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CHEMILUMINESCENCE AND THE FORMATION OF SINGLET OXYGEN IN THE OXIDATION OF CERTAIN POLYPHENOLS AND QUINONES
Author(s) -
Slawinska Danuta
Publication year - 1978
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1978.tb06947.x
Subject(s) - chemistry , chemiluminescence , photochemistry , autoxidation , cumene hydroperoxide , hydroquinone , benzoquinone , pyrogallol , light emission , organic chemistry , catalysis , physics , optoelectronics
— The possibility of 1 O 2 ( 1 Δ g ) participation in the oxidation of polyphenols and quinones has been investigated in two systems: (1) the system involving autooxidation leading to oxidative polymerization and destruction, and (2) the modified Trautz‐Schorigin reaction, i.e. oxidation of polyphenols and HCHO with H 2 O 2 in concentrated alkaline solutions. The red band with maximum at 635 nm observed in chemiluminescence of pyrocatechol, adrenaline, pyrogallol, gallic acid, adrenochrome and p ‐benzoquinone corresponds to the transition 2O 2 ( 1 Δ g ) → 2O 2 ( 3 Σ ‐ g ). Emission bands in the range 475–540 nm arise from the superposition of the 2O 2 ( 1 Δ g ) → 2O 2 ( 3 Σ ‐ g ) transition and radiative deactivation of excited oxidation products. In system (2) chemiluminescence has a broad band from 580 nm beyond 800 nm and much higher intensity than in system (1). Formaldehyde was found to enhance light emission in system (1) by a factor of about 30. The influence of solvents, including D 2 O in which 1 O 2 has varying lifetimes, on kinetics of chemiluminescence as well as quenching effect of β‐carotene, hydroquinone, cysteine, bilirubin and biliverdin strongly support the involvement of 1 O 2 in the chemiluminescence of both systems.