Synthesis, characterization and spectral properties of substituted tetraphenylporphyrin iron chloride complexes

Molecules

Volumn 16, Issue 4, 2011, Pages 2960-2970

  Sun, Zhi Cheng ^a   She, Yuan Bin ^a   Zhou, Yang ^a   Song, Xu Feng ^a   Li, Kai ^a  

^a BEIJING UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Iron porphyrin; Porphyrin; Spectra property; Synthesis

Indexed keywords

FERROUS CHLORIDE; FERROUS ION; PORPHYRIN; TETRAPHENYLPORPHYRIN;

ARTICLE; CHEMISTRY; INFRARED SPECTROPHOTOMETRY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

FERROUS COMPOUNDS; PORPHYRINS; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 79955538271     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16042960     Document Type: Article

References (30)

1. Haber, J.; Matachowski, L.; Pamin, K.; Poltowicz, J. The effect of peripheral substituents in metalloporphyrins on their catalytic activity in Lyons system. J. Mol. Catal. A: Chem. 2003, 198, 215-221.
2. Zakharieva, O.; Trautwein, A.X.; Veeger, C. Porphyrin-Fe(III)- hydroperoxide and porphyrin- Fe(III)-peroxide anion as catalytic intermediates in cytochrome P450-catalyzed hydroxylation reactions: a molecular orbital study. Biophys. Chem. 2000, 88, 11-34.
3. Bourre, L.; Simonneaux, G.; Ferrand, Y.; Thibaut, S.; Lajat, Y.; Patrice, T. Synthesis, and in vitro and in vivo evaluation of a diphenylchlorin sensitizer for photodynamic therapy. J. Photochem. Photobiol. B, Biol. 2003, 69, 179-192. (Pubitemid 36503387)
4. Biesaga, M.; Orska, J.; Fiertek, D.; Izdebski, J.; Trojanowicz, M. Immobilized metal-ion affinity chromatography of peptides on metalloporphyrin stationary phases. Fresenius J. Anal. Chem. 1999, 364, 160-164.
5. Drain, C.M.; Russell, K.C.; Lehn, J.M. Self-assembly of a multi-porphyrin supramolecular macrocycle by hydrogen bond molecular recognition. Chem. Commun. 1996, 3, 337-338. (Pubitemid 126443243)
6. Adachi, S.; Nagano, S.; Ishimori, K.; Watanabe, Y.; Morishima, I.; Egawa, T.; Kitagawa, T.; Makino, R. Roles of proximal ligand in heme proteins: replacement of proximal histidine of human myoglobin with cysteine and tyrosine by site-directed mutagenesis as models for P-450, chloroperoxidase, and catalase. Biochemistry 1993, 32, 241-252. (Pubitemid 23033342)
7. Nebert, D.W.; Dalton, T.P. The role of cytochrome P450 enzymes in endogenous signalling pathways and environmental carcinogenesis. Nat. Rev. Cancer 2006, 6, 947-960. (Pubitemid 44862679)
8. Yuan, Y.; Ji, H.B.; Chen, Y.X.; Han, Y.; Song, X.F.; She, Y.B.; Zhong, R.G. Oxidation of cyclohexane to adipic acid using Fe-porphyrin as a biomimetic catalyst. Org. Process Res. Dev. 2004, 8, 418-420. (Pubitemid 38829040)
9. Wang, L.Z.; She, Y.B.; Zhong, R.G.; Ji, H.B.; Zhang, Y.H.; Song, X.F. A green process for oxidation of p-nitrotoluene catalyzed by metalloporphyrins under mild conditions. Org. Process Res. Dev. 2006, 10, 757-761.
10. Rahimi, R.; Tehrani, A.A.; Fard, M.A.; Sadegh, B.M.M.; Khavasi, H.R. First catalytic application of metal complexes of porpholactone and dihydroxychlorin in the sulfoxidation reaction. Catal. Commun. 2009, 11, 232-235.
11. Meunier, B. Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage. Chem. Rev. 1992, 92, 1411-1456.
12. Rothemund, P. A new porphyrin synthesis. The synthesis of porphin. J. Am. Chem. Soc. 1936, 58, 625-627.
13. Adler, A.D.; Longo, F.R.; Finarelli, J.D.; Assour, J.; Korsakoff, L. A simplified synthesis for meso-tetraphenylporphine. J. Org. Chem. 1967, 32, 476.
14. Lindsey, J.S.; Schreiman, I.C.; Hsu, H.C.; Kearney, P.C.; Marguerettaz, A.M. Rothemund and Adler-Longo reactions revisited: synthesis of tetraphenylporphyrins under equilibrium conditions. J. Org. Chem. 1987, 52, 827-836.
15. Kumar, A.; Maji, S.; Abhilash, G.J.; Pandey, S.; Sarkar, S. One-pot general synthesis of metalloporphyrins. Tetrahedron Lett. 2007, 48, 7287-7290. (Pubitemid 47381539)
16. Sharghi, H.; Nejad, A.H. Phosphorus pentachloride (PCl5) mediated synthesis of tetraarylporphyrins. Helv. Chim. Acta 2003, 86, 408-414. (Pubitemid 36348392)
17. Nguyen, L.T.; Senge, M.O.; Smith, K.M.; Simple methodology for syntheses of porphyrins possessing multiple peripheral substituents with an element of symmetry. J. Org. Chem. 1996, 61, 998-1003. (Pubitemid 126585696)
18. Johnston, M.R.; Latter, M.J.; Warrener, R.N. Porphyrin-containing molecular capsules: metal mediated dimerization of a bis-porphyrin cavity. Org. Lett. 2002, 4, 2165-2168.
19. Rocha Gonsalves, A.M.d'A.; Varejao, J.M.T.B.; Pereira, M.M. Some new aspects related to the synthesis of meso-substituted porphyrins. J. Heterocycl. Chem. 1991, 28, 635-640.
20. Serra, A.C.; Rocha Gonsalves, A.M.d'A. Controlled porphyrinogen oxidation for the selective synthesis of meso-tetraarylchlorins. Tetrahedron Lett. 2010, 51, 4192-4194.
21. Geier, G.R., III; Chick, J.F.B.; Callinan, J.B.; Reid, C.G.; Auguscinski, W.P. A survey of acid catalysis and oxidation conditions in the two-step, one-flask synthesis of meso-substituted corroles via dipyrromethanedicarbinols and pyrrole. J. Org. Chem. 2004, 69, 4159-4169. (Pubitemid 38736480)
22. Ono, N.; Kawamura, H.; Bougauchi, M.; Maruyama, K. Porphyrin synthesis from nitrocompounds. Tetrahedron 1990, 46, 7483-7496.
23. Rothemund, P. Formation of porphyrins from pyrroles and aldehydes. J. Am. Chem. Soc. 1935, 57, 2010-2011.
24. Rothemund, P.; Menotti, A.R. Porphyrin studies. IV. The synthesis of α, β, γ, δ-tetraphenylporphine. J. Am. Chem. Soc. 1941, 63, 267-270.
25. Adler, A.D.; Longo, F.R.; Shergalis, W. Mechanistic investigation of porphyrin syntheses. I. Preliminary studies on ms-tetraphenylporphin. J. Am. Chem. Soc. 1964, 86, 3145-3149.
26. Lindsey, J.S.; MacCrum, K.A.; Tyhonas, J.S.; Chuang, Y.Y. Investigation of a synthesis of meso-porphyrins employing high concentration conditions and an electron transport chain for aerobic oxidation. J. Org. Chem. 1994, 59, 579-587.
27. Li, F.R.; Yang, K.X.; Tyhonas, J.S.; Maccrum, K.A.; Lindsey, J.S. Beneficial effects of salts on an acid-catalyzed condensation leading to porphyrin formation. Tetrahedron 1997, 53, 12339-12360. (Pubitemid 27380295)
28. Adler, A.D.; Longo, F.R.; Kampas, F.; Kim, J. On the preparation of metalloporphyrins. J. Inorg. Nucl. Chem. 1970, 32, 2443-2445.
29. Johnstone, R.A.W.; Nunes, M.L.P.G.; Pereira, M.M.; Rocha Gonsalves, A.M.d'A.; Serra, A.C. Improved syntheses of 5, 10, 15, 20-tetrakisaryl- and tetrakisalkylporphyrins. Heterocycles 1996, 43, 1423-1437.
30. Prendergast, K.; Spiro, T.G. Core expansion, ruffling, and doming effects on metalloporphyrin vibrational frequencies. J. Am. Chem. Soc. 1992, 114, 3793-3801.