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Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers.
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-06-29 , DOI: 10.3762/bjoc.16.127
Alberto Rubin Pedrazzo 1 , Fabrizio Caldera 1 , Marco Zanetti 1 , Silvia Lucia Appleton 1 , Nilesh Kumar Dhakar 1 , Francesco Trotta 1
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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 synthesized 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 carbonyl group of the NS.

中文翻译:

机械化学绿色合成超交联的环糊精聚合物。

环糊精纳米海绵(CD-NS)是由环糊精组成的纳米结构交联聚合物。CD的反应性羟基使它们充当能够交联至双官能或多官能化学物质的多官能单体。NS最常见的合成途径是将所选的CD和合适的交联剂溶解在有机极性非质子液体(例如NN-二甲基甲酰胺或二甲基亚砜),会影响最终结果,尤其是对于潜在的生物医学应用而言。本文介绍了通过机械化学,特别是通过球磨并使用1,1-羰基二咪唑作为交联剂的绿色合成途径。得到的聚合物表现出与在溶剂中合成的基于CD的碳酸酯NS相同的特性。此外,在合成后,通过亲核羧酸基团与三种不同的有机染料(荧光素,甲基红和若丹明B)和NS的仍活泼的咪唑基羰基反应,聚合物易于官能化。
更新日期:2020-06-29
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