Micelle-Enhancing Effect on a Flavin-Photosensitized Reaction of Benzyl Alcohols in Aqueous Solution
- 1 March 2003
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 76 (3), 601-605
- https://doi.org/10.1246/bcsj.76.601
Abstract
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.Keywords
This publication has 12 references indexed in Scilit:
- Photooxidation of Benzyl Alcohol Derivatives By Oxygen, Catalyzed By Protonated Flavin AnaloguesResearch on Chemical Intermediates, 1999
- Photochemistry of Flavins in Micelles: Specific Effects of Anionic Surfactants on the Monomerization of Thymine Cyclobutane Dimers Photosensitized by Tetra-O-acyl RiboflavinsPhotochemistry and Photobiology, 1998
- Mechanistic analysis of the 3-methyllumiflavin-promoted oxidative deamination of benzylamine. A potential model for monoamine oxidase catalysisJournal of the American Chemical Society, 1993
- Flavin-photosensitized monomerization of dimethylthymine cyclobutane dimer: remarkable effects of perchloric acid and participation of excited-singlet, triplet, and chain-reaction pathwaysJournal of the American Chemical Society, 1992
- Naturally occurring 5-deazaflavin coenzymes: biological redox rolesAccounts of Chemical Research, 1986
- Flavin analog-metal ion complexes acting as efficient photocatalysts in the oxidation of p-methylbenzyl alcohol by oxygen under irradiation with visible lightJournal of the American Chemical Society, 1985
- Photochemical and photophysical studies of amines with excited flavins. Relevance to the mechanism of action of the flavin-dependent monoamine oxidaseJournal of the American Chemical Society, 1982
- Flavin coenzymes: at the crossroads of biological redox chemistryAccounts of Chemical Research, 1980
- Kinetics of Fluorescence Quenching by Electron and H‐Atom TransferIsrael Journal of Chemistry, 1970
- EXCITED STATES OF FLAVINE COENZYMES‐III. FLUORESCENCE AND PHOSPHORESCENCE EMISSIONSPhotochemistry and Photobiology, 1968