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1H‐INDENYLFURAN AND THIOPHENE DERIVATIVES– A NEW CLASS OF SINGLET OXYGEN SENSITIZERS
Author(s) -
D'AURIA MAURIZIO,
VANTAGGI ANNA
Publication year - 1991
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.1751-1097.1991.tb03921.x
Subject(s) - singlet oxygen , photochemistry , intersystem crossing , thiophene , chemistry , dabco , singlet state , octane , reactivity (psychology) , oxygen , quantum yield , fluorescence , excited state , organic chemistry , medicine , physics , alternative medicine , pathology , quantum mechanics , nuclear physics
— Photophysical and photochemical properties of 1H‐indenylfuran and thiophene derivatives were studied. UV spectra showed that all the compounds tested absorbed UV light in the region 350–380 nm. The fluorescence spectra of 4a‐e showed bands in the region 410–470 nm and quantum yields (φ F ) in the range 0.25–0.88. Attempts to calculate the triplet energy of 4a‐e failed except for 4c and 4d , which showed E T = 43–44 kcal mol ‐1 . These compounds are a new class of singlet oxygen sensitizers. The sensitized reaction of 2,5‐dimethylfuran with singlet oxygen was followed showing that 4a and 4e are more reactive than α‐terthiophene (4.0 and 2.5 times respectively), while the other compounds show the same reactivity as 1 . This behavior can be explained considering the different intersystem crossing quantum yields of compounds 4a‐e . Diazabicyclo[2. 2. 2]octane is a quencher of singlet oxygen in this reaction, while we can exclude superoxide ion formation using the photooxidation of α, α‐dimethylstilbene.