Cargando…
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...
Autores principales: | , , , , , , , , , |
---|---|
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 |
_version_ | 1783628591871819776 |
---|---|
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. |
format | Online Article Text |
id | pubmed-7765906 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT giofresalvatorev ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT tieccomatteo ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT celesticonsuelo ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT patanesalvatore ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT trioloclaudia ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT gulinoantonino ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT spitaleriluca ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT scalesesilvia ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT scuderimario ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT iannazzodaniela ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent |