Porphyrin–Nanodiamond Hybrid Materials—Active, Stable and Reusable Cyclohexene Oxidation Catalysts

The quest for active, yet “green” non-toxic catalysts is a continuous challenge. In this work, covalently linked hybrid porphyrin–nanodiamonds were prepared via ipso nitro substitution reaction and characterized by X-ray photoelectron spectroscopy (XPS), fluorescence spectroscopy, infrared spectrosc...

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Bibliographic Details
Published in:Catalysts 2020-12, Vol.10 (12), p.1402
Main Authors: Dias, Lucas D., Rodrigues, Fábio M. S., Calvete, Mário J. F., Carabineiro, Sónia A. C., Scherer, Marisa D., Caires, Anderson R. L., Buijnsters, Josephus G., Figueiredo, José L., Bagnato, Vanderlei S., Pereira, Mariette M.
Format: Article
Language:English
Subjects:
Additives
Biocompatibility
Carbon
Catalysts
Catalytic oxidation
Chemical reactions
Copper
Copper compounds
Cyclohexene
Cytotoxicity
Diamonds
Fluorescence
Fourier transforms
Infrared spectroscopy
Nanomaterials
Nanostructure
Nanostructured materials
Optics
Oxidation
Oxidizing agents
Photoelectrons
Porphyrins
Solvents
Substitution reactions
Thermogravimetry
Toxicity
X ray photoelectron spectroscopy
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Summary:The quest for active, yet “green” non-toxic catalysts is a continuous challenge. In this work, covalently linked hybrid porphyrin–nanodiamonds were prepared via ipso nitro substitution reaction and characterized by X-ray photoelectron spectroscopy (XPS), fluorescence spectroscopy, infrared spectroscopy (IR) and thermogravimetry-differential scanning calorimetry (TG-DSC). The amine-functionalized nanodiamonds (ND@NH2) and 2-nitro-5,10,15,20-tetra(4-trifluoromethylphenyl)porphyrin covalently linked to nanodiamonds (ND@βNH-TPPpCF3) were tested using Allium cepa as a plant model, and showed neither phytotoxicity nor cytotoxicity. The hybrid nanodiamond–copper(II)–porphyrin material ND@βNH-TPPpCF3-Cu(II) was also evaluated as a reusable catalyst in cyclohexene allylic oxidation, and displayed a remarkable turnover number (TON) value of ≈265,000, using O2 as green oxidant, in the total absence of sacrificial additives, which is the highest activity ever reported for said allylic oxidation. Additionally, ND@βNH-TPPpCF3-Cu(II) could be easily separated from the reaction mixture by centrifugation, and reused in three consecutive catalytic cycles without major loss of activity.
ISSN:2073-4344
2073-4344
DOI:10.3390/catal10121402