Facile fabrication of ultrafine palladium nanoparticles with size- and location-control in click-based porous organic polymers

ACS Nano

Volumn 8, Issue 5, 2014, Pages 5352-5364

  Li, Liuyi ^a   Zhao, Huaixia ^a   Wang, Jinyun ^a   Wang, Ruihu ^a  

^a FUJIAN INSTITUTE OF RESEARCH ON THE STRUCTURE OF MATTER   (China)

Author keywords

click reaction; heterogeneous catalysis; nanoparticles; palladium; porous organic polymers

Indexed keywords

CATALYSIS; CHARCOAL; ELECTRONIC PROPERTIES; NANOPARTICLES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM;

CATALYTIC PERFORMANCE; CLICK REACTION; COMPUTATIONAL CALCULATIONS; CONFINEMENT EFFECTS; NMR AND IR SPECTRUM; PALLADIUM NANOPARTICLES; POROUS ORGANIC POLYMERS; UNIFORM DISTRIBUTION;

ORGANIC POLYMERS;

EID: 84901650331     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn501853g     Document Type: Article

References (69)

1. Zaera, F. Nanostructured Materials for Applications in Heterogeneous Catalysis Chem. Soc. Rev. 2013, 42, 2746-2762
2. Dhakshinamoorthy, A.; Garcia, H. Catalysis by Metal Nanoparticles Embedded on Metal-Organic Frameworks Chem. Soc. Rev. 2012, 41, 5262-5284
3. Burda, C.; Chen, X.; Narayanan, R.; El-Sayed, M. A. Chemistry and Properties of Nanocrystals of Different Shapes Chem. Rev. 2005, 105, 1025-1102
4. Vajda, S.; Pellin, M. J.; Greeley, J. P.; Marshall, C. L.; Curtiss, L. A.; Ballentine, G. A.; Elam, J. W.; Catillon-Mucherie, S.; Redfern, P. C.; Mehmood, F. Subnanometre Platinum Clusters as Highly Active and Selective Catalysts for the Oxidative Dehydrogenation of Propane Nat. Mater. 2009, 8, 213-216
5. Qiao, B.; Wang, A.; Yang, X.; Allard, L. F.; Jiang, Z.; Cui, Y.; Liu, J.; Li, J.; Zhang, T. Single-Atom Catalysis of CO Oxidation Using Pt1/FeOx Nat. Chem. 2011, 3, 634-641
6. Li, Z.; Liu, J.; Xia, C.; Li, F. Nitrogen-Functionalized Ordered Mesoporous Carbons as Multifunctional Supports of Ultrasmall Pd Nanoparticles for Hydrogenation of Phenol ACS Catal. 2013, 2440-2448
7. Kibata, T.; Mitsudome, T.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Investigation of Size-Dependent Properties of Sub-Nanometer Palladium Clusters Encapsulated within a Polyamine Dendrimer Chem. Commun. 2013, 49, 167-169
8. White, R. J.; Luque, R.; Budarin, V. L.; Clark, J. H.; Macquarrie, D. J. Supported Metal Nanoparticles on Porous Materials. Methods and Applications Chem. Soc. Rev. 2009, 38, 481-494
9. Ott, L. S.; Finke, R. G. Transition-Metal Nanocluster Stabilization for Catalysis: A Critical Review of Ranking Methods and Putative Stabilizers Coord. Chem. Rev. 2007, 251, 1075-1100
10. Pileni, M.-P. The Role of Soft Colloidal Templates in Controlling the Size and Shape of Inorganic Nanocrystals Nat. Mater. 2003, 2, 145-150
11. Gascon, J.; Aktay, U.; Hernandezalonso, M.; Vanklink, G.; Kapteijn, F. Amino-Based Metal-Organic Frameworks as Stable, Highly Active Basic Catalysts J. Catal. 2009, 261, 75-87
12. Cárdenas-Lizana, F.; Berguerand, C.; Yuranov, I.; Kiwi-Minsker, L. Chemoselective Hydrogenation of Nitroarenes: Boosting Nanoparticle Efficiency by Confinement within Highly Porous Polymeric Framework J. Catal. 2013, 301, 103-111
13. Li, X.-H.; Antonietti, M. Metal Nanoparticles at Mesoporous N-Doped Carbons and Carbon Nitrides: Functional Mott-Schottky Heterojunctions for Catalysis Chem. Soc. Rev. 2013, 42, 6593-6604
14. Liu, B.; Jie, S. Y.; Li, B. G. Metal-Organic Frameworks for Heterogeneous Catalysis Prog. Chem. 2013, 25, 36-45
15. Vilhelmsen, L. B.; Walton, K. S.; Sholl, D. S. Structure and Mobility of Metal Clusters in MOFs: Au, Pd, and AuPd Clusters In MOF-74 J. Am. Chem. Soc. 2012, 134, 12807-12816
16. Aijaz, A.; Karkamkar, A.; Choi, Y. J.; Tsumori, N.; Ronnebro, E.; Autrey, T.; Shioyama, H.; Xu, Q. Immobilizing Highly Catalytically Active Pt Nanoparticles inside the Pores of Metal-Organic Framework: A Double Solvents Approach J. Am. Chem. Soc. 2012, 134, 13926-13929
17. Zhu, Q. L.; Li, J.; Xu, Q. Immobilizing Metal Nanoparticles to Metal-Organic Frameworks with Size and Location Control for Optimizing Catalytic Performance J. Am. Chem. Soc. 2013, 135, 10210-10213
18. Lu, G.; Li, S.; Guo, Z.; Farha, O. K.; Hauser, B. G.; Qi, X.; Wang, Y.; Wang, X.; Han, S.; Liu, X. Imparting Functionality to a Metal-Organic Framework Material by Controlled Nanoparticle Encapsulation Nat. Chem. 2012, 4, 310-316
19. Moon, H. R.; Lim, D. W.; Suh, M. P. Fabrication of Metal Nanoparticles in Metal-Organic Frameworks Chem. Soc. Rev. 2013, 42, 1807-1824
20. Ma, L.; Lin, W. Designing Metal-Organic Frameworks for Catalytic Applications Top. Curr. Chem. 2010, 293, 175-205
21. 2 and Its Characterization by MAS NMR J. Phys. Chem. C 2009, 113, 13906-13917
22. Zou, X. Q.; Ren, H.; Zhu, G. S. Topology-Directed Design of Porous Organic Frameworks and their Advanced Applications Chem. Commun. 2013, 49, 3925-3936
23. Dawson, R.; Cooper, A. I.; Adams, D. J. Nanoporous Organic Polymer Networks Prog. Polym. Sci. 2012, 37, 530-563
24. Patel, H. A.; Karadas, F.; Byun, J.; Park, J.; Deniz, E.; Canlier, A.; Jung, Y.; Atilhan, M.; Yavuz, C. T. Highly Stable Nanoporous Sulfur-Bridged Covalent Organic Polymers for Carbon Dioxide Removal Adv. Funct. Mater. 2013, 23, 2270-2276
25. Zhao, H.; Jin, Z.; Su, H.; Zhang, J.; Yao, X.; Zhao, H.; Zhu, G. Target Synthesis of a Novel Porous Aromatic Framework and Its Highly Selective Separation of CO(2)/CH(4) Chem. Commun. 2013, 49, 2780-2782
26. Fang, Q.; Gu, S.; Zheng, J.; Zhuang, Z.; Qiu, S.; Yan, Y. 3D Microporous Base-Functionalized Covalent Organic Frameworks for Size-Selective Catalysis Angew. Chem., Int. Ed. 2014, 53, 2878-2882
27. Jiang, J. X.; Wang, C.; Laybourn, A.; Hasell, T.; Clowes, R.; Khimyak, Y. Z.; Xiao, J.; Higgins, S. J.; Adams, D. J.; Cooper, A. I. Metal-Organic Conjugated Microporous Polymers Angew. Chem., Int. Ed. 2011, 50, 1072-1075
28. Chen, L.; Yang, Y.; Jiang, D. CMPs as Scaffolds for Constructing Porous Catalytic Frameworks: A Built-in Heterogeneous Catalyst with High Activity and Selectivity Based on Nanoporous Metalloporphyrin Polymers J. Am. Chem. Soc. 2010, 132, 9138-9143
29. Ding, S. Y.; Wang, W. Covalent Organic Frameworks (COFs): From Design to Applications Chem. Soc. Rev. 2013, 42, 548-568
30. Medina, D. D.; Werner, V.; Auras, F.; Tautz, R.; Dogru, M.; Schuster, J.; Linke, S.; Doblinger, M.; Feldmann, J.; Knochel, P. et al. Oriented Thin Films of a Benzodithiophene Covalent Organic Framework ACS Nano 2014, 10.1021/nn5000223
31. Zhang, Y. G.; Riduan, S. N. Functional Porous Organic Polymers for Heterogeneous Catalysis Chem. Soc. Rev. 2012, 41, 2083-2094
32. Li, Z.; Liu, J.; Huang, Z.; Yang, Y.; Xia, C.; Li, F. One-Pot Synthesis of Pd Nanoparticle Catalysts Supported on N-Doped Carbon and Application in the Domino Carbonylation ACS Catal. 2013, 3, 839-845
33. Zhang, P.; Weng, Z.; Guo, J.; Wang, C. Solution-Dispersible, Colloidal, Conjugated Porous Polymer Networks with Entrapped Palladium Nanocrystals for Heterogeneous Catalysis of the Suzuki-Miyaura Coupling Reaction Chem. Mater. 2011, 23, 5243-5249
34. Ding, S. Y.; Gao, J.; Wang, Q.; Zhang, Y.; Song, W. G.; Su, C. Y.; Wang, W. Construction of Covalent Organic Framework for Catalysis: Pd/COF-LZU1 in Suzuki-Miyaura Coupling Reaction J. Am. Chem. Soc. 2011, 133, 19816-19822
35. Hasell, T.; Wood, C. D.; Clowes, R.; Jones, J. T. A.; Khimyak, Y. Z.; Adams, D. J.; Cooper, A. I. Palladium Nanoparticle Incorporation in Conjugated Microporous Polymers by Supercritical Fluid Processing Chem. Mater. 2010, 22, 557-564
36. Zhang, Q.; Yang, Y.; Zhang, S. Novel Functionalized Microporous Organic Networks Based on Triphenylphosphine Chem.-Eur. J. 2013, 19, 10024-10029
37. Chan-Thaw, C. E.; Villa, A.; Prati, L.; Thomas, A. Triazine-Based Polymers as Nanostructured Supports for the Liquid-Phase Oxidation of Alcohols Chem.-Eur. J. 2011, 17, 1052-1057
38. Zhou, Y.; Xiang, Z.; Cao, D.; Liu, C. J. Covalent Organic Polymer Supported Palladium Catalysts for CO Oxidation Chem. Commun. 2013, 49, 5633-5635
39. Chan-Thaw, C. E.; Villa, A.; Katekomol, P.; Su, D.; Thomas, A.; Prati, L. Covalent Triazine Framework as Catalytic Support for Liquid Phase Reaction Nano Lett. 2010, 10, 537-541
40. Xie, Z.; Wang, C.; deKrafft, K. E.; Lin, W. Highly Stable and Porous Cross-Linked Polymers for Efficient Photocatalysis J. Am. Chem. Soc. 2011, 133, 2056-2059
41. Wan, Y.; Wang, H.; Zhao, Q.; Klingstedt, M.; Terasaki, O.; Zhao, D. Ordered Mesoporous Pd/Silica-Carbon as a Highly Active Heterogeneous Catalyst for Coupling Reaction of Chlorobenzene in Aqueous Media J. Am. Chem. Soc. 2009, 131, 4541-4550
42. Liang, L.; Astruc, D. The Copper(I)-Catalyzed Alkyne-Azide Cycloaddition (CuAAC) "Click" Reaction and Its Applications. An Overview Coord. Chem. Rev. 2011, 255, 2933-2945
43. Barner-Kowollik, C.; Du Prez, F. E.; Espeel, P.; Hawker, C. J.; Junkers, T.; Schlaad, H.; Van Camp, W. "Clicking" Polymers or Just Efficient Linking: What is the Difference? Angew. Chem., Int. Ed. 2011, 50, 60-62
44. Juríček, M.; Kouwer, P. H. J.; Rowan, A. E. Triazole: A Unique Building Block for the Construction of Functional Materials Chem. Commun. 2011, 47, 8740-8749
45. Juríček, M.; Felici, M.; Contreras-Carballada, P.; Lauko, J.; Bou, S. R.; Kouwer, P. H. J.; Brouwer, A. M.; Rowan, A. E. Triazole-Pyridine Ligands: A Novel Approach to Chromophoric Iridium Arrays J. Mater. Chem. 2011, 21, 2104-2111
46. Fleischel, O.; Wu, N.; Petitjean, A. Click-Triazole: Coordination of 2-(1,2,3-Triazol-4-yl)-Pyridine to Cations of Traditional Tetrahedral Geometry (Cu(I), Ag(I)) Chem. Commun. 2010, 46, 8454-8456
47. Wang, D.; Denux, D.; Ruiz, J.; Astruc, D. The Clicked Pyridyl-Triazole Ligand: From Homogeneous to Robust, Recyclable Heterogeneous Mono- and Polymetallic Palladium Catalysts for Efficient Suzuki-Miyaura, Sonogashira, and Heck Reactions Adv. Synth. Catal. 2013, 355, 129-142
48. Li, L. Y.; Wang, J. Y.; Wu, T.; Wang, R. H. Click Ionic Liquids: A Family of Promising Tunable Solvents and Application in Suzuki-Miyaura Cross-Coupling Chem.-Eur. J. 2012, 18, 7842-7851
49. Pandey, P.; Farha, O. K.; Spokoyny, A. M.; Mirkin, C. A.; Kanatzidis, M. G.; Hupp, J. T.; Nguyen, S. T. A "Click-Based" Porous Organic Polymer from Tetrahedral Building Blocks J. Mater. Chem. 2011, 21, 1700-1703
50. Holst, J. R.; Stöckel, E.; Adams, D. J.; Cooper, A. I. High Surface Area Networks from Tetrahedral Monomers: Metal-Catalyzed Coupling, Thermal Polymerization, and "Click" Chemistry Macromolecules 2010, 43, 8531-8538
51. Plietzsch, O.; Schilling, C. I.; Grab, T.; Grage, S. L.; Ulrich, A. S.; Comotti, A.; Sozzani, P.; Muller, T.; Brase, S. Click Chemistry Produces Hyper-Cross-Linked Polymers with Tetrahedral Cores New J. Chem. 2011, 35, 1577-1581
52. 2-Capture Ability of a Porous Organic Polymer Bifunctionalized with Carboxy and Triazole Groups Chem.-Eur. J. 2013, 19, 11590-11597
53. Li, L.; Chen, Z.; Zhong, H.; Wang, R. Urea-Based Porous Organic Frameworks: Effective Supports for Catalysis in Neat Water Chem.-Eur. J. 2014, 20, 3050-3060
54. Li, L. Y.; Wang, J. Y.; Zhou, C. S.; Wang, R. H.; Hong, M. C. pH-Responsive Chelating N-Heterocyclic Dicarbene Palladium(II) Complexes: Recoverable Precatalysts for Suzuki-Miyaura Reaction in Pure Water Green Chem. 2011, 13, 2071-2077
55. Devadoss, A.; Chidsey, C. E. Azide-Modified Graphitic Surfaces for Covalent Attachment of Alkyne-Terminated Molecules by "Click" Chemistry J. Am. Chem. Soc. 2007, 129, 5370-5371
56. Bebensee, F.; Bombis, C.; Vadapoo, S. R.; Cramer, J. R.; Besenbacher, F.; Gothelf, K. V.; Linderoth, T. R. On-Surface Azide-Alkyne Cycloaddition on Cu(111): Does It "Click" in Ultrahigh Vacuum? J. Am. Chem. Soc. 2013, 135, 2136-2139
57. Guan, B.; Ciampi, S.; Le Saux, G.; Gaus, K.; Reece, P. J.; Gooding, J. J. Different Functionalization of the Internal and External Surfaces in Mesoporous Materials for Biosensing Applications Using "Click" Chemistry Langmuir 2011, 27, 328-334
58. 2 Fixation to Cyclic Carbonates J. Mater. Chem. A 2013, 1, 5517-5523
59. Ben, T.; Pei, C.; Zhang, D.; Xu, J.; Deng, F.; Jing, X.; Qiu, S. Gas Storage in Porous Aromatic Frameworks (PAFs) Energy Environ. Sci. 2011, 4, 3991-3999
60. Weber, J.; Schmidt, J.; Thomas, A.; Bohlmann, W. Micropore Analysis of Polymer Networks by Gas Sorption and 129Xe NMR Spectroscopy: Toward a Better Understanding of Intrinsic Microporosity Langmuir 2010, 26, 15650-15656
61. Dawson, R.; Laybourn, A.; Clowes, R.; Khimyak, Y. Z.; Adams, D. J.; Cooper, A. I. Functionalized Conjugated Microporous Polymers Macromolecules 2009, 42, 8809-8816
62. Liang, Q.; Liu, J.; Wei, Y.; Zhao, Z.; MacLachlan, M. J. Palladium Nanoparticles Supported on a Triptycene-Based Microporous Polymer: Highly Active Catalysts for CO Oxidation Chem. Commun. 2013, 49, 8928-8930
63. Yuan, B.; Pan, Y.; Li, Y.; Yin, B.; Jiang, H. A Highly Active Heterogeneous Palladium Catalyst for the Suzuki-Miyaura and Ullmann Coupling Reactions of Aryl Chlorides in Aqueous Media Angew. Chem., Int. Ed. 2010, 49, 4054-4058
64. Martis, M.; Mori, K.; Fujiwara, K.; Ahn, W.-S.; Yamashita, H. Amine-Functionalized MIL-125 with Imbedded Palladium Nanoparticles as an Efficient Catalyst for Dehydrogenation of Formic Acid at Ambient Temperature J. Phys. Chem. C 2013, 117, 22805-22810
65. Radkevich, V. Z.; Senko, T. L.; Wilson, K.; Grishenko, L. M.; Zaderko, A. N.; Diyuk, V. Y. The Influence of Surface Functionalization of Activated Carbon on Palladium Dispersion and Catalytic Activity in Hydrogen Oxidation Appl. Catal. A: Gen. 2008, 335, 241-251
66. Huang, Y.; Liu, S.; Lin, Z.; Li, W.; Li, X.; Cao, R. Facile Synthesis of Palladium Nanoparticles Encapsulated in Amine-Functionalized Mesoporous Metal-Organic Frameworks and Catalytic for Dehalogenation of Aryl Chlorides J. Catal. 2012, 292, 111-117
67. Yuan, S.; Kirklin, S.; Dorney, B.; Liu, D.; Yu, L. Nanoporous Polymers Containing Stereocontorted Cores for Hydrogen Storage Macromolecules 2009, 42, 1554-1559
68. Leininger, S.; Stang, P. J.; Huang, S. P. Synthesis and Characterization of Organoplatinum Dendrimers with 1,3,5-Triethynylbenzene Building Blocks Organometallics 1998, 17, 3981-3987
69. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; et al. Gaussian 03, Revision D.02; Gaussian, Inc.: Wallingford, CT, 2004.