Ordered-mesoporous-carbon-bonded cobalt phthalocyanine: A bioinspired catalytic system for controllable hydrogen peroxide activation

ACS Applied Materials and Interfaces

Volumn 6, Issue 8, 2014, Pages 5869-5876

  Li, Nan ^a   Lu, Wangyang ^a   Pei, Kemei ^a   Yao, Yuyuan ^a   Chen, Wenxing ^a  

^a ZHEJIANG SCI TECH UNIVERSITY   (China)

Author keywords

bioinspired catalysis; cobalt phthalocyanine; hydrogen peroxide activation; ordered mesoporous carbon

Indexed keywords

AZO DYES; CARBON; CATALYSIS; COBALT; ENZYMES; FUNCTIONAL MATERIALS; HYDROGEN PEROXIDE; MESOPOROUS MATERIALS; PEROXIDES; PORPHYRINS; QUANTUM CHEMISTRY;

BIOINSPIRED CATALYSIS; COBALT PHTHALOCYANINE; COBALT TETRAAMINOPHTHALOCYANINE; DODECYLBENZENE SULFONATES; ENHANCED CATALYTIC ACTIVITY; FUNCTIONAL MODIFICATION; HYDROGEN PEROXIDE ACTIVATION; ORDERED MESOPOROUS CARBON;

CATALYTIC OXIDATION;

CARBON; COBALT PHTHALOCYANINE; HYDROGEN PEROXIDE; INDOLE DERIVATIVE; METALLOPORPHYRIN; ORGANOMETALLIC COMPOUND; PEROXIDASE;

CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; POROSITY;

CARBON; CATALYSIS; HYDROGEN PEROXIDE; INDOLES; METALLOPORPHYRINS; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PEROXIDASE; POROSITY;

EID: 84899579745     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am500766a     Document Type: Article

References (52)

1. Brégeault, J. M. Transition-Metal Complexes for Liquid-Phase Catalytic Oxidation: Some Aspects of Industrial Reactions and of Emerging Technologies Dalton Trans. 2003, 3289-3302
2. Mahammed, A.; Gross, Z. Albumin-Conjugated Corrole Metal Complexes: Extremely Simple Yet Very Efficient Biomimetic Oxidation Systems J. Am. Chem. Soc. 2005, 127, 2883-2887
3. Sharma, R. K.; Gulati, S.; Pandey, A.; Adholeya, A. Novel, Efficient and Recyclable Silica Based Organic-Inorganic Hybrid Nickel Catalyst for Degradation of Dye Pollutants in a Newly Designed Chemical Reactor Appl. Catal., B 2012, 125, 247-258
4. Piera, J.; Bäckvall, J. E. Catalytic Oxidation of Organic Substrates by Molecular Oxygen and Hydrogen Peroxide by Multistep Electron Transfer-A Biomimetic Approach Angew. Chem., Int. Ed. 2008, 47, 3506-3523
5. Sorokin, A. B. Phthalocyanine Metal Complexes in Catalysis Chem. Rev. 2013, 113, 8152-8191
6. Collins, T. J. TAML Oxidant Activators: A New Approach to the Activation of Hydrogen Peroxide for Environmentally Significant Problems Acc. Chem. Res. 2002, 35, 782-790
7. Berglund, G. I.; Carlsson, G. H.; Smith, A. T.; Szöke, H.; Henriksen, A.; Hajdu, J. The Catalytic Pathway of Horseradish Peroxidase at High Resolution Nature 2002, 417, 463-468
8. Filizola, M.; Loew, G. H. Role of Protein Environment in Horseradish Peroxidase Compound I Formation: Molecular Dynamics Simulations of Horseradish Peroxidase-HOOH Complex J. Am. Chem. Soc. 2000, 122, 18-25
9. Reid, T. J., III; Murthy, M. R.; Sicignano, A.; Tanaka, N.; Musick, W. D.; Rossmann, M. G. Structure and Heme Environment of Beef Liver Catalase at 2.5 Å Resolution Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 4767-4771
10. Ghosh, A.; Mitchell, D. A.; Chanda, A.; Ryabov, A. D.; Popescu, D. L.; Upham, E. C.; Collins, G. J.; Collins, T. J. Catalase-Peroxidase Activity of Iron(III)-TAML Activators of Hydrogen Peroxide J. Am. Chem. Soc. 2008, 130, 15116-15126
11. IV-Oxo Species J. Am. Chem. Soc. 2005, 127, 6573-6582
12. 4 Nanorods-Reduced Graphene Oxide with Intrinsic Peroxidase-Like Activity and Catalysis in the Degradation of Methylene Blue ACS Appl. Mater. Interfaces 2013, 5, 3809-3815
13. Ball, Z. T. Designing Enzyme-like Catalysts: A Rhodium(II) Metallopeptide Case Study Acc. Chem. Res. 2013, 46, 560-570
14. Kuwabara, J.; Stern, C. L.; Mirkin, C. A. A Coordination Chemistry Approach to a Multieffector Enzyme Mimic J. Am. Chem. Soc. 2007, 129, 10074-10075
15. Wulff, G. Enzyme-like Catalysis by Molecularly Imprinted Polymers Chem. Rev. 2002, 102, 1-28
16. Zhuang, X.; Wan, Y.; Feng, C.; Shen, Y.; Zhao, D. Highly Efficient Adsorption of Bulky Dye Molecules in Wastewater on Ordered Mesoporous Carbons Chem. Mater. 2009, 21, 706-716
17. Liang, C.; Li, Z.; Dai, S. Mesoporous Carbon Materials: Synthesis and Modification Angew. Chem., Int. Ed. 2008, 47, 3696-3717
18. 2 Batteries ACS Appl. Mater. Interfaces 2013, 5, 13426-13431
19. 2-Ordered Mesoporous Carbon Nanocomposite as an Anode Material for Lithium-Ion Batteries ACS Appl. Mater. Interfaces 2013, 5, 2182-2187
20. Zhou, Z.; Hartmann, M. Progress in Enzyme Immobilization in Ordered Mesoporous Materials and Related Applications Chem. Soc. Rev. 2013, 42, 3894-3912
21. Lu, W.; Li, N.; Chen, W.; Yao, Y. The Role of Multiwalled Carbon Nanotubes in Enhancing the Catalytic Activity of Cobalt Tetraaminophthalocyanine for Oxidation of Conjugated Dyes Carbon 2009, 47, 3337-3345
22. Lu, W.; Li, N.; Bao, S.; Chen, W.; Yao, Y. The Coupling of Metallophthalocyanine with Carbon Nanotubes to Produce a Nanomaterial-Based Catalyst for Reaction-Controlled Interfacial Catalysis Carbon 2011, 49, 1699-1709
23. Lu, W.; Chen, W.; Li, N.; Xu, M.; Yao, Y. Oxidative Removal of 4-Nitrophenol Using Activated Carbon Fiber and Hydrogen Peroxide to Enhance Reactivity of Metallophthalocyanine Appl. Catal., B 2009, 87, 146-151
24. Chen, W.; Lu, W.; Yao, Y.; Xu, M. Highly Efficient Decomposition of Organic Dyes by Aqueous-Fiber Phase Transfer and in Situ Catalytic Oxidation Using Fiber-Supported Cobalt Phthalocyanine Environ. Sci. Technol. 2007, 41, 6240-6245
25. Wang, X.; Liang, C.; Dai, S. Facile Synthesis of Ordered Mesoporous Carbons with High Thermal Stability by Self-Assembly of Resorcinol-Formaldehyde and Block Copolymers under Highly Acidic Conditions Langmuir 2008, 24, 7500-7505
26. El-Merraoui, M.; Tamai, H.; Yasuda, H.; Kanata, T.; Mondori, J.; Nadai, K.; Kaneko, K. Pore Structures of Activated Carbon Fibers from Organometallics/Pitch Composites by Nitrogen Adsorption Carbon 1998, 36, 1769-1776
27. Darmstadt, H.; Roy, C.; Kaliaguine, S.; Choi, S. J.; Ryoo, R. Surface Chemistry of Ordered Mesoporous Carbons Carbon 2002, 40, 2673-2683
28. Bazuła, P. A.; Lu, A. H.; Nitz, J. J.; Schüth, F. Surface and Pore Structure Modification of Ordered Mesoporous Carbons via a Chemical Oxidation Approach Microporous Mesoporous Mater. 2008, 108, 266-275
29. Tao, X.; Ma, W.; Zhang, T.; Zhao, J. Efficient Photooxidative Degradation of Organic Compounds in the Presence of Iron Tetrasulfophthalocyanine under Visible Light Irradiation Angew. Chem., Int. Ed. 2001, 40, 3014-3016
30. Chen, S. L.; Huang, X. J.; Xu, Z. K. Effect of a Spacer on Phthalocyanine Functionalized Cellulose Nanofiber Mats for Decolorizing Reactive Dye Wastewater Cellulose 2012, 19, 1351-1359
31. Afanasiev, P.; Kudrik, E. V.; Albrieux, F.; Briois, V.; Koifman, O. I.; Sorokin, A. B. Generation and Characterization of High-Valent Iron Oxo Phthalocyanines Chem. Commun. 2012, 48, 6088-6090
32. Kudrik, E. V.; Afanasiev, P.; Alvarez, L. X.; Du-bourdeaux, P.; Clémancey, M.; Latour, J.; Blondin, G.; Bouchu, D.; Albrieux, F.; Nefedov, S. E.; Sorokin, A. B. An N-Bridged High-Valent Diiron-Oxo Species on a Porphyrin Platform That Can Oxidize Methane Nat. Chem. 2012, 4, 1024-1029
33. Que, L.; Tolman, W. B. Biologically Inspired Oxidation Catalysis Nature 2008, 455, 333-340
34. Collman, J. P.; Sorrell, T. N.; Dawson, J. H.; Trudell, J. R.; Bunnenberg, E.; Djerassi, C. Magnetic Circular Dichroism of Ferrous Carbonyl Adducts of Cytochromes P-450 and P-420 and Their Synthetic Models: Further Evidence for Mercaptide as the Fifth Ligand to Iron Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 6-10
35. Werck-Reichhart, D.; Feyereisen, R. Cytochromes P450: A Success Story Genome Biol. 2000, 1, 3003.1-3003.9
36. Thomas, C. M.; Ward, T. R. Artificial Metalloenzymes: Proteins as Hosts for Enantioselective Catalysis Chem. Soc. Rev. 2005, 34, 337-346
37. Du, J.; Li, Q.; Li, W.; Lin, H.; Guo, G. Hexaaquacobalt(II) 4-Hydroxybenzenesulfonate Dehydrate Acta Crystallogr., Sect. E: Struct. Rep. Online 2007, E63, m2597-m2597
38. Couldwell, C.; Prout, K.; Robey, D.; Taylor, R. The Crystal and Molecular Structures of Hexaaquacopper(II) Benzenesulphonate, Toluene-4-sulphonate and D-Camphor-10-sulphonate Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1978, B34, 1491-1499
39. Kosnic, E. J.; McClymont, E. L.; Hodder, R. A.; Squattrito, P. J. Synthesis and Structures of Layered Metal Sulfonate Salts Inorg. Chim. Acta 1992, 201, 143-151
40. Cai, J.; Chen, C.; Liao, C.; Feng, X.; Chen, X. Solid-State Structures of Group 1 and Group 2 Metal 1,5-Naphthalenedisulfonates: Systematic Investigation of Lamellar Three-Dimensional Networks Constructed by Metal Arenedisulfonate Acta Crystallogr., Sect. B: Struct. Sci. 2001, B57, 520-530
41. 2 N,N′)copper(II) Dehydrate Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, E65, m1678-m1679
42. Murase, I.; Vuckovic, G.; Kodera, M.; Harada, H.; Matsumoto, N.; Kida, S. Synthesis and Characterization of Copper(II), Nickel(II), and Cobalt(II) Binuclear Complexes with a New Tricyclic Octadentate Ligand, 1,5,8,12,15,19,22,26-Octaazatricyclo[17.9.2.25,15]dotriacontane (tcoa): Trapping of Carbon Dioxide in a Neutral Aqueous Solution Inorg. Chem. 1991, 30, 728-733
43. 2 Acta Chem. Scand. 1993, 47, 1173-1178
44. Cocker, T. M.; Bachman, R. E. Isolation and Crystal Structure of a Novel Dinuclear Nickel(II) O-bound Sulfinate from the Oxidation of 2,2′-Bipyridine-1,2-benzenedithiolatonickel(II) Chem. Commun. 1999, 875-876
45. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Heme-Containing Oxygenases Chem. Rev. 1996, 96, 2841-2888
46. Gupta, G.; Slanac, D. A.; Kumar, P.; Wiggins-Camacho, J. D.; Wang, X.; Swinnea, S.; More, K. L.; Dai, S.; Stevenson, K. J.; Johnston, K. P. Highly Stable and Active Pt-Cu Oxygen Reduction Electrocatalysts Based on Mesoporous Graphitic Carbon Supports Chem. Mater. 2009, 21, 4515-4526
47. Pan, Z.; Wang, Q.; Sheng, X.; Horner, J. H.; Newcomb, M. Highly Reactive Porphyrin-Iron-Oxo Derivatives Produced by Photolyses of Metastable Porphyrin-Iron(IV) Diperchlorates J. Am. Chem. Soc. 2009, 131, 2621-2628
48. Rittle, J.; Green, M. T. Cytochrome P450 Compound I: Capture, Characterization, and C-H Bond Activation Kinetics Science 2010, 330, 933-937
49. Sorokin, A. B.; Tuel, A. Metallophthalocyanine Functionalized Silicas: Catalysts for the Selective Oxidation of Aromatic Compounds Catal. Today 2000, 57, 45-59
50. 2 Dalton Trans. 2011, 40, 701-710
51. tBuOOH in the Presence of Supported Iron Phthalocyanine New J. Chem. 2009, 33, 1031-1037
52. Afanasiev, P.; Bouchu, D.; Kudrik, E. V.; Millet, J. J. M.; Sorokin, A. B. Stable N-Bridged Diiron(IV) Phthalocyanine Cation Radical Complexes: Synthesis and Properties Dalton Trans. 2009, 9828-9836