Micelle-Enhancing Effect on a Flavin-Photosensitized Reaction of Benzyl Alcohols in Aqueous Solution
The tetra-O-acetylriboflavin (Fl)-photosensitized dehydrogenation of benzyl alcohols 1 proceeded more efficiently in aqueous solutions in the presence of sodium dodecyl sulfate (H2O/SDS) than acetonitrile solutions. The fluorescence quenching of Fl with 1 occurred efficiently in H2O/SDS. The apparen...
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Published in | Bulletin of the Chemical Society of Japan Vol. 76; no. 3; pp. 601 - 605 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
TOKYO
The Chemical Society of Japan
01.03.2003
Chemical Soc Japan Chemical Society of Japan |
Subjects | |
Online Access | Get full text |
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Summary: | The tetra-O-acetylriboflavin (Fl)-photosensitized dehydrogenation of benzyl alcohols 1 proceeded more efficiently in aqueous solutions in the presence of sodium dodecyl sulfate (H2O/SDS) than acetonitrile solutions. The fluorescence quenching of Fl with 1 occurred efficiently in H2O/SDS. The apparent rate constants (kQ) for the fluorescence quenching were determined by Stern–Volmer plots. The plots of kQ vs the free-energy changes for the electron transfer from 1 to the excited singlet of Fl showed the Rehm–Weller-type correlation. However, plots for H2O/SDS were deviated from a curve calculated by the Rehm–Weller equation, although plots for MeCN were fitted to the calculated curve. The deviation in H2O/SDS is attributable to the incorporation of Fl and 1 into the hydrophobic domain of the SDS micelle, where the condensation, less-polar medium, and exteior negative charge operate favorably for efficient electron transfer. |
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ISSN: | 0009-2673 1348-0634 |
DOI: | 10.1246/bcsj.76.601 |