Silicon phthalocyanine covalently functionalized N-doped ultrasmall reduced graphene oxide decorated with Pt nanoparticles for hydrogen evolution from water

ACS Applied Materials and Interfaces

Volumn 7, Issue 6, 2015, Pages 3732-3741

  Huang, Jie ^a,b   Wu, Yijie ^a   Wang, Dandan ^a   Ma, Yufei ^b   Yue, Zongkuan ^a   Lu, Yongtao ^a   Zhang, Mengxin ^b   Zhang, Zhijun ^b   Yang, Ping ^a  

^a SOOCHOW UNIVERSITY   (China)

^b SUZHOU INSTITUTE OF NANO TECH AND NANO BIONICS   (China)

Author keywords

hydrogen evolution; N doped ultrasmall graphene; photocatalysis; silicon phthalocyanine

Indexed keywords

ATOMIC FORCE MICROSCOPY; CATALYST ACTIVITY; DOPING (ADDITIVES); FLUORESCENCE; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GRAPHENE; HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY; HYDROGEN PRODUCTION; IRRADIATION; LIGHT; METAL NANOPARTICLES; PHOTOCATALYSIS; PHOTOCATALYTIC ACTIVITY; PHOTOELECTRON SPECTROSCOPY; PLATINUM; QUENCHING; REDUCED GRAPHENE OXIDE; ULTRAVIOLET VISIBLE SPECTROSCOPY; X RAY PHOTOELECTRON SPECTROSCOPY;

1 ,3-DIPOLARCYCLOADDITION; AZOMETHINE YLIDES; HYDROGEN EVOLUTION; PHOTO-INDUCED ELECTRON TRANSFER; PHOTOCURRENT RESPONSE; ULTRA-SMALL; UV-VIS SPECTROSCOPY; VISIBLE-LIGHT IRRADIATION;

SILICON;

EID: 84923242859     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am508476d     Document Type: Article

References (72)

1. 4 Composites for Enhanced Hydrogen Evolution Performance ACS Appl. Mater. Interfaces 2014, 6, 13841-13849
2. 4 Photocatalyst Green Chem. 2011, 13, 2500-2506
3. Qu, Y. Q.; Duan, X. F. Progress, Challenge and Perspective of Heterogeneous Photocatalysts Chem. Soc. Rev. 2013, 42, 2568-2580
4. 3 Microspheres for Photocatalytic Water Splitting Int. J. Hydrogen Energy 2014, 39, 13481-13485
5. 2 Evolution ACS Sustainable Chem. Eng. 2014, 2, 1429-1438
6. Zhang, G. G.; Wang, X. C. A Facile Synthesis of Covalent Carbon Nitride Photocatalysts by Co-Polymerization of Urea and Phenylurea for Hydrogen Evolution J. Catal. 2013, 307, 246-253
7. Zhang, W. X.; Cui, J. C.; Tao, C. A.; Wu, Y. G.; Li, Z. P.; Ma, L.; Wen, Y. Q.; Li, G. T. A Strategy for Producing Pure Single-Layer Graphene Sheets Based on a Confined Self-Assembly Approach Angew. Chem., Int. Ed. 2009, 48, 5864-5868
8. Li, D.; Müller, M. B.; Gilje, S.; Kaner, R. B.; Wallace, G. G. Processable Aqueous Dispersions of Graphene Nanosheets Nat. Nanotechnol. 2008, 3, 101-105
9. 4 Hybrid Functional Material for the Electrocatalytic Reduction of Oxygen ACS Appl. Mater. Interfaces 2014, 6, 2692-2699
10. Wang, X.; Zhi, L. J.; Müllen, K. Transparent, Conductive Graphene Electrodes for Dye-Sensitized Solar Cells Nano Lett. 2008, 8, 323-331
11. Kongkanand, A.; Domínguez, R. M.; Kamat, P. V. Single Wall Carbon Nanotube Scaffolds for Photoelectrochemical Solar Cells. Capture and Transport of Photogenerated Electrons Nano Lett. 2007, 7, 676-688
12. Guldi, D. M.; Rahman, G. M. A.; Sgobba, V.; Kotov, N. A.; Bonifazi, D.; Prato, M. CNT-CdTe Versatile Donor-Acceptor Nanohybrids J. Am. Chem. Soc. 2006, 128, 2315-2323
13. Farrow, B.; Kamat, P. V. CdSe Quantum Dot Sensitized Solar Cells. Shuttling Electrons through Stacked Carbon Nanocups J. Am. Chem. Soc. 2009, 131, 11124-11131
14. Rao, C. N. R.; Sood, A. K.; Subrahmanyam, K. S.; Govindaraj, A. Graphene: The New Two-Dimensional Nanomaterial Angew. Chem., Int. Ed. 2009, 48, 7752-7777
15. Wei, D. C.; Liu, Y. Q.; Wang, Y.; Zhang, H. L.; Huang, L. P.; Yu, G. Synthesis of N-Doped Graphene by Chemical Vapor Deposition and Its Electrical Properties Nano Lett. 2009, 9, 1752-1758
16. Li, X. L.; Wang, H. L.; Robinson, J. T.; Sanchez, H.; DianKov, G.; Dai, H. J. Simultaneous Nitrogen Doping and Reduction of Graphene Oxide J. Am. Chem. Soc. 2009, 131, 15939-15944
17. Qu, L. T.; Liu, Y.; Baek, J. B.; Dai, L. M. Nitrogen-Doped Graphene as Efficient Metal-Free Electrocatalyst for Oxygen Reduction in Fuel Cells ACS Nano 2010, 4, 1321-1326
18. Zhu, M. S.; Li, Z.; Xiao, B.; Lu, Y. T.; Du, Y. K.; Yang, P.; Wang, X. M. Surfactant Assistance in Improvement of Photocatalytic Hydrogen Production with the Porphyrin Noncovalently Functionalized Graphene Nanocomposite ACS Appl. Mater. Interfaces 2013, 5, 1732-1740
19. Yin, H. J.; Tang, H. J.; Wang, D.; Gao, Y.; Tang, Z. Y. Facile Synthesis of Surfactant-Free Au Cluster/Graphene Hybrids for High-Performance Oxygen Reduction Reaction ACS Nano 2012, 6, 8288-8297
20. Zhang, J.; Zhao, F.; Zhang, Z. P.; Chen, N.; Qu, L. T. Dimension-Tailored Functional Graphene Structures for Energy Conversion and Storage Nanoscale 2013, 5, 3112-3126
21. Li, H. Y.; Liu, S.; Tian, J. Q.; Wang, L.; Lu, W. B.; Luo, Y. L.; Asiri, A. M.; Al-Youbi, A. O.; Sun, X. P. Ternary Nanocomposites of Porphyrin, Angular Au Nanoparticles and Reduced Graphene Oxide: Photocatalytic Synthesis and Enhanced Photocurrent Generation ChemCatChem 2012, 4, 1079-1083
22. Chen, Y. Z.; Huang, Z. H.; Yue, M. B.; Kang, F. Y. Integrating Porphyrin Nanoparticles into a 2D Graphene Matrix for Free-Standing Nanohybrid Films with Enhanced Visible-Light Photocatalytic Activity Nanoscale 2014, 6, 978-985
23. Khan, Z.; Chetia, T. R.; Vardhaman, A. K.; Barpuzary, D.; Sastri, C. V.; Qureshi, M. Visible Light Assisted Photocatalytic Hydrogen Generation and Organic Dye Degradation by CdS-Metal Oxide Hybrids in Presence of Graphene Oxide RSC Adv. 2012, 2, 12122-12128
24. El-Khouly, M. E.; Kim, J. H.; Kay, K. Y.; Choi, C. S.; Ito, O.; Fukuzumi, S. Synthesis and Photoinduced Intramolecular Processes of Light-Harvesting Silicon Phthalocyanine-Naphthalenediimide-Fullerene Connected Systems Chem. - Eur. J. 2009, 15, 5301-5310
25. Linssen, T. G.; Dürr, K.; Hanack, M.; Hirsch, A. A Green Fullerene: Synthesis and Electrochemistry of a Diels-Alder Adduct of [60]Fullerene with a Phthalocyanine J. Chem. Soc. Chem. Commun. 1995, 103-104
26. D'Souza, F.; Ito, O. Photoinduced Electron Transfer in Supramolecular Systems of Fullerenes Functionalized with Ligands Capable of Binding to Zinc Porphyrins and Zinc Phthalocyanines Coord. Chem. Rev. 2005, 249, 1410-1422
27. Fukuzumi, S.; Ohkubo, K.; Ortiz, J.; Gutiérrez, A. M.; Fernández-Lázaro, F.; Sastre-Santos, á. Formation of a Long-Lived Charge-Separated State of a Zinc Phthalocyanine-Perylenediimide Dyad by Complexation with Magnesium Ion Chem. Commun. 2005, 41, 3814-3816
28. Xue, J. G.; Uchida, S.; Rand, B. P.; Forrest, S. R. 4.2% Efficient Organic Photovoltaic Cells with Low Series Resistances Appl. Phys. Lett. 2004, 84, 3013-3015
29. Calvete, M. J. F.; Dini, D.; Flom, S. R.; Hanack, M.; Pong, R. G. S.; Shirk, J. S. Synthesis of a Bisphthalocyanine and Its Nonlinear Optical Properties Eur. J. Org. Chem. 2005, 2005, 3499-3509
30. Bottari, G.; Torre, G.; Guldi, D. M.; Torres, T. Covalent and Noncovalent Phthalocyanine-Carbon Nanostructure Systems: Synthesis, Photoinduced Electron Transfer, and Application to Molecular Photovoltaics Chem. Rev. 2010, 110, 6768-6816
31. 2 Films by a Near-IR-Absorbing Unsymmetrical Zinc Phthalocyanine Angew. Chem., Int. Ed. 2007, 46, 373-376
32. 2 under Visible Light Energy Environ. Sci. 2010, 3, 1789-1795
33. Takanabe, K.; Kamata, K.; Wang, X.; Antonietti, M.; Kubota, J.; Domen, K. Photocatalytic Hydrogen Evolution on Dye-Sensitized Mesoporous Carbon Nitride Photocatalyst with Magnesium Phthalocyanine Phys. Chem. Chem. Phys. 2010, 12, 13020-13025
34. Yeh, T. F.; Teng, C. Y.; Chen, S. J.; Teng, H. Nitrogen-Doped Graphene Oxide Quantum Dots as Photocatalysts for Overall Water-Splitting under Visible Light Illumination Adv. Mater. 2014, 26, 3297-3303
35. Peng, J.; Gao, W.; Gupta, B. K.; Liu, Z.; Romero-Aburto, R.; Ge, L. H.; Song, L.; Alemany, L. B.; Zhan, X. B.; Gao, G. H.; Vithayathil, S. A.; Kaipparettu, B. A.; Marti, A. A.; Hayashi, T.; Zhu, J. J.; Ajayan, P. M. Graphene Quantum Dots Derived from Carbon Fibers Nano Lett. 2012, 12, 844-849
36. Jiang, B. J.; Tian, C. G.; Wang, L.; Sun, L.; Chen, C.; Nong, X. Z.; Qiao, Y. J.; Fu, H. G. Highly Concentrated, Stable Nitrogen-Doped Graphene for Supercapacitors: Simultaneous Doping and Reduction Appl. Surf. Sci. 2012, 258, 3438-3443
37. Quintana, M.; Spyrou, K.; Grzelczak, M.; Browne, W. R.; Rudolf, P.; Ptato, M. Functionalization of Graphene via 1,3-Dipolar Cycloaddition ACS Nano 2010, 4, 3527-3533
38. Zhang, X. Y.; Hou, L. L.; Cnossen, A.; Coleman, A. C.; Ivashenko, O.; Rudolf, P.; Wees, B. J.; Browne, W. R.; Feringa, B. L. One-Pot Functionalization of Graphene with Porphyrin through Cycloaddition Reactions Chem. - Eur. J. 2011, 17, 8957-8964
39. Ragoussi, M. E.; Malig, J.; Katsukis, G.; Butz, B.; Spiecker, E.; Torre, G.; Torres, T.; Guldi, D. M. Linking Photo- and Redoxactive Phthalocyanines Covalently to Graphene Angew. Chem., Int. Ed. 2012, 51, 6421-6425
40. Martín-Gomis, L.; Ohkubo, K.; Fernández-Lázaro, F.; Fukuzumi, S.; Sastre-Santos, A. Synthesis and Photophysical Studies of a New Nonaggregated C60-Silicon Phthalocyanine-C60 Triad Org. Lett. 2007, 9, 3441-3444
41. El-Khouly, M. E.; Kang, E. S.; Kay, K. Y.; Choi, C. S.; Aaraki, Y.; Ito, O. Silicon-Phthalocyanine-Cored Fullerene Dendrimers: Synthesis and Prolonged Charge-Separated States with Dendrimer Generations Chem. - Eur. J. 2007, 13, 2854-2863
42. Li, Z.; Chen, Y. J.; Du, Y. K.; Wang, X. M.; Yang, P.; Zhen, J. W. Triphenylamine-Functionalized Graphene Decorated with Pt Nanoparticles and Its Application in Photocatalytic Hydrogen Production Int. J. Hydrogen Energy 2012, 37, 4880-4888
43. Kraeutler, B.; Bard, A. J. Heterogeneous Photocatalytic Preparation of Supported Catalysts. Photodeposition of Platinum on Titanium Dioxide Powder and Other Substrates J. Am. Chem. Soc. 1978, 100, 4317-4318
44. Huang, J.; Zhang, L. M.; Chen, B.; Ji, N.; Chen, F. H.; Zhang, Y.; Zhang, Z. J. Nanocomposites of Size-Controlled Gold Nanoparticles and Graphene Oxide: Formation and Applications in SERS and Catalysis Nanoscale 2010, 2, 2733-2738
45. Huang, J.; Zong, C.; Shen, H.; Liu, M.; Chen, B.; Ren, B.; Zhang, Z. J. Mechanism of Cellular Uptake of Graphene Oxide Studied by Surface-Enhanced Raman Spectroscopy Small 2012, 8, 2577-2584
46. Si, Y.; Samulski, E. T. Synthesis of Water Soluble Graphene Nano Lett. 2008, 8, 1679-1682
47. Bose, S.; Kuila, T.; Mishra, A. K.; Kim, N. H.; Lee, J. H. Dual Role of Glycine as a Chemical Functionalizer and a Reducing Agent in the Preparation of Graphene: An Environmentally Friendly Method J. Mater. Chem. 2012, 22, 9696-9703
48. Zhang, H.; Kuila, T.; Kim, N. H.; Yu, D. S.; Lee, J. H. Simultaneous Reduction, Exfoliation, and Nitrogen Doping of Graphene Oxide via a Hydrothermal Reaction for Energy Storage Electrode Materials Carbon 2014, 69, 66-78
49. Orthmann, E.; Wegner, G. Catalysis of the Polycondensation of Dihydroxysiliconphthalocyanine Makromol. Chem. Rapid Commun. 1986, 7, 243-247
50. Wijekoon, W. M. K. P.; Kama, S. P. Comparative Raman, Infrared and Optical Spectroscopic Studies of Thin Films of an Axially Substituted Phthalocyanine Compound J. Raman Spectrosc. 1994, 25, 949-952
51. Shin, H.-J.; Kim, K. K.; Benayad, A.; Yoon, S.-M.; Park, H. K.; Jung, I.-S.; Jin, M. H.; Jeong, H.-K.; Kim, J. M.; Choi, J.-Y.; Lee, Y. H. Efficient Reduction of Graphite Oxide by Sodium Borohydride and Its Effect on Electrical Conductance Adv. Funct. Mater. 2009, 19, 1987-1992
52. Chunder, A.; Pal, T.; Khondaker, S. I.; Zhai, L. Reduced Graphene Oxide/Copper Phthalocyanine Composite and Its Optoelectrical Properties J. Phys. Chem. C 2010, 114, 15129-15135
53. Malig, J.; Jux, N.; Kiessling, D.; Cid, J.-J.; Vázquez, P.; Torres, T.; Guldi, D. M. Towards Tunable Graphene/Phthalocyanine-PPV Hybrid Systems Angew. Chem., Int. Ed. 2011, 50, 3561-3565
54. Reddy, A. L. M.; Srivastava, A.; Gowda, S. R.; Gullapalli, H.; Dubey, M.; Ajayan, P. M. Synthesis of Nitrogen-Doped Graphene Films for Lithium Battery Application ACS Nano 2010, 4, 6337-6342
55. Casanovas, J.; Ricart, J. M.; Rubio, J.; Illas, F.; Jiménez-Mateos, J. M. Origin of the Large N 1s Binding Energy in X-ray Photoelectron Spectra of Calcined Carbonaceous Materials J. Am. Chem. Soc. 1996, 118, 8071-8076
56. Li, Z. Y.; Lieberman, M. XPS and SERS Study of Silicon Phthalocyanine Monolayers: Umbrella vs Octopus Design Strategies for Formation of Oriented SAMs Langmuir 2001, 17, 4887-4894
57. Brédas, J. L.; Thémans, B.; André, J. M. Bipolarons in Polypyrrole Chains Phys. Rev. B 1983, 27, 7827-7830
58. Torre, G. De la; Vázquez, P.; Agullo-López, F.; Torres, T. Role of Structural Factors in the Nonlinear Optical Properties of Phthalocyanines and Related Compounds Chem. Rev. 2004, 104, 3723-3750
59. Biyiklioʇlu, Z.; Cakir, D. Novel Axially Disubstituted Non-Aggregated Silicon Phthalocyanines Spectrochim. Acta, Part A 2012, 98, 178-182
60. Tackley, D. R.; Dent, G.; Smith, W. E. Phthalocyanines: Structure and Vibrations Phys. Chem. Chem. Phys. 2001, 3, 1419-1426
61. Wang, A. J.; Long, L. L.; Zhao, W.; Song, Y. L.; Humphrey, M. G.; Cifuentes, M. P.; Wu, X. Z.; Fu, Y. S.; Zhang, D. D.; Li, X. F.; Zhang, C. Increased Optical Nonlinearities of Graphene Nanohybrids Covalently Functionalized by Axially-Coordinated Porphyrins Carbon 2013, 53, 327-338
62. Robinson, J. T.; Tabakman, S. M.; Liang, Y. Y.; Wang, H. L.; Casalongue, H. S.; Vinh, D.; Dai, H. J. Ultrasmall Reduced Graphene Oxide with High Near-Infrared Absorbance for Photothermal Therapy J. Am. Chem. Soc. 2011, 133, 6825-6831
63. Kim, J. H.; El-khouly, M. E.; Araki, Y.; Ito, O.; Kay, K. Y. Photoinduced Processes of Subphthalocyanine-Diazobenzene-Fullerene Triad as an Efficient Excited Energy Transfer System Chem. Lett. 2008, 37, 544-545
64. Wojcik, A.; Kamat, P. V. Reduced Graphene Oxide and Porphyrin. An Interactive Affair in 2-D ACS Nano 2010, 4, 6697-6706
65. Zhang, X. Q.; Feng, Y. Y.; Tang, S. D.; Feng, W. Preparation of a Graphene Oxide-Phthalocyanine Hybrid through Strong π-π Interactions Carbon 2010, 48, 211-216
66. y Decorated Graphene Nanohybrid Photocatalyst for Highly Efficient Photocatalytic Hydrogen Evolution Chem. Commun. 2014, 50, 5037-5039
67. 2-Modified Cds/Reduced Graphene Oxide Nanocomposite with Enhanced Photocatalytic Activity for Hydrogen Production under Visible Light Irradiation J. Phys. Chem. C 2014, 118, 22896-22903
68. McNeill, C. R.; Hwang, I.; Greenham, N. C. Photocurrent Transients in All-Polymer Solar Cells: Trapping and Detrapping Effects J. Appl. Phys. 2009, 106, 024507
69. Xu, H.; Yu, D. H.; Liu, L. L.; Yan, P. F.; Jia, L. W.; Li, G. M.; Yue, Z. Y. Small Molecular Glasses Based on Multiposition Encapsulated Phenyl Benzimidazole Iridium(III) Complexes: Toward Efficient Solution-Processable Host-Free Electrophosphorescent Diodes J. Phys. Chem. B 2010, 114, 141-150
70. Yang, J. H.; Wang, D.; Han, H. X.; Li, C. Roles of Cocatalysts in Photocatalysis and Photoelectrocatalysis Acc. Chem. Res. 2013, 46, 1900-1909
71. Li, Q.; Guo, B. D.; Yu, J. G.; Ran, J. R.; Zhang, B. H.; Yan, H. J.; Gong, J. R. Highly Efficient Visible-Light-Driven Photocatalytic Hydrogen Production of CdS-Cluster-Decorated Graphene Nanosheets J. Am. Chem. Soc. 2011, 133, 10878-10884
72. Kamat, P. V. Graphene-Based Nanoarchitectures. Anchoring Semiconductor and Metal Nanoparticles on a Two-Dimensional Carbon Support J. Phys. Chem. Lett. 2009, 1, 520-527