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

Beilstein Journal of Organic Chemistry

卷:16

Yizhou Wang¹  Masato Morita¹  Takuya Higashida¹  Tsutomu Konno¹  Shigeyuki Yamada¹  Takuya Hosokai²  Kaveenga Rasika Koswattage²  Kaveendra Maduwantha² 

[1] Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan;

[2] National Metrology Institute of Japan, National Institute of Advanced Industrial Science and Technology, 1-1-1 Umezono, Tsukuba 305-8560, Japan;

关键词: alkyne oxidation;    benzils;    bistolanes;    fluorinated compounds;    phosphorescence;   

DOI  :  10.3762/bjoc.16.102

来源: DOAJ

【 摘 要 】

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 PdCl2-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 (λPL) of around 400 nm and phosphorescence with a PL band at a λPL 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.

【 授权许可】

Unknown