Phototransformation of anthraquinone-2-sulphonate in aqueous solution

Photochemical and Photobiological Sciences

Volumn 11, Issue 9, 2012, Pages 1445-1453

  Bedini, Andrea ^a   De Laurentiis, Elisa ^a   Sur, Babita ^a,b   Maurino, Valter ^a   Minero, Claudio ^a   Brigante, Marcello ^c,d   Mailhot, Gilles ^c,d   Vione, Davide ^a  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF CALCUTTA   (India)

^c UNIVERSITÉ CLERMONT AUVERGNE   (France)

^d ICCF   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84962425344     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c2pp25111f     Document Type: Article

References (48)

1. A. Ter Halle C. Richard Simulated solar light irradiation of mesotrione in natural waters Environ. Sci. Technol. 2006 40 3842 3847
2. C. K. Remucal K. McNeill Photosensitized amino acid degradation in the presence of riboflavin Environ. Sci. Technol. 2011 45 5230 5237
3. I. Grgic L. I. Nieto-Gligorovski S. Net B. Temime-Roussel S. Gligorovski H. Wortham Light induced multiphase chemistry of gas-phase ozone on aqueous pyruvic and oxalic acids Phys. Chem. Chem. Phys. 2010 12 698 707
4. J. L. Packer J. J. Werner D. E. Latch K. McNeill W. A. Arnold Photochemical fate of pharmaceuticals in the environment: naproxen, diclofenac, clofibric acid, and ibuprofen Aquat. Sci. 2003 65 342 351
5. S. Canonica T. Kohn M. Mac F. J. Real J. Wirz U. Von Gunten Photosensitizer method to determine rate constants for the reaction of carbonate radical with organic compounds Environ. Sci. Technol. 2005 39 9182 9188
6. Y. Yu M. J. Ezell A. Zelenyuk D. Imre L. Alexander J. Ortega J. L. Thomas K. Gogna D. J. Tobias B. D'Anna C. W. Harmon S. N. Johnson B. J. Finlayson-Pitts Nitrate ion photochemistry at interfaces: a new mechanism for oxidation of α-pinene Phys. Chem. Chem. Phys. 2008 10 3063 3071
7. H. Gorner Electron transfer from aromatic amino acids to triplet quinones J. Photochem. Photobiol., B 2007 88 83 89
8. T. Delatour T. Douki C. D'Ham J. Cadet Photosensitization of thymine nucleobase by benzophenone through energy transfer, hydrogen abstraction and one-electron oxidation J. Photochem. Photobiol., B 1998 44 191 198
9. S. Lacombe H. Cardy M. Simon A. Khoukh J. P. Soumillion M. Ayadim Oxidation of sulfides and disulfides under electron transfer or singlet oxygen photosensitization using soluble or grafted sensitizers Photochem. Photobiol. Sci. 2002 1 347 354
10. J. Wenk U. von Gunten S. Canonica Effect of dissolved organic matter on the transformation of contaminants induced by excited triplet states and the hydroxyl radical Environ. Sci. Technol. 2011 45 1334 1340
11. V. Maurino A. Bedini D. Borghesi D. Vione C. Minero Phenol transformation photosensitised by quinoid compounds Phys. Chem. Chem. Phys. 2011 13 11213 11221
12. P. R. Maddigapu C. Minero V. Maurino D. Vione M. Brigante G. Mailhot Enhancement by anthraquinone-2-sulphonate of the photonitration of phenol by nitrite: implication for the photoproduction of nitrogen dioxide by coloured dissolved organic matter in surface waters Chemosphere 2010 81 1401 1406
13. P. R. Maddigapu M. Minella D. Vione V. Maurino C. Minero Modeling phototransformation reactions in surface water bodies: 2,4-dichloro-6- nitrophenol as a case study Environ. Sci. Technol. 2011 45 209 214
14. D. Vione P. R. Maddigapu E. De Laurentiis M. Minella M. Pazzi V. Maurino C. Minero S. Kouras C. Richard Modelling the photochemical fate of ibuprofen in surface waters Water Res. 2011 45 6725 6736
15. I. Loeff A. Treinin H. Linschitz Photochemistry of 9,10-anthraquinone-2- sulfonate in solution. 1. Intermediates and mechanism J. Phys. Chem. 1983 87 2536 2544
16. P. R. Maddigapu A. Bedini C. Minero V. Maurino D. Vione M. Brigante G. Mailhot M. Sarakha The pH-dependent photochemistry of anthraquinone-2-sulfonate Photochem. Photobiol. Sci. 2010 9 323 330
17. H. J. Kuhn S. E. Braslavsky R. Schmidt Chemical actinometry Pure Appl. Chem. 2004 76 2105 2146
18. S. E. Braslavsky Glossary of terms used in photochemistry Pure Appl. Chem. 2007 79 293 465
19. K. P. Clark H. I. Stonehill Photochemistry and radiation chemistry of anthraquinone-2-sodium-sulphonate in aqueous solution. Part 1. Photochemical kinetics in aerobic solution J. Chem. Soc., Faraday Trans. 1 1972 68 577 590
20. J. B. Foresman and A. Frisch, Exploring Chemistry with Electronic Structure Methods, Gaussian, Inc., Pittsburgh, PA, 1996
21. J. A. Pople P. M. W. Gill B. G. Johnson Kohn-Sham density-functional theory within a finite basis set Chem. Phys. Lett. 1992 199 557 560
22. R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989
23. D. Becke Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993 98 5648 5652
24. C. E. H. Dessent, A density functional theory study of the anthracene anion Chem. Phys. Lett. 2000 330 180 187
25. K. E. Wise A. K. Grafton R. A. Wheeler Trimethyl-p-benzoquinone provides excellent structural, spectroscopic, and thermochemical models for plastoquinone-1 and its radical anion J. Phys. Chem. A 1997 101 1160 1165
26. A. K. Grafton A. E. Boesch R. A. Wheeler Structures and properties of vitamin K and its radical anion predicted by a hybrid Hartree-Fock/density functional method J. Mol. Struct. (THEOCHEM) 1997 392 1 11
27. D. Jacquemin J. Preat M. Charlot V. Wathelet J. M. Andre E. A. Perpete Theoretical investigation of substituted anthraquinone dyes J. Chem. Phys. 2004 121 1736 1743
28. R. Krishnan J. S. Binkley R. Seeger J. A. Pople Self consistent molecular orbital methods. XX. A basis set for correlated wave functions J. Chem. Phys. 1980 72 650 654
29. A. D. McLean G. S. Chandler Contracted Gaussian basis sets for molecular. calculations. I. Second row atoms, Z = 11-18 J. Chem. Phys. 1980 72 5639 5648
30. S. Miertus E. Scrocco J. Tomasi Electrostatic interaction of a solute with a continuum: a direct utilization of ab initio molecular potentials for the prevision of solvent effects J. Chem. Phys. 1981 55 117 129
31. E. Runge E. K. U. Gross Density-functional theory for time-dependent systems Phys. Rev. Lett. 1984 52 997 1000
32. M. Cossi V. Barone Time-dependent density functional theory for molecules in liquid solutions J. Chem. Phys. 2001 115 4708 4717
33. R. W. Browne N. M. O'Boyle J. J. McGarvey J. G. Vos Elucidating excited state electronic structure and intercomponent interactions in multicomponent and supramolecular systems Chem. Soc. Rev. 2005 34 641 663
34. 2+: a spectroscopic and computational study Inorg. Chem. 2009 48 1469 1481
35. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr., 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. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, 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, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle and J. A. Pople, GAUSSIAN 03 (Revision B.05), Gaussian, Inc., Pittsburgh, PA, 2003
36. N. M. O'Boyle and J. G. Vos, GaussSum, version 1.0.5, Dublin City University, Dublin, Ireland, 2005. http://gausssum.sourceforge.net, last accessed September 2011
37. R. S. K. A. Gamage B. M. Peake J. Simpson X-Ray crystal structure determination of some sodium anthraquinone sulfonate derivatives Aust. J. Chem. 1993 46 1595 1604
38. V. Maurino D. Borghesi D. Vione C. Minero Transformation of phenolic compounds upon UVA irradiation of anthraquinone-2-sulfonate Photochem. Photobiol. Sci. 2008 7 321 327
39. B. Sui X. Fu Novel application of 1-/2-phenyl substituted 9,10-anthraquinones in solid electrochromic devices J. Solid State Electrochem. 2009 13 1889 1895
40. A. E. Alegría A. Ferrer G. Santiago E. Sepúlveda W. Flores Photochemistry of water-soluble quinones. Production of hydroxyl radical, singlet oxygen and the superoxide ion J. Photochem. Photobiol., A 1999 127 57 65
41. J. N. Moore D. Phillips R. E. Hester Time-resolved resonance Raman spectroscopy applied to the photochemistry of the sulfonated derivatives of 9,10-anthraquinone J. Phys. Chem. 1988 92 5619 5627
42. I. Loeff S. Goldstein A. Treinin H. Linschitz Interactions of formate ion with triplets of anthraquinone-2-sulfonate, 1,4-naphthoquinone, benzophenone-4-carboxylate, and benzophenone-4-sulfonate J. Phys. Chem. 1991 95 4423 4430
43. B. E. Hulme E. J. Land G. O. Phillip Pulse radiolysis of 9,10-anthraquinones. Part 1. Radicals J. Chem. Soc., Faraday Trans. 1 1972 68 1992 2002
44. J. N. Moore D. Phillips N. Nakashima K. Yoshihara Photochemistry of 9,10-anthraquinone-2,6-disulphonate J. Chem. Soc., Faraday Trans. 2 1986 82 745 761
45. D. Phillips J. N. Moore R. E. Hester Time-resolved resonance Raman spectroscopy applied to anthraquinone photochemistry J. Chem. Soc., Faraday Trans. 2 1986 82 2093 2104
46. B. Sur M. Rolle C. Minero V. Maurino D. Vione M. Brigante G. Mailhot Formation of hydroxyl radicals by irradiated 1-nitronaphthalene (1NN): oxidation of hydroxyl ions and water by the 1NN triplet state Photochem. Photobiol. Sci. 2011 10 1817 1824
47. R. S. Silva D. E. Nicodem Deuterium isotope effects on the photoreduction of 9,10-phenanthrenequinone and benzophenone by 2-propanol J. Photochem. Photobiol., A 2008 194 76 80
48. H. Nagakubo G. Kubota K. Kubo T. Kaneko T. Sakurai H. Inoue Self-sensitized photolysis of N-(1-naphthoyl)-N-phenyl-O-(benzoyl-substituted benzoyl)hydroxylamines Bull. Chem. Soc. Jpn. 1996 69 2603 2611