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...
| Main Authors: | , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-12-01
|
| Series: | Nanomaterials |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2079-4991/10/12/2549 |
| _version_ | 1797544253047439360 |
|---|---|
| author | Salvatore V. Giofrè Matteo Tiecco Consuelo Celesti Salvatore Patanè Claudia Triolo Antonino Gulino Luca Spitaleri Silvia Scalese Mario Scuderi Daniela Iannazzo |
| author_facet | Salvatore V. Giofrè Matteo Tiecco Consuelo Celesti Salvatore Patanè Claudia Triolo Antonino Gulino Luca Spitaleri Silvia Scalese Mario Scuderi Daniela Iannazzo |
| author_sort | Salvatore V. Giofrè |
| collection | DOAJ |
| 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 <i>N</i>-methyl nitrone <b>1a</b> and the newly synthesized <i>C</i>-diethoxyphosphorylpropilidene <i>N</i>-benzyl nitrone <b>1b</b> with the surface of GQDs, affording the isoxazolidine cycloadducts <i>isox</i>-GQDs <b>2a</b> and <i>isox</i>-GQDs <b>2b</b>. 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. |
| first_indexed | 2024-03-10T13:57:53Z |
| format | Article |
| id | doaj.art-2baadc15d5ef4659820b6748656401c6 |
| institution | Directory Open Access Journal |
| issn | 2079-4991 |
| language | English |
| last_indexed | 2024-03-10T13:57:53Z |
| publishDate | 2020-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Nanomaterials |
| spelling | doaj.art-2baadc15d5ef4659820b6748656401c62023-11-21T01:27:34ZengMDPI AGNanomaterials2079-49912020-12-011012254910.3390/nano10122549Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic SolventSalvatore V. Giofrè0Matteo Tiecco1Consuelo Celesti2Salvatore Patanè3Claudia Triolo4Antonino Gulino5Luca Spitaleri6Silvia Scalese7Mario Scuderi8Daniela Iannazzo9Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, I-98168 Messina, ItalyDepartment of Chemistry, Biology and Biotechnology, University of Perugia, I-06123 Perugia, ItalyDepartment of Engineering, University of Messina, I-98166 Messina, ItalyDepartment of Mathematical and Computer Sciences, Physical Sciences and Earth Sciences, University of Messina, I-98166 Messina, ItalyDepartment of Civil, Energy, Environmental and Materials Engineering, Mediterranea University, I-89122 Reggio Calabria, ItalyDepartment of Chemical Sciences, University of Catania and I.N.S.T.M. UdR of Catania, I-95125 Catania, ItalyDepartment of Chemical Sciences, University of Catania and I.N.S.T.M. UdR of Catania, I-95125 Catania, ItalyInstitute for Microelectronics and Microsystems, National Research Council (CNR-IMM), Ottava Strada n.5, I-95121 Catania, ItalyInstitute for Microelectronics and Microsystems, National Research Council (CNR-IMM), Ottava Strada n.5, I-95121 Catania, ItalyDepartment of Engineering, University of Messina, I-98166 Messina, ItalyDue 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 <i>N</i>-methyl nitrone <b>1a</b> and the newly synthesized <i>C</i>-diethoxyphosphorylpropilidene <i>N</i>-benzyl nitrone <b>1b</b> with the surface of GQDs, affording the isoxazolidine cycloadducts <i>isox</i>-GQDs <b>2a</b> and <i>isox</i>-GQDs <b>2b</b>. 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.https://www.mdpi.com/2079-4991/10/12/2549graphene quantum dots1,3-dipolar cycloadditionsnatural deep eutectic solventseco-friendly reactions |
| spellingShingle | Salvatore V. Giofrè Matteo Tiecco Consuelo Celesti Salvatore Patanè Claudia Triolo Antonino Gulino Luca Spitaleri Silvia Scalese Mario Scuderi Daniela Iannazzo Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent Nanomaterials graphene quantum dots 1,3-dipolar cycloadditions natural deep eutectic solvents eco-friendly reactions |
| 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 | graphene quantum dots 1,3-dipolar cycloadditions natural deep eutectic solvents eco-friendly reactions |
| url | https://www.mdpi.com/2079-4991/10/12/2549 |
| work_keys_str_mv | AT salvatorevgiofre ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT matteotiecco ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT consuelocelesti ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT salvatorepatane ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT claudiatriolo ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT antoninogulino ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT lucaspitaleri ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT silviascalese ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT marioscuderi ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent AT danielaiannazzo ecofriendly13dipolarcycloadditionreactionsongraphenequantumdotsinnaturaldeepeutecticsolvent |