Cyclodextrin nanosponges (CD-NS) are nanostructured crosslinked polymers made up of cyclodextrins. The reactive hydroxy groups of CDs allow them to act as multifunctional monomers capable of crosslinking to bi- or multifunctional chemicals. The most common NS synthetic pathway consists in dissolving the chosen CD and an appropriate crosslinker in organic polar aprotic liquids (e.g., N,N-dimethylformamide or dimethyl sulfoxide), which affect the final result, especially for potential biomedical applications. This article describes a new, green synthetic pathway through mechanochemistry, in particular via ball milling and using 1,1- carbonyldiimidazole as the crosslinker. The polymer obtained exhibited the same characteristics as a CD-based carbonate NS syn- thesized in a solvent. Moreover, after the synthesis, the polymer was easily functionalized through the reaction of the nucleophilic carboxylic group with three different organic dyes (fluorescein, methyl red, and rhodamine B) and the still reactive imidazoyl car- bonyl group of the NS

Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

Rubin Pedrazzo, Alberto
;
Caldera, Fabrizio;Zanetti, Marco;Appleton, Silvia Lucia;Trotta, Francesco
2020

Abstract

Cyclodextrin nanosponges (CD-NS) are nanostructured crosslinked polymers made up of cyclodextrins. The reactive hydroxy groups of CDs allow them to act as multifunctional monomers capable of crosslinking to bi- or multifunctional chemicals. The most common NS synthetic pathway consists in dissolving the chosen CD and an appropriate crosslinker in organic polar aprotic liquids (e.g., N,N-dimethylformamide or dimethyl sulfoxide), which affect the final result, especially for potential biomedical applications. This article describes a new, green synthetic pathway through mechanochemistry, in particular via ball milling and using 1,1- carbonyldiimidazole as the crosslinker. The polymer obtained exhibited the same characteristics as a CD-based carbonate NS syn- thesized in a solvent. Moreover, after the synthesis, the polymer was easily functionalized through the reaction of the nucleophilic carboxylic group with three different organic dyes (fluorescein, methyl red, and rhodamine B) and the still reactive imidazoyl car- bonyl group of the NS
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β-cyclodextrin; ball-milling; crosslinking; green chemistry; mechanochemistry; nanosponges
Rubin Pedrazzo, Alberto; Caldera, Fabrizio; Zanetti, Marco; Appleton, Silvia Lucia; Dahkar, Nilesh Kumar; Trotta, Francesco
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/1743162
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