Fundamental aspects on the catalytic activity of metallomacrocyclics for the electrochemical reduction of O2

N4-Macrocyclic Metal Complexes

Volumn , Issue , 2006, Pages 41-82

  Zagal, José H ^a   Páez, Maritza A ^a   Silva, J Francisco ^a  

^a UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84892081777     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-0-387-28430-9_2     Document Type: Chapter

References (126)

1. Jasinski, R. (1964). A new fuel-cell cathode catalyst. Nature 201, 1212-1213.
2. van den Brink, F., E. Barendrecht, and W. Visscher (1980). The cathodic reduction of oxygen-A review with emphasis on macrocyclic organic metal-complexes as electrocatalysts. Recl. Trav. Chim. Pays-Bas, 99, 253-262.
3. Rayushkina, K.A. and M.R. Tarasevich (1986). Electrocatalytic properties of pyrolytic polymers produced from N4-complexes (review). Translated from Electrokhimiya 22, 1155-1170.
4. 2 reduction. Electrochim. Acta 29, 1527- 1537.
5. Vasudevan, P., S.N. Mann, and S. Tyagi (1990). Transition-metal complexes of porphyrins and phthalocyanines as electrocatalysts for dioxygen reduction. Transition Met. Chem. 15, 81-90.
6. Zagal, J.H. (1992). Metallophthalocyanines as catalysts in electrochemical reactions. Coord. Chem. Rev. 119, 89-136.
7. Adzic, R. (1998). Recent advances in the kinetics of oxygen reduction. In J. Lipkowski and P.N. Ross (ed), Electrocatalysis, Frontiers in Science. Wiley-VCH, New York, 197-242.
8. Zagal, J.H. (2003). Macrocycles. In W. Vielstich, A. Lamm and H.A. Gasteiger (eds.), Handbook of Fuel Cells-Fundamentals, Technology and Applications, Vol. 2, Part 5. John Wiley & Sons Ltd, Chichester, pp. 544-554.
9. Collman, J.P., R. Boulatov, and C.J. Sunderland (2003). Functional and structural analogs of the dioxygen reduction site in terminal oxidases. In K.M. Kadish, K.M. Smith, and R. Guilard (eds.), The Porphyrin Handbook, Chapter 23. Academic Press, Boston, pp. 1-49.
10. Zagal, J.H., M. Ṕaez, A.A. Tanaka, J.R. dos Santos, and C. Linkous (1992). Electrocatalytic activity of metal phthalocyanines for oxygen reduction. J. Electroanal. Chem. 339, 13-30.
11. 2. J. Porphyrins Phthalocyanines 1, 3-16.
12. Pavez, J., M. Ṕaez, A. Ringued́e, F. Bedioui, and J.H. Zagal (2005). Effect of film thickness on the electro-reduction of molecular oxygen on electropolymerized cobalt tetra-aminophthalocyanine films. Solid State Electrochem. 9, 21-29.
13. Ramirez, G., E. Trollund, M. Isaacs, J. Zagal, J.C. Costamagna, and M.J. Aguirre (2002). Electroreduction of dioxygen on poly-fetetraaminophthalocyanine modified electrodes. Electroanalysis 14, 540-545.
14. 2 catalyzed by vitamin B12 adsorbed on a graphite electrode. J .Electroanal. Chem. 237, 145-148.
15. Qiu, Q. and S. Dong (1993). Rapid determination of kinetic parameters for the electrocatalytic reduction of dioxygen by vitamin B12 adsorbed on glassy carbon. Electrochim. Acta 38, 2297-2302.
16. 2 reduction kinetics on a graphite electrode modified with adsorbed vitamin B12. J. Electroanal. Chem. 437, 45-52.
17. Steiger, B. and F.C. Anson (1995). Evidence of the importance of back-bonding in determining the behavior of ruthenated cyanophenyl cobalt porphyrins as electrocatalysts for the reduction of dioxygen. Inorg. Chem. 34, 3355-3357.
18. Durand, R.R., C.S. Bencosme, J.P. Collman, and F.C. Anson (1983). Mechanistic aspects of the catalytic reduction of dioxygen by cofacial metalloporphyrins. J. Am. Chem. Soc. 105, 2710-2718.
19. Lalande, G., R. Cote, D. Guay, J.P. Dodelet, L.T. Weng, and P. Bertrand (1997). Is nitrogen important in the formulation of Fe-based catalysts for oxygen reduction in solid polymer fuel-cells? Electrochim. Acta 42, 1378-1388.
20. Bouwkamp-Wijnoltz, A.L., W. Visscher, and J.A.R. Van Veen (1998). The selectivity of oxygen reduction by pyrolysed iron porphyrin supported on carbon. Electrochim. Acta 43, 3141-3152.
21. Lefevre, M., J.P. Dodelet, and P. Bertrand (2002). Molecular oxygen reduction in PEM fuel cells: Evidence for the simultaneous presence of two active sites in Febased catalysts. J. Phys. Chem., B 106, 8705-8713.
22. Bouwkamp-Wijnoltz, A.L., W. Visscher, J.A.R. Van Veen, J.A.R. Boellaard, A.M. Van Der Kraan, and S.C. Tang (2002). On active-site heterogeneity in pyrolyzed carbon supported iron porphyrin catalysts for the electrochemical reduction of oxygen: An in situ M̈ossbauer study. J. Phys. Chem., B 106, 12993-13001.
23. Lefevre, M. and J.P. Dodelet (2003). Fe-based catalysts for the reduction of oxygen in polymer electrolyte membrane fuel cell conditions: Determination of the amount of peroxide released during electroreduction and its influence on the stability of the catalysts. Electrochim. Acta 48, 2749-2760.
24. Kobayashi, N. and W.A. Nevin (1996). Electrocatalytic reduction of oxygen using water-soluble iron and cobalt phthalocyanines and porphyrins. Appl. Organomet. Chem. 10, 579-590.
25. Bytheway, I. and M.B. Hall (1994). Theoretical calculations of metal-dioxygen complexes. Chem. Rev. 94, 639-658.
26. 2 reduction on transition metal chelates. J. Electroanal. Chem. 221, 95-104.
27. Zecevic, S., B. Simic-Glavaski, E. Yeager, A.B.P. Lever, and P.C. Minor (1985). Spectroscopic and electrochemical studies of transition metal tetrasulfonated phthalocyanines: Part V. Voltammetric studies of adsorbed tetrasulfonated phthalocyanines (MTsPc) in aqueous solutions. J. Electroanal. Chem. 196, 339-358.
28. Ni, C.L. and F.C. Anson (1984). Relation between the potentials where adsorbed and unadsorbed cobalt(III) tetrakis(N-methylpyridinium-4-yl)porphyrin is reduced and those where it catalyzes the electroreduction of dioxygen. Inorg. Chem. 24, 4754- 4756.
29. Shi, C. and F. C. Anson (1990). Catalytic pathways for the electroreduction of oxygen by iron tetrakis(4-N-methylpyridyl)porphyrin or iron tetraphenylporphyrin adsorbed on edge plane pyrolytic graphite electrodes. Inorg. Chem. 29, 4298-4305.
30. van Veen, J.A.R. and C. Visser (1979). Oxygen reduction on monomeric transition metal phthalocyanines in acid electrolyte. Electrochim. Acta 24, 921-928.
31. van Veen, J.A.R., J.F. van Baar, C.J. Croese, J.G.F. Coolegem, N. de Wit, and H.A. Colijin (1981). Oxygen reduction on transition metal porphyrins in acid electrolyte: I activity. Ber. Bunsenges. Phys. Chem. 85, 693-700.
32. 2 on electrodes modified with N-4 macrocyclics. In F.C. Anson, R.R. Adzic, and K. Kinoshita, Oxygen Electrochemistry. The Electrochemical Society Symposium Series 95-26, pp. 89-100.
33. Zagal, J.H., M. Gulppi, M. Isaacs, G. Ćardenas-Jiŕon, and M.J. Aguirre (1998). Linear vs. volcano correlations between electrocatalytic activity and redox properties of metallophthalocyanines. Electrochim. Acta 44, 1349-1357.
34. Ćardenas-Jiŕon, G., M.A. Gulppi, C.A. Caro, R. del Rio, M. Paez, and J.H. Zagal (2001). Reactivity of electrodes modified with substituted metallophthalocyanines. Correlations with redox potentials, Hammett parameters and donor-acceptor intermolecular hardness. Electrochim. Acta 46, 3227-3235.
35. Zagal, J.H. and G. Ćardenas-Jiron (2000). Reactivity of immobilized cobalt phthalocyanines for the electroreduction of molecular oxygen in terms of molecular hardness. J. Electroanal. Chem. 489, 96-100.
36. Ćardenas-Jiŕon, G.I. and J.H. Zagal (2001). Donor-acceptor intermolecular hardness on charge transfer reactions of substituted cobalt phthalocyanines. J. Electroanal. Chem. 497, 55-60.
37. Schlettwein, D. and T.Yoshida (1998). Electrochemical reduction of substituted cobalt phthalocyanines adsorbed on graphite. J. Electroanal. Chem. 441, 148.
38. Zagal, J.H., M.A. Gulppi, and G. Ćardenas-Jiŕon (2000). Metal-centered redox chemistry of substituted cobalt phthalocyanines adsorbed on graphite and correlations with MO calculations and Hammett parameters. Electrocatalytic reduction of disulfide. Polyhedron 19, 2255-2260.
39. Newton, M.D. (1991). Quantum chemical probes of electron-transfer kinetics: The nature of donor-acceptor interactions. Chem. Rev. 91, 767-792.
40. Pearson, R.G. (1986). Absolute electronegativity and hardness correlated with molecular orbital theory. Proc. Natl Acad. Sci. USA 83, 8440-8441.
41. Parr, R.G. and R.G. Pearson (1983). Absolute hardness: Companion parameter to absolute electronegativity. J. Am. Chem. Soc, 105, 7512-7516.
42. Ulstrup, J. (1977). Catalysis of the electrochemical reduction of molecular dioxygen by metal phthalocyanines. J. Electroanal. Chem. 79, 191-197.
43. Rosa, A. and E.J. Baerends (1994). Metal macrocycle interaction in phthalocyanines- density functional calculations of ground and excited states. Inorg. Chem. 33, 584-595.
44. Hipps, K.W., X. Lung, X.D. Wang, and U. Manzur (1996). Metal d-orbital occupation-dependent images in the scanning tunnelling microscopy of metal phthalocyanines. J. Phys. Chem., B 100, 11207-11210.
45. Theodoridou, E., A.D. Jannakoudakis, P.D. Jannakoudakis, and J.O. Besenhard (1992). Carbon fibre based conductive ion exchangers as support for metal and ligand charged metalloporphyrin electrocatalysts. J. Appl. Electrochem. 22, 733-737.
46. Hinnen, C., F. Coowar, and M. Savy (1989). Oxygen reduction in acid media: Investigations by electroreflectance on adsorbed iron phthalocyanine and naphthalocyanine layers. J. Electroanal. Chem. 264, 167-180.
47. van den Ham, D., C. Hinnen, G. Magner, and M. Savy (1987). Electrocatalytic oxygen reduction: The role of oxygen bridges as a structural factor in the activity of transition-metal phthalocyanines. J. Phys. Chem. 91, 4743-4748.
48. 2 reduction to water in different acid media by iron naphthalocyanines. J. Electroanal. Chem. 246, 119-138.
49. Elzing, A., A. van der Putten, W. Visscher, and E. Barendrecht (1987). The cathodic reduction of oxygen at metal tetrasulfonato-phthalocyanines: Influence of adsorption conditions on electrocatalysis. J. Electroanal. Chem. 233, 99-112.
50. Elzing, A., A. van der Putten, W. Visscher, and E. Barendrecht (1986). The cathodic reduction of oxygen at cobalt phthalocyanine: Influence of electrode preparation on electrocatalysis. J. Electroanal. Chem. 200, 313-322.
51. Fierro, C.A., M. Mohan, and D.A. Scherson (1990). In situ Mossbauer spectroscopy of a species irreversibly adsorbed on an electrode surface. Langmuir 6, 1338-1342.
52. Ouyang, J., K. Shigehara, A. Yamada, and F.C. Anson (1991). Hexadecafluoro- and octacyano phthalocyanines as electrocatalysts for the reduction of dioxygen. J. Electroanal. Chem., 297, 489-498.
53. van der Putten, A., A. Elzing, W. Visscher, and E. Barendrecht (1986). Oxygen reduction on vacuum-deposited and absorbed transition-metal phthalocyanine films. J. Electroanal. Chem. 214, 523-533.
54. Shi, C. and F. C. Anson (1992). Electrocatalysis of the reduction of molecular oxygen to water by tetraruthenated cobalt meso-tetrakis(4-pyridyl) porphyrin adsorbed on graphite electrodes. Inorg. Chem. 31, 5078-5083.
55. 2 reduction on water soluble phthalocyanines adsorbed on graphite electrodes. J. Electrochem. Soc. 127, 1506-1517.
56. Ikeda, O., H. Fukuda, and H. Tamura (1986). The effect of heat treatment on group VIII B porphyrins as electrocatalysts in the cathodic reduction of oxygen. J. Chem. Soc. Farad. Trans. I 82, 1561-1573.
57. van Veen, J.A.R., J.F. van Baar, and K.J. Krose (1981). Effect of heat treatment on the performance of carbon-supported transition-metal chelates in the electrochemical reduction of oxygen. J. Chem. Soc. Farad. Trans. 77, 2827-2843.
58. van Veen, J.A.R. and H.A. Colijn (1981). Oxygen reduction on transition-metal porphyrins in acid electrolyte. Stability. Ber Bunsenges. Phys. Chem. 85, 700-704.
59. Shamsipur, M., A. Salimi, H. Haddadzadeh, and M.F. Mousavi (2001). Electrocatalytic activity of cobaloxime complexes adsorbed on glassy carbon electrodes toward the reduction of dioxygen. J. Electroanal. Chem. 517, 37-44.
60. Salimi, A. and M. Ghadermazi (2001). Electrocatalytic reduction of dioxygen on a glassy carbon electrode modified with adsorbed cobaloxime complex. Anal. Sci. 17, 1165-1170.
61. Chan, R.J., Y.O. Su, and T. Kuwana (1985). Electrocatalysis of oxygen reduction. 5. Oxygen to Hydrogen peroxide conversion by cobalt (II) tetrakis (N-methyl-4pyridyl) porphyrin. Inorg. Chem. 24, 3777-3784.
62. Atoguchi, T., A. Aramata, A. Kazusaka, and M. Enyo (1991). Cobalt (II)- tetraphenylporphyrin-pyridine complex fixed on a glassy carbon electrode and its prominent catalytic activity for reduction of carbon dioxide. J. Chem. Soc. Chem. Commun. 156-157.
63. Zeng, Z.Y., S.L. Gupta, H. Huang, and E.B Yeager (1991). Oxygen reduction on poly (4-vinylpyridine)-modified ordinary pyrolytic graphite electrodes with adsorbed cobalt tetra-sulphonated phthalocyanine in acid solution. J. Appl. Electrochem. 21, 973-981.
64. 2O. J. Mol. Struct. (Theochem) 180, 309-318.
65. Anson, F.C., C. Shi, and B. Steiger (1997). Novel multinuclear catalysts for the electroreduction of dioxygen directly to water. Acc. Chem. Res. 30, 437-449.
66. Gupta, S., C. Fierro and E.Yeager (1991). The effects of cyanide on the electrochemical properties of transition metal macrocycles for oxygen reduction in alkaline solutions. J. Electroanal. Chem. 306, 239-250.
67. D'Souza, F., Y.Y. Hsieh, and G.R. Deviprasad (1997). Electrocatalytic reduction of molecular oxygen using non-planar cobalt tetrakis-(4- sulfonatophenyl)?- octabromoporphyrin. J. Electroanal. Chem. 426, 17-21.
68. Coutanceau, C., A. Rakotondrainibe, P. Crouigneau, J.M. Ĺeger and C. Lamy (1995). Spectroscopic investigations of polymer-modified electrodes containing cobalt phthalocyanine: Application to the study of oxygen reduction at such electrodes. J. Electroanal. Chem. 386, 173-182.
69. Elzing, A., A. van der Putten, W. Visscher, E. Barendrecht, and C. Hinnen (1990). Spectroscopic measurements on metal tetrasulphonato-phthalocyanines. J. Electroanal. Chem. 279, 137-156.
70. Phougat, N. and P. Vasudevan (1997). Electrocatalytic activity of some metal phthalocyanine compounds for oxygen reduction in phosphoric acid. J. Power Sources 69, 161-163.
71. Lin, A.S. and J.C. Huang (2003). Oxygen reduction on Nafion-bound unpyrolyzed metal macrocyclic complexes. J. Electroanal. Chem. 541, 147-151.
72. Chung, T.D. and F.C. Anson (2001). Catalysis of the electroreduction of O2by cobalt 5, 10, 15, 20-tetraphenylporphyrin dissolved in thin layers of benzonitrile on graphite electrodes. J. Electroanal. Chem. 508, 115-122.
73. Steiger, B. and F.C. Anson (2000). Examination of cobalt "picket fence" porphyrin and its complex with 1-methylimidazole as catalysts for the reduction of dioxygen. Inorg. Chem. 39, 4579-4585.
74. Hutchison, J.E., T.A. Postlethweite, and R.W. Murray (1993). Molecular films of thiol-derivatized tetraphenylporphyrins on gold: Film formation and electrocatalytic dioxygen reduction. Langmuir 9, 3277-3283.
75. Postlethweite, T.A., J.E. Hutchison, K.W. Hathcock, and R.W. Murray (1995). Optical electrochemical, and electrocatalytic properties of self-assembled thiolderivatized porphyrins on transparent gold electrodes. Langmuir 11, 4109-4116.
76. Lever, A.B.P., E.R. Milaeva, and G. Speir (1993). The redox chemistry of metallophthalocyanines in solution. In C.C. Leznoff, A.B.P. Lever (eds), Phthalocyanines, Properties and Applications, Vol. 3, VCH Publishers, New York, pp. 1-70.
77. Lever, A.B.P. (1999). The phthalocyanines-molecules of enduring value, a two dimensional analysis of redox potentials. J. Porphyrins Phthalocyanines, 3, 488-499.
78. Paliteiro, A., A. Hamnett, and J.B. Goodenough (1984). Cathodic reduction of oxygen by platinum phthalocyanine thin films. J. Electroanal. Chem. 160, 359-367.
79. Collman, J.P., M. Marrocco, P. Denisevich, C. Koval, and F.C. Anson (1979). Potent catalysis of the electroreduction of oxygen to water by dicobalt porphyrin dimers adsorbed on graphite electrodes. J. Electroanal. Chem. 101, 117-122.
80. Collman, J.P., P. Denisevich, Y. Konai, M. Marrocco, C. Koval, and F.C. Anson (1980). Electrocatalysis of the four-electron reduction of oxygen to water by dicobalt face-to-face porphyrins. J. Am. Chem. Soc. 102, 6027-6036.
81. Chang, C.K., H.Y. Liu, and I. Abdalmuhdi (1984). Electroreduction of oxygen by pillared cobalt(II) cofacial diporphyrin catalysts. J. Am. Chem. Soc. 106, 2725-2726.
82. van der Putten, A., A. Elzing, W. Visscher, and E. Barendrecht (1986). The fourelectron reduction of oxygen to water on a planar cobalt chelate. J. Chem. Soc. Chem. Commun. 477-479.
83. Janda, P., N. Kobayashi, P.R. Auburn, H. Lam, C.C. Leznoff, and A.B.P. Lever (1989). Dioxgen reduction at a graphite electrode modified by mononuclear tetraneopentoxyphthalocyaninatocobalt (II) and Related Polynuclear Species. Can. J. Chem. 67, 1109-1119.
84. Biloul, A., F. Coower, O. Contamin, G. Scarbeck, M. Savy, D. van den Ham, J. Riga, and J.J. Verbist (1993). Oxygen reduction in an acid medium: Electrocatalysis by CoNPc(1, 2) impregnated on a carbon black support; effect of loading and heat treatment. J. Electroanal. Chem. 350, 189-204.
85. Biloul, A., O. Contamin, G. Scarbeck, M. Savy, B. Palys. J. Riga, and J. Verbist (1994). Oxygen reduction in acid media: influence of the activity of CoNPc(1, 2) bilayer deposits in relation to their attachment to the carbon black support and role of surface groups as a function of heat treatment. J. Electroanal. Chem. 365, 239-246.
86. Anson, F.C., C.L. Ni, and J.M. Saveant (1985). Electrocatalysis at redox polymer electrodes with separation of the catalytic and charge propagation roles. Reduction of dioxygen to hydrogen peroxide as catalyzed by cobalt(II) tetrakis(4- N-methylpyridyl)porphyrin. J. Am. Chem. Soc. 107, 3442-3450.
87. Shi and F.C. Anson (1991). Multiple intramolecular electron transfer in the catalysis of the reduction of dioxygen by cobalt meso-tetratrakis(4pyridyl) porphyrin to which four Ru(NH3)5 groups are coordinated. J. Am Chem. Soc. 113, 9564-9570.
88. Steiger, B., C. Shi, and F.C. Anson (1993). Electrocatalysis of the reduction of dioxygen by adsorbed cobalt 5, 10, 15, 20-tetraarylporphyrins to which one, two, or three pentaammineruthenium(2+) centers are coordinated. Inorg. Chem. 32, 2107-2113.
89. Steiger, B. and F.C. Anson (1994). New electrocatalysts for the four-electron reduction of dioxygen based on (5, 10, 15- tris(pentaammineruthenium(II)-4-cyanophenyl)- 20-(1methylpyridinium-4-yl) porphyrinato)cobalt(II) immobilized on graphite electrodes. Inorg. Chem. 33, 5767-5779.
90. Shi, C. and F.C. Anson (1995). Coordination chemistry in electrocatalysis. Pure Appl. Chem. 67, 319-322.
91. Steiger, B. and F.C. Anson (1997). (5, 10, 15, 20-Tetrakis(4- ((pentaammineruthenio)- cyano)phenyl)porphyrinato)cobalt(II) immobilized on graphite electrodes catalyzes the electroreduction of O2 to H2O, but the corresponding 4-cyano-2, 6- dimethylphenyl derivative catalyzes the reduction only to H2O2, Inorg. Chem. 36, 4138-4140.
92. n+(n = 2, 3) groups are coordinated to the porphyrin ring. Inorg. Chem. 35, 7928-7931.
93. Zhong, H.-Z., J.S. Baskin, B. Steiger, F.C. Anson, and A.H. Zewail (1999). Femtosecond dynamics and electrocatalysis of the reduction of O2: Tetraruthenated cobalt porphyrins. J. Am. Chem. Soc. 121, 484-485.
94. Imaoka, T. and K. Yamamoto (2001). Electrochemistry of Co-Ru hetero-dinuclear porphyrin complex in a Nafion matrix. Phys. Chem. Chem. Phys. 3, 4462-4468.
95. Bettelheim, A., D. Ozer, R. Harth, and R. Ydgar (1990). Dioxygen reduction and hydrogen peroxide dismutation using electropolymerized bilayers of cobalt + manganese tetrakis(o-aminophenyl)porphyrins. J. Electroanal. Chem. 281, 147-161.
96. Yamamoto, K. and D. Taneichi (1999). Electrochemical catalytic reduction of oxygen by self-doped polyaniline-Co porphyrin complex-modified glassy carbon electrode. J. Inorg. Organomet. Polymers. 9, 231-243.
97. Matsufuji, A., S. Nakazawa, and K. Yamamoto (2001). Electrocatalysis of the reduction of dioxygen by π-conjugated polymer complexes with dinuclear cobalt porphyrin. J. Inorg. Organomet. Polym. 11, 47-61.
98. Kobayashi, N., K. Sudo, and T. Osa (1990). Preparation of iron and cobalt phthalocyanine- 1, 2:3, 4:8, 9;10, 11:15, 16:22, 23:24, 25-octakis(N- decyldicarboximide) and their catalytic behavior for electroreduction of oxygen, Bull. Chem. Soc. Jpn 63, 571-575.
99. 2 reduction. J. Chem. Soc. Farad. Trans. 94, 3393-3399.
100. Oyaizu, K., A. Haryono, J. Natori, and E. Tsuchida (1998). (μ-peroxo)bis [pyridine( phthalocyanato)iron(III)] as a convenient catalyst for the four-electron reduction of dioxygen. J. Chem. Soc. Farad. Trans. 94, 3737-3742.
101. 2O. Bull. Che. Soc. Jpn 73, 1153-1163.
102. Shi, C., B. Steiger, M. Yuasa, and F.C. Anson (1997). Electroreduction of O2 to H2O at unusually positive potentials catalyzed by the simplest of the cobalt porphyrins. Inorg. Chem. 36, 4294-4295.
103. 2O. Inorg. Chem. 37, 1037-1043.
104. Chaves, J.A.P., M.F.A. Araujo, J. de J.G. Varela J́unior, and A.A. Tanaka (2003). Electrocat́alise da reaçao de reduçao de oxigenio sobre eletrodos de grafite modificados com ftalocianina tetracarboxilada de ferro. Ecl. Qúim., Sao Paulo 28, 9-20.
105. Tanaka, A.A., C. Fierro, D.A. Scherson, and E. Yeager (1989). Oxygen reduction on adsorbed iron tetrapyridinoporphyrazine. Mat. Chem. Phys. 22, 431-456.
106. Sawaguchi, T., T. Matsue, K. Itaya, and I. Uchida (1991). Electrochemical catalytic reduction of molecular oxygen by iron porphyrin ion-complex modified electrode. Electrochim. Acta 36, 703-708.
107. Elzing, A., A. van der Putten, W. Visscher, and E. Barendrecht (1987). The mechanism of oxygen reduction at iron tetrasulfonato-phthalocyanine incorporated in polypyrrole. J. Electroanal. Chem. 233, 113-123.
108. Elzing, A., A van der Putten, W. Visscher, and E. Barendrecht (1990). Models for adsorption of dioxygen on metal-chelates. Recl. Trav. Chim. Pays-Bas 109, 31-39.
109. Zagal, J.H., M. Ṕaez, J. Sturm, and S. Ureta-Zãnartu (1984). Electroreduction of oxygen on mixtures of phthalocyanines co-adsorbed on a graphite electrode. J. Electroanal. Chem. 181, 295-300.
110. Sheldon, R.A. and J.K. Kochi (1981). Metal-Catalysed Oxidations of Organic Compounds. Academic Press, New York.
111. van Veen, J.A.R. and J.F. van Baar (1982). Electrocatalysis on transition metal chelates. Rev. Inorg. Chem. 4, 293-327.
112. Shigehara, K. and F.C. Anson (1982). Electrocatalytic activity of three iron porphyrins in the reduction of dioxygen and hydrogen peroxide at graphite cathodes. J. Phys. Chem. 86, 2776-2783.
113. van den Brink, F., W. Visscher, and E. Barendrecht (1984). Electrocatalysis of cathodic oxygen reduction by metal phthalocyanines: Part III. Iron phthalocyanine as electrocatalyst: Experimental part. J. Electroanal. Chem. 172, 301-325.
114. Liu, H.Y., I. Abdalmuhdi, C.K. Chang, and F.C. Anson (1986). Catalysis of the electroreduction of dioxygen and hydrogen peroxide by an anthracene-linked dimeric cobalt porphyrin. J. Phys. Chem. 89, 665-670.
115. Anderson, A.B. and R.A. Sidik (2004). Oxygen electroreduction on FeII and FeIII coordinated to N4 chelates. Reversible potentials for the intermediate steps from quantum theory. J. Phys. Chem. B 108, 5031-5035.
116. Abraham, K.M., M. Alamgir, E.B. Willstaedt, and W.P. Kilroy (1992). Metal phthalocyanine-catalysed Li/SOCl2 cells. Electrochim. Acta 37, 531-543.
117. Collman, J.P. and K. Kim (1986). Electrocatalytic four-electron reduction of dioxygen by iridium porphyrins adsorbed on graphite. J. Am. Chem. Soc. 108, 7847-7849.
118. 2 reduction and evolution in alkaline media. J. Electrochem. Soc., 128, 1674-1680.
119. Bettelheim, A., D. Ozer, R. Harth, and R.W. Murray (1988). Redox and electrocatalytic properties towards dioxygen reduction of ruthenium tetra(orthoaminophenyl) porphyrin complexes with various axial ligands. J. Electroanal. Chem. 246, 139-154.
120. Convert, P., C. Coutanceau, P. Crouigneau, F. Gloagen, and C. Lamy (2001). Electrodes modified by electrodeposition of CoTAA complexes as selective oxygen cathodes in a direct methanol fuel cell. J. Appl. Electrochem. 31, 945-952.
121. Jiang, R. and D. Chu (2000). Remarkably active catalysts for the electroreduction of O2 to H2O for use in an acidic electrolyte containing concentrated methanol. J. Electrochem. Soc. 147, 4605-4609.
122. Gupta, S., D. Tryk, S.K. Zecevic, W. Aldred, D. Guo, and R.F. Savinell (1998). Methanol-tolerant electrocatalysts for oxygen reduction in a polymer electrolyte membrane fuel cell. J. Appl. Electrochem. 28, 673-682.
123. Sun, G.Q., J.T. Wang, S. Gupta, and R.F. Savinell (2001). Iron(III) tetramethoxyphenylporphyrin (FeTMPP-Cl) as electrocatalyst for oxygen reduction in direct methanol fuel cells. J. Appl. Electrochem. 31, 1025-1031.
124. Bettelheim, A., L. Soifer, E. Korin (2004). Electropolymerized porphyrin films as methanol barriers in direct methanol fuel cells. J. Electroanal. Chem. 571, 265-272.
125. Shentu, B, K. Oyaizu, and H. Nishide (2004). Electroreduction of oxygen at a Pt/C-modified electrode with a cobalporphyrin complex. Bull. Soc. Chem. Jpn 77, 401-405.
126. Shentu, B., K. Oyaizu, and H. Nishide (2004), Preparation of a tetraphenylporphyrinato- cobalt(II)-poly(3, 4-azopyridylene)complex and its oxygen enrichment effect at an oxygen electrode. J. Mater. Chem. 14, 3308-3311.