Controllable Synthesis and Catalytic Performance of Gold Nanoparticles with Cucurbit[n]urils (n = 5–8)
Abstract
:1. Introduction
2. Materials and Methods
2.1. Instrumentation
2.2. Materials
2.3. Synthesis of CB[n]-AuNPs by In Situ Reduction of KAuCl4
2.4. Catalytic Reduction of 4-Nitrophenol
3. Results and Discussion
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
- Xia, Y.N.; Campbell, C.T. Nanoparticles for catalysts. Acc. Chem. Res. 2013, 46, 1671–1672. [Google Scholar] [CrossRef] [PubMed]
- Cuenya, B.R. Synthesis and catalytic properties of metal nanoparticles: Size, shape, support, composition, and oxidation state effects. Thin. Solid Films 2010, 518, 3127–3150. [Google Scholar] [CrossRef]
- Dykman, L.; Khlebtsov, N. Gold nanoparticles in biomedical applications: Recent advances and perspectives. Chem. Soc. Rev. 2012, 41, 2256–2282. [Google Scholar] [CrossRef] [PubMed]
- Xu, P.; Feng, Q.; Yang, X.R.; Liu, S.M.; Xu, C.; Huang, L.; Chen, M.; Liang, F.; Cheng, Y. Near Infrared Light Triggered Cucurbit[7]uril-Stabilized Gold Nanostars as a Supramolecular Nanoplatform for Combination Treatment of Cancer. Bioconj. Chem. 2018, 29, 2855–2866. [Google Scholar] [CrossRef] [PubMed]
- Ye, R.; Hurlburt, T.J.; Sabyrov, K.; Alayoglu, S.; Somorjai, G.A. Molecular catalysis science: Perspective on unifying the fields of catalysis. Proc. Natl. Acad. Sci. USA 2016, 113, 5159–5166. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Henderson, M.A. A surface science perspective on TiO2 photocatalysis. Surf. Sci. Rep. 2011, 66, 185–297. [Google Scholar] [CrossRef]
- Kukovecza, Á.; Kordásc, k.; Kissd, J.; Kónyaa, Z. Atomic scale characterization and surface chemistry of mental modified titanate nanotubes and nanowires. Surf. Sci. Rep. 2016, 71, 473–546. [Google Scholar] [CrossRef] [Green Version]
- Wu, Z.L.; Jiang, D.; Mann, A.K.; Mullins, D.R.; Qiao, Z.N.; Allard, L.F.; Zeng, C.Z.; Jin, R.C.; Overbury, S.H. Thiolate Ligands as a Double-Edged Sword for CO Oxidation on CeO2 Supported Au25(SCH2CH2Ph)18 Nanoclusters. J. Am. Chem. Soc. 2014, 136, 6111–6122. [Google Scholar] [CrossRef]
- Chen, H.W.; Hong, C.Y.; Kung, C.W.; Mou, C.Y.; Wu, K.W.; Ho, K.C. A gold surface plasmon enhanced mesoporous titanium dioxide photoelectrode for the plastic-based flexible dye-sensitized solar cells. J. Power Sources 2015, 288, 221–228. [Google Scholar] [CrossRef]
- Wang, L.; Liu, C.H.; Nemoto, Y.; Fukata, N.; Wu, K.W.; Yamauchi, Y. Rapid synthesis of biocompatible gold nanoflowers with tailored surface textures with the assistance of amino acid molecules. RSC Adv. 2012, 2, 4608–4611. [Google Scholar] [CrossRef]
- Montes-Garcia, V.; Perez-Juste, J.; Pastoriza-Santos, I.; Liz-Marzan, L.M. Metal Nanoparticles and Supramolecular Macrocycles: A Tale of Synergy. Chem. Eur. J. 2014, 20, 10874–10883. [Google Scholar] [CrossRef] [PubMed]
- Lu, J.; Lin, J.X.; Cao, M.; Cao, R. Cucurbituril: A promising organic building block for the design of coordination compounds and beyond. Coord. Chem. Rev. 2013, 57, 1334–1356. [Google Scholar] [CrossRef]
- Shetty, D.; Khedkar, J.K.; Park, K.M.; Kim, K. Can we beat the biotin–avidin pair?: Cucurbit[7]uril-based ultrahigh affinity host–guest complexes and their applications. Chem. Soc. Rev. 2015, 44, 8747–8761. [Google Scholar] [CrossRef] [PubMed]
- Barrow, S.J.; Kasera, S.; Rowland, M.J.; Barrio, J.; Scherman, O.A. Cucurbituril-Based Molecular Recognition. Chem. Rev. 2015, 115, 12320–12406. [Google Scholar] [CrossRef] [PubMed]
- Gong, W.J.; Yang, X.R.; Zavalij, P.Y.; Isaacs, L.; Zhao, Z.Y.; Liu, S.M. From Packed “Sandwich” to “Russian Doll”: Assembly by Charge-Transfer Interactions in Cucurbit[10]uril. Chem. Eur. J. 2016, 22, 17612–17618. [Google Scholar] [CrossRef] [PubMed]
- Gong, W.J.; Ma, J.; Zhao, Z.Y.; Gao, F.; Liang, F.; Zhang, H.J.; Liu, S.M. Inhibition and Stabilization: Cucurbituril Induced Distinct Effects on the Schiff Base Reaction. J. Org. Chem. 2017, 82, 3298–3301. [Google Scholar] [CrossRef] [PubMed]
- Yang, X.R.; Liu, F.; Zhao, Z.Y.; Liang, F.; Zhang, H.J.; Liu, S.M. Cucurbit[10]uril-based chemistry. Chin. Chem. Lett. 2018, 29, 1560–1566. [Google Scholar] [CrossRef]
- Katz, E.; Willner, I. Integrated Nanoparticle–Biomolecule Hybrid Systems: Synthesis, Properties, and Applications. Angew. Chem. Int. Ed. 2004, 43, 6042–6108. [Google Scholar] [CrossRef]
- Kim, H.J.; Lee, M.H.; Mutihac, L.; Vicens, L.; Kim, J.S. Host–guest sensing by calixarenes on the surfaces. Chem. Soc. Rev. 2012, 41, 1173–1190. [Google Scholar] [CrossRef]
- Zhao, Y.; Huang, Y.; Zhu, H.; Zhu, Q.; Xia, Y. Three-in-One: Sensing, Self-Assembly, and Cascade Catalysis of Cyclodextrin Modified Gold Nanoparticles. J. Am. Chem. Soc. 2016, 138, 16645–16654. [Google Scholar] [CrossRef]
- Lee, T.C.; Scherman, O.A. Formation of dynamic aggregates in water by cucurbit[5]uril capped with gold nanoparticles. Chem. Commun. 2010, 46, 2438–2440. [Google Scholar] [CrossRef] [PubMed]
- Premkumar, T.; Geckeler, K.E. Cucurbit[7]uril as a Tool in the Green Synthesis of Gold Nanoparticles. Chem. Asian J. 2010, 5, 2468–2476. [Google Scholar] [CrossRef] [PubMed]
- Lu, X.; Masson, E. Formation and Stabilization of Silver Nanoparticles with Cucurbit[n]urils (n = 5–8) and Cucurbituril-Based Pseudorotaxanes in Aqueous Medium. Langmuir 2011, 27, 3051–3058. [Google Scholar] [CrossRef] [PubMed]
- Lee, T.C.; Scherman, O.A. A Facile Synthesis of Dynamic Supramolecular Aggregates of Cucurbit[n]uril (n = 5–8) Capped with Gold Nanoparticles in Aqueous Media. Chem. Eur. J. 2012, 18, 1628–1633. [Google Scholar] [CrossRef] [PubMed]
- Benyettou, F.; Milosevic, I.; Lalatonne, Y.; Warmont, F.; Assah, R.; Olsen, J.; Jouaid, M.; Motte, L.; Platas-Iglesias, C.; Trabolsi, A. Toward theranostic nanoparticles: CB[7]-functionalized iron oxide for drug delivery and MRI. J. Mater. Chem. B 2013, 1, 5076–5082. [Google Scholar] [CrossRef]
- Premkumar, T.; Geckeler, K.E. Synthesis of honeycomb-like palladium nanostructures by using cucurbit[7]uril and their catalytic activities for reduction of 4-nitrophenol. Mater. Chem. Phys. 2014, 148, 772–777. [Google Scholar] [CrossRef]
- Qiu, X.; Zhou, Y.; Jin, X.; Qi, A.; Yang, Y. One-pot solvothermal synthesis of biocompatible magnetic nanoparticles mediated by cucurbit[n]urils. J. Mater. Chem. C 2015, 3, 3517–3521. [Google Scholar] [CrossRef]
- Han, Y.W.; Yang, X.R.; Liu, Y.; Ai, Q.; Liu, S.M.; Sun, C.; Liang, F. Supramolecular Controlled Cargo Release via Near Infrared Tunable Cucurbit[7]uril-Gold Nanostars. Sci. Rep. 2016, 6, 22239. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- An, Q.; Li, G.T.; Tao, C.; Li, Y.; Wu, Y.; Zhang, W. A general and efficient method to form self-assembled cucurbit[n]uril monolayers on gold surfaces. Chem. Commun. 2008, 17, 1989–1991. [Google Scholar] [CrossRef] [PubMed]
- Blanco, E.; Esteve-Adell, I.; Atienzar, P.; Casas, J.A.; Hernández, P.; Quintana, C. Cucurbit[7]uril-stabilized gold nanoparticles as catalysts of the nitro compound reduction reaction. RSC. Adv. 2016, 6, 86309–86315. [Google Scholar] [CrossRef] [Green Version]
- Blanco, E.; Atienzar, P.; Hernandez, P.; Quintana, C. The Langmuir–Hinshelwood approach for kinetic evaluation of cucurbit[7]uril-capped gold nanoparticles in the reduction of the antimicrobial nitrofurantoin. Phys. Chem. Chem. Phys. 2017, 19, 18913–18923. [Google Scholar] [CrossRef] [PubMed]
- Pozo, M.D.; Blanco, E.; Hernandez, P.; Casas, J.A.; Quintana, C. Catalystic efficiency of microcylic-capped gold nanoparticles: Cucurbit[n]urils versus cyclodextrins. J. Nanopart. Res. 2018, 20, 121. [Google Scholar] [CrossRef]
- Liao, Y.T.; Chen, J.; Isida, Y.; Yonezawa, T.; Chang, W.C.; Alshehri, S.; Yamauchi, Y.; Wu, K.W. De Novo Synthesis of Gold-Nanoparticle-Embedded, Nitrogen-Doped Nanoporous Carbon Nanoparticles (Au@NC) with Enhanced Reduction Ability. ChemCatChem 2016, 8, 502–509. [Google Scholar] [CrossRef]
- Zhao, P.; Feng, X.; Huang, D.; Yang, G.; Astruc, D. Basic concepts and recent advances in nitrophenol reduction by gold- and other transition metal nanoparticles. Coord. Chem. Rev. 2015, 287, 114–136. [Google Scholar] [CrossRef]
- Aditya, T.; Pal, A.; Pal, T. Nitroarene reduction: A trusted model reaction to test nanoparticle catalysts. Chem. Commun. 2015, 51, 9410–9431. [Google Scholar] [CrossRef] [PubMed]
- Herves, P.; Perez-Lorenzo, M.; Liz-Marzan, L.M.; Dzubiell, J.; Lu, Y.; Ballauff, M. Catalysis by metallic nanoparticles in aqueous solution: Model reactions. Chem. Soc. Rev. 2012, 41, 5577–5587. [Google Scholar] [CrossRef] [PubMed]
- Ma, T.; Yang, W.S.; Liu, S.M.; Zhang, H.J.; Liang, F. A Comparison Reduction of 4-Nitrophenol by Gold Nanospheres and Gold Nanostars. Catalysts 2017, 7, 38. [Google Scholar] [CrossRef]
- Ma, T.; Liang, F.; Chen, R.S.; Liu, S.M.; Zhang, H.J. Synthesis of Au-Pd Bimetallic Nanoflowers for Catalytic Reduction of 4-Nitrophenol. Nanomaterials 2017, 7, 239. [Google Scholar] [CrossRef] [PubMed]
- Subramanian, V.; Wolf, E.E.; Kamat, P.V. Catalysis with TiO2/Gold Nanocomposites Effect of Mental Paeticle Size on the Fermi Level Equilibration. J. Am. Chem. Soc. 2004, 16, 4943–4950. [Google Scholar] [CrossRef]
- Haiss, W.; Thanh, N.T.; Aveyard, J.; Fernig, D.G. Determination of Size and Concentration of Gold Nanoparticles from UV−Vis Spectra. Anal. Chem. 2007, 79, 4215–4221. [Google Scholar] [CrossRef]
- Palma, R.D.; Peeters, S.; Bael, M.J.; Rul, V.; Bonroy, K.; Laureyn, W.; Mullens, J.; Borghs, G.; Maes, G. Silane Ligand Exchange to Make Hydrophobic Superparamagnetic Nanoparticles Water-Dispersible. Chem. Mater. 2007, 19, 1821–1831. [Google Scholar] [CrossRef]
- Siyam, M.A.; Christopher, L.K. Impact of Gold Nanoparticle Stabilizing Ligands on the Colloidal Catalytic Reduction of 4-Nitrophenol. ACS. Catal. 2016, 6, 5553–5560. [Google Scholar]
- Menumerov, E.; Hughes, R.A.; Neretina, S. Catalytic Reduction of 4-Nitrophenol: A Quantitative Assessment of the Role of Dissolved Oxygen in Determining the Induction Time. Nano. Lett. 2016, 16, 7791–7797. [Google Scholar] [CrossRef] [PubMed]
- Cao, H.L.; Huang, H.B.; Chen, Z.; Karadeniz, B.; Lü, J.; Cao, R. Ultrafine Silver Nanoparticles Supported on a Conjugated Microporous Polymer as High-Performance Nanocatalysts for Nitrophenol Reduction. ACS Appl. Mater. Interfaces 2017, 9, 5231–5236. [Google Scholar] [CrossRef] [PubMed]
- Wunder, S.; Polzer, F.; Lu, Y.; Mei, Y.; Ballauff, M. Kinetic Analysis of Catalytic Reduction of 4-Nitrophenol by Metallic Nanoparticles Immobilized in Spherical Polyelectrolyte Brushes. J. Phys. Chem. C 2010, 114, 8814–8820. [Google Scholar] [CrossRef]
- Wunder, S.; Lu, Y.; Albrecht, M.; Ballauff, M. Catalytic Activity of Faceted Gold Nanoparticles Studied by a Model Reaction: Evidence for Substrate-Induced Surface Restructuring. ACS Catal. 2011, 1, 908–916. [Google Scholar] [CrossRef]
- Quaresma, P.; Soares, L.; Contar, L.; Miranda, A.; Osorio, I.; Carvalho, P.A.; Franco, R.; Pereira, E. Green photocatalytic synthesis of stable Au and Ag nanoparticles. Green. Chem. 2009, 11, 1889–1893. [Google Scholar] [CrossRef]
- Nigra, M.M.; Ha, J.M.; Katz, A. Identification of site requirements for reduction of 4-nitrophenol using gold nanoparticle catalysts. Catal. Sci. Technol. 2013, 3, 2976–2983. [Google Scholar] [CrossRef]
- Ansar, S.M.; Haputhanthri, R.; Edmonds, B.; Liu, D.; Yu, L.Y.; Sygula, A.; Zhang, D.M. Determination of the Binding Affinity, Packing, and Conformation of Thiolate and Thione Ligands on Gold Nanoparticles. J. Phys. Chem. C 2011, 115, 653–660. [Google Scholar] [CrossRef]
- Siriwardana, K.; Gadogbe, M.; Ansar, S.M.; Vasquez, E.S.; Collier, W.E.; Zou, S.L.; Walters, K.B.; Zhang, D.M. Ligand Adsorption and Exchange on Pegylated Gold Nanoparticles. J. Phys. Chem. C 2014, 118, 11111–11119. [Google Scholar] [CrossRef]
- Zhang, D.M.; Ansar, S.M. Ratiometric Surface Enhanced Raman Quantification of Ligand Adsorption onto a Gold Nanoparticle. Anal. Chem. 2010, 82, 5910–5914. [Google Scholar] [CrossRef] [PubMed]
- Ge, J.; Xue, S.; Zhu, Q.; Tao, Z.; Zhang, J. Interaction of Cucurbit[n = 6∼8]urils and Benzimidazole Derivatives. J. Incl. Phenom. Macrocycl. Chem. 2006, 58, 63–69. [Google Scholar] [CrossRef]
- Koner, A.L.; Ghosh, I.; Saleh, N.; Nau, W.M. Supramolecular encapsulation of benzimidazole-derived drugs by cucurbit[7]uril. Can. J. Chem. 2001, 89, 139–147. [Google Scholar] [CrossRef]
- Smitka, J.; Lemos, A.; Porel, M.; Jockusch, S.; Belderrain, T.R.; Tesarova, E.; Da Silva, J.P. Phototransformation of benzimidazole and thiabendazole inside cucurbit[8]uril. Photochem. Photobiol. Sci. 2014, 13, 310–315. [Google Scholar] [CrossRef] [PubMed]
- Gong, J.L. Structure and Surface Chemistry of Gold-Based Model Catalysts. Chem. Rev. 2012, 112, 2987–3054. [Google Scholar] [CrossRef]
- Pina, C.D.; Falletta, E.; Rossi, M. Update on selective oxidation using gold. Chem. Soc. Rev. 2012, 41, 350–369. [Google Scholar] [CrossRef]
AuNPs Composite | Portal Diameter of CB[n] (nm) 2 | Cavity Diameter of CB[n] (nm) 2 | Diameter (nm) 3 | Diameter (nm) 4 |
---|---|---|---|---|
CB[5]/AuNPs | 0.24 | 0.44 | 3.6 ± 1.0 | 4.6 ± 0.7 |
CB[6]/AuNPs | 0.39 | 0.58 | 10.0 ± 4.4 | 10.4 ± 1.6 |
CB[7]/AuNPs | 0.54 | 0.73 | 3.3 ± 1.1 | 12.4 ± 1.8 |
CB[8]/AuNPs | 0.69 | 0.88 | 7.7 ± 2.9 | 15.5 ± 2.5 |
AuNPs Composite | Weight Loss % | Packing Density (molecules/nm2) | Coverage (%) | kapp (min−1) 3 | Induction Time (s) 3 |
---|---|---|---|---|---|
CB[5]/AuNPs | 1.08 | 0.08 | 1.3 | 11.55 ± 1.4 | ND 4 |
CB[6]/AuNPs | 4.61 | 0.97 | 25.6 | 7.17 ± 0.34 | 3.75 ± 0.45 |
CB[7]/AuNPs | 4.78 | 1.04 | 43.8 | 5.98 ± 0.17 | 10.24 ± 1.62 |
CB[8]/AuNPs | 5.77 | 1.38 | 83.9 | 1.95 ± 0.09 | 16.59 ± 0.71 |
AuNPs-citrate (4 nm) 2 | N/A 5 | N/A 5 | N/A | 13.39 ± 1.9 | ND 4 |
AuNPs-citrate (16 nm) 2 | N/A 5 | N/A 5 | N/A | 7.22 ± 0.35 | 2.01 ± 0.02 |
© 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Zhang, L.; Liu, S.; Wang, Y.; Zhang, H.; Liang, F. Controllable Synthesis and Catalytic Performance of Gold Nanoparticles with Cucurbit[n]urils (n = 5–8). Nanomaterials 2018, 8, 1015. https://doi.org/10.3390/nano8121015
Zhang L, Liu S, Wang Y, Zhang H, Liang F. Controllable Synthesis and Catalytic Performance of Gold Nanoparticles with Cucurbit[n]urils (n = 5–8). Nanomaterials. 2018; 8(12):1015. https://doi.org/10.3390/nano8121015
Chicago/Turabian StyleZhang, Liangfeng, Simin Liu, Yuhua Wang, Haijun Zhang, and Feng Liang. 2018. "Controllable Synthesis and Catalytic Performance of Gold Nanoparticles with Cucurbit[n]urils (n = 5–8)" Nanomaterials 8, no. 12: 1015. https://doi.org/10.3390/nano8121015