Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules

Pure organic phosphorescent molecules are attractive alternatives to transition-metal-complex-based phosphores for biomedical and technological applications owing to their abundance and nontoxicity. This article discloses the design, synthesis, and photophysical properties of fluorinated benzil and...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2020-05, Vol.16 (1), p.1154-1162
Main Authors: Yamada, Shigeyuki, Higashida, Takuya, Wang, Yizhou, Morita, Masato, Hosokai, Takuya, Maduwantha, Kaveendra, Koswattage, Kaveenga Rasika, Konno, Tsutomu
Format: Article
Language:English
Subjects:
alkyne oxidation
benzils
bistolanes
Carbon
Chemistry
Chromatography
Dimethyl sulfoxide
fluorinated compounds
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Light emitting diodes
NMR
Nuclear magnetic resonance
Oxidation
Palladium chloride
Phosphorescence
Photons
Theory
Toluene
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Summary:Pure organic phosphorescent molecules are attractive alternatives to transition-metal-complex-based phosphores for biomedical and technological applications owing to their abundance and nontoxicity. This article discloses the design, synthesis, and photophysical properties of fluorinated benzil and bisbenzil derivatives as potential pure organic room-temperature phosphorescent molecules. These compounds were separately converted from the corresponding fluorinated bistolanes via PdCl 2 -catalyzed oxidation by dimethyl sulfoxide, while nonfluorinated bistolane provided the corresponding bisbenzil derivatives exclusively in a similar manner. Intensive investigations of the photophysical properties of the benzil and bisbenzil derivatives in toluene at 25 °C showed both fluorescence with a photoluminescence (PL) band at a maximum wavelength (λ PL ) of around 400 nm and phosphorescence with a PL band at a λ PL of around 560 nm. Interestingly, intersystem crossing effectively caused fluorinated benzils to emit phosphorescence, which may arise from immediate spin-orbit coupling involving the 1 (n, π)→ 3 (π, π) transition, unlike the case of fluorinated or nonfluorinated bisbenzil analogues. These findings offer a useful guide for developing novel pure organic room-temperature phosphorescent materials.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.16.102