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THE CHEMILUMINESCENCE OF INDOLE DERIVATIVES IN DIMETHYL SULFOXIDE*
Author(s) -
BERGER A. W.,
DRISCOLL J. N.,
DRISCOLL J. S.,
PIROG J. A.,
LINSCHITZ H.
Publication year - 1968
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.1751-1097.1968.tb07403.x
Subject(s) - chemiluminescence , dimethyl sulfoxide , indole test , chemistry , autoxidation , skatole , peroxide , yield (engineering) , sulfoxide , photochemistry , fluorescence , medicinal chemistry , stereochemistry , chromatography , organic chemistry , materials science , physics , quantum mechanics , metallurgy
The chemiluminescent autoxidation of over fifty indoles has been measured in dimethyl sulfoxide (DMSO). The 3‐alkylindole derivatives represent the brightest and most efficient members of this group. The chemiluminescence yield (per mole) of skatole is (1·5 ± 0·6) × 10 ‐3 . The chemiluminescence spectrum of skatole is identical with the fluorescence spectrum of o‐formamidoacetophenone in the same environment Similar results for 2,3‐dimethylindole lead to the identification of the acylamide anion as the emitter in indole chemiluminescence. A peroxide ring cleavage excitation mechanism is proposed.