Water-soluble silver(II) and gold(III) porphyrins: The effect of structural distortion on the photophysical and photochemical behavior

Inorganic Chemistry Communications

Volumn 14, Issue 11, 2011, Pages 1756-1761

  Harrach, Gergely ^a   Valicsek, Zsolt ^a   Horváth, Ottó ^a  

^a UNIVERSITY OF PANNONIA   (Hungary)

Author keywords

Gold; Photochemistry; Photodynamic therapy; Porphyrin; Silver; Sitting atop features

Indexed keywords

EID: 80053564264     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2011.08.003     Document Type: Article

References (52)

1. F. Haurowitz, E. Clar, Z. Hermann, H. Kittel, and F.K. Munzberg Eigenschaften der Porphyrin-Metall-Komplexe und ihre Abhangigkeit von der Wertigkeit und Susceptibilitat ihrer Metallatome Ber. Dtsch. Chem. Ges. 68 1935 1795 1806
2. K.M. Kadish The electrochemistry of metalloporphyrins in nonaqueous media Prog. Inorg. Chem. 34 1986 435 605
3. H.N. Po, and S.E. Jones Heterogeneous electron transfer rate constants of substituted tetraphenylporphinatosilver(II) complexes Inorg. Chim. Acta 48 1981 37 39
4. S.E. Jones, and H.N. Po The effect of substituents on the oxidation potentials of substituted tetraphenyporhinatosilver(II) complexes Inorg. Chim. Acta 42 1980 95 99
5. A. Harriman, M.C. Richoux, and P. Neta Redox chemistry of metalloporphyrins in aqueous solution J. Phys. Chem. 87 1983 4957 4965
6. D. Karweik, N. Winograd, D.G. Davis, and K.M. Kadish X-ray photoelectron spectroscopic studies of silver(III) octaethylporphyrin J. Am. Chem. Soc. 96 1974 591 592
7. A. Kumar, and P. Neta Reduction and demetalation of silver porphyrins in aqueous solutions J. Phys. Chem. 85 1981 2830 2832
8. K.M. Kadish, X.Q. Lin, J.Q. Ding, Y.T. Wu, and C. Araullo A reinvestigation of silver porphyrin electrochemistry. Reactions of Ag(III), Ag(II), and Ag(I) Inorg. Chem. 25 1986 3236 3242
9. A. Giraudeau, A. Louati, H.J. Callot, and M. Gross Electrochemical reduction and demetalation of silver and thallium porphyrins Inorg. Chem. 20 1981 769 772
10. S. Fukuzumi, K. Ohkubo, W. Zhu, M. Sintic, T. Khoury, P.J. Sintic, W. E., Z. Ou, M.J. Crossley, and K.M. Kadish Androgynous Porphyrins. Silver(II) quinoxalinoporphyrins act as both good electron donors and acceptors J. Am. Chem. Soc. 130 2008 9451 9458 (Pubitemid 352031156)
11. A. Antipas, D. Dolphin, M. Gouterman, and E.C. Johnson Porphyrins. 38. Redox potentials, charge transfer transitions, and emission of copper, silver, and gold complexes J. Am. Chem. Soc. 100 1978 7705 7709
12. M. Krishnamurthy, J.R. Sutter, and P. Hambright Monomer-dimer equilibration of water-soluble porphyrins as a function of the co-ordinated metal ion J. Chem. Soc. Chem. Commun. 1 1975 13 14
13. M. Krishnamurthy, and J.R. Sutter Kinetic and equilibrium study of the monomer-dimer reaction of [tetrakis(p-(trimethylammonio)phenyl)porphinato] silver(III) in aqueous medium Inorg. Chem. 24 1985 1943 1946
14. A. MacCragh, C.B. Storm, and W.S. Koski Solvent and substituent effects on the spin resonance spectra of metalloporphyrins J. Am. Chem. Soc. 87 1965 1470 1476
15. M. Ghazzali, A.M. Morsy, K. Abu-Youssef, Ö. Larsson, A. Hansson, T. Amer, and L. Tamm Öhrström, Synthesis, EPR and DFT calculations of rare Ag(II)porphyrins and the crystal structure of [Zn(II)tetrakis(4-bromo-2- thiophene)porphyrin] Inorg. Chem. Commun. 11 2008 1019 1022
16. S. Igarashi, K. Uchiyama, and T. Yotsuyanagi Spectrophotometric determination of sulfide ion with watersoluble porphyrin complex of silver(I) Bunseki Kagaku 37 1988 331 332
17. -7 M levels of thiol compounds using silver(I)-5,10,15,20-tetrakis(4- sulfophenyl)porphine complex Chem. Pharm. Bull. 44 1996 226 228
18. H. Kunkely, and A. Vogler Photodemetalation of silver(II) tetraphenylporphyrin Inorg. Chem. Commun. 10 2007 479 481
19. F.K. Kneubühl, W.S. Koski, and W.S. Caughey An electron spin resonance study of silver porphyrin J. Am. Chem. Soc. 83 1961 1607 1609
20. A. MacCragh, and W.S. Koski The electron paramagnetic resonance spectrum of silver phthalocyanine J. Am. Chem. Soc. 85 1963 2375 2376
21. O. Horváth, R. Huszánk, Z. Valicsek, and G. Lendvay Photophysics and photochemistry of kinetically labile, water-soluble porphyrin complexes Coord. Chem. Rev. 250 2006 1792 1803
22. Z. Valicsek, and O. Horváth Formation, photophysics and photochemistry of thallium(III) 5,10,15,20-tetrakis(4-sulphonatophenyl) porphyrin: New supports of typical sitting-atop features J. Photoch. Photobio. A 186 2007 1 7
23. Z. Valicsek, G. Lendvay, and O. Horváth Equilibrium, photophysical, photochemical, and quantum chemical examination of anionic mercury(II) mono- and bisporphyrins J. Phys. Chem. B 112 2008 14509 14524
24. R.D. Shannon Revised effective ionic radii and systematic studies of interatomic distances in halides and chalcogenides Acta Crystallogr. Sect. A: Found. Crystallogr. 32 1976 751 767
25. D.K. Lavallee Kinetics and mechanisms of metalloporphyrin term reactions Coord. Chem. Rev. 61 1985 55 96
26. S.C.M. Gandini, E.L. Gelamo, R. Itri, and M. Tabak Small angle X-Ray scattering study of meso-tetrakis(4-sulfonatophenyl) porphyrin in aqueous solution:a self-aggregation model Biophys. J. 85 2003 1259 1268 (Pubitemid 36909686)
27. M.P. Eng, T. Ljungdahl, J. Andreasson, J. Martensson, and B. Albinsson Triplet Photophysics of Gold(III) Porphyrins J. Phys. Chem. A 109 2005 1776 1784 (Pubitemid 40406840)
28. R.E. Haddad, S. Gazeau, J. Pécaut, J.-C. Marchon, C.J. Medforth, and J.A. Shelnutt Origin of the red shifts in the optical absorption bands of nonplanar tetraalkylporphyrins J. Am. Chem. Soc. 125 2003 1253 1268 (Pubitemid 36159836)
29. J.M. Okoh, and M. Krishnamurthy Solution chemistry of silver porphyrins. Oxidation of 5,10,15,20-tetra(3-N-methylpyridinio)porphyrinatodisilver(I) J. Chem. Soc. Dalton Trans. 2 1986 449 451
30. J.M. Okoh, and M. Krishnamurthy Kinetics of the demetallation and oxidation of the tetrakis-(p-(trimethylammonio)phenyl)porphine-silver complex Inorg. Chim. Acta 189 1991 233 236
31. G.D. Dorough, J.R. Miller, and F.M. Huennekens Spectra of the metallo-derivatives of alpha, beta, gamma, delta-tetraphenylporphine J. Am. Chem. Soc. 73 1951 4315 4320
32. J.M. Okoh, N. Bowles, and M. Krishnamurthy Solution chemistry of silver-porphyrins 3. Silver(I) porphyrins Polyhedron 3 1984 1077 1081
33. Z. Valicsek, O. Horváth, and K.L. Stevenson Photophysics and photochemistry of water-soluble, sitting-atop bis-thallium(I) 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin Photochem. Photobiol. Sci. 3 2004 669 673 (Pubitemid 39139937)
34. D.Y. Dawson, and J. Arnold Ionic versus covalent bonding in dilithium porphyrins: X-ray structure of dilithium tetraphenylporphyrin bis(etherate) J. Porphyr. Phthalocya. 1 1997 121 124 (Pubitemid 127534547)
35. M.E. Jamin, and R.T. Iwamoto Gold porphyrin complexes. Evidence for electrochemically inert gold(III) Inorg. Chim. Acta 27 1977 135 143
36. W. Levason, and M.D. Spicer The chemistry of copper and silver in their higher oxidation states Coord. Chem. Rev. 76 1987 45 120
37. T.C.W. Mak, and X.-L. Zhao Silver: Inorganic & Coordination Chemistry R.B. King, Encyclopedia of Inorganic Chemistry Second edition 2005 John Wiley & Sons Chichester 5187 5197
38. H.N. Po Heterocyclic and macrocyclic amine complexes of silver(II) and silver(III) Coord. Chem. Rev. 20 1976 171 195
39. J.A. McMillan Higher oxidation states of silver Chem. Rev. 62 1962 65 80
40. A. Harriman Luminescence of porphyrins and metalloporphyrins. Part 1. - Zinc(II), nickel(II) and manganese(II) porphyrins J. Chem. Soc. Faraday Trans. 1 76 1980 1978 1985
41. V.S. Chirvonyi, B.M. Dzhagarov, Y.V. Timinskii, and G.P. Gurinovich Picosecond flash-photolysis of Ni(II)- and Ag(II)-porphyrins Chem. Phys. Lett. 70 1980 79 83
42. Z. Valicsek, O. Horváth, G. Lendvay, I. Kikaš, and I. Škorić Formation, photophysics, and photochemistry of cadmium(II) complexes with 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin and its octabromo derivative: The effects of bromination and the axial hydroxo ligand J. Photoch. Photobio. A 218 2011 143 155
43. O. Horváth, Z. Valicsek, and A. Vogler Unique photoreactivity of mercury(II) 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin Inorg. Chem. Commun. 7 2004 854 857
44. K. Kalyanasundaram Photochemistry of Polypyridine and Porphyrin Complexes 1996 Academic Press London
45. A. Melaiye, Z. Sun, K. Hindi, A. Milsted, D. Ely, D.H. Reneker, C.A. Tessier, and W.J. Youngs Silver(I) - imidazole cyclophane gem-diol complexes encapsulated by electrospun tecophilic nanofibers: Formation of nanosilver particles and antimicrobial activity J. Am. Chem. Soc. 127 2005 2285 2291 (Pubitemid 40270533)
46. V. Sambhy, M.M. MacBride, B.R. Peterson, and A. Sen Silver bromide nanoparticle/polymer composites: Dual action tunable antimicrobial materials J. Am. Chem. Soc. 128 2006 9798 9808 (Pubitemid 44147964)
47. J.A. Cowan, and J.K.M. Sanders Reductive demetallation of porphyrins: Evidence for peripheral and axial modes of reduction Tetrahedron Lett. 27 1986 1201 1204
48. Electron transfer K.M. Kadish, K.M. Smith, and R. Guilar The Porphyrin Handbook 2000 Academic Press San Diego 74 75
49. J.R. McCarthy, P.J. Melfi, S.H. Capetta, and C. Brückner Use of Ag(II) as a removable template in porphyrin chemistry: diol cleavage products of [meso-tetraphenyl-2,3-cis-diolchlorinato]silver(II) Tetrahedron 59 2003 9137 9146 (Pubitemid 37329562)
50. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Cliord, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J.J. Dannenberg, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, and J.A. Pople Gaussian 98 Revision A.11.4 2002 Gaussian Inc Pittsburgh PA
51. W.R. Scheidt, J.U. Mondal, C.W. Eigenbrot, A. Adler, L.J. Radonovich, and J.L. Hoard Crystal and molecular structure of the silver(II) and zinc(II) derivates of meso-tetraphenylporphyrin. An exploration of crystal-packing effects on bond distance Inorg. Chem. 25 1986 795 799
52. J.W. Barnes, and G.D. Dorough Exchange and replacement reactions of alpha, beta, gamma, delta-tetraphenyl-metalloporphins J. Am. Chem. Soc. 72 1950 4045 4050