Highly Functionalized SWCNTs with a Dopamine Derivative as a Support for Pd Nanoparticles: A Recyclable Catalyst for the Reduction of Nitro Compounds and the Heck Reaction

Single-walled carbon nanotubes (SWCNTs) were functionalized with a dopamine derivative in which the amine group was converted to azide (dopamine azide). The direct reaction of SWCNTs and dopamine azide in o-dichlorobenzene at high temperature (160 °C) led to very highly functionalized CNTs (≈60 wt%)...

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Bibliographic Details
Published in:Chemistry : a European journal 2023-10, Vol.29 (58), p.e202301238-e202301238
Main Authors: Campisciano, Vincenzo, Valentino, Laura, Alfieri, Maria Laura, La Parola, Valeria, Napolitano, Alessandra, Giacalone, Francesco, Gruttadauria, Michelangelo
Format: Article
Language:English
Subjects:
Carbon
Catalysts
Chemical composition
Chemistry
Dichlorobenzene
Dopamine
Electrons
High temperature
Nanoparticles
Nanotechnology
Nanotubes
Nitro compounds
Palladium
Phenolic compounds
Phenols
Photoelectron spectroscopy
Photoelectrons
Raman spectroscopy
Reduction
Single wall carbon nanotubes
Spectroscopy
Spectrum analysis
Transmission electron microscopy
X ray photoelectron spectroscopy
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Summary:Single-walled carbon nanotubes (SWCNTs) were functionalized with a dopamine derivative in which the amine group was converted to azide (dopamine azide). The direct reaction of SWCNTs and dopamine azide in o-dichlorobenzene at high temperature (160 °C) led to very highly functionalized CNTs (≈60 wt%). Surprisingly, despite this high degree of functionalization, Raman spectroscopy detected a low disruption of the π-network of the carbonaceous support. This finding was justified by the rehybridization from sp3 to sp2 of the sidewall carbon atoms of CNTs involved in the functionalization process. Further characterization by means of different techniques such as X-ray photoelectron spectroscopy (XPS) analysis and transmission electron microscopy (TEM) allowed to shed some light on the chemical composition and morphology of the obtained material. Moreover, the estimation of the total content of phenolic units and their reducing potential after CNTs functionalization was also assessed using Folin and Ciocalteu and 2,2-diphenyl-1-picryl hydrazide (DPPH) assays. The functionalization of CNTs was exploited to immobilize palladium(II) species that were subsequently reduced with NaBH4 leading to the formation of Pd nanoparticles (NPs). The so obtained hybrid material was used as a recyclable heterogeneous catalyst for the reduction of nitro compounds and the Heck reaction.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202301238