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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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Autores principales: Yamada, Shigeyuki, Higashida, Takuya, Wang, Yizhou, Morita, Masato, Hosokai, Takuya, Maduwantha, Kaveendra, Koswattage, Kaveenga Rasika, Konno, Tsutomu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
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Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277987/
https://www.ncbi.nlm.nih.gov/pubmed/32550930
http://dx.doi.org/10.3762/bjoc.16.102
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author Yamada, Shigeyuki
Higashida, Takuya
Wang, Yizhou
Morita, Masato
Hosokai, Takuya
Maduwantha, Kaveendra
Koswattage, Kaveenga Rasika
Konno, Tsutomu
author_facet Yamada, Shigeyuki
Higashida, Takuya
Wang, Yizhou
Morita, Masato
Hosokai, Takuya
Maduwantha, Kaveendra
Koswattage, Kaveenga Rasika
Konno, Tsutomu
author_sort Yamada, Shigeyuki
collection PubMed
description 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.
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spelling pubmed-72779872020-06-17 Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules Yamada, Shigeyuki Higashida, Takuya Wang, Yizhou Morita, Masato Hosokai, Takuya Maduwantha, Kaveendra Koswattage, Kaveenga Rasika Konno, Tsutomu Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2020-05-29 /pmc/articles/PMC7277987/ /pubmed/32550930 http://dx.doi.org/10.3762/bjoc.16.102 Text en Copyright © 2020, Yamada et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://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 Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Yamada, Shigeyuki
Higashida, Takuya
Wang, Yizhou
Morita, Masato
Hosokai, Takuya
Maduwantha, Kaveendra
Koswattage, Kaveenga Rasika
Konno, Tsutomu
Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules
title Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules
title_full Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules
title_fullStr Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules
title_full_unstemmed Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules
title_short Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules
title_sort development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277987/
https://www.ncbi.nlm.nih.gov/pubmed/32550930
http://dx.doi.org/10.3762/bjoc.16.102
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