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Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent

Due to their outstanding physicochemical properties, the next generation of the graphene family—graphene quantum dots (GQDs)—are at the cutting edge of nanotechnology development. GQDs generally possess many hydrophilic functionalities which allow their dispersibility in water but, on the other hand...

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Autores principales: Giofrè, Salvatore V., Tiecco, Matteo, Celesti, Consuelo, Patanè, Salvatore, Triolo, Claudia, Gulino, Antonino, Spitaleri, Luca, Scalese, Silvia, Scuderi, Mario, Iannazzo, Daniela
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7765906/
https://www.ncbi.nlm.nih.gov/pubmed/33352966
http://dx.doi.org/10.3390/nano10122549
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author Giofrè, Salvatore V.
Tiecco, Matteo
Celesti, Consuelo
Patanè, Salvatore
Triolo, Claudia
Gulino, Antonino
Spitaleri, Luca
Scalese, Silvia
Scuderi, Mario
Iannazzo, Daniela
author_facet Giofrè, Salvatore V.
Tiecco, Matteo
Celesti, Consuelo
Patanè, Salvatore
Triolo, Claudia
Gulino, Antonino
Spitaleri, Luca
Scalese, Silvia
Scuderi, Mario
Iannazzo, Daniela
author_sort Giofrè, Salvatore V.
collection PubMed
description Due to their outstanding physicochemical properties, the next generation of the graphene family—graphene quantum dots (GQDs)—are at the cutting edge of nanotechnology development. GQDs generally possess many hydrophilic functionalities which allow their dispersibility in water but, on the other hand, could interfere with reactions that are mainly performed in organic solvents, as for cycloaddition reactions. We investigated the 1,3-dipolar cycloaddition (1,3-DCA) reactions of the C-ethoxycarbonyl N-methyl nitrone 1a and the newly synthesized C-diethoxyphosphorylpropilidene N-benzyl nitrone 1b with the surface of GQDs, affording the isoxazolidine cycloadducts isox-GQDs 2a and isox-GQDs 2b. Reactions were performed in mild and eco-friendly conditions, through the use of a natural deep eutectic solvent (NADES), free of chloride or any metal ions in its composition, and formed by the zwitterionic trimethylglycine as the -bond acceptor, and glycolic acid as the hydrogen-bond donor. The results reported in this study have for the first time proved the possibility of performing cycloaddition reactions directly to the p-cloud of the GQDs surface. The use of DES for the cycloaddition reactions on GQDs, other than to improve the solubility of reactants, has been shown to bring additional advantages because of the great affinity of these green solvents with aromatic systems.
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spelling pubmed-77659062020-12-28 Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent Giofrè, Salvatore V. Tiecco, Matteo Celesti, Consuelo Patanè, Salvatore Triolo, Claudia Gulino, Antonino Spitaleri, Luca Scalese, Silvia Scuderi, Mario Iannazzo, Daniela Nanomaterials (Basel) Article Due to their outstanding physicochemical properties, the next generation of the graphene family—graphene quantum dots (GQDs)—are at the cutting edge of nanotechnology development. GQDs generally possess many hydrophilic functionalities which allow their dispersibility in water but, on the other hand, could interfere with reactions that are mainly performed in organic solvents, as for cycloaddition reactions. We investigated the 1,3-dipolar cycloaddition (1,3-DCA) reactions of the C-ethoxycarbonyl N-methyl nitrone 1a and the newly synthesized C-diethoxyphosphorylpropilidene N-benzyl nitrone 1b with the surface of GQDs, affording the isoxazolidine cycloadducts isox-GQDs 2a and isox-GQDs 2b. Reactions were performed in mild and eco-friendly conditions, through the use of a natural deep eutectic solvent (NADES), free of chloride or any metal ions in its composition, and formed by the zwitterionic trimethylglycine as the -bond acceptor, and glycolic acid as the hydrogen-bond donor. The results reported in this study have for the first time proved the possibility of performing cycloaddition reactions directly to the p-cloud of the GQDs surface. The use of DES for the cycloaddition reactions on GQDs, other than to improve the solubility of reactants, has been shown to bring additional advantages because of the great affinity of these green solvents with aromatic systems. MDPI 2020-12-18 /pmc/articles/PMC7765906/ /pubmed/33352966 http://dx.doi.org/10.3390/nano10122549 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Giofrè, Salvatore V.
Tiecco, Matteo
Celesti, Consuelo
Patanè, Salvatore
Triolo, Claudia
Gulino, Antonino
Spitaleri, Luca
Scalese, Silvia
Scuderi, Mario
Iannazzo, Daniela
Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent
title Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent
title_full Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent
title_fullStr Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent
title_full_unstemmed Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent
title_short Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent
title_sort eco-friendly 1,3-dipolar cycloaddition reactions on graphene quantum dots in natural deep eutectic solvent
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7765906/
https://www.ncbi.nlm.nih.gov/pubmed/33352966
http://dx.doi.org/10.3390/nano10122549
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