Electron transport properties through graphene oxide-cobalt phthalocyanine complexes

Journal of Physical Chemistry C

Volumn 117, Issue 45, 2013, Pages 23664-23675

  Cárdenas Jirón, Gloria I ^a   León Plata, Paola ^b   Cortes Arriagada, Diego ^a   Seminario, Jorge M ^b,c  

^a UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

^b Department of Electrical and Computer Engineering   (United States)

^c TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER PROPERTIES; COBALT PHTHALOCYANINE; FRONTIER MOLECULAR ORBITALS; FUNCTIONALIZATIONS; FUNCTIONALIZED GRAPHENE; HYDROXYL FUNCTIONALIZATION; INTRINSIC ELECTRICAL PROPERTY; PHTHALOCYANINE COMPLEXES;

ADSORPTION; BINDING ENERGY; ELECTRIC PROPERTIES; ELECTRON TRANSPORT PROPERTIES; HYBRID MATERIALS; MOLECULAR ORBITALS;

GRAPHENE;

EID: 84887869152     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp405951p     Document Type: Article

References (96)

1. Novoselov, K. S.; Jiang, D.; Schedin, F.; Booth, T. J.; Khotkevich, V. V.; Morozov, S. V.; Geim, A. K. Two-Dimensional Atomic Crystals Proc. Natl. Acad. Sci. U.S.A. 2005, 102 (30) 10451-10453
2. Novoselov, K. S.; Geim, A. K.; Morozov, S. V.; Jiang, D.; Zhang, Y.; Dubonos, S. V.; Grigorieva, I. V.; Firsov, A. A. Electric Field Effect in Atomically Thin Carbon Films Science 2004, 306 (5696) 666-669
3. Geim, A. K.; Novoselov, K. S. The Rise of Graphene Nat. Mater. 2007, 6 (3) 183-191
4. Lee, C.; Wei, X.; Kysar, J. W.; Hone, J. Measurement of the Elastic Properties and Intrinsic Strength of Monolayer Graphene Science 2008, 321 (5887) 385-388
5. Balandin, A. A.; Ghosh, S.; Bao, W.; Calizo, I.; Teweldebrhan, D.; Miao, F.; Lau, C. N. Superior Thermal Conductivity of Single-Layer Graphene Nano Lett. 2008, 8 (3) 902-907
6. Stankovich, S.; Dikin, D. A.; Dommett, G. H. B.; Kohlhaas, K. M.; Zimney, E. J.; Stach, E. A.; Piner, R. D.; Nguyen, S. T.; Ruoff, R. S. Graphene-Based Composite Materials Nature 2006, 442 (7100) 282-286
7. Liang, M.; Zhi, L. Graphene-Based Electrode Materials for Rechargeable Lithium Batteries J. Mater. Chem. 2009, 19 (33) 5871-5878
8. Yong-Hui, Z.; Ya-Bin, C.; Kai-Ge, Z.; Cai-Hong, L.; Jing, Z.; Hao-Li, Z.; Yong, P. Improving Gas Sensing Properties of Graphene by Introducing Dopants and Defects: A First-Principles Study Nanotechnology 2009, 20 (18) 185504
9. Kang, X.; Wang, J.; Wu, H.; Liu, J.; Aksay, I. A.; Lin, Y. A Graphene-Based Electrochemical Sensor for Sensitive Detection of Paracetamol Talanta 2010, 81 (3) 754-759
10. Heersche, H. B.; Jarillo-Herrero, P.; Oostinga, J. B.; Vandersypen, L. M. K.; Morpurgo, A. F. Bipolar Supercurrent in Graphene Nature 2007, 446 (7131) 56-59
11. Sofo, J. O.; Chaudhari, A. S.; Barber, G. D. Graphane: A Two-Dimensional Hydrocarbon Phys. Rev. B 2007, 75 (15) 153401
12. Hashimoto, A.; Suenaga, K.; Gloter, A.; Urita, K.; Iijima, S. Direct Evidence for Atomic Defects in Graphene Layers Nature 2004, 430 (7002) 870-873
13. 60 and Some Related Species Chem. Phys. Lett. 1986, 128 (5-6) 501-503
14. El-Barbary, A. A.; Telling, R. H.; Ewels, C. P.; Heggie, M. I.; Briddon, P. R. Structure and Energetics of the Vacancy in Graphite Phys. Rev. B 2003, 68 (14) 144107
15. Banhart, F.; Kotakoski, J.; Krasheninnikov, A. V. Structural Defects in Graphene ACS Nano 2010, 5 (1) 26-41
16. Geim, A. K.; Kim, P. Carbon Wonderland Sci. Am. 2008, 90-97
17. Hummers, W. S.; Offeman, R. E. Preparation of Graphitic Oxide J. Am. Chem. Soc. 1958, 80 (6) 1339-1339
18. Niyogi, S.; Bekyarova, E.; Itkis, M. E.; McWilliams, J. L.; Hamon, M. A.; Haddon, R. C. Solution Properties of Graphite and Graphene J. Am. Chem. Soc. 2006, 128 (24) 7720-7721
19. Lerf, A.; He, H.; Forster, M.; Klinowski, J. Structure of Graphite Oxide Revisited J. Phys. Chem. B 1998, 102 (23) 4477-4482
20. 13C-Labeled Graphite Oxide Science 2008, 321 (5897) 1815-1817
21. Cote, L. J.; Kim, F.; Huang, J. Langmuir-Blodgett Assembly of Graphite Oxide Single Layers J. Am. Chem. Soc. 2008, 131 (3) 1043-1049
22. Schniepp, H. C.; Li, J.-L.; McAllister, M. J.; Sai, H.; Herrera-Alonso, M.; Adamson, D. H.; Prud'homme, R. K.; Car, R.; Saville, D. A.; Aksay, I. A. Functionalized Single Graphene Sheets Derived from Splitting Graphite Oxide J. Phys. Chem. B 2006, 110 (17) 8535-8539
23. Pandey, D.; Reifenberger, R.; Piner, R. Scanning Probe Microscopy Study of Exfoliated Oxidized Graphene Sheets Surf. Sci. 2008, 602 (9) 1607-1613
24. Yan, J.-A.; Chou, M. Y. Oxidation Functional Groups on Graphene: Structural and Electronic Properties Phys. Rev. B 2010, 82 (12) 125403
25. Zhiping, X.; Kun, X. Engineering Graphene by Oxidation: A First-Principles Study Nanotechnology 2010, 21 (4) 045704
26. Hernández Rosas, J.; Ramírez Gutiérrez, R.; Escobedo-Morales, A.; Chigo Anota, E. First Principles Calculations of the Electronic and Chemical Properties of Graphene, Graphane, and Graphene Oxide J. Mol. Model. 2011, 17 (5) 1133-1139
27. Zhu, Y.; Murali, S.; Cai, W.; Li, X.; Suk, J. W.; Potts, J. R.; Ruoff, R. S. Graphene and Graphene Oxide: Synthesis, Properties, and Applications Adv. Mater. 2010, 22 (35) 3906-3924
28. Ghaderi, N.; Peressi, M. First-Principle Study of Hydroxyl Functional Groups on Pristine, Defected Graphene, and Graphene Epoxide J. Phys. Chem. C 2010, 114 (49) 21625-21630
29. Al-Aqtash, N.; Vasiliev, I. Ab Initio Study of Carboxylated Graphene J. Phys. Chem. C 2009, 113 (30) 12970-12975
30. Yoon, H. J.; Jun, D. H.; Yang, J. H.; Zhou, Z.; Yang, S. S.; Cheng, M. M.-C. Carbon Dioxide Gas Sensor Using a Graphene Sheet Sens. Actuators, B 2011, 157 (1) 310-313
31. 3 Nanopore Sensors for Sensitive Detection of DNA and DNA-Protein Complexes ACS Nano 2011, 6 (1) 441-450
32. Ganhua, L.; Leonidas, E. O.; Junhong, C. Reduced Graphene Oxide for Room-Temperature Gas Sensors Nanotechnology 2009, 20 (44) 445502
33. Sundaram, R. S.; Gómez-Navarro, C.; Balasubramanian, K.; Burghard, M.; Kern, K. Electrochemical Modification of Graphene Adv. Mater. 2008, 20 (16) 3050-3053
34. Robinson, J. T.; Perkins, F. K.; Snow, E. S.; Wei, Z.; Sheehan, P. E. Reduced Graphene Oxide Molecular Sensors Nano Lett. 2008, 8 (10) 3137-3140
35. Lu, C.-H.; Yang, H.-H.; Zhu, C.-L.; Chen, X.; Chen, G.-N. A Graphene Platform for Sensing Biomolecules Angew. Chem. 2009, 121 (26) 4879-4881
36. 2/Graphene Oxide Nanocomposite Talanta 2010, 82 (5) 1637-1641
37. Yin, Z.; Sun, S.; Salim, T.; Wu, S.; Huang, X.; He, Q.; Lam, Y. M.; Zhang, H. Organic Photovoltaic Devices Using Highly Flexible Reduced Graphene Oxide Films as Transparent Electrodes ACS Nano 2010, 4 (9) 5263-5268
38. Kim, R.-H.; Bae, M.-H.; Kim, D. G.; Cheng, H.; Kim, B. H.; Kim, D.-H.; Li, M.; Wu, J.; Du, F.; Kim, H.-S. Stretchable, Transparent Graphene Interconnects for Arrays of Microscale Inorganic Light Emitting Diodes on Rubber Substrates Nano Lett. 2011, 11 (9) 3881-3886
39. Wu, J.; Agrawal, M.; Becerril, H. C. A.; Bao, Z.; Liu, Z.; Chen, Y.; Peumans, P. Organic Light-Emitting Diodes on Solution-Processed Graphene Transparent Electrodes ACS Nano 2009, 4 (1) 43-48
40. Ghosh, A.; Rao, K. V.; George, S. J.; Rao, C. N. R. Noncovalent Functionalization, Exfoliation, and Solubilization of Graphene in Water by Employing a Fluorescent Coronene Carboxylate Chem.-Eur. J. 2010, 16 (9) 2700-2704
41. Wuest, J. D.; Rochefort, A. Strong Adsorption of Aminotriazines on Graphene Chem. Commun. 2010, 46 (17) 2923-2925
42. Mao, J.; Zhang, H.; Jiang, Y.; Pan, Y.; Gao, M.; Xiao, W.; Gao, H. J. Tunability of Supramolecular Kagome Lattices of Magnetic Phthalocyanines Using Graphene-Based Moiré Patterns as Templates J. Am. Chem. Soc. 2009, 131 (40) 14136-14137
43. Cárdenas-Jirón, G. I.; Caro, C. A.; Venegas-Yazigi, D.; Zagal, J. H. Theoretical Study of the Interaction Energy Profile of Cobalt Phthalocyanine and 2-Mercaptoethanol. Effect of the Graphite on the Global Reactivity J. Mol. Struct. 2002, 580 (1-3) 193-200
44. Cortez, L.; Berríos, C.; Yáñez, M.; Cárdenas-Jirón, G. I. Theoretical Study of the Binding Nature of Glassy Carbon with Nickel(II) Phthalocyanine Complexes Chem. Phys. 2009, 365 (3) 164-169
45. Cárdenas-Jirón, G. I.; Leon-Plata, P. A.; Cortes-Arriagada, D.; Seminario, J. M. Electrical Characteristics of Cobalt Phthalocyanine Complexes Adsorbed on Graphene J. Phys. Chem. C 2011, 115 (32) 16052-16062
46. Zagal, J. H.; Griveau, S.; Silva, J. F.; Nyokong, T.; Bedioui, F. Metallophthalocyanine-Based Molecular Materials as Catalysts for Electrochemical Reactions Coord. Chem. Rev. 2010, 254 (23-24) 2755-2791
47. Cárdenas-Jirón, G. I.; Gonzalez, C.; Benavides, J. Nitric Oxide Oxidation Mediated by Substituted Nickel Phthalocyanines: A Theoretical Viewpoint J. Phys. Chem. C 2012, 116 (32) 16979-16984
48. Cortés-Arriagada, D.; Cárdenas-Jirón, G. I. A Through-Space Charge Transfer Mechanism for Explaining the Oxidation of 2-Chlorophenol on a Tetrasulphonated Nickel(III) Phthalocyanine Comput. Theor. Chem. 2011, 963 (1) 161-167
49. Cárdenas-Jirón, G. I.; Berríos, C. Theoretical Evidence of the Ni(III) Participation in the Chlorophenol Oxidation on Tetrasulphonated Nickel Phthalocyanine Int. J. Quantum Chem. 2008, 108 (13) 2586-2594
50. Cárdenas-Jirón, G. I.; Paredes-García, V.; Venegas-Yazigi, D.; Zagal, J. H.; Páez, M.; Costamagna, J. Theoretical Modeling of the Oxidation of Hydrazine by Iron(II) Phthalocyanine in the Gas Phase. Influence of the Metal Character J. Phys. Chem. A 2006, 110 (42) 11870-11875
51. Paredes-García, V.; Cárdenas-Jirón, G. I.; Venegas-Yazigi, D.; Zagal, J. H.; Páez, M.; Costamagna, J. Through-Space and Through-Bond Mixed Charge Transfer Mechanisms on the Hydrazine Oxidation by Cobalt(II) Phthalocyanine in the Gas Phase J. Phys. Chem. A 2005, 109 (6) 1196-1204
52. Young, S. J.; Hart, J. P.; Dowman, A. A.; Cowell, D. C. The Non-Specific Inhibition of Enzymes by Environmental Pollutants: A Study of a Model System Towards the Development of Electrochemical Biosensor Arrays Biosens. Bioelectron. 2001, 16 (9-12) 887-894
53. Mugadza, T.; Nyokong, T. Facile Electrocatalytic Oxidation of Diuron on Polymerized Nickel Hydroxo Tetraamino-Phthalocyanine Modified Glassy Carbon Electrodes Talanta 2010, 81 (4-5) 1373-1379
54. Lane, P. A.; Rostalski, J.; Giebeler, C.; Martin, S. J.; Bradley, D. D. C.; Meissner, D. Electroabsorption Studies of Phthalocyanine/Perylene Solar Cells Sol. Energy Mater. Sol. Cells 2000, 63 (1) 3-13
55. Motoyoshi, R.; Suzuki, A.; Kikuchi, K.; Oku, T. Formation and Characterization of Copper Tetrakis (4-cumylphenoxy) Phthalocyanine: Perylene Solar Cells Synth. Met. 2009, 159 (13) 1345-1348
56. Liang, F.; Shi, F.; Fu, Y.; Wang, L.; Zhang, X.; Xie, Z.; Su, Z. Donor-Acceptor Conjugates-Functionalized Zinc Phthalocyanine: Towards Broad Absorption and Application in Organic Solar Cells Sol. Energy Mater. Sol. Cells 2010, 94 (10) 1803-1808
57. Bechara, R.; Petersen, J.; Gernigon, V.; Léveîque, P.; Heiser, T.; Toniazzo, V.; Ruch, D.; Michel, M. PEDOT:PSS-Free Organic Solar Cells Using Tetrasulfonic Copper Phthalocyanine as Buffer Layer Sol. Energy Mater. Sol. Cells 2012, 98 (0) 482-485
58. Sarker, A. K.; Kang, M. G.; Hong, J.-D. A Near-Infrared Dye for Dye-Sensitized Solar Cell: Catecholate-Functionalized Zinc Phthalocyanine Dyes Pigm. 2012, 92 (3) 1160-1165
59. Zhang, X.-F.; Xi, Q. A Graphene Sheet as an Efficient Electron Acceptor and Conductor for Photoinduced Charge Separation Carbon 2011, 49 (12) 3842-3850
60. Zhu, J.; Li, Y.; Chen, Y.; Wang, J.; Zhang, B.; Zhang, J.; Blau, W. J. Graphene Oxide Covalently Functionalized with Zinc Phthalocyanine for Broadband Optical Limiting Carbon 2011, 49 (6) 1900-1905
61. 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 (15) 3561-3565
62. 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 (35) 15129-15135
63. Kamada, S.; Nomoto, H.; Fukuda, K.; Fukawa, T.; Shirai, H.; Kimura, M. Noncovalent Wrapping of Chemically Modified Graphene with π-Conjugated Disk-Like Molecules Colloid Polym. Sci. 2011, 289 (8) 925-932
64. Li, N.; Zhu, M.; Qu, M.; Gao, X.; Li, X.; Zhang, W.; Zhang, J.; Ye, J. Iron-Tetrasulfophthalocyanine Functionalized Graphene Nanosheets: Attractive Hybrid Nanomaterials for Electrocatalysis and Electroanalysis J. Electroanal. Chem. 2011, 651 (1) 12-18
65. Zhu, Q.; Lu, Y. H.; Jiang, J. Z. Stability and Properties of Two-Dimensional Graphene Hydroxide J. Phys. Chem. Lett. 2011, 2 (11) 1310-1314
66. Giannozzi, P.; Car, R.; Scoles, G. Oxygen Adsorption on Graphite and Nanotubes J. Chem. Phys. 2003, 118 (3) 1003-1006
67. 2, and NO on Graphene: A First-Principles Study Phys. Rev. B 2008, 77 (12) 125416
68. Paulo, V. C. M.; Mota, F. D. B.; Artur, J. S. M.; Caio, M. C. D. C. Adsorption of Monovalent Metal Atoms on Graphene: A Theoretical Approach Nanotechnology 2010, 21 (11) 115701
69. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77 (18) 3865-3868
70. 2 and NO Adsorption on Heteroatom-Doped Graphenes Including the van der Waals Interaction J. Phys. Chem. C 2011, 115 (22) 10971-10978
71. Zhao, Y.; Truhlar, D. G. Density Functionals for Noncovalent Interaction Energies of Biological Importance J. Chem. Theory Comput. 2007, 3 (1) 289-300
72. Staroverov, V. N.; Scuseria, G. E.; Tao, J.; Perdew, J. P. Comparative Assessment of a New Nonempirical Density Functional: Molecules and Hydrogen-Bonded Complexes J. Chem. Phys. 2003, 119 (23) 12129-12137
73. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. Design of Density Functionals by Combining the Method of Constraint Satisfaction with Parametrization for Thermochemistry, Thermochemical Kinetics, and Noncovalent Interactions J. Chem. Theory Comput. 2006, 2 (2) 364-382
74. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. Exchange-Correlation Functional with Broad Accuracy for Metallic and Nonmetallic Compounds, Kinetics, and Noncovalent Interactions J. Chem. Phys. 2005, 123 (16) 161103-161104
75. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Gaussian 09, revision A.01; Gaussian, Inc.: Wallingford CT, 2009.
76. + (M = Fe, Co, Ni and Ru, Rh, Pd) J. Phys. Chem. A 2012, 116 (18) 4560-4568
77. Flener-Lovitt, C.; Woon, D. E.; Dunning, T. H.; Girolami, G. S. A DFT and ab Initio Benchmarking Study of Metal-Alkane Interactions and the Activation of Carbon-Hydrogen Bonds J. Phys. Chem. A 2009, 114 (4) 1843-1851
78. Roetti, C. The CRYSTAL Code. In Quantum-Mechanical ab-Initio Calculation of the Properties of Crystalline Materials; Pisani, C., Ed.; Springer-Verlag: Berlin, Germany, 1996; Vol. 67, pp 125-137.
79. Dovesi, R.; Saunders, V. R.; Roetti, R.; Orlando, R.; Zicovich-Wilson, C. M.; Pascale, F.; Civalleri, B.; Doll, K.; Harrison, N. M.; D'Arco, P.; CRYSTAL06 User's Manual; University of Torino: Torino, Italy, 2006.
80. Seminario, J. M.; Yan, L. Ab Initio Analysis of Electron Currents in Thioalkanes Int. J. Quantum Chem. 2005, 102, 711-723
81. Bautista, E. J.; Yan, L.; Seminario, J. M. Ab Initio Analysis of Electron Transport in Oligoglycines J. Phys. Chem. C 2007, 111 (39) 14552-14559
82. Salazar-Salinas, K.; Jauregui, L. A.; Kubli-Garfias, C.; Seminario, J. M. Molecular Biosensor Based on a Coordinated Iron Complex J. Chem. Phys. 2009, 130 (10) 105101
83. Rangel, N. L.; Seminario, J. M. Single Molecule Detection Using Graphene Electrodes J. Phys. B: At., Mol. Opt. Phys. 2010, 43 (11) 115101
84. Rangel, N. L.; Seminario, J. M. Vibronics and Plasmonics Based Graphene Sensors J. Chem. Phys. 2010, 132 (12) 125102-125104
85. Derosa, P. A.; Seminario, J. M. Electron Transport through Single Molecules: Scattering Treatment Using Density Functional and Green Function Theories J. Phys. Chem. B 2000, 105 (2) 471-481
86. Seminario, J. M.; Zacarias, A. G.; Derosa, P. A. Analysis of a Dinitro-Based Molecular Device J. Chem. Phys. 2002, 116 (4) 1671-1683
87. Sotelo, J. C.; Yan, L.; Wang, M.; Seminario, J. M. Field-Induced Conformational Changes in Bimetallic Oligoaniline Junctions Phys. Rev. A 2007, 75 (2) 022511
88. Afshar, C. E.; Katz, A. K.; Carrell, H. L.; Amin, S.; Desai, D.; Glusker, J. P. Three-Dimensional Structure of Anti-5,6-dimethylchrysene-1,2-dihydrodiol- 3,4-epoxide: A Diol Epoxide with a Bay Region Methyl Group Carcinogenesis 1999, 20 (8) 1549-1554
89. 6 J. Am. Chem. Soc. 2006, 128 (37) 12268-12280
90. Tang, S.; Zhang, S. Adsorption of Epoxy and Hydroxyl Groups on Zigzag Graphene Nanoribbons: Insights from Density Functional Calculations Chem. Phys. 2012, 392 (1) 33-45
91. 3-δ (Ln = La, Pr and Nd; x > 0.60) Mater. Res. Bull. 2005, 40 (6) 990-1000
92. -) Complexes Eur. J. Inorg. Chem. 2009, 2009 (31) 4675-4685
93. OuYang, F.; Huang, B.; Li, Z.; Xiao, J.; Wang, H.; Xu, H. Chemical Functionalization of Graphene Nanoribbons by Carboxyl Groups on Stone-Wales Defects J. Phys. Chem. C 2008, 112 (31) 12003-12007
94. Al-Aqtash, N.; Vasiliev, I. Carboxylation of Boron- and Nitrogen-Doped Graphene and Carbon Nanotubes: First Principles Study. In NSTI Nanotechnology Conference and Expo, Anaheim, CA, 2010; Vol. 2, pp 729-732.
95. Wang, G.; Qian, F.; Saltikov, C.; Jiao, Y.; Li, Y. Microbial Reduction of Graphene Oxide by Shewanella Nano Res. 2011, 4 (6) 563-570
96. Gurunathan, S.; Han, J. W.; Eppakayala, V.; Kim, J.-H. Microbial Reduction of Graphene Oxide by Escherichia Coli: A Green Chemistry Approach Colloids Surf., B 2013, 102 (0) 772-777