Reduction of 4,4′-stilbenequinone and 4,4′-diphenoquinone upon reaction with photogenerated radicals

Photochemistry and Photobiology

Volumn 86, Issue 6, 2010, Pages 1202-1207

  Görner, Helmut ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

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[No Author keywords available]

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TETRA;

EID: 78649682052     PISSN: 00318655     EISSN: 17511097     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2010.00798.x     Document Type: Article

References (48)

1. Maruyama, K., and, A. Osuka, (1988) Recent advances in the photochemistry of quinones. In The Chemistry of the Quinoide Compounds, Vol. 2 (Edited by, S. Patei, and, Z. Rappoport,), pp. 757-875. Wiley, New York.
2. Maruyama, K., and, Y. Kubo, (1994) Photochemical hydrogen abstraction of quinones. In CRC Handbook of Organic Photochemistry and Photobiology (Edited by, W. M. Horspool, and, P.-S. Song,), pp. 748-756. CRC Press, Boca Raton.
3. Serpa, C., and, L. G. Arnaut, (2000) Does molecular size matter in photoinduced electron transfer reactions? J. Phys. Chem. A 104, 11075-11086.
4. Görner, H., (2003) Photoreduction of p-benzoquinones: Effects of alcohols and amines on the intermediates and reactivities in solution. Photochem. Photobiol. 78, 440-448.
5. Görner, H., (2003) Photoprocesses of p-benzoquinones in aqueous solution. J. Phys. Chem. A 107, 11587-11595.
6. Gollnick, K., S. Held, D. O. Mártire, and, S. E. Braslavsky, (1992) Hydroxyanthraquinones as sensitizers of singlet oxygen reactions: Quantum yields of triplet formation and singlet oxygen generation in acetonitrile. J Photochem. Photobiol. A: Chem. 69, 155-165.
7. Alegría, A., E. Ferrer, G. Santiago, E. Sepúlveda, and, W. Flores, (1999) Photochemistry of water-soluble quinones. Production of the hydroxyl radical, singlet oxygen and the superoxide ion. J. Photochem. Photobiol. A: Chem. 127, 57-65.
8. Görner, H., (2005) Photoreactions of 1,4-naphthoquinones: Effects of substituents and water on the intermediates and reactivity. Photochem. Photobiol. 81, 376-383.
9. Görner, H., (2003) Photoreduction of 9,10-anthraquinone derivatives: Transient spectroscopy and effects of alcohols and amines on reactivity in solution. Photochem. Photobiol. 77, 171-179.
10. Görner, H., (2007) Oxygen uptake upon photolysis of 1,4-benzoquinones and 1,4-naphthoquinones in air-saturated aqueous solution in the presence of formate, amines, ascorbic acid and alcohols. J. Phys. Chem. A 111, 2814-2819.
11. Steenken, S., and, P. Neta, (2003) Transient phenoxyl radicals: Formation and properties in aqueous solutions. In The Chemistry of Phenols (Edited by, Z. Rappoport,), pp. 1107-1152. Wiley, New York.
12. Görner, H., (2004) Photoreactions of 2-methyl-5-isopropyl-1,4- benzoquinone. J. Photochem. Photobiol. A: Chem. 165, 215-222 and references cited therein.
13. 1) and plastoquinone-1 in solution. Photochem. Photobiol. Sci. 2, 524-535.
14. 1: Effects of alcohols and amines on the reactivity in solution. Photochem Photobiol. Sci. 3, 71-78.
15. Jovanovic, S. V., K. Kánya, and, J. C. Scaiano, (1995) Redox reactions of 3,5-di-tert-butyl-1,2-benzoquinone. Implications for reversal of paper yellowing. Can. J. Chem. 73, 1803-1810.
16. Brede, O., S. Naumov, and, R. Hermann, (2002) Sterically hindered phenols are extremely efficient light quenchers. Chem. Phys. Lett. 355, 1-7.
17. Lehmann, M. W., and, D. H. Evans, (2001) Mechanism of the electrochemical reduction of 3,5-di-tert-butyl-1,2-benzoquinone. Evidence for a concerted electron and proton transfer reaction involving a hydrogen-bonded complex as reactant. J. Phys. Chem. B 105, 8877-8884.
18. Bradley, W., and, J. D. Sanders, (1962) Derivatives of stilbenequinone. J. Chem. Soc. 480-486.
19. Li, S., and, K. Lundquist, (2005) Stereoisomers of 3,3′-dimethoxy- 4,4′-stilbenequinone. Holzforschung 59, 282-284.
20. Kovářová, J., J. Rotschová, O. Brede, and, M. Burgers, (1995) The effect of transformation products of the antioxidant BHT on the initial stages of thermo- and photo-oxidation of LDPE. Can. J. Chem. 73, 1862-1868.
21. Brede, O., M. Burgers, J. Kovářová, and, I. Kúdelka, (1996) Pulse radiolysis and laser flash photolysis studies of stabiliser transformation products. Rad. Phys. Chem. 47, 47-52.
22. Friaa, O., V. Chaleix, M. Lecouvey, and, D. Brault, (2008) Reaction between the anesthetic agent propofol and the free radical DPPH• in semiaqueous media: Kinetics and characterization of the products. Free Radic. Biol. Med. 45, 1011-1018.
23. Casellato, U., S. Tamburini, P. A. Vigato, A. De Stefani, M. Vidali, and, D. E. Fenton, (1983) The preparation of binuclear complexes and their catalytic behaviour in the oxidation of 3,5-di-t-butycatechol. Inorg. Chim. Acta 69, 45-51.
24. Zippel, F., F. Ahlers, R. Werner, W. Haase, H.-F. Nolting, and, B. Krebs, (1996) Structural and functional models for the dinuclear copper active site in catechol oxidases: Syntheses, X-ray crystal structures, magnetic and spectral properties and X-ray absorption spectroscopic studies in solid state and in solution. Inorg. Chem. 35, 3409-3419.
25. Oyaizu, K., K. Saito, and, E. Tsuchida, (2000) Copper-catalyzed oxidative coupling of 2,4,6- trimethylphenol with oxygen. Chem. Lett. 1318-1319.
26. Chun, H., C. N. Verani, P. Chaudhuri, E. Bothe, E. Bill, T. Weyhermüller, and, K. Wieghardt, (2001) Molecular and electronic structure of octahedral o-aminophenolato and o-iminobenzo-semiquinonato complexes of V(V), Cr(III), Fe(III), and Co(III). Experimental determination of oxidation levels of ligands and metal ions. Inorg. Chem. 40, 4157-4166.
27. Mukherjee, S., T. Weyhermüller, E. Bothe, K. Wieghardt, and, P. Chaudhuri, (2004) Dinuclear and mononuclear manganese(IV)-radical complexes and their catalytic catecholase activity. Dalton Trans. 3842-3853.
28. Szigyártó, I. C., L. I. Simándi, L. Párkányi, L. Korecz, and, G. Schlosser, (2006) Biomimetic oxidation of 3,5-di-tert-butylcatechol by dioxygen via Mn-enhanced base catalysis. Inorg. Chem. 45, 7480-7487.
29. Jockusch, S., H. J. Timpe, Ch.-H. Fischer, and, W. Schnabel, (1992) On the photoreduction of crystal violet, phenosafranine and methylene blue by benzophenone. J. Photochem. Photobiol. A: Chem. 63, 217-226.
30. Jockusch, S., H.-J. Timpe, W. Schnabel, and, N. J. Turro, (1996) Photoreduction of organic dyes in ketone amine systems. J. Photochem. Photobiol. A: Chem. 96, 129-136.
31. Jockusch, S., H.-J. Timpe, W. Schnabel, and, N. J. Turro, (1997) Photoinduced energy and electron transfer between ketone triplets and organic dyes. J. Phys. Chem. A 101, 440-445.
32. Jockusch, S., and, N. J. Turro, (1999) Radical addition rate constants to acrylates and oxygen: α-hydroxy and α-amino radicals produced by photolysis of photoinitiators. J. Am. Chem. Soc. 121, 3921-3925.
33. Gruen, H., and, H. Görner, (2009) Reduction of the polynuclear quinonoid dyes 16,17-dihydroxy- and dimethoxyviolanthrone with photogenerated radicals. Photochem. Photobiol. Sci. 8, 1164-1171.
34. Gruen, H., and, H. Görner, (2010) Properties of 16,17-disubstituted dihydroviolanthrones formed by reaction of violanthrones with photogenerated radicals. Photochem. Photobiol. Sci. 9, 1088-1093.
35. Gruen, H., H. Steffen, and, D. Schulte-Frohlinde, (1981) Formation of singlet oxygen by photo-excitation of substituted aromatic azo-compounds in oxygenated solution. J. Soc. Dyers Col. 97, 430-435.
36. Heller, H. G., and, J. R. Langan, (1981) Photochromic heterocyclic fulgides. Part 3. The use of (E)-α-(2,5-dimethyl-3-furylethylidene) (isopropylidene)succinic anhydride as a simple convenient chemical actinometer. J. Chem. Soc. Perkin Trans. 2 341-343.
37. Carmichael, I., and, G. L. Hug, (1986) Triplet-triplet absorption spectra of organic molecules in condensed phases. J. Phys. Ref. Data 15, 1-250.
38. Adams, G. E., and, R. L. Willson, (1973) Ketyl radicals in aqueous solution pulse radiolysis study. J. Chem. Soc. Faraday Trans. 1 69, 719-729.
39. a, and reduction potential of phenoxyl radical from 4,4′-biphenol in aqueous medium. J. Phys. Chem. A 105, 5954-5959.
40. Tripathi, G. N. R., and, D. M. Chipman, (2002) Structure and proton reactivity of the semiquinone anion and dianion of biphenol in water. J. Phys. Chem. A 106, 8908-8916.
41. Nelsen, S. F., M. N. Weaver, and, J. P. Telo, (2007) Charge localization in a 17-bond mixed-valence quinone radical anion. J. Phys. Chem. A 111, 10993-10997.
42. Görner, H., (2006) Oxygen uptake and involvement of superoxide radicals upon photolysis of ketones in air-saturated aqueous alcohol, formate, amine or ascorbic acid solutions. Photochem. Photobiol. 82, 801-808.
43. 2. J. Mol. Catal. A, Chem. 117, 299-309.
44. Türk, H., and, Y. Çimen, (2005) Oxidation of 2,6-di-tert-butylphenol with tert-butylhydroperoxide catalyzed by cobalt(II) phthalocyanine tetrasulfonate in a methanol-water mixture and formation of an unusual product 4,4′-dihydroxy-3,3′,5,5′-tetra-tert- butylbiphenyl. J. Mol. Catal. A, Chem. 234, 19-24.
45. Božič, M., S. Pricelius, G. M. Guebitz, and, V. Kokol, (2010) Enzymatic reduction of complex redox dyes using NADH-dependent reductase from Bacillus subtilis coupled with cofactor regeneration. Appl Microbiol. Biotechn. 85, 563-571.
46. Meredith, P., and, T. Sarna, (2006) The physical and chemical properties of eumelanin. Pigment Cell Res. 19, 572-594.
47. Valgimigli, L., R. Amorati, M. G. Fumo, G. A. DiLabio, G. F. Pedulli, K. U. Ingold, and, D. A. Pratt, (2008) The unusual reaction of semiquinone radicals with molecular oxygen. J. Org. Chem. 73, 1830-1841.
48. Görner, H., D. Döpp, and, A. Dittmann, (2000) Photoreduction of electron-deficient azaarenes by di- and trialkylamines. J. Chem. Soc. Perkin Trans. 2 1723-1733.