Photochemistry of metal complexes of 3-hydroxyflavone: Towards a better understanding of the influence of solar light on the metal-soil organic matter interactions

Photochemical and Photobiological Sciences

Volumn 7, Issue 1, 2007, Pages 109-119

  Protti, Stefano ^a,b   Mezzetti, Alberto ^a   Lapouge, Christine ^a   Cornard, Jean Paul ^a  

^a UNIVERSITÉ DES SCIENCES ET TECHNOLOGIES DE LILLE   (France)

^b UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 3 PHENYL 1,2 INDANDIONE; 3 HYDROXYFLAVONE; ALUMINUM; LEAD; METAL COMPLEX; METHANOL; OXYGEN; PHENINDIONE; SOIL ORGANIC MATTER; UNCLASSIFIED DRUG; WATER; ZINC;

ARTICLE; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; DESORPTION; FLUORESCENCE; INFRARED SPECTROSCOPY; LIGHT; MOLECULAR INTERACTION; PHOTOCHEMISTRY; PRIORITY JOURNAL; RAMAN SPECTROMETRY; SOLAR ENERGY; SOLAR RADIATION; ULTRAVIOLET RADIATION;

EID: 37749050338     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b709682h     Document Type: Article

References (60)

1. R. L. Wershaw and G. R. Aiken, in Humic substances in soils, sediments and water, Wiley Interscience, New York, 1995
2. G. Sposito, in The chemistry of soils, Oxford Univeristy Press, New York, 1989, 277
3. P. Doelman L. Haanstra Effect of lead on soil respiration and on the decomposition of organic matter Soil Biol. Biochem. 1979 11 475 479
4. E. Baath Effects of heavy metals in soil on microbial processes and populations (a review) Water Air Soil Poll. 1989 47 335 379
5. I. V. Sokolova O. N. Tchaikovskaya Fluorescence and photochemical properties of humic acids Atmos. Oceanic. Opt. 2006 19 220 222
6. D. E. Latch R. McNeil Microheterogeneity of Singlet Oxygen Distributions in Irradiated Humic Acid Solutions Science 2006 311 1743 1747
7. W. L. Miller Effects of UV radiation on aquatic humus: photochemical principles and experimental considerations Ecol. Studies 1998 133 125 143
8. R. G. Zepp G. L. Baughman P. F. Schlotzhauer Comparison of photochemical behaviour of various humic substances in water: I. Sunlight, induced reactions of aquatic pollutants photosensitized by humic substances Chemosphere 1981 10 109 117
9. R. G. Zepp G. L. Baughman P. F. Schlotzhauer Comparison of photochemical behavior of various humic substances in water: II. Photosensitized, oxygenations Chemosphere 1981 10 119 26
10. D. Vialaton C. Richard Phototransformation of aromatic pollutants in solar light: Photolysis versus photosensitized reactions under natural water conditions Aquat. Sci. 2002 64 207 215
11. B. C. Faust J. Hoignè Sensitized photooxidation of phenols by fulvic acids and in natural waters Environ. Sci. Technol. 1987 21 957 964
12. J. Buschmann S. Canonica L. Sigg Photoinduced oxidation of Antimony(iii) in the presence of humic acids Environ. Sci. Technol. 2005 39 5335 5341
13. The flavonoids: advances in research since 1986, ed., J. B. Harborne,, Chapman-Hall, London, 1994
14. C. Rice-Evans Flavonoids antioxidants Curr. Med. Chem. 2001 8 797 807
15. P. J. Pietta Flavonoids as antioxidants J. Nat. Products 2000 63 1035 1042
16. A. S. Klymchenko C. Kenfack G. Duportail Y. Mély Effect of polar protic solvents on dual emissions of 3-hydroxychromones J. Chem. Sci. 2007 119 83 89
17. D. McMorrow M. Kasha Proton transfer spectroscopy of 3-hydroxychromones. Extreme sensitivity to hydrogen-bonding perturbations J. Am. Chem. Soc. 1983 105 5133 5134
18. D. McMorrow M. Kasha Proton-transfer spectroscopy on 3-hydroxyflavone in an isolated-site crystal matrix Proc. Natl. Acad. Sci. USA 1984 81 3375 3378
19. D. McMorrow M. Kasha Intramolecular excited-state proton transfer in 3-hydroxyflavone. Hydrogen-bonding solvent perturbations J. Phys. Chem. 1984 88 2235 2243
20. I. Yokoe K. Higugi Y. Shirataki M. Komatsu Photochemistry of Flavonoids. III. Photorearrangement, of Flavonols Chem. Pharm. Bull. 1981 29 894 898
21. S. L. Studer W. E. Brewer M. L. Martinez P.-T. Chou Time-resolved Study of the Photooxygenation of 3-Hydroxyflavone J. Am. Chem. Soc. 1989 111 7643 7644
22. B. J. Schwartz L. A. Peteanu C. B. Harris Direct observation of fast proton transfer: femtosecond photophysics of 3-hydroxyflavone J. Phys. Chem. 1992 96 3591 3598
23. J. Woolfe P. J. Thistlethwaite Direct observation of Excited State Intramolecular Proton Transfer Kinetics in 3-Hydroxyflavone J. Am. Chem. Soc. 1981 103 6916 6923
24. P. Chou D. McMorrow T. J. Aartsma M. Kasha The proton-transfer laser: gain spectrum and amplification of spontaneous emissiom of 3-hydroxyflavone J. Phys. Chem. 1984 88 4596 4599
25. E. Biagtan E. Goldberg R. Stephens E. Valeroso J. Harmon Gamma radiation dose rate effects on a polymer scintillator containing a large Stokes shift dye, 3-hydroxyflavone Nucl. Instrum. Methods Phys. Res., Sect. B 1996 114 88 90
26. S. Carturan A. Quaranta G. Maggioni M. Bonafini G. Della Mea, 3-Hydroxyflavone-based wavelength shifting system for near UV optical sensors Sens. Actuators, A 2004 113 288 292
27. B. Gerard G. Jones II J. A. Porco, Jr. A biomimetic approach to the rocaglamides employing photogeneration of oxidopyryliums derived from 3-hydroxyflavones J. Am. Chem. Soc. 2004 126 13620 13621
28. J. A. Porco, Jr., B. Gerald, G. Jones II, Synthesis of rocaglamide natural products via photochemical generation of oxydopyrylium species, PCT Int. Appl., WO2005-US10005-20050323, 2005
29. V. V. Shynkar A. S. Klymchenko C. Kunzelmann G. Duportail C. D. Muller A. P. Demchenko J.-M. Freyssinet Y. Mely Fluorescent biomembrane probe for ratiometric detection of apoptosis J. Am. Chem. Soc. 2007 129 2187 2193
30. 3+ in methanol Polyhedron 2007 26 6 10
31. J.-P. Cornard L. Dangleterre C. Lapouge DFT and TD-DFT investigation and spectroscopic characterization of the molecular and electronic structure of Zn(ii)-3-hydroxyflavone complex Chem. Phys. Lett. 2006 419 304 308
32. L. Dangleterre J.-P. Cornard Interation of lead(ii) chloride with hydroxyflavones in methanol: A spectroscopic study Polyhedron 2005 24 1593 1598
33. C. Lapouge J. P. Cornard time dependent density functional theory study of electronic absorption properties of lead(ii) complexes with a series of hydroxyflavones J. Phys. Chem. A 2005 109 6752 6761
34. A.-C. Boudet J.-P. Cornard J.-C. Merlin Conformational and spectroscopic investigation of 3-hydroxyflavone-aluminium chelates Spectrochim. Acta, Part A 2000 56 829 839
35. D. S. Smith J. R. Kramer Multisite metal binding to fulvic acid determined using multiresponse fluorescence Anal. Chim. Acta 2000 416 211 220
36. D. S. Smith J. R. Kramer Fluorescence analysis for multi-site aluminum binding to natural organic matter Environ. Inter. 1999 25 295 306
37. C. B. Coulson R. I. Davies D. A. Lewis Polyphenols in plant, humus and soil. I. Polyphenols, of leaves litter and superficial humus from mull and more sites J. Soil Sci. 1960 11 20 29
38. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople, GAUSSIAN 03 (Revision B.04), Gaussian, Inc., Wallingford, CT, 2003
39. A. D. Becke Density-functional thermochemistry. III. The, role of exact exchange J. Chem. Phys. 1993 98 5648 5652
40. C. Lee W. Yang R. G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 1988 37 785 789
41. R. Bauernschmitt R. Ahlrichs Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory Chem. Phys. Lett. 1996 256 454 464
42. M. Cossi G. Scalmani N. Rega V. Barone New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution J. Chem. Phys. 2002 117 43 54
43. P. K. Mandal A. Samanta Evidence of ground-state proton-transfer reaction of 3-hydroxyflavone in neutral alcoholic solvents J. Phys. Chem A 2003 107 6334 6339
44. J.-P. Cornard L. Vrielynck J.-C. Merlin J.-C. Wallet Structural and vibrational study of 3-hydroxyflavone and 3-methoxyflavone Spectrochim. Acta, Part A 1995 51 913 923
45. M. Wang T. Teslova F. Xu T. Spataru J. R. Lombardi R. L. Birke Raman and surface enhanced Raman scattering of 3-Hydroxyflavone J. Phys. Chem. C 2007 111 3038 3043
46. E. B. Wilson The Normal Modes and Frequencies of Vibration of the Regular Plane Hexagon Model of the Benzene Molecule Phys. Rev. 1934 45 706 714
47. G. Varsanyi, in Assignment for vibrational spectra of seven hundreds benzene derivatives, ed., L. Lang,, Hilger, Budapest, 1974
48. T. Matsuura T. Takemoto R. Nakashima Photoinduced reactions-LXXI. Photorearrengements, of 3-hydroxyflavones to 3-aryl-3-Hydroxy-1,2-indandione Tetrahedron 1973 29 3337 3340
49. R. Ficarra P. Ficarra S. Tommasini S. Campagna G. Guglielmo Photochemistry of flavonoids. Solvent effect on photochemical of 3-hydroxyflavone Boll. Chim. Farm. 1994 665 669
50. S. Tommasini M. L. Calabroprime; P. Donato D. Raneri G. Guglielmo P. Ficarra R. Ficarra J. Pharm. Biomed. Anal. 2004 35 389 397
51. C. Reichardt, in Solvents and solvent effects in organic chemistry, VCH, Weinheim, Germany, 1988, p. 378, ch. 7
52. F. L. Urbach A. Timnick Spectrophotometric and spectrofluorimetric study of Flavonol-Aluminum chelates in absolute ethyl alcohol Anal. Chem. 1968 40 1269 1272
53. M. Katyal Flavones as analytical reagents - A review Talanta 1968 15 98 106
54. P. C. H. Hollman J. M. P. van Trijp M. N. C. P. Buysman Fluorescence detection of flavonols in HPLC by postcolumn chemation with Aluminum Anal. Chem. 1996 68 3511 3515
55. M. Shozaki T. Hiraoka Photochemistry of β-hydroxy-γ-pyrone. A new synthesis of 3-methylcyclopent-2-en-2-ol-1-one from maltol Tetrahedron Lett. 1972 13 4655 4658
56. K. Tokumura M. Kurauchi N. Yagata M. Itoh Phototautomerization of 3-hydroxyflavone in the lowest triplet state Chem. Phys. Lett. 1996 258 495 500
57. M. Itoh Y. Tanimoto K. Tokumura Transient absorption study of the intramolecular excited state and ground-state proton transfer in 3-hydroxyflavone and 3-hydroxychromone J. Am. Chem. Soc. 1983 105 3339 3340
58. W. E. Brewer S. L. Studer M. Standiford P.-T. Chou Dynamics of the triplet state and reverse proton transfer of 3-hydroxyflavone J. Phys. Chem. 1989 93 6088 6094
59. A. J. Strandjord P. F. Barbara Proton-transfer kinetics of 3-hydroxyflavone: solvent effects J. Phys. Chem. 1985 89 2355 2361
60. B. L. Tran S. M. Cohen Flavothionato metal complexes: implications for the use of Hydroxyflavothiones as green pesticides Chem. Commun. 2006 203 205