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Copper(II)-Bis-Cyclen Intercalated Graphene Oxide as an Efficient Two-Dimensional Nanocomposite Material for Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction

We report stable and heterogeneous graphene oxide (GO)–intercalated copper as an efficient catalyst for the organic transformations in green solvents. The GO-intercalated copper(II) complex of bis(1,4,7,10-tetraazacyclododecane) [Cu(II)-bis-cyclen] was prepared by a facile synthetic approach with a...

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Autores principales: Samuel, Angel Green, Subramanian, Sowmya, Vijendran, Vijaikanth, Bhagavathsingh, Jebasingh
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8782203/
https://www.ncbi.nlm.nih.gov/pubmed/35071181
http://dx.doi.org/10.3389/fchem.2021.754734
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author Samuel, Angel Green
Subramanian, Sowmya
Vijendran, Vijaikanth
Bhagavathsingh, Jebasingh
author_facet Samuel, Angel Green
Subramanian, Sowmya
Vijendran, Vijaikanth
Bhagavathsingh, Jebasingh
author_sort Samuel, Angel Green
collection PubMed
description We report stable and heterogeneous graphene oxide (GO)–intercalated copper as an efficient catalyst for the organic transformations in green solvents. The GO-intercalated copper(II) complex of bis(1,4,7,10-tetraazacyclododecane) [Cu(II)-bis-cyclen] was prepared by a facile synthetic approach with a high dilution technique. The as-prepared GO-Cu(II)-bis-cyclen nanocomposite was used as a click catalyst for the 1,3 dipolar Huisgen cycloaddition reaction of terminal alkyne and azide substrates. On directing a great deal of attention toward the feasibility of the rapid electron transfer rate of the catalyst in proliferating the yield of 1,2,3-triazole products, the click catalyst GO-Cu(II)-bis-cyclen nanocomposite was designed and synthesized via non-covalent functionalization. The presence of a higher coordination site in an efficient 2D nanocomposite promotes the stabilization of Cu(I) L-acetylide intermediate during the catalytic cycle initiated by the addition of reductants. From the XRD analysis, the enhancement in the d-interlayer spacing of 1.04 nm was observed due to the intercalation of the Cu(II)-bis-cyclen complex in between the GO basal planes. It was also characterized by XPS, FT-IR, RAMAN, UV, SEM, AFM, and TGA techniques. The recyclability of the heterogeneous catalyst [GO-Cu(II)-cyclen] with the solvent effect has also been studied. This class of GO-Cu(II)-bis-cyclen nanocomposite paves the way for bioconjugation of macromolecules through the click chemistry approach.
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spelling pubmed-87822032022-01-22 Copper(II)-Bis-Cyclen Intercalated Graphene Oxide as an Efficient Two-Dimensional Nanocomposite Material for Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction Samuel, Angel Green Subramanian, Sowmya Vijendran, Vijaikanth Bhagavathsingh, Jebasingh Front Chem Chemistry We report stable and heterogeneous graphene oxide (GO)–intercalated copper as an efficient catalyst for the organic transformations in green solvents. The GO-intercalated copper(II) complex of bis(1,4,7,10-tetraazacyclododecane) [Cu(II)-bis-cyclen] was prepared by a facile synthetic approach with a high dilution technique. The as-prepared GO-Cu(II)-bis-cyclen nanocomposite was used as a click catalyst for the 1,3 dipolar Huisgen cycloaddition reaction of terminal alkyne and azide substrates. On directing a great deal of attention toward the feasibility of the rapid electron transfer rate of the catalyst in proliferating the yield of 1,2,3-triazole products, the click catalyst GO-Cu(II)-bis-cyclen nanocomposite was designed and synthesized via non-covalent functionalization. The presence of a higher coordination site in an efficient 2D nanocomposite promotes the stabilization of Cu(I) L-acetylide intermediate during the catalytic cycle initiated by the addition of reductants. From the XRD analysis, the enhancement in the d-interlayer spacing of 1.04 nm was observed due to the intercalation of the Cu(II)-bis-cyclen complex in between the GO basal planes. It was also characterized by XPS, FT-IR, RAMAN, UV, SEM, AFM, and TGA techniques. The recyclability of the heterogeneous catalyst [GO-Cu(II)-cyclen] with the solvent effect has also been studied. This class of GO-Cu(II)-bis-cyclen nanocomposite paves the way for bioconjugation of macromolecules through the click chemistry approach. Frontiers Media S.A. 2022-01-07 /pmc/articles/PMC8782203/ /pubmed/35071181 http://dx.doi.org/10.3389/fchem.2021.754734 Text en Copyright © 2022 Samuel, Subramanian, Vijendran and Bhagavathsingh. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Samuel, Angel Green
Subramanian, Sowmya
Vijendran, Vijaikanth
Bhagavathsingh, Jebasingh
Copper(II)-Bis-Cyclen Intercalated Graphene Oxide as an Efficient Two-Dimensional Nanocomposite Material for Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction
title Copper(II)-Bis-Cyclen Intercalated Graphene Oxide as an Efficient Two-Dimensional Nanocomposite Material for Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction
title_full Copper(II)-Bis-Cyclen Intercalated Graphene Oxide as an Efficient Two-Dimensional Nanocomposite Material for Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction
title_fullStr Copper(II)-Bis-Cyclen Intercalated Graphene Oxide as an Efficient Two-Dimensional Nanocomposite Material for Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction
title_full_unstemmed Copper(II)-Bis-Cyclen Intercalated Graphene Oxide as an Efficient Two-Dimensional Nanocomposite Material for Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction
title_short Copper(II)-Bis-Cyclen Intercalated Graphene Oxide as an Efficient Two-Dimensional Nanocomposite Material for Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction
title_sort copper(ii)-bis-cyclen intercalated graphene oxide as an efficient two-dimensional nanocomposite material for copper-catalyzed azide–alkyne cycloaddition reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8782203/
https://www.ncbi.nlm.nih.gov/pubmed/35071181
http://dx.doi.org/10.3389/fchem.2021.754734
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