Electroreduction of CO2 catalyzed by metallomacrocyclics

N4-Macrocyclic Metal Complexes

Volumn , Issue , 2006, Pages 191-254

  Costamagna, Juan A ^a   Isaacs, Mauricio ^b   Aguirre, María J ^a   Ramírez, Galo ^a   Azocar, Ignacio ^a  

^a UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

^b UNIVERSITY OF CHILE   (Chile)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 35048817552     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-0-387-28430-9_5     Document Type: Chapter

References (170)

1. Bockris, J.O.M. (1989). Modern aspects electrochemistry. Electrochemical and Photoelectrochemical Reduction of Carbon Dioxide. Plenum Press, New York.
2. Vasudevan, P., N. Phougat, and A.K. Shukla (1996). Metal phthalocyanines as electrocatalysts for redox reactions. Appl. Organometal. Chem. 10(8), 591-604.
3. Udupa, K.S., G.S. Subramanian, and H.V.K. Udupa (1971). The electrolytic reduction of carbon dioxide to formic acid. Electrochim. Acta, 16(9) 1593-1598 and references therein.
4. Russell, P.G., N. Kovac, S. Srinivasan, and M. Steinberg (1977). The electrochemical reduction of carbon dioxide, formic acid, and formaldehyde. J. Electrochem. Soc. 124(9), 1329-1338 and references therein.
5. 2 on differently prepared copper electrodes: The influence of electrode treatment on the current efficiencies. J. Electroanal. Chem. 322(1-2), 233-246.
6. Arana, C., S. Yan, M. Keshavaraz, K.K.T. Pots, and H.D. Abrũna (1992). Electrocatalytic reduction of carbon dioxide with iron, cobalt, and nickel complexes of terdentate ligands. Inorg Chem. 31, 3680-3682.
7. Ogura, K. and H. Uchida (1987). Electrocatalytic reduction of carbon dioxide to methanol. Part 5. Relationship between the ability of metal complexes to engage in homogeneous catalysis and their coordination chemistry. J. Chem. Soc. Dalton Trans. 6, 1377-1380.
8. Frese, K.W. and S. Leach (1985). Electrochemical reduction of carbon dioxide to methane, methanol, and CO on Ru electrodes. J. Electrochem. Soc. 132, 259-261.
9. 2 at chemically modified electrodes. J. Chem. Soc. Chem. Commun. 20, 1416-1417.
10. Ogura, K. and K. Takamagari (1986). Electrocatalytic reduction of carbon dioxide to methanol. Part 2. Effects of metal complex and primary alcohol. J. Chem. Soc. Dalton Trans. 10, 1519-1523.
11. 2Cl. J. Am. Chem. Soc. 106, 5367-5368.
12. Naitoh, A., K. Otha, T. Mizuno, H. Yoshida, M. Sakai, and H. Noda (1993). Electrochemical reduction of carbon dioxide in methanol at low temperature. Electrochim. Acta 38(15) 2177-2179.
13. Fujita, E. (1996). DOE Report, DE 96007, 869, 66.
14. Behr, A. (1988). Carbon Dioxide Activation by Metal Complexes. VCH, New York.
15. Abrũna, H.D. (1988). Coordination chemistry in two dimensions: Chemically modified electrodes. Coord. Chem. Rev. 86, 135-189.
16. Collin, J.P. and J.P. Sauvage (1989). Electrochemical reduction of carbon dioxide mediated by molecular catalysts. Coord. Chem. Rev. 93(2), 245-268.
17. Vigato, P.A., S. Tamburrini, and D.E. Fenton (1990). The activation of small molecules by dinuclear complexes of copper and other metals. Coord. Chem. Rev. 106, 25-170.
18. Sullivan, B.P. (ed) (1993). Electrochemical and Electrocatalytic Reduction of Carbon Dioxide. Elsevier, Amsterdam.
19. Fujita, E., B.S. Brunschwig, T. Ogata, and S. Yanagida (1994). Toward photochemical carbon dioxide activation by transition metal complexes. Coord. Chem. Rev. 132, 195-200.
20. Costamagna, J., G. Ferraudi, J. Canales, and J. Vargas (1996). Carbon dioxide activation by aza-macrocyclic complexes. Coord. Chem. Rev. 148, 221-248.
21. Costamagna, J., G. Ferraudi, B. Matsuhiro, M. Campos-Vallette, J. Canales, M. Villagŕan, J. Vargas, and M.J. Aguirre (2000). Complexes of macrocycles with pendant arms as models for biological molecules. Coord. Chem. Rev. 196(1), 125-164.
22. Zagal, J.H., M.J. Aguirre, M. Isaacs, and J. Pavez (2003). Electrocat́alisis sobre electrodos modificados con complejos macroćiclicos. In N. Alonso-Vante (ed), Electroqúimica y Electrocat́alisis. Nuevos Materiales: Aspectos Fundamentales y Aplicaciones. e-libro.net, Buenos Aires.
23. Scibioh, M.A. and V.R. Vijayaraghavan (1998). Electrocatalytic reduction of carbon dioxide: Its relevance and importance. J. Sci. Ind. Res. 57(3), 111-123.
24. 2 on a new SPE-based system. J. Appl. Electrochem. 34(7), 757-762.
25. Yin, X. and J.R. Moss (1999). Recent developments in the activation of carbon dioxide by metal complexes. Coord. Chem. Rev. 181(1), 27-59.
26. Latimer, W.L. (1952). The Oxidation States of the Elements and Their Potentials in Aqueous Solutions, 2nd edition. Prentice Hall, USA.
27. Bard, A.J., R. Parsons, and J. Jordan (eds) (1985). Standard Potentials in Aqueous Solutions. IUPAC, Physical and Analytical Chemistry Divisions. Marcel Dekker, New York.
28. Schwarz, H.A., C. Creuz, and N. Suttin (1985). Cobalt(I) polypyridine complexes. Redox and substitutional kinetics and thermodynamics in the aqueous 2, 2'-bipyridine and 4, 4'-dimethyl-2, 2'-bipyridine series studied by the pulseradiolysis technique. Inorg. Chem. 24, 433-439.
29. Amatore, C. and J.M. Saveant (1981). Mechanism and kinetic characteristics of the electrochemical reduction of carbon dioxide in media of low proton availability. J. Am. Chem. Soc. 103, 5021-5023.
30. Frese, Jr., K.W. (1993). in B.P. Sullivan, K. Krist, H.E. Guard, (eds), Electrochemical and Electrocatalytic Reduction of Carbon Dioxide. Elsevier, Amsterdam, Chapter 6, and references therein.
31. 2 at metal-electrodes in aqueous hydrogen carbonate solution. Chem. Lett. 11, 1695.
32. 3 media. J. Electrochem. Soc. 137(6), 1772-1778.
33. Hori, Y., K. Kikuchi, A. Murata, and S. Suzuki (1986). Production of methane and ethylene in electrochemical reduction of carbon-dioxide at copper electrode in aqueous hydrogen carbonate solution. Chem. Lett. 6, 897.
34. Hori, Y., A. Murata, R. Takahashi, and S. Suzuki (1988). Enhanced formation of ethylene and alcohols at ambient temperature and pressure in electrochemical reduction of carbon dioxide at a copper electrode. J. Chem. Soc. Chem. Commun. 1, 17-19.
35. Hori, Y., A. Murata, and R. Takahashi (1989). Formation of hydrocarbons in the electrochemical reduction of carbon dioxide at a copper electrode in aqueous solution, J. Chem. Soc. Faraday Trans. 1, 5(8), 2309-2326.
36. DeWulf, D., T. Jin, and A. Bard (1989). Electrochemical and surface studies of carbon dioxide reduction to methane and ethylene at copper electrodes in aqueous solutions. J. Electrochem. Soc. 13, 1686-1691.
37. 2 and CO to methane on Cu foil electrodes. J. Electroanal. Chem. 245(1-2), 223-244.
38. Cook, R., R. MacDuff, and A. Sammels (1988). On the electrochemical reduction of carbon dioxide at in situ electrodeposited copper. J. Electrochem. Soc. 135(6), 1320-1326.
39. Wasmus, S., E. Cattaneo, and W. Vielstich (1990). Reduction of carbon dioxide to methane and ethane: An on-line MS study with rotating electrodes. Electrochim. Acta 35(4), 771-775.
40. 2 hydrogenation over Rh by metal oxides: The influence of oxide Lewis acidity and reducibility. J. Catal. 149(1), 149-158.
41. 2 on Ni electrodes. J. Electrochem. Soc. 140(6), 1541-1545.
42. 2. Electrochim. Acta 38(10), 1391-1394.
43. Schwartz, M., R.L. Cook, V.M. Kehoe, R.C. MacDuff, J. Patel, and A.F. Sammels (1993). Carbon dioxide reduction to alcohols using Perouskite-type electrocatalysis. J. Electrochem. Soc. 140(3), 614-618.
44. 2 on n-GaAs electrodes and selective methanol synthesis. J. Electrochem. Soc. 131(12), 2518-2522.
45. Kondelka, M., A. Monnier, and J. Augustyniski (1984). Electrocatalysis of the cathodic reduction of carbon dioxide on platinized titanium dioxide film electrode. J. Electrochem. Soc. 131(4), 745-750.
46. n films in aqueous media: Parameters influencing the reaction selectivity. J. Electroanal. Chem. 444, 253-260.
47. 2 pressures. J. Electroanal. Chem. 513(1), 45-51.
48. 2 to ethylene at a three-phase interface on copper(I) halide-confined Cu-mesh electrodes in acidic solutions of potassium halides. J. Electroanal. Chem. 565(2), 287-293.
49. 2 on Cu-Ag alloy electrodes. J. Electrochem. Soc. 147(5), 1864-1867.
50. 2 on a polypyrrole electrode modified by rhenium and copper-rhenium microalloy in methanol media. J. Electroanal. Chem. 533(1-2), 167-175.
51. 2, Catal. Lett. 26(3-4), 373-381.
52. 2 at a series of copper single crystal electrodes. J. Phys. Chem. B 106, 15-17.
53. 2 at copper single crystal Cu(S)-[n(111)×(111)] and Cu(S)-[n(110)×(100)] electrodes. J. Electroanal. Chem. 533(1-2), 135-143.
54. Shibata, M., K. Yoshida, and N. Furuya (1998). Electrochemical synthesis of urea at gas-diffusion electrodes III. Simultaneous reduction of carbon dioxide and nitrite ions with various metal catalysts. J. Electrochem. Soc. 145(2), 595-600.
55. a) Shibata, M., K. Yoshida, and N. Furuya (1998). Electrochemical synthesis of urea at gas-diffusion electrodes-IV. Simultaneous reduction of carbon dioxide and nitrate ions with various metal catalysts. J. Electrochem. Soc. 145(7), 2348-2353.
56. Shibata, M., K. Yoshida, and N. Furuya (1995). Electrochemical synthesis of urea on reduction of carbon dioxide with nitrate and nitrite ions using Cu-loaded gasdiffusion electrode. J. Electroanal. Chem. 387(1-2), 143-145 .
57. Shibata, M., K. Yoshida, and N. Furuya (1998). Electrochemical synthesis of urea at gas-diffusion electrodes-Part II. Simultaneous reduction of carbon dioxide and nitrite ions at Cu, Ag and Au catalysts. J. Electroanal. Chem. 442(1-2), 67-72.
58. 2, Electrochim. Acta 46(19), 3015-3022.
59. Ogawa, S., T. Yamaguchi, and N. Gotoh (1974). Synthesis of a novel macrocyclic compound and of its copper complex. J. Chem. Soc. Chem. Commun. 10, 577-579.
60. Ogawa, S., T. Yamaguchi, and N. Gotoh (1974). Preparation of a conjugated tautomer of 1, 14:7, 8-diethenotetrapyrido-[2, 1, 6-de:2, 1, 6-gh:2, 1, 6-kl:2, 1, 6na][1, 3, 5, 8, 10, 12] hexa-azacyclotetradecine and its metal derivatives]. J. Chem. Soc. Perkin Trans. 1, 976-978.
61. Ogawa, S., (1977). Preparation of macrocyclic compounds by thermal dimerization of 1, 10-phenanthroline derivatives. J. Chem. Soc. Perkin Trans. 12, 214-216.
62. Seno, M., S. Tsuchida, and S. Ogawa (1977). Electronic structure of macrocyclic compounds revealed by X-ray photoelectron spectroscopy. J. Am. Chem. Soc. 99(9), 3014-3018.
63. Cheng, C.-C., Y.-N. Kuo, K.-S. Chuang, C.-F. Luo, and W.J. Wang (1999). A new Co-II complex as a bulge-specific probe for DNA. Angew. Chem. Int. Ed. 38(9), 1255-1257.
64. Costamagna, J., J. Canales, J. Vargas, M. Camalli, F. Caruso, and E. Rivarola (1993). Precursors of aza-macrocycles-characterization of substituted phenanthrolines and related bases-crystal and molecular-structure of dichloro-di-n-butyl(2, 2-, 6, 6-bipyrimidine)-tin(IV). Pure Appl. Chem. 65(7), 1521-1526.
65. Lewis, J. and T. O'Donoghue (1980). Chemistry of polydentate ligands. Part 5. Complexes of 2, 9-dihydrazino-derivates of 1, 10-phenanthroline. Dependence of coordination number of a ligand on the anion present. J. Chem. Soc. Dalton.Trans. 5, 736-742.
66. Costamagna, J., J. Canales, J. Vargas, A. Alvarado, and G. Ferraudi (1993). Spectroscopic and electrochemical characterization of some complexes with azamacrocyclic ligands. J. Indian Chem. Soc. 70(11-12), 877-883.
67. Costamagna, J., J. Canales, J. Vargas, and G. Ferraudi (1995). Electrochemical reduction of carbon-dioxide by hexa-azamacrocyclic complexes. Pure Appl. Chem. 67(7), 1045-1052.
68. Estiu, G., A. Jubert, J. Molina, J. Costamagna, J. Canales, and J. Vargas (1995). Semiempirical SCF/CI interpretation of the origin of the catalytic activity of transition metal-macrocycle complexes. J. Mol. Struct: Teochem. 330(1-3), 201-210.
69. Estíu, G. and A. Jubert (1995). A theoretical investigation of the structure and electronic spectra of porphyrin homologue macrocycles. Hexaazacyclophane and its nickel and copper complexes. Inorg. Chem. 34, 1212-1220.
70. 2 by aza-macrocyclic complexes of Ni(II), Co(II), and Cu(II). Theoretical contribution to probable mechanisms. Inorg. Chim. Acta 339, 224-232.
71. Canales, J., J. Raḿirez, G. Estíu, and J. Costamagna (2000). Bis-bipyridine hexa-azamacrocycle complexes of zinc(II) and nickel(II) and the catalytic reduction of carbon dioxide. Polyhedron 19(22-23), 2373-2381.
72. 2 catalyzed by a cobalt(II) macrocyclic complex. J. Coord. Chem. 56(14), 1193-1201.
73. Kadish, K., M. Royal, E. Van Caemelbecke, and L. Gueletti (2000). Metalloporphyrins in nonaqueous Media: Database of Redox Potentials. In K.M. Kadish, K.M. Smith, and R. Guilard (eds), The Porphyrin Handbook, Vol. 9. Chapter 1, Academic Press, New York.
74. Lever, A.B.P., E.R. Milaneva, and G. Speir (1993). The redox chemistry of metallophthalocyanines in solution. in C.C. Leznoff and A.B.P.Lever, (eds), Phthalocyanines Properties and Applications, Vol. 3, Chapter 1, VCH, Weinheim.
75. Day, P., H.A.O. Hill, and M.G. Price (1968). Some reaction of cobalt phthalocyanines. J. Chem. Soc. A 1, 90-93.
76. Nevin, W.A., W. Liu, M. Melnick, and A.B.P. Lever (1986). Spectro-electrochemistry of cobalt and iron tetrasulphonated phthalocyanines. J. Electroanal. Chem. 213(2), 217-234.
77. Ardiles, P., E. Trollund, M. Isaacs, F. Armijo, and M.J. Aguirre (2001). Evidence of a stable charge-transfer adduct between 2-mercaptoethanol and cobalt-poly-tetraaminophthalocyanine. J. Coord. Chem. 54(3-4), 183-191.
78. + in water: Study of the factors affecting the efficiency and the selectivity of the process. J. Am. Chem. Soc. 108, 7461-7467.
79. 2 in water. J. Chem. Soc. Chem. Commun. 19, 1315-1316.
80. Pearce, D.J. and D. Pletcher (1986). A study of the mechanism for the electrocatalysis of carbon dioxide reduction by nickel and cobalt square planar complexes in solution, J. Electroanal. Chem. 197(1-2), 317-330.
81. 2 by nickel(II) cyclam: Study of the reduction mechanism on mercury by cyclic voltammetry, polarography and electrocapillarity. J. Electroanal. Chem. 292(1-2), 199-215.
82. Grant, J.L., K. Goswami, L.O. Spreer, J.W. Otvos, and M. Calvin (1987). Photochemical reduction of carbon dioxide to carbon monoxide in water using nickel(II) tetra-azamacrocycle complex as catalyst, J. Chem. Soc. Dalton Trans. 9, 2105-2109.
83. Collin, J.P., A. Jouaiti, and J.P. Sauvage (1988). Electrocatalytic properties of Ni(cyclam)2+ and Ni2(biscyclam)4+ with respect to CO2 and H2O reduction. Inorg. Chem. 27, 1986-1990.
84. 2, J. Electroanal. Chem. 322(1-2), 325-345 .
85. 2. J. Electroanal. Chem. 361(1-2), 149-157.
86. 2 Coordinate to a Ni(1) complex? An ab-initio MO/SD-CI study. J. Am. Chem. Soc. 11(2), 7813-7814.
87. Smith, C.I., J.A. Crayston, and R.W. Hay (1993). Reduction of carbon dioxide by nickel macrocyclic catalysts adsorbed on a mercury electrode or a copper rotating disc electrode. J. Chem. Soc. Dalton Trans. 21, 3267-3269.
88. 2( cyclam). J. Am. Chem. Soc. 114, 2055-2062.
89. Shionoya, M., E. Kimura, and Y. Iitaka (1990). Mono-, di-, and tetrafluorinated cyclams. J. Am. Chem. Soc. 112, 9231-9245.
90. 2 for carbon dioxide reduction (HTIM = 2, 3, 9, 10-tetramethyl-l, 4, 8, 11- tetraazacyclotetradecane, DMC = C-meso-5, 12-dimethyl-l, 4, 8, 11-tetraazacyclotetradecane). Inorg. Chem. 33, 4627- 4628.
91. Abbi, F., G. de Santis, L. Fabbrizzi, M. Licchelli, A.M.P. Manotti-Lanfredi, P. Pallavicini, A. Poggi, F. Ugozzoliz (1994). Nickel(II) complexes of azacyclams: oxidation and reduction behavior and catalytic effects in the electroreduction of carbon dioxide. Inorg. Chem. 33, 1366-1375.
92. Zilbermann, I., M. Winnik, D. Sagiv, A. Rotman, A.H. Cohen, and D. Meyerstein (1995). Properties of monovalent nickel complexes with tetraaza-macrocyclic ligands in aqueous solutions. Inorg. Chim. Acta 240(1-2), 503-514.
93. Lovecchio, F.V., E.S. Gore, and D.H. Busch (1974). The oxidation and reduction behavior of macrocyclic complexes of nickel. Electron spin resonance studies. J. Am. Chem. Chem. 96(10), 3109-3118.
94. Kobiro, K., A. Nakayama, T. Hiro, M. Suwa, and Y. Tobe (1992). Synthesis and molecular structures of nickel(II) alkyl-substituted cyclam complexes. Inorg. Chem. 31, 676-685.
95. Beer, P. D., P.A. Gale, and D.K. Smith (1999). Supramolecular Chemistry. Oxford University Press, New York.
96. Kaifer, A. and M. Gomez-Kaifer (1999). Supramolecular Electrochemistry. Wiley- VCH, Weinheim, Germany.
97. Lehn, J.-M. (1992). In A.F. Williams, C. Floriani, and A.E. Merbach (eds), Perspectives in Coordination Chemistry. VHCA, Basel p. 447.
98. Kr̈amer, R., J.-M. Lehn, A. De Cian, and J. Fisher (1993). Self-assembly, structure, and spontaneous resolution of a trinuclear triple helix from an oligobipyridine ligand and NiII Ions. Angew. Chem. In. Ed. Engl. 32(5), 703-706.
99. De Blas, A., G. De Santis, L. Fabrizzi, M. Licchelli, A.M. Manotti, L.P. Pallavicini, A. Poggi, and F. Ugozzoli (1993). Pyridines with an appended metallocyclam subunit. Versatile building blocks to supramolecular multielectron redox systems. Inorg. Chem. 32, 106-113.
100. Kimura, E., S. Wada, M. Shionoya, and Y. Okazaki (1994). New series of multifunctionalized nickel(II)-cyclam (cyclam = 1, 4, 8, 1l tetraazacyclotetradecane) complexes. Application to the photoreduction of carbon dioxide. Inorg. Chem. 33, 770-778.
101. Taraszewska, J., G. Roslonek, Y.D. Lampeka, and I.M. Maloshtan (1998). Oxalatebridged dinuclear nickel azacyclam macrocyclic complexes: Synthesis and electrochemical study. J. Electroanal. Chem. 452(1), 49-56.
102. Taraszewska, J., L. Tsymbal, and Y.D. Lampeka (1999). Polynuclear oxalate-bridged nickel complexes based on bis(macrocyclic) building blocks: Synthesis, spectral and electrochemical studies. Supramol. Chem. 10(4), 287-295.
103. Taraszewska, J., G. Roslonek, and B. Korybut-Daszkiewicz (2000). Redox properties of novel dinuclear Ni(II) bis-tetraazamacrocyclic complex. Supramol. Chem. 12(1), 115-121.
104. de Alwis, C., J. Crayston, T. Cromie, T. Eisenbl̈atter, R. Hay, Y.D. Lampeka, and L. Tsymbal (2000). Cyclic voltammetry study of the electrocatalysis of carbon dioxide reduction by bis(polyazamacrocyclic) nickel complexes. Electrochim. Acta 45(13), 2061-2074.
105. 2 by nickel(II) complex. Eur. J. Inorg. Chem. 17, 3242-3249.
106. Rowinski, P. and R. Bilewicz (2001). Carbon dioxide electrochemical sensor based on lipid cubic phase containing tetraazamacrocyclic complexes of Ni(II). Materials Science and Engineering C 18(1-2), 177-183.
107. Jarzebinska, A., P. Rowinski, I. Zawisza, R. Bilewicz, L. Siegfried, and T. Kaden (1999). Modified electrode surfaces for catalytic reduction of carbon dioxide. Anal. Chim. Acta 396(1), 1-12.
108. 2- towards a voltammetric sensor for the gas phase. Electroanal. 15(18), 1437-1444.
109. Ganjali, M., M. Yousefi, M. Javanbakht, T. Poursaberi, M. Salavati-Niasari, L. Hajiagha-Babael, E. Latifi, and M. Shamsipur (2002). Determination of SCN- in urine and saliva of smokers and non-smokers by SCN-selective polymeric membrane containing a nickel(II)-azamacrocycle complex coated on a graphite electrode. Anal. Sci. 18(8), 887-892.
110. Kashiwagi, Y., C. Kikuchi, F. Kurashima, and J. Anzai (2002). Electrocatalytic reduction of aldehydes and ketones on nickel(II) tetraazamacrocyclic complex-modified graphite felt electrode. J. Organomet. Chem. 662(1-2), 9-13.
111. Rowinski, P., R. Bilewicz, M.J. St́eb́e, and E. Rogalska (2002). A concept for immobilizing catalytic complexes on electrodes: Cubic phase layers for carbon dioxide sensing. Anal. Chem. 74(7), 1154-1559.
112. Mahmood, M.N., D. Masheder, and C.J. Harty (1987). Use of gas-diffusion electrodes for high-rate electrochemical reduction of carbon dioxide. II. Reduction at metal phthalocyanine-impregnated electrodes. J. Appl. Electrochem. 17(6), 1223-1227.
113. 2 by CoPc-coated edge graphite electrodes. J. Electroanal. Chem. 241(1-2), 361-371.
114. Kapusta, S. and N. Hackerman (1984). Carbon dioxide reduction at a metal phthalocyanine catalyzed carbon electrode. J. Electrochem. Soc. 131(7), 1511-1514.
115. Tanabe, H. and K. Ohno (1987). Electrocatalysis of metal phthalocyanine thin film prepared by the plasma-assisted deposition on a glassy carbon in the reduction of carbon dioxide. Electrochim. Acta, 32(7), 1121-1124.
116. Zagal, J.H. (1992). Metallophthalocyanines as catalysts in electrochemical reactions. Coord. Chem. Rev. 119, 89-136.
117. Eggins, B.R., J.T.S. Irvine, and J. Grimshaw (1998). The voltammetry of mixed solutions of carbon dioxide and metal phthalocyanines in DMSO. J. Electroanal. Chem. 266, 125-131.
118. Gangi, D.A., R.R. Dur and, Jr., (1986). Binding of carbon dioxide to cobalt and nickel tetra-aza macrocycles. J. Chem. Soc. Chem. Commun. 9, 697-699.
119. 2. J. Phys. Chem. A 104(48), 11332-11339.
120. 2 reduction in the aqueous phase using cobalt phthalocyanine/poly-4- vinylpyridine modified electrodes. J. Electroanal. Chem. 385(2), 209-225.
121. 2 reduction with cobalt phthalocyanine incorporated in a polyvinylpyridine membrane coated on a graphite electrode. J. Electroanal. Chem. 412(1-2), 125-132.
122. 2 reduction by cobalt octabutoxyphthalocyanine coated on graphite electrode. J. Mol. Catal. A 112(1), 55-61.
123. 2 reduction catalysed by cobalt octacyanophthalocyanine and its mechanism. J. Porhyrins Phthalocyanines 1, 315-321.
124. IIporphyrins. J. Chem. Soc. Commun. 21, 1471- 1472.
125. Prasad, R., V.K. Gupta, and A. Kumar (2004). Metallo-tetraazaporphyrin based anion sensors: Regulation of sensor characteristics through central metal ion coordination. Anal. Chim. Acta 508, 61-70.
126. Hammouche, M., D. Lexa, M. Momentau, and J.-M. Saveant (1991). Chemical catalysis of electrochemical reactions. Homogeneous catalysis of the electrochemical reduction of carbon dioxide by iron ("O") porphyrins. Role of the addition of magnesium cations. J. Am. Chem. Soc. 113(22), 8455-8466.
127. 2. Radiation chemical, photochemical, and electrochemical studies. J. Phys. Chem. A 102(17), 2870-2877.
128. 2 with cobalt and iron porphyrins. Interaction between CO and reduced metalloporphyrins. J. Phys. Chem. A 103(38), 7742-7748.
129. Swistak, C. and K.M. Kadish (1987). Electrochemistry of iron porphyrins under a CO atmosphere. Interactions between CO and pyridine. Inorg. Chem. 26, 405-412.
130. BF) of alkylated iron and cobalt porphyrins [(por)-M-R]. J. Porphyrins Phthalocyanines 1, 125-134.
131. Guilard, R., F. J́er̂ome, J.M. Barbe, C. Gross, Z. Ou, J. Shao, J. Fischer, R. Weiss, and K.M. Kadish (2001). Alkyl and aryl substituted corroles. 2. Synthesis and characterization of linked "face-to-face" biscorroles. X-ray structure of (BCA)Co-2(py)(3), where BCA represents a biscorrole with an anthracenyl bridge. Inorg. Chem. 40(19), 4845-4855.
132. Guilard, R., D.T. Gryko, G. Canard, J.M. Barbe, B. Koszarna, S. Brandes, and M. Tasior (2002). Synthesis of corroles bearing up to three different meso substituents. Org. Lett. 4(25), 4491-4494.
133. 2. J. Phys. Chem. A 106(18), 4772-4778.
134. Bhugun, I., D. Lexa, and J.M. Saveant (1996). Catalysis of the electrochemical reduction of carbon dioxide by iron(0) porphyrins: Synergystic effect of weak Br̈onsted acids. J. Am. Chem. Soc. 118, 1769-1776.
135. Bhugun, I., D. Lexa, and J.M. Saveant (1996). Catalysis of the electrochemical reduction of carbon dioxide by iron(0) porphyrins. Synergistic effect of Lewis acid cations. J. Phys. Chem. 100, 19981-19985.
136. Anson, F.C., C. Shi, and B. Steiger (1997). Novel multinuclear catalysts for the electroreduction of dioxygen directly to water. Acc. Chem. Res. 30, 437-444.
137. Toma, H. and K. Araki (2000). Supramolecular assemblies of ruthenium complexes and porphyrins. Coord. Chem. Rev. 196(1), 307-329.
138. Souza, F.D. (2002). Recent advances in the electrochemistry of porphyrins and phthalocyanines. J. Porphyrins Phthalocyanines 6(4), 285-288.
139. Prodi, A., M.T. Indelli, C.J. Kleverlaan, E. Alessio, and F. Scandola (2002). Energy transfer pathways in pyridylporphyrin metal adducts and side-to-face arrays. Coord. Chem. Rev. 229(1-2), 51-58.
140. Baerends, E.J., G. Ricciardi, A. Rosa, and S.J.A. van Gisbergen (2002). A DFT/TDDFT interpretation of the ground and excited states of porphyrin and porphyrazine complexes. Coord. Chem. Rev. 230(1-2), 5-27.
141. Iengo, E., E. Zangrando, and E. Alessio (2003). Discrete supramolecular assemblies of porphyrins mediated by coordination compounds. Eur. J. Inorg. Chem. 13, 2371-2384.
142. Araki, K. and H.E. Toma (1994). Spectroelectrochemistry and electrocatalytic properties of a tetraruthenated nickel porphyrin. J. Chem. Res. (S) 7, 290-290.
143. Araki, K. and H.E. Toma (1994). Synthesis and properties of a new polymetallated iron porphyrin. J. Chem. Res. (M). 3, 82-83.
144. Meshituka, S., M. Ichikawa, and K. Tamaru (1974). Electrocatalysis by metal phthalocyanines in the reduction of carbon dioxide. J. Chem. Soc. Chem. Commun. 5, 158-159.
145. 2 reduction electrocatalyzed by a cobalt tetramethylpyridoporphyrazine on the disk and detected as CO on a platinum ring. J. Electroanal. Chem. 403(1-2), 93-100.
146. 3Br] complexes incorporated into coated nafion membrane (bpy = 2, 2-bipyridine; terpy = 2, 2; 6, 2-terpyridine). J. Chem. Soc. Chem. Commun. 7, 631-633.
147. 2 reduction in methanol catalyzed by mono-, di-, and electropolymerized phthalocyanine complexes. Russ. Chem. Bull. Int. Ed. 51(5), 805-812.
148. Riquelme, A., M. Isaacs, M. Lucero, E. Trollund, and M. J. Aguirre (2003). Electrocatalytic reduction of carbon dioxide at polymeric cobalt tetra (3-amino (phenyl) porphyrin glassy carbon-modified electrodes. J. Chil. Chem. Soc. 48(2), 89-92.
149. Furuya, N. and K. Matsui (1989). Electroreduction of carbon dioxide on gasdiffusion electrodes modified by metal phthalocyanines. J. Electroanal. Chem. 271(1-2), 181-191.
150. 2. Electrochem. Commun. 1(6), 213-216.
151. Shibata, M. and N. Furuya (2001). Electrochemical synthesis of urea at gas-diffusion electrodes: Part VI. Simultaneous reduction of carbon dioxide and nitrite ions with various metallophthalocyanine catalysts. J. Electroanal. Chem. 507(1-2), 177-184.
152. Shibata, M. and N. Furuya (2003). Simultaneous reduction of carbon dioxide and nitrate ions at gas-diffusion electrodes with various metallophthalocyanine catalysts. Electrochim. Acta 48(25-26), 3953-3958.
153. 2 with transition metal phthalocyanine and porphyrin complexes supported on activated carbon fibers. J. Electrochem. Soc. 149(6), D89-D95.
154. 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. 13, 156-157.
155. 2 reduction. J. Electroanal. Chem. 318(1-2), 309-320.
156. Tanaka, H. and A. Aramata (1997). Aminopyridyl cation radical method for bridging between metal complex and glassy carbon: Cobalt(II) tetraphenylporphyrin bonded on glassy carbon for enhancement of CO2 electroreduction. J. Electroanal.Chem. 437(1-2) 29-35.
157. Aga, H., A. Aramata, and Y. Hisaeda (1997). The electroreduction of carbon dioxide by macrocyclic cobalt complexes chemically modified on a glassy carbon electrode. J. Electronal. Chem. 437(1-2), 11-118.
158. , M. Lucero, A. Riquelme, M. Villagŕan, J. Costamagna, E. Trollund, and M.J. Aguirre (2004). A supramolecular cobalt-porphyrin-modified electrode, toward the electroreduction of CO2. J. Coord. Chem. 57(3), 249-255.
159. Floriani, C., and F. Calderazzo (1969). Oxygen adducts of Schiffs base complexes of cobalt prepared in solution. J. Chem. Soc. A 6, 946-953.
160. Cariati, F., D. Galizzioli, F. Morazzoni, and C. Busetto (1975). New adducts of phthalocyaninatocobalt( II) with pyridine and 4-methylpyridine and their vibrational, magnetic, and electronic properties. Part 1. Reactivity towards oxygen. J. Chem. Soc. Dalton Trans. 7, 556-561.
161. Collman, J.P., R.R. Gagne, J. Kouba, and H. Ljusberg-Wahren (1974). Reversible oxygen adduct formation in cobalt(I1) picket fence porphyrins. J. Am. Chem. Soc. 96(21), 6800-6802.
162. Floriani, C. and G. Fachinetti (1974). Sodium [N, N'-ethylenebis (salicylideneiminato) cobaltate(I)], a reversible carbon dioxide carrier. J. Chem. Soc. Chem. Commun. 15, 615-616.
163. Gambarotta, S., F. Arena, C. Floriani, and P. Zanazzi (1982). Carbon dioxide fixation. Bifunctional complexes containing acidic and basic sites working as reversible carriers. J. Am. Chem. Soc. 104(19), 5082-5092.
164. Schmidt, M.H., G.M. Miskelley, and N.S. Lewis (1990). Effects of redox potential, steric configuration, solvent, and alkali-metal cations on the binding of carbondioxide to cobalt(I) and nickel(I) macrocycles. J. Am. Chem. Soc. 112(9), 3420-3426.
165. Zeng, Z.Y., S.L. Gupta, H. Huang, and E.B. Yeager (1991). Oxygen reduction on poly(4-vinyl pyridine)-modified ordinary pyrolytic graphite electrodes with adsorbed cobalt tetra-sulphonated phthalocyanine in acid solutions. J. Appl. Electrochem. 21(11), 973-981.
166. Furuya, N. and S. Koide (1991). Electroreduction of carbon dioxide by metal phthalocyanines. Electrochim. Acta 36(8), 1309-1313.
167. Zagal, J., M. Ṕaez, and C. Fierro (1997). In: S. Srinivasan, S. Wagner, and H. Wrobloba (eds), Electrode Materials and Processes for Energy Conversion and Storage. Electrochemical Society, Pennington, New York.
168. Rodŕiguez-Ḿendez, M.L., R. Aroca, and A. De Saja (1993). Electrochromic and gas adsorption properties of Langmuir-Blodgett films of lutetium bisphthalocyanine complexes. Chem. Mater. 4, 933-937.
169. 2 with epoxides. Russ. Chem. Bull. 47(11), 2137-2145.
170. Heskett, A., B. Plummer, and C. Messmer (1984). A correlation between anomalous electronic and vibrational properties of Chemisorbed molecules. Surf. Sci. 139(2-3), 558-568.