Catalytic Activity of Silicon Nanowires Decorated with Gold and Copper Nanoparticles Deposited by Pulsed Laser Ablation
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials
2.2. General Procedure for Caryl–N Cross Coupling
2.3. General Procedure for Carbonylation of Haloarenes
2.4. General Procedure for Reduction of Nitroarenes
3. Results and Discussion
3.1. Structural Properties of Catalysts Nanocomposites
3.2. Catalytic Activity in Caryl–N Coupling Reactions
3.3. Carbonylation of Haloarenes
3.4. Reduction of Nitroarenes
3.5. Mechanistic Insights
4. Conclusions
- (i)
- an unexpected activity for some chemical transformations like Caryl–N couplings and subsequent carbonylations that have no precedents in the literature for gold and copper catalysts, respectively;
- (ii)
- an extraordinary activity, attested by the very high TON values (about ten up to hundred times higher than those of the most commonly used catalysts (Figure 5)), surely due to the uniform coverage along the NW length and absence of the chemical shell surrounding the MeNPs;
- (iii)
- a high recyclability, with more than ten recycling runs occurring with limited loss of activity, which can be ascribed to two main effects: (a) the high availability of MeNPs all over the length of NWs, notwithstanding the initial depletion in the upper layer of wires, and (b) the strong covalent interaction at the Me–Si interface by virtue of metal “silicides” formation. This confines the metal catalyst to the voids among the wires, transforming them into “micro-reactors” (Figure 9).
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Run | X | R | Amine (R1NH2) | Yield (%) (b) | |
---|---|---|---|---|---|
CuNPs@SiNWs | AuNPs@SiNWs | ||||
1 | I | H | BuNH2 | 96 | 95 |
2 | I | H | AllylNH2 | 80 | 85 |
3 | I | H | BnNH2 | 99 | 98 |
4 | I | H | HO(CH2)4NH2 | 75 (c) | 80 (c) |
5 | I | H | H2N(CH2)4NH2 | 99 (d) | 95 (d) |
6 | I | H | CyNH2 | 98 | 97 |
7 | I | H | 2-NH2CyNH2 | 99 (e) | 99 (e) |
8 | I | H | n-C12H25NH2 | 82 | 79 |
9 | I | I | Bu2NH | 20 | 19 |
10 | I | H | PhNH2 | 15 | 18 |
11 | I | 4-NO2 | BuNH2 | 99 | 96 |
12 | I | 4-Br | BuNH2 | 50 | 55 |
13 | I | 4-MeO | BuNH2 | 40 | 49 |
14 | I | 4-CH3 | BuNH2 | 94 | 98 |
15 | I | 2-CH3 | BuNH2 | 72 | 73 |
16 | Br | H | BuNH2 | 15 | 10 |
17 | Br | 4-CN | BuNH2 | 19 | 20 |
18 | I | H | HO(CH2)4SH (f) | 90 | 95 |
19 | I | H | HO(CH2)4OH | <1 | 3 |
Run | R | R′-NH2 | Product | Yields (b) (%) | Sel. (b) (%) |
---|---|---|---|---|---|
1 | H | BuNH2 | 97 | 84 | |
2 | H | AllylNH2 | 89 | 85 | |
3 | H | BnNH2 | 90 | 80 | |
4 | H(c) | 4-AB | 95 | 83 | |
5 | H | CyNH2 | 92 | 82 | |
6 | 4-NO2 | BuNH2 | 99 | 55 (d) | |
7 | 4-Br | BuNH2 | 98 | 64 | |
8 | 4-MeO | BuNH2 | 85 | 88 | |
9 | 4-Me | BuNH2 | 88 | 86 | |
10 | 2-Me | BuNH2 | 75 | 85 | |
11 | H (e) | BuNH2 | <5 | - |
Run | R′-OH | Product | Yields (b) (%) | Sel. (b) (%) |
---|---|---|---|---|
1 | Me-OH | 89 | 90 | |
2 | Bu-OH | 82 | 95 | |
3 | iPr-OH | 62 | 93 | |
4 | Allyl-OH | 72 | 92 | |
5 | Cy-OH | 68 | 91 | |
6 | Bn-OH | 90 | 65 | |
7 | 1,3-BD (c) | 66 | 55 | |
8 | Ph-OH (c) | <5 | - |
Run | Catalyst | TOF (b) | Ref. |
---|---|---|---|
1 | AuNPs@SiNWs | 123 | This work |
2 | CuNPs@SiNWs | 255 | This work |
3 | CuNPs@SiNWs | 220 | [33] |
5 | Au/CeO2 | 240 | [64] |
6 | Cu cubes | 136 | [65] |
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Casiello, M.; Picca, R.A.; Fusco, C.; D’Accolti, L.; Leonardi, A.A.; Lo Faro, M.J.; Irrera, A.; Trusso, S.; Cotugno, P.; Sportelli, M.C.; et al. Catalytic Activity of Silicon Nanowires Decorated with Gold and Copper Nanoparticles Deposited by Pulsed Laser Ablation. Nanomaterials 2018, 8, 78. https://doi.org/10.3390/nano8020078
Casiello M, Picca RA, Fusco C, D’Accolti L, Leonardi AA, Lo Faro MJ, Irrera A, Trusso S, Cotugno P, Sportelli MC, et al. Catalytic Activity of Silicon Nanowires Decorated with Gold and Copper Nanoparticles Deposited by Pulsed Laser Ablation. Nanomaterials. 2018; 8(2):78. https://doi.org/10.3390/nano8020078
Chicago/Turabian StyleCasiello, Michele, Rosaria Anna Picca, Caterina Fusco, Lucia D’Accolti, Antonio Alessio Leonardi, Maria Josè Lo Faro, Alessia Irrera, Sebastiano Trusso, Pietro Cotugno, Maria Chiara Sportelli, and et al. 2018. "Catalytic Activity of Silicon Nanowires Decorated with Gold and Copper Nanoparticles Deposited by Pulsed Laser Ablation" Nanomaterials 8, no. 2: 78. https://doi.org/10.3390/nano8020078