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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 3
BKCSDE 32(3)
March 20, 2011 

Spectroscopic Properties of Quercetin-3-O-rhamnoside and Quercetin-3-O-rutinoside in Aerosol-OT Reverse Micelles
Hyoung Ryun Park, Hai Bo Liu, Sung Chul Shin, Jong Keun Park, Ki Min Bark*
Quercetin, AOT reverse micelle, Intramolecular proton transfer, Intramolecular charge transfer
The anomalous spectroscopic properties of quercetin-3-O-rhamnoside (QCRM) and quercetin-3-O-rutinoside (QCRT) in AOT reverse micelle were studied. The excited state intramolecular proton transfer (ESIPT) occurs through the strong hydrogen bond between the –OH at position 5 and the carbonyl oxygen. Because the ESIPT can only happens in the S1 state and the Franck-Condon factor involved in the S2 → S1 internal conversion is small, the S2 → So emission alone appears. Because the molecular planarity is improved at the interior of the micelle, the excited state intramolecular charge transfer in the S1 state is extended, and the excited state is more tolerable for any quenching effects in the micelle. Therefore, an S1 → So emission was newly discovered under this micelle microenvironment. For the S2 → So emission, the quantum yields increase but the quantum yield of the S1 → So emission approximately decreases as the water concentration in the micelle increases.
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