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Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

Alberto Rubin Pedrazzo, Fabrizio Caldera, Marco Zanetti, Silvia Lucia Appleton, Nilesh Kumar Dhakar and Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563. https://doi.org/10.3762/bjoc.16.127

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Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

Alberto Rubin Pedrazzo, Fabrizio Caldera, Marco Zanetti, Silvia Lucia Appleton, Nilesh Kumar Dhakar and Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563. https://doi.org/10.3762/bjoc.16.127

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Rubin Pedrazzo, A.; Caldera, F.; Zanetti, M.; Appleton, S. L.; Dhakar, N. K.; Trotta, F. Beilstein J. Org. Chem. 2020, 16, 1554–1563. doi:10.3762/bjoc.16.127

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TY  - JOUR
A1  - Rubin Pedrazzo, Alberto
A1  - Caldera, Fabrizio
A1  - Zanetti, Marco
A1  - Appleton, Silvia Lucia
A1  - Dhakar, Nilesh Kumar
A1  - Trotta, Francesco
T1  - Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers
JF  - Beilstein Journal of Organic Chemistry
PY  - 2020///
VL  - 16
SP  - 1554
EP  - 1563
SN  - 1860-5397
DO  - 10.3762/bjoc.16.127
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.16.127
KW  - β-cyclodextrin
KW  - ball-milling
KW  - crosslinking
KW  - green chemistry
KW  - mechanochemistry
KW  - nanosponges
N2  - 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.
ER  -

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