Cupric oxide nanowires on three-dimensional copper foam for application in click reaction

Wang, Chunxia; Yang, Fan; Cao, Yan; He, Xing; Tang, Yushu; Li, Yongfeng

doi:10.1039/c7ra00014f

Cited by 30 publications

(13 citation statements)

References 48 publications

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“…This result is consistent with a recently reported work using CuO nanowires as a heterogeneous catalyst for a click reaction in solution. 45 Figure 4 shows SEM studies of the key steps illustrated in Schemes 1 and 2 for CuO nanowires. The pristine CuO nanowires are shown in Figure 4a,b.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“Clickable” Metal-Oxide Nanomaterials Surface-Engineered by Gas-Phase Covalent Functionalization with Prop-2-ynoic Acid

Janzen

Bai

et al. 2019

Chem. Mater.

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The surface properties of metal-oxide nanomaterials (MONMs) can be tuned by reacting them with a variety of organic compounds. Reactions of the oxides with functionalized carboxylic (R−COOH) or phosphonic acids (R−PO(OH) 2 ) and various approaches utilizing silylation (such as with R−Si(X) 3 , where the X could be Cl or −OCH 3 ) are often used to deliver the target modifier R to the oxide surface. However, the liquid-phase reactions between metal oxides and these agents often cause agglomeration or multilayer growth, morphology change, or surface etching. In this paper, we report a novel approach that circumvents all of these problems. The proposed two-step functionalization approach utilizes exposure of the oxide materials to prop-2-ynoic acid (HCC−COOH, propiolic acid) in the gas phase as a first step. The second step can then utilize the created CC for post-modification that introduces any predesigned functionality to the surface via "click" chemistry with azides (R−N 3 ). Gas-phase exposure of prop-2-ynoic acid was carried out onto surfaces of different MONMs (ZnO nanorods, CuO nanowires, TiO 2 nanoparticles, and CeO 2 nanoparticles) under medium vacuum (×10 −2 Torr), and this step was demonstrated to preserve the nanostructure of all the materials studied. The surface modification with "click" chemistry was tested via Cu(I)-catalyzed reaction of benzyl azide, with an added bonus of the CuO materials not requiring the presence of the copper catalyst. The combination of microscopic and spectroscopic investigations including scanning electron microscopy, Xray photoelectron spectroscopy, and solid-state nuclear magnetic resonance spectroscopy was used to follow the process and to compare with the traditional liquid-phase modification schemes.

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Section: ■ Results and Discussionmentioning

confidence: 99%

“Clickable” Metal-Oxide Nanomaterials Surface-Engineered by Gas-Phase Covalent Functionalization with Prop-2-ynoic Acid

Janzen

Bai

et al. 2019

Chem. Mater.

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“…9 Also, CuONPs have attracted attention as efficient catalysts to promote sustainable chemical transformations. For instance, CuONPs were reported as catalysts for CO 2 electroreduction yielding ethylene, 10 electrocatalytic water oxidation, 11 click chemistry reactions, 12 photocatalytic degradations of organic dyes, 13 dehydrogenation of alcohols, 14 C−N cross-coupling reactions, 15 and nitroarene reduction. 16−19 Regarding nitroarene reductions, these transformations are of industrial importance to prepare high-value-added bulk and fine aminoarene chemicals that are applied in the civil and automobile industries and in the manufacture of dyes, plastics, agrochemicals, pharmaceuticals, and polymers.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Also, CuONPs have attracted attention as efficient catalysts to promote sustainable chemical transformations. For instance, CuONPs were reported as catalysts for CO 2 electroreduction yielding ethylene, electrocatalytic water oxidation, click chemistry reactions, photocatalytic degradations of organic dyes, dehydrogenation of alcohols, C–N cross-coupling reactions, and nitroarene reduction. − …”

Section: Introductionmentioning

confidence: 99%

Improved Mechanochemical Fabrication of Copper(II) Oxide Nanoparticles with Low E-Factor. Efficient Catalytic Activity for Nitroarene Reduction in Aqueous Medium

Schio

Soares

Machado³

et al. 2021

ACS Sustainable Chem. Eng.

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Copper(II) oxide nanoparticles (CuONPs) have become an essential material with a wide range of applications in different areas. Although different methodologies are available to fabricate CuONPs, most of them are solvent based, which generate a high amount of waste. Therefore, synthetic methodologies under dry conditions are an interesting alternative for seeking high yields, scale-up, and waste minimization. In this work, we describe an improved and lower environmental impact methodology to synthesize CuONPs through one-step high-energy mechanochemical milling under dry conditions. The methodology proved itself efficient to prepare CuONPs in gram-scale quantities, with 88% yield after 20 min at 1000 rpm and in the absence of additional heat treatment. The CuONPs exhibited a predominantly quasi-spherical morphology and an average size of 7.84 ± 2.08 nm. The nanoparticles showed a surface area of 68 ± 10 m2 g–1 and an energy gap value of 2.28 eV. The catalytic activity of the mechanochemically obtained CuONPs was successfully explored for nitroarene reduction in an aqueous medium. Conversion and selectivity both reached 99% for eight nitroarene examples. The catalyst was reused up to five times in consecutive runs without a significant decrease in the catalytic activity.

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“…Recently, it has been shown that Cu x O nanomaterials can be utilized as heterogeneous catalysts for alkyne–azide click cycloaddition, − in which possible reduction processes have been discussed to produce surface Cu(I) species desired for the catalytic cycloaddition process, − suggesting a possibility of designing surface functionalization schemes where the surface itself could serve as a catalyst. In this communication, we demonstrate that a convenient two-step sensitization of CuO nanostructures can be performed without any additional catalysts and without any solvents.…”

Section: Introductionmentioning

confidence: 99%

Self-Catalyzed Sensitization of CuO Nanowires via a Solvent-free Click Reaction

Cai

Wei

et al. 2020

Langmuir

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Recent advances in organic surface sensitization of metal oxide nanomaterials focused on two-step approaches with the first step providing a convenient functionalized chemical “hook”, such as an alkyne functionality connected to a carboxylic group in prop-2-ynoic acid. The second step then took advantage of copper-catalyzed click chemistry to deliver the desired structure (such as benzyl or perylene) attached to an azide to react with the surface-bound alkyne. The use of this approach on CuO not only resulted in a successful morphology preserving chemical modification but also has demonstrated that surface Cu(I) can be obtained during the process and promote a surface-catalyzed click reaction without additional copper catalyst. Here, it is demonstrated that this surface-catalyzed chemistry can be performed on a surface of the CuO nanomaterial without a solvent, as a “dry click” reaction, as confirmed with spectroscopic and microscopic investigations with X-ray photoelectron spectroscopy, Fourier transform infrared spectroscopy, X-ray diffraction, solid-state nuclear magnetic resonance, and scanning electron microscopy. Computational studies provided instructive information on the interaction between the surface prop-2-yonate and azide functional group to better understand the mechanism of this surface-catalyzed click reaction.

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Cupric oxide nanowires on three-dimensional copper foam for application in click reaction

Abstract: CuO nanowires can be synthesized by facile thermal oxidation of 3D Cu foam in air, which were found to be effective heterogeneous catalysts for the 1,3-dipolar cycloaddition reactions without using any additional support and bases.

Cited by 30 publications

References 48 publications

“Clickable” Metal-Oxide Nanomaterials Surface-Engineered by Gas-Phase Covalent Functionalization with Prop-2-ynoic Acid

“Clickable” Metal-Oxide Nanomaterials Surface-Engineered by Gas-Phase Covalent Functionalization with Prop-2-ynoic Acid

Improved Mechanochemical Fabrication of Copper(II) Oxide Nanoparticles with Low E-Factor. Efficient Catalytic Activity for Nitroarene Reduction in Aqueous Medium

Self-Catalyzed Sensitization of CuO Nanowires via a Solvent-free Click Reaction

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