Metalloporphyrin-functionalized hexagonal mesoporous silica: Synthesis, structural properties and catalytic activity as cytochrome P450 model

Microporous and Mesoporous Materials

Volumn 168, Issue , 2013, Pages 37-45

  Bolzon, Lucas B ^a   Airoldi, Heide R ^a   Zanardi, Fabrício B ^a   Granado, Juliana G ^a   Iamamoto, Yassuko ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Biomimetic catalysis; HMS; Metalloporphyrins; Oxidation; PhIO

Indexed keywords

BIOMIMETIC MATERIALS; BIOMIMETICS; CATALYSTS; CATALYTIC OXIDATION; CHLORINE COMPOUNDS; MESOPOROUS MATERIALS; OXIDATION; PORE SIZE; PORPHYRINS;

ADSORPTION DESORPTION ISOTHERMS; BIOMIMETIC CATALYSIS; EFFECT OF THE SUPPORT; HEXAGONAL MESOPOROUS SILICA; MESOPOROUS STRUCTURES; METALLO-PORPHYRINS; OXIDATION OF CYCLOHEXANE; PHIO;

CATALYST ACTIVITY;

EID: 84867901070     PISSN: 13871811     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.micromeso.2012.09.039     Document Type: Article

References (65)

1. P.R. Ortiz de Montellano, Chem. Rev. 110 (2010) 932.
2. D. Dolphin, T.G. Traylor, L.Y. Xie, Acc. Chem. Res. 30 (1997) 251.
3. P.R. Ortiz de Montellano, J. De Voss, in: P.R. Ortiz de Montellano (Ed.), Cytochrome P450: Structure, Mechanism and Biochemistry, 3rd ed., Kluwer Academic/Plenum Publisher, New York, 2005, p. 183.
4. J.T. Groves, Y.Z. Han, in: P.R. Ortiz de Montellano (Ed.), Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed., Kluwer Academic/Plenum Publisher, New York, 1995, p. 3.
5. J.T. Groves, J. Inorg. Biochem. 100 (2006) 434.
6. S.P. Visser, W. Nam, in: K.M. Kadish, K.M. Smith, R. Guilard (Ed.), Handbook of Porphyrin Science, v.10 Part 1,World Scientific Publishing Co. Pte. Ltd., Singapore, 2010, p. 85.
7. J. Rittle, J.M. Younker, M.T. Green, Inorg. Chem. 49 (2010) 3610.
8. Z. Pan, Q. Wang, X. Sheng, J.H. Horner, M. Newcomb, J. Am. Chem. Soc. 131 (2009) 2621.
9. E.Y. Tshuva, S.J. Lippard, Chem. Rev. 104 (2004) 987.
10. L. Que Jr., W.B. Tolman, Nature 455 (2008) 333.
11. M. Costas, M.P. Mehn, M.P. Jensen, L. Que Jr., Chem. Rev. 104 (2004) 939.
12. S.V. Kryatov, E.V. Rybak-Akimova, S. Schindler, Chem. Rev. 105 (2005) 2175.
13. A.E. Shilov, G.B. Shul'pin, Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes, Kluwer, Dordrecht, 2000.
14. B. Meunier, Chem. Rev. 92 (1992) 1411.
15. D. Mansuy, Coord. Chem. Rev. 125 (1993) 129.
16. J.R. Lindsay Smith, in: R.A. Sheldon (Ed.), Metalloporphyrins in Catalytic Oxidations, Marcel Dekker, New York, 1994, p. 325.
17. D. Mansuy, P. Battioni, in: K.M. Kadish, K.M. Smith, R. Guilard (Eds.), The Porphyrin Handbook, vol. 4, Academic Press, San Diego, 2000, p. 1.
18. J.T. Groves, K. Shalyaev, J. Lee, in: K.M. Kadish, K.M. Smith, R. Guilard (Eds.), The Porphyrin Handbook, vol. 4, Academic Press, San Diego, 2000, p. 17.
19. K. Suslick, in: K.M. Kadish, K.M. Smith, R. Guilard (Eds.), The Porphyrin Handbook, vol. 4, Academic Press, San Diego, 2000, p. 41.
20. W. Nam, S.Y. Oh, Y.J. Sun, J. Kim, W.K. Kim, S.K. Woo, W. Shin, J. Org. Chem. 68 (2003) 7903.
21. T.G. Traylor, Y. Iamamoto, T. Nakano, J. Am. Chem. Soc. 108 (1986) 3530.
22. F.S. Vinhado, M.E.F. Gandini, Y. Iamamoto, A.M.G. Silva, M.M.Q. Simões, M.G.P.M.S. Neves, A.C. Tomé, S.L.H. Rebelo, A.M.V.M. Pereira, J.A.S. Cavaleiro, J. Mol. Catal. A 239 (2005) 138.
23. J.R. Lindsay Smith, Y. Iamamoto, F.S. Vinhado, J. Mol. Catal. A 252 (2006) 23.
24. E. Brulé, Y.R. de Miguel, Org. Biomol. Chem. 4 (2006) 599.
25. C.M.C. Prado-Manso, E.A. Vidoto, F.S. Vinhado, H.C. Sacco, K.J. Ciuffi, P.R. Martins, A.G. Ferreira, J.R. Lindsay-Smith, O.R. Nascimento, Y. Iamamoto, J. Mol. Catal. A 150 (1999) 251.
26. F.S. Vinhado, C.M.C. Prado-Manso, H.C. Sacco, Y. Iamamoto, J. Mol. Catal. A 174 (2001) 279.
27. A.D.Q. Ferreira, F.S. Vinhado, Y. Iamamoto, J. Mol. Catal. A 243 (2006) 111.
28. H.C. Sacco, Y. Iamamoto, J.R. Lindsay Smith, J. Chem. Soc., Perkin Trans. 2 (2001) 181.
29. M.D. Assis, J.R. Lindsay Smith, J. Chem. Soc. Perkin Trans. 2 (1998) 2221.
30. M.E.F. Gandini, C.R. Neri, F.S. Vinhado, T.S. Minorin, O.R. Nascimento, O.A. Serra, Y. Iamamoto, J. Braz. Chem. Soc. 19 (2008) 344.
31. P. Battioni, E. Cardin, M. Louloudi, B. Schöllorn, G.A. Spyroulias, D. Mansuy, T.G. Traylor, J. Chem. Soc. Chem. Commun. (1996) 2037.
32. K.J. Ciuffi, H.C. Sacco, J.C. Biazzotto, A. Vidoto, O.R. Nascimento, C.A.P. Leite, O.A. Serra, Y. Iamamoto, J. Non-Cryst. Solids 273 (2000) 100.
33. I.L. Viana Rosa, C.M.C. Prado-Manso, O.A. Serra, Y. Iamamoto, J. Mol. Catal. A 160 (2000) 199.
34. F.C. Skrobot, I.L. Viana Rosa, A.P.A. Marques, P.R. Martins, J. Rocha, A.A. Valente, Y. Iamamoto, J. Mol. Catal. A 237 (2005) 86.
35. A.A. Costa, G.F. Ghesti, J.L. Macedo, V.S. Braga, M.M. Santos, J.A. Dias, S.C.L. Dias, J. Mol. Catal. A 282 (2008) 149.
36. Z. Li, C.G. Xia, X.M. Zhang, J. Mol. Catal. A 185 (2002) 47.
37. R. Zhang, W.Y. Yu, H.Z. Sun, W.S. Liu, C.M. Che, Chem. Eur. J. 8 (2002) 2495.
38. S. Evans, J.R. Lindsay Smith, J. Chem. Soc. Perkin Trans. 2 (2001) 174.
39. P.T. Tanev, T.J. Pinnavaia, Science 267 (1995) 865.
40. P.T. Tanev, T.J. Pinnavaia, Chem. Mater. 8 (1996) 2068.
41. L. Mercier, T.J. Pinnavaia, Chem. Mater. 12 (2000) 188.
42. T.R. Pauly, T.J. Pinnavaia, Chem. Mater. 13 (2001) 987.
43. P.M. Price, J.H. Clark, D.J. Macquarrie, J. Chem. Soc. Dalton Trans. (2000) 101.
44. K. Wilson, A.F. Lee, D.J. Macquarrie, J.H. Clark, Appl. Catal. A 228 (2002) 127.
45. A.R. Silva, K. Wilson, A.C. Whitwood, J.H. Clark, C. Freire, Eur. J. Inorg. Chem. (2006) 1275.
46. D.J. Macquarrie, Chem. Commun. (1996) 1961.
47. A.G.S. Prado, C. Airoldi, J. Mater. Chem. 12 (2002) 3823.
48. A.G.S. Prado, E. DeOliviera, J. Coll. Interface Sci. 291 (2005) 53.
49. E. DeOliveira, A.G.S. Prado, J. Mol. Catal. A 271 (2007) 63.
50. E. DeOliveira, C.R. Neri, A.O. Ribeiro, V.S. Garcia, L.L. Costa, A.O. Moura, A.G.S. Prado, O.A. Serra, Y. Iamamoto, J. Coll. Interface Sci. 323 (2008) 98.
51. P. Battioni, O. Brigaud, H. Desvaux, D. Mansuy, T.G. Traylor, Tetrahedron Lett. 32 (1991) 2893.
52. R.M. Silverstein, F.X. Webster, D.J. Kiemle, Spectrometric Identification of Organic Compounds, seventh ed., John Wiley & Sons, New York, 2005.
53. L. Boucher, J. Coord. Chem. Rev. 7 (1972) 289.
54. K.J. Balkus Jr., A.G. Gabrielov, S.L. Bell, Inorg. Chem. 33 (1994) 67.
55. M.F. Toney, C.A. Evans Jr, S. Wilson, in: C.R. Brundle (Ed.), Encyclopedia of Materials Characterization, Butterworth, Heineman, Stoneham, 1992.
56. Y. Iamamoto, M.D. Assis, K.J. Ciuffi, C.M.C. Prado, B.Z. Prellwitz, M. Moraes, O.R. Nascimento, H.C. Sacco, J. Mol. Catal. A 116 (1997) 365.
57. J.T. Groves, T.E. Nemo, J. Am. Chem. Soc. 105 (1984) 5786.
58. J.T. Groves, J. Lee, S.S. Marla, J. Am. Chem. Soc. 119 (1997) 6269.
59. J.T. Groves, T.E. Nemo, R.S. Myers, J. Am. Chem. Soc. 101 (1979) 1032.
60. T.S. Minorin, Master Degree Dissertation, Universidade de São Paulo, Brazil, 2008.
61. M.E.F. Gandini, Doctorate Thesis, Universidade de São Paulo, Brazil, 2006.
62. J.T. Groves, G.A. McClusky, J. Am. Chem. Soc. 98 (1976) 859.
63. S. Shaik, S.P. De Visser, in: P.R. Ortiz de Montellano (Ed.), Cytochrome P450: Structure, third ed., Mechanism and Biochemistry, Kluwer Academic/Plenum Publisher, New York, 2005, p. 45.
64. B. Meunier, S.P. DeVisser, S. Shaik, Chem. Rev. 104 (2004) 3947.
65. M.A. Schiavon, Y. Iamamoto, O.R. Nascimento, M.D. Assis, J. Mol. Catal. A 174 (2001) 213.