C–O–C in the pyranose ring, respectively.…”

Section: Resultsmentioning

confidence: 99%

Extraction of Cellulose Polymeric Material from Populus tremula Fibers: Characterization and Application to the Adsorption of Methylene Blue and Crystal Violet

2021

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Cellulose is the most widely available biopolymer which is extensively used for several applications including textiles, composites, pharmaceutical, water treatment, etc. In this investigation, cellulose was chemically extracted from Populus tremula seed fibers. Samples were characterized using FT-IR, SEM, XRD, and TGA-DTA analyses. FT-IR spectrum of the extracted cellulose confirmed that hemicellulose and lignin were removed during alkali and bleaching treatments. SEM images showed the partially roughened surface of the fiber due to the removal of non-cellulosic elements and surface impurities during chemical modification. The crystallinity index values for untreated Populus tremula fibers and extracted cellulose were calculated to be 32.8% and 58.9%, respectively. The obvious increase in the crystallinity index for the extracted cellulose confirmed the removal of amorphous compounds present in raw populus. Alkali-treated populus fibers were more thermally stable than raw fibers. All changes observed after alkali and bleaching treatments evidenced the removal of amorphous contents and non-cellulosic components in raw populus fibers. Extracted cellulose exhibited excellent adsorption capacities of methylene blue (140.4 mg g−1) and crystal violet (154 mg g−1). The pseudo second order equation fitted well the kinetic data indicating a chemi-sorption process. The Freundlich model complied well with the experimental data suggesting that the adsorption of the studied dyes was multilayer.

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“…Eventually, either a sol-gel process or a precipitation polymerization can be observed, leading to the formation of a monolithic block or a precipitate, respectively. Also, in those cases in which the cross-linker is in the liquid form, and able to solubilize the CD, a melt polymerization can be performed [36,37].…”

Section: General Synthesis Protocolmentioning

confidence: 99%

“…Once the synthesis is completed, the solvent, the catalyst, eventual unreacted monomers, and by-products are removed from the synthesized product by purification with water or other volatile solvents. In the end, a dry solid powder is collected [37][38][39]. Another well-known approach to synthesize CD-NSs is achieved through simple dehydration reactions.…”

Section: General Synthesis Protocolmentioning

confidence: 99%

Strategies to Develop Cyclodextrin-Based Nanosponges for Smart Drug Delivery

Hoti¹,

Appleton²,

Pedrazzo³

et al. 2022

Smart Drug Delivery

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In recent years, the development of various cyclodextrin (CD)-based nanosponges (NSs) has gained great importance in the controlled and-or targeted release of drugs due to their versatility and simple preparation. In this chapter, an introduction of different administration routes is explained. Further, different ways to obtain CD-NSs and their classification are shown with a brief explanation of the characterization of the inclusion complexes. Finally, illustrative examples in diverse processes or diseases will be reviewed and explained to demonstrate the potential of CD-NSs. Therefore, this division will serve to compile information on CD-NSs in recent years and to illustrate to readers how to generate and apply different derivatives of interest.

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Sustainable synthesis of cyclodextrin-based polymers by exploiting natural deep eutectic solvents

Abstract: Natural deep eutectic solvents (NADES) represent an environmentally-friendly replacement of petroleum-based solvents, for this reason, they are a major field of research which aims to reduce the industrial emissions, looking...

Cited by 30 publications

References 57 publications

Effect of the Cross-Linking Density on the Swelling and Rheological Behavior of Ester-Bridged β-Cyclodextrin Nanosponges

Effect of the Cross-Linking Density on the Swelling and Rheological Behavior of Ester-Bridged β-Cyclodextrin Nanosponges

Extraction of Cellulose Polymeric Material from Populus tremula Fibers: Characterization and Application to the Adsorption of Methylene Blue and Crystal Violet

Strategies to Develop Cyclodextrin-Based Nanosponges for Smart Drug Delivery

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