Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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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)
  • Received : 2012.09.17
  • Accepted : 2012.11.01
  • Published : 2013.01.20
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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

Acknowledgement

Supported by : National Research Foundation of Korea

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