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http://dx.doi.org/10.5012/bkcs.2013.34.1.211

Spectroscopic Properties of Flavonoids in Various Aqueous-Organic Solvent Mixtures  

Park, Hyoung-Ryun (Department of Chemistry and Research Institute of Basic Science, Chonnam National University)
Daun, Yu (Department of Chemistry and Research Institute of Life Science, Gyeongsang National University)
Park, Jong Keun (Department of Chemical Education and Research Institute of Life Science, Gyeongsang National University)
Bark, Ki-Min (Department of Chemical Education and Research Institute of Life Science, Gyeongsang National University)
Publication Information
Bulletin of the Korean Chemical Society / v.34, no.1, 2013 , pp. 211-220 More about this Journal
Abstract
The characteristic fluorescence properties of quercetin (QCT) and apigenin (API) were studied in various $CH_3OH-H_2O$ and $CH_3CN-H_2O$ mixed solvents. The structure of QCT is completely planar. API is not planar at the ground state but becomes nearly planar at the excited state. If the molecules are excited to the $S_1$ state in organic solvents, QCT exhibits no fluorescence due to excited state intramolecular proton transfer (ESIPT) between the -OH and the carbonyl oxygen, but API shows significant fluorescence because ESIPT occurs slowly. If the molecules are excited to the $S_2$ state, both QCT and API exhibit strong $S_2{\rightarrow}S_o$ emission without any dual fluorescence. As the $H_2O$ composition of both solvents increases, the fluorescence intensity decreases rapidly due to the intermolecular hydrogen bonding interaction. The theoretical calculation further supports these results. The change in fluorescence properties as a function of the solvatochromic parameters was also studied.
Keywords
Flavonoids; Fluorescence spectroscopy; Intramolecular charge transfer; Intramolecular proton transfer;
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1 Middleton, E., Jr.; Kandaswami, C. The Impact of Plant Flavonoids on Mammalian Biology; Harborne, J. B., Ed.; Chapman and Hall: London, UK, 1994; p 619.
2 Iwashina, T. J. Plant Res. 2000, 113, 287.   DOI
3 Butkoviæ, V.; Klasinc, V.; Bors, W. J. Agric. Food Chem. 2004, 52, 2816.   DOI   ScienceOn
4 Exarchou, V.; Nenadis, N.; Tsimidou, M.; Gerothanassis, I. P.; Troganis, A.; Boskou, D. J. Agric. Food Chem. 2002, 50, 5294.   DOI   ScienceOn
5 Miyake, Y.; Yamamoto, K.; Morimitsu, Y.; Osawa, T. J. Agric. Food. Chem. 1997, 45, 4619.   DOI   ScienceOn
6 Jovanovic, S. V.; Steenken, S.; Tosic, M.; Marjanovic, B.; Simic, M. G. J. Am. Chem. Soc. 1994, 116, 4846.   DOI   ScienceOn
7 Lapouge, C.; Dangleterre, L.; Cornard, J. P. J. Phys. Chem. 2006, 110, 12494.   DOI   ScienceOn
8 Li, Y. Q.; Zhou, F. C.; Gao, F.; Bian, J. S.; Shan, F. J. Agric. Food Chem. 2009, 57, 11463.   DOI   ScienceOn
9 Liu, W.; Rong, G. J. Coll. Interf. Sci. 2006, 302, 625.   DOI   ScienceOn
10 Cornard, J. P.; Merlin, J. C. J. Inorg. Biochem. 2002, 92, 19.   DOI   ScienceOn
11 Baranac, J. M.; Petranovi , N. A.; Dimitri -Markovi , M. D. J. M. J. Agric. Food Chem. 1997, 45, 1694.   DOI   ScienceOn
12 Gutierrez, A. C.; Gehlen, M. H. Spectrochim. Acta A 2002, 58, 83.   DOI   ScienceOn
13 Rossi, M.; Rickles, L. F.; Halpin, W. A. Bioorgan. Chem. 1986, 14, 55.   DOI
14 Leopoldini, M.; Marino, T.; Russo, N.; Toscano, M. Theor. Chem. Acc. 2004, 111, 210.   DOI
15 Falkovskaia, E.; Sengupta, P. K.; Kasha, M. Chem. Phys. Lett. 1998, 297, 109.   DOI   ScienceOn
16 Sengupta, P. K.; Kasha, M. Chem. Phys. Lett. 1979, 68, 382.   DOI   ScienceOn
17 Smith, G. J.; Markham, K. R. J. Photochem. Photobiol. A 1998, 118, 99.   DOI   ScienceOn
18 Hollman, P. C. H.; van Trijp, J. M. P.; Buysman, M. N. C. P. Anal. Chem. 1996, 68, 3511.   DOI   ScienceOn
19 Liu, H. B.; Daun, Y.; Shin, S. C.; Park, H. R.; Park, J. K.; Bark, K. M. Photochem. Photobiol. 2009, 85, 934.   DOI   ScienceOn
20 Park, H. R.; Liu, H. B.; Shin, S. C.; Park, J. K.; Bark, K. M. Bull. Korean Chem. Soc. 2011, 32, 981.
21 Navarro-Nunez, L.; Lozano, M. L.; Palomo, M.; Martinez, C.; Vicente, V.; Castillo, J.; Benavente-Garcia, O.; Diaz-Ricart, M.; Escolar, G.; Rivera, J. J. Agric. Food Chem. 2008, 56, 2970.   DOI   ScienceOn
22 Yuan, J. L.; Liu, H.; Kang, X.; Lv, Z.; Zou, G. L. J. Mole. Struct. 2008, 891, 333.   DOI   ScienceOn
23 Yuan, J. L.; Iv, Z.; Liu, Z. G.; Hu, Z.; Zou, G. L. J. Photochem. Photobiol. A 2007, 191, 104.   DOI   ScienceOn
24 Zsila, F.; Bikádi, Z.; Simonyi, M. Biochem. Pharmacol. 2003, 65, 447.   DOI   ScienceOn
25 Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH, Weinheim, Germany, 1988; p 372.
26 Eaton, D. F. Reference Compounds for Fluorescence Measurement; IUPAC Organic Chemistry Division, Washington DC, USA. 1987; p 1.
27 Frish, M. J.; Trucks, G. W.; Head-Gordon, M. H.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C. R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 03; Gaussian Inc., Pittsburgh, PA, USA. 2003.
28 Favaro, G.; Clementi, C.; Romani, A.; Vickackaite, V. J. Fluoresc. 2007, 17, 707.   DOI
29 Hochstrasser, R. M.; Marzzacco, C. J. Chem. Phys. 1968, 49, 971.   DOI
30 Cornard, J. P.; Boudet, A. C.; Merlin, J. C. J. Mol. Struct. 1999, 508, 37.   DOI   ScienceOn
31 Cornard, J. P.; Merlin, J. C.; Boudet, A. C.; Vrielynck, L. Biospect. 1997, 3, 183.   DOI
32 Mendoza-Wilson, A. M.; Glossman-Mitnik, D. J. Mol. Struct. (Theochem) 2004, 681, 71.   DOI   ScienceOn
33 Saskia, A. B.; van Acker, E.; de Groot, M. J.; van den Berg, D. J.; Tromp, M. N. J. L.; den Kelder, G. D. O.; van der Vijgh, W. J. F.; Bast, A. Chem. Res. Toxicol. 1996, 9, 1305.   DOI   ScienceOn
34 Cody, V.; Luft, J. R. J. Mol. Struct. 1994, 317, 89.   DOI   ScienceOn
35 Amat, A.; Clementi, C.; De Angelis, F.; Sgamellotti, A.; Fantacci, S. J. Phys. Chem. A 2009, 113, 15118.   DOI   ScienceOn
36 Matías Funes, N.; Correa, M.; Silber, J. J.; Biasutti, M. A. Photochem. Photobiol. 2007, 83, 486.   DOI   ScienceOn
37 Martinez, M. L.; Studer, S. L.; Chou, P. T. J. Am. Chem. Soc. 1991, 113, 5881.   DOI