Effect of amine substituted at ortho and para positions on the electrochemical and electrocatalytic properties of cobalt porphyrins self-assembled on glassy carbon surface

Electrochimica Acta

Volumn 115, Issue , 2014, Pages 197-205

  Muthukumar, Palanisamy ^a   John, S Abraham ^a  

^a GANDHIGRAM RURAL UNIVERSITY   (India)

Author keywords

Cyclic voltammetry; Electronic effect; Oxygen reduction; Self assembled monolayer; Tetraaminoporphyrinatocobalt(II)

Indexed keywords

ELECTROCATALYTIC PROPERTIES; ELECTROCHEMICAL REDUCTIONS; ELECTRONIC EFFECTS; GLASSY CARBON ELECTRODES; OXYGEN REDUCTION; REFLECTANCE SPECTROSCOPY; TETRAAMINOPORPHYRINATOCOBALT(II); THERMODYNAMICS AND KINETICS;

ADDITION REACTIONS; COBALT; CYCLIC VOLTAMMETRY; ELECTROLYTIC REDUCTION; GLASS; ORGANIC POLYMERS; PHOTOELECTRONS; PORPHYRINS; SELF ASSEMBLED MONOLAYERS; X RAY PHOTOELECTRON SPECTROSCOPY;

GLASS MEMBRANE ELECTRODES;

EID: 84887780731     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2013.10.157     Document Type: Article

References (74)

1. K.M. Kadish, K.M. Smith, and R. Guilard The Porphyrin Handbook 11 2000 Academic Press SanDiego 100
2. S. Nardis, D. Monti, C. Di Natale, A. D'Amico, P. Siciliano, A. Forleo, M. Epifani, A. Taurino, R. Rella, and R. Paolesse Preparation and characterization of cobalt porphyrin modified tin dioxide films for sensor applications Sensors and Actuators B: Chemical 103 2004 339 343 (Pubitemid 40329226)
3. Y. Kuramochi, A. Satake, and Y. Kobuke Light-harvesting macroring accommodating a tetrapodal ligand based on complementary and cooperative coordinations Journal of the American Chemical Society 126 2004 8668 8669 (Pubitemid 38955728)
4. G. Zuo, H. Yuan, J. Yang, R. Zuo, and X. Lu Study of orientation mode of cobalt-porphyrin on the surface of gold electrode by electrocatalytic dioxygen reduction Journal of Molecular Catalysis A: Chemical 269 2007 46 52 (Pubitemid 46507856)
5. H.L. Anderson Building molecular wires from the colours of life: conjugated porphyrin oligomers Chemical Communications (Cambridge) 23 1999 2323 2330
6. K. Araki, M.J. Wagner, and M.S. Wrighton Layer-by-layer growth of electrostatically assembled multilayer porphyrin films Langmuir 12 1996 5393 5398 (Pubitemid 126562239)
7. M.G. Walter, and C.C. Wamser Synthesis and characterization of electropolymerized nanostructured aminophenylporphyrin films The Journal of Physical Chemistry C 114 2010 7563 7574
8. W. Chen, J. Akhigbe, C. Bruckner, C.M. Li, and Y. Lei Electrocatalytic four-electron reduction of dioxygen by electrochemically deposited poly{[meso-tetrakis(2-thienyl)porphyrinato]cobalt(II)} The Journal of Physical Chemistry C 114 2010 8633 8638
9. A. Bettelheim, B.A. White, S.A. Raybuck, and R.W. Murray Electrochemical polymerization of amino-, pyrrole- and hydroxy-substituted tetraphenylporphyrins Inorganic Chemistry 26 1987 1009 1017
10. A. Bettelheim, B.A. White, and R.W. Murray Electrocatalysis of dioxygen reduction in aqueous acid and base by multimolecular layer films of electropolymerized cobalt tetra(o-aminophenyl)porphyrin Journal of Electroanalytical Chemistry 217 1987 271 286
11. S-M. Chen, and Y.L. Chen The electropolymerization and electrocatalytic properties of polymerized MnTAPP film modified electrodes in aqueous solutions Journal of Electroanalytical Chemistry 573 2004 277 287
12. G. Ramirez, G. Cornejo, M. Lucero, A. Riquelme, I. Azocar, F. Armijo, M.J. Aguirre, and E. Trollund Chemical metallation of poly-p- tetraaminophenylporphyrin films grown by cyclic voltammetry on conducting glass electrodes Journal of the Chilean Chemical Society 49 2004 261 266 (Pubitemid 39286602)
13. A. Bettelheim, R. Harth, D. Ozer, and R. Ydgar Dioxygen fixation by a cobalt(II)-ammoniacal complex and its electroreduction in a nafion coated solid-state three-electrode cell Journal of the Chemical Society Chemical Communications 7 1990 521 522
14. G.G. Robert Langmuir-Blodgett Films 1990 Plenum Press New York and London
15. A. Manivannan, L.A. Nagahara, K. Hashimoto, A. Fujishima, H. Yanagi, T. Kouzeki, and M. Ashida Imaging of vanadylnaphthalocyanine aggregates by scanning tunneling microscopy Langmuir 9 1993 771 775
16. F.J. Kampas, K. Yamashita, and J. Fajer Photoelectrochemical properties of metalloporphyrins Nature 284 1980 40 42
17. T.A. Eberspacher, J.P. Collman, C.E.D. Chidsey, D.L. Donohue, and H.V. Ryswyk Modular assembly and air-stable electrochemistry of ruthenium porphyrin monolayers Langmuir 19 2003 3814 3821
18. A. Gulino, P. Mineo, S. Bazzano, D. Vitalini, and I. Fragala Optical pH meter by means of a porphyrin monolayer covalently assembled on a molecularly engineered silica surface Chemistry of Materials 17 2005 4043 4045 (Pubitemid 41173781)
19. D. Monti, M. Stefanelli, M. Raggio, N. Colozza, M. Venanzi, R. Lettieri, L. Luvidi, G. Laguzzi, S. Bonacchi, D. Weber, L. Prodi, C. Di Natale, and R. Paolesse Solid state deposition of chiral amphiphilic porphyrin derivatives on glass surface Journal of Porphyrins and Phthalocyanines 15 2011 1209 1219
20. N. Minamijima, N. Furuta, S. Wakunami, and T. Mizutani Functionalization of silica surface by tetrahydroxyporphyrin via Si-O linkages Bulletin of the Chemical Society of Japan 84 2011 794 801
21. G. Zuo, X. Liu, J. Yang, X. Li, and X. Lu Study of the adsorption kinetics of thiol-derivatized porphyrin on the surface of gold electrode Journal of Electroanalytical Chemistry 605 2007 81 88 (Pubitemid 46946943)
22. X. Lu, B. Lv, Z. Xue, M. Li, L. Zhang, and J. Kang Self-assembled monolayers of a thiol-derivatized porphyrin on gold electrode: film formation and electrocatalytic dioxygen reaction Thin Solid Films 488 2005 230 235 (Pubitemid 41068360)
23. X. Lu, M. Li, C. Yang, L. Zhang, Y. Li, L. Jiang, H. Li, L. Jiang, C. Liu, and W. Hu Electron transport through a self-assembled monolayer of thiol-end-functionalized tetraphenylporphines and metal tetraphenylporphines Langmuir 22 2006 3035 3039
24. J. Zak, H. Yuan, M. Ho, K. Woo, and M.D. Porter Thiol-derivatized metalloporphyrins: monomolecular films for the electrocatalytic reduction of dioxygen at gold electrodes Langmuir 9 1993 2772 2774
25. J.E. Hutchison, T.A. Postlethwaite, C.-H. Chen, K.W. Hathcock, R.S. Ingram, W. Ou, R.W. Linton, R.W. Murray, D.A. Tyvoll, L.L. Chng, and J.P. Collman Electrocatalytic activity of an immobilized cofacial diporphyrin depends on the electrode material Langmuir 13 1997 2143 2148 (Pubitemid 127651440)
26. T.A. Postlethwaite, J.E. Hutchison, K.W. Hathcock, and R.W. Murray Optical, electrochemical and electrocatalytic properties of self-assembled thiol-derivatized porphyrins on transparent gold films Langmuir 11 1995 4109 4116
27. H. Imahori, H. Norieda, K. Ozawa, K. Ushida, H. Yamada, T. Azuma, K. Tamaki, and Y. Sakata Chain length effect on photocurrent from polymethylene-linked porphyrins in self-assembled monolayers Langmuir 14 1998 5335 5338 (Pubitemid 128590358)
28. M.S. Boeckl, A.L. Bramblett, K.D. Hauch, T. Sasaki, B.D. Ratner, and J.W. Rogers Self-assembly of tetraphenylporphyrin monolayers on gold substrates Langmuir 16 2000 5644 5653
29. J. Yang, M. Li, H. Li, Y. Yang, Y. Kashimura, C. Wang, K. Torimitsu, X. Lu, and H. Hu Characterization and application of self-assembly porphyrin with four clips on gold surface The Journal of Physical Chemistry C 114 2010 12320 12324
30. C.M. Cordas, A.S. Viana, S. Leupold, F.-P. Montforts, and L.M. Abrantes Self-assembled monolayer of an iron(III)porphyrin disulphide derivative on gold Electrochemistry Communications 5 2003 36 41
31. X. Lu, L. Zhang, M. Li, X. Wang, Y. Zhang, X. Liu, and G. Zuo Electrochemical characterization of self-assembled thiol-porphyrin monolayers on gold electrodes by SECM ChemPhysChem 7 2006 854 862
32. N. Nishimura, M. Ooi, K. Shimazu, H. Fujii, and K. Uosaki Post-assembly insertion of metal ions into thiol-derivatized porphyrin monolayers on gold Journal of Electroanalytical Chemistry 473 1999 75 84 (Pubitemid 30507119)
33. D.A. Offord, S.B. Sachs, M.S. Ennis, T.A. Eberspacher, J.H. Griffin, C.E.D. Chidesy, and J.P. Collman Synthesis and properties of metalloporphyrin monolayers and stacked multilayers bound to an electrode via site specific axial ligation to a self-assembled monolayer Journal of the American Chemical Society 120 1998 4478 4487 (Pubitemid 28261209)
34. H.V. Ryswyk, R.S. Gabor, S. Awasthi, D.J. Bodzin, and K.S. Orosz Kinetics of metalloporphyrin chemisorption onto monolayer-confined ligands and subsequent distal ligand exchange Langmuir 20 2004 11815 11817 (Pubitemid 40049658)
35. A. Dreas-Woldarczak, M. Mullneritsch, T. Juffmann, C. Cioffi, M. Arndt, and M. Mayor Immobilization of zinc porphyrin complexes on pyridine- functionalized glass surfaces Langmuir 26 2010 10822 10826
36. S. Zou, R.S. Clegg, and F.C. Anson Attachment of cobalt Picket Fence porphyrin to the surface of gold electrodes coated with 1-(10-mercaptodecyl) imidazole Langmuir 18 2002 3241 3246 (Pubitemid 35383784)
37. M.A. Mezour, R. Cornut, E.M. Hussien, M. Morin, and J. Mauzeroll Detection of hydrogen peroxide produced during the oxygen reduction reaction at self-assembled thiol-porphyrin monolayers on gold using SECM and nanoelectrodes Langmuir 26 2010 13000 13006
38. D.A. Van Galen, and M. Majda Irreversible self-assembly of monomolecular layers of a cobalt(II)hexadecyltetrapyridylporphyrin amphiphile at gold electrodes and its catalysis of oxygen reduction Analytical Chemistry 60 1988 1549 1553
39. A. Ulman Formation and structure of self-assembled monolayers Chemical Reviews 96 1996 1533 1554 (Pubitemid 126639367)
40. I. Gallardo, J. Pinson, and N. Vila Spontaneous attachment of amines to carbon and metallic surfaces The Journal of Physical Chemistry B 110 2006 19521 19529 (Pubitemid 44626432)
41. K.M. Kadish, E.V. Caemelbecke, and G. Royal K.M. Kadish, K.M. Smith, R. Guilard, The Porphyrin Handbook 8 2000 Academic Press Burlington, MA 1 114
42. A. Ghosh Substituent effects on valence ionization potentials of free base porphyrins: a local density functional study Journal of the American Chemical Society 117 1995 4691 4699
43. R. Koerner, J.L. Wright, X.D. Ding, M.J.M. Nesset, K. Aubrecht, R.A. Watson, R.A. Barber, L.M. Mink, A.R. Tipton, C.J. Norvell, K. Skidmore, U. Simonis, and F.A. Walker Electronic effects in transition metal porphyrins. 9. Effect of phenyl ortho substituents on the spectroscopic and redox properties and axial ligand binding constants of iron(III)tetraphenylporphyrinates Inorganic Chemistry 37 1998 733 745 (Pubitemid 128501390)
44. B.D. McLees, and W.S. Caughey Substituted deuteroporphyrins: V. Structures, stabilities and properties of nickel(II)complexes with axial ligands Biochemistry 7 1968 642 652
45. M.K. Safo, G.P. Gupta, F.A. Walker, and W.R. Scheidt Models of the cytochromes b. Control of axial ligand orientation with a hindered porphyrin system Journal of the American Chemical Society 113 1991 5497 5510
46. F.A. Walker, E. Hui, and J.M. Walker Electronic effects in transition metal porphyrins. I. Reaction of piperidine with a series of para- and meta-substituted nickel(II) and vanadium(IV)tetraphenylporphyrins Journal of the American Chemical Society 97 1975 2390 2397
47. F.A. Walker, M-W. Lo, and M.T. Ree Electronic effects in transition metal porphyrins. The reactions of imidazoles and pyridines with a series of para-substituted tetraphenylporphyrin complexes of chloroiron(III) Journal of the American Chemical Society 98 1976 5552 5559
48. J.E. Falk Porphyrins and Metalloporphyrins 1964 Elsevier New York 28, 42, 69, 93
49. E. Rose, M. Soleilhavoup, L. Christ-Tommasino, G. Moreau, J.P. Collman, M. Quelquejeu, and A. Straumanis Bis-faced aminoporphyrin templates for the synthesis of chiral catalysts and hemeprotein analogues The Journal Organic Chemistry 63 1998 2042 2044
50. S.R. Loewe, A. Ambroise, K. Muthukumaran, K. Padmaja, A.B. Lysenko, G. Mathur, Q. Li, D.F. Bocian, V. Misra, and J.S. Lindsey Porphyrins bearing mono or tripodal benzylphosphonic acid tethers for attachment to oxide surfaces The Journal of Organic Chemistry 69 2004 1453 1460 (Pubitemid 38292093)
51. G.A. Schick, I.C. Schreiman, R.W. Wagner, J.S. Lindsey, and D.F. Bocian Spectroscopic characterization of porphyrin monolayer assemblies Journal of the American Chemical Society 111 1989 1344 1350
52. J.A.M. Sondag-Huethorst, and L.G.J. Fokkink Electrochemical characterization of functionalized alkanethiol monolayers on gold Langmuir 11 1995 2237 2241
53. E. Laviron General expressions of the linear potential sweep voltammogram in the case of diffusionless electrochemical system Journal of Electroanalytical Chemistry 101 1979 19 28
54. P. Zanello Inorganic electrochemistry: theory, practice and applications Royal Society of Chemistry 2003 579
55. M. Charton The application of the Hammett equation to ortho-substituted benzene reaction series Canadian Journal of Chemistry 38 1960 2493 2499
56. T. Lukasczyk, K. Flechtner, L.R. Merte, N. Jux, F. Maier, J.M. Gottfried, and H.-P. Steinruck Interaction of cobalt(II)tetraarylporphyrins with a Ag(111) surface studied with photoelectron spectroscopy The Journal of Physical Chemistry C 111 2007 3090 3098 (Pubitemid 46384321)
57. J.M. Gottfried, K. Flechtner, A. Kretchmann, T. Luckasczyk, and H-P. Steinruck Direct synthesis of a metalloporphyrin complex on a surface Journal of the American Chemical Society 128 2006 5644 5645 (Pubitemid 43724361)
58. S. Berner, H. Lidbaum, G. Ledung, J. Ahlund, K. Nilson, J. Schiessling, U. Gelius, J.-E. Backvall, C. Puglia, and S. Oscarsson Electronic and structural studies of immobilized thiol-derivatized cobalt porphyrins on gold surfaces Applied Surface Science 253 2007 7540 7548 (Pubitemid 46873794)
59. R. Zanoni, A. Aurora, F. Cattaruzza, F. Decker, P. Fastiggi, V. Menichetti, P. Tagliatesta, A.-L. Capodilupo, and A. Lembo Metalloporphyrins as molecular precursors of electroactive hybrids: a characterization of their actual electronic states on Si(1 0 0) and (1 1 1) by AFM and XPS Material Science and Engineering C 27 2007 1351 1354 (Pubitemid 47211819)
60. L. Elbaz, E. Korin, L. Soifer, and A. Bettelheim Evidence for the formation of cobalt porphyrin-quinone complexes stabilized at carbon-based surfaces toward the design of efficient non-noble-metal oxygen reduction catalysts Journal of Physical Chemistry Letters 1 2010 398 401
61. J.O.M. Bockris, A.K.N. Reddy, and M. Gamboda-Aldeco second ed. Modern Electrochemistry 2A 1998 Plenum Publishers New York
62. H.M. Schessler, D.S. Karpovich, and G.J. Blanchard Quantitating the balance between enthalpic and entropic forces in alkanethiol/gold monolayer self assembly Journal of the American Chemical Society 118 1996 9645 9651
63. A.N. Frumkin, and B.B. Damaskin Adsorption of organic compounds at electrodes J.O'M. Bockris, B.E. Conway, Modern Aspects of Electrochemistry 3 1964 Butterworth London 149 223
64. E. Castellini, A. Ranieri, D.A. Simari, and G.D. Rocco Thermodynamic aspects of the adsorption of cytochrome c and its mutants on kaolinite Langmuir 25 2009 6849 6855
65. J.D. Tirado, A. Acevedo, R.L. Bredz, and H.D. Abruna Adsorption dynamics of electroactive self-assembling molecules Langmuir 10 1994 1971 1979
66. J.P. Collman, P. Denisevich, Y. Konai, M. Marrocco, C. Koval, and F.C. Anson Electrode catalysis of the four-electron reduction of oxygen to water by dicobalt face-to-face porphyrins Journal of the American Chemical Society 102 1980 6027 6036
67. R.R. Durand, C.S. Bencosme, J.P. Collman, and F.C. Anson Mechanistic aspects of the catalytic reduction of dioxygen by cofacial metalloporphyrins Journal of the American Chemical Society 105 1983 2710 2718 (Pubitemid 13061086)
68. Y.L. Mest, C. Inisan, A. Laouenan, M. L'Her, J. Talarmin, E.M. Khalifa, and J.-Y. Sailard Reactivity toward dioxygen of dicobalt face-to-face diporphyrins in aprotic media. experimental and theoretical aspects: possible mechanistic implication in the reduction of dioxygen Journal of the American Chemical Society 119 1997 6095 6106 (Pubitemid 27314843)
69. C.J. Chang, Y. Deng, C. Shi, C.K. Chang, F.C. Anson, and D.G. Nocera Electrocatalytic four-electron reduction of oxygen to water by a highly flexible cofacial cobalt bisporphyrin Chemical Communications 15 2000 1355 1356 (Pubitemid 30621905)
70. W. Lu, C. Wang, Q. Lv, and X. Zhou Electrocatalytic reduction of dioxygen on the surface of glassy carbon electrodes modified with dicobalt diporphyrin complexes Journal of Electroanalytical Chemistry 588 2003 59 63
71. R.S. Nicholson, and I. Shain Theory of stationary electrode polarography: single scan and cyclic methods applied to reversible, irreversible, and kinetic systems Analytical Chemistry 36 1964 706 723.
72. A.J. Bard, and L.R. Faulkner Electrochemical Methods 1980 Wiley New York
73. D. Morales-Acosta, D.L. de la Fuente, L.G. Arriaga, G.V. Gutierrez, and F.J.R. Varela Electrochemical investigation of Pt-Co/MWCNT as an alcohol tolerant ORR catalyst for direct oxidation fuel cells International Journal of Electrochemical Science 6 2001 1835 1854
74. D.T. Sawyer Oxygen Chemistry 1991 Oxford University Press London