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SPECTROSCOPY AND PHOTOCHEMISTRY OF 8‐SUBSTITUTED 5‐DEAZAFLAVINS
Author(s) -
Link Paul A. J.,
Plas Henk C. VAN DER,
Müller Franz
Publication year - 1987
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.1751-1097.1987.tb07380.x
Subject(s) - substituent , chemistry , phosphorescence , photochemistry , fluorescence , dimer , medicinal chemistry , organic chemistry , physics , quantum mechanics
— Absorption, fluorescence and phosphorescence spectra as well as fluorescence and phosphorescence quantum yields of 8‐X‐5‐deazaflavins (X = C1, NO 2 , p ‐NO 2 ‐C 6 H 4 , N(CH 3 ) 2 , NH 2 , p ‐NH 2 ‐C 6 H 4 , p ‐N(CH 3 ) 2 ‐C 6 H 4 ‐N=N) were determined. It was found that all these data are highly influenced by the substituent at position 8 of the 5‐deazaisoalloxazine skeleton. Also the photoreduction of 8‐X‐5‐deazaflavins in the presence of electron donors was studied. It was established that the photoreduction leads to the formation of a 5,5‘‐dimer and/or a 6,7‐dihydro compound. Reduction of the C(6)‐C(7) bond is promoted by strong electron‐donating substituents and bulky electron donors. 5‐Deazaftavins with a reducible substituent at position 8 exhibit reduction of the substituent prior to the reduction of the 5‐deazaisoalloxazine skeleton.