,
,
Beilstein Arch. 2020, 202031. https://doi.org/10.3762/bxiv.2020.31.v1
Published 23 Mar 2020
Pure organic phosphorescent molecules are attractive alternatives to transition metal complexes-based phosphores for biomedical and technological applications owing to their abundance and nontoxicity. This article discloses the design, synthesis, and photophysical property 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 non-fluorinated bistolane provided the corresponding bisbenzil derivatives exclusively in a similar manner. Intensive investigation 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 be due to immediate spin-orbit coupling involving the 1(n, π)→3(π, π) transition, unlike the case of fluorinated or non-fluorinated bisbenzil analogues. These findings would become useful tool to develop novel pure organic room-temperature phosphorescent materials.
Keywords: alkyne-oxidation; benzils; bistolanes; fluorinated compounds; phosphorescence
| Format: PDF | Size: 4.6 MB | Download |
When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:
Yamada, S.; Higashida, T.; Wang, Y.; Morita, M.; Hosokai, T.; Maduwantha, K.; Koswattage, K. R.; Konno, T. Beilstein Arch. 2020, 202031. doi:10.3762/bxiv.2020.31.v1
Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and
Zotero.
© 2020 Yamada et al.; licensee Beilstein-Institut.
This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.
The license is subject to the Beilstein Archives terms and conditions: (https://www.beilstein-archives.org/xiv/terms)
