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Wavelength selective photoactivated autocatalytic oxidation of 5,12-dihydrobenzo[b]phenazine and its application in metal-free synthesis

Photochemical stability of 5,12-dihydrobenzo[b]phenazine (DHBP) was investigated with LEDs with central emission wavelengths in a range of 365 to 595 nm. Photochemical conversion of DHBP to benzo[b]phenazine (BP) was observed with wavelengths upto 516 nm. Light of 490 and 516 nm is not absorbed by D...

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Autores principales: Bian, Lei, Ma, Jie, Feng, Xiaotong, Wang, Yuanhang, Zhao, Lizhi, Zhao, Lei, Wang, Xiayan, Guo, Guangsheng, Pu, Qiaosheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9050338/
https://www.ncbi.nlm.nih.gov/pubmed/35498597
http://dx.doi.org/10.1039/d0ra01495h
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author Bian, Lei
Ma, Jie
Feng, Xiaotong
Wang, Yuanhang
Zhao, Lizhi
Zhao, Lei
Wang, Xiayan
Guo, Guangsheng
Pu, Qiaosheng
author_facet Bian, Lei
Ma, Jie
Feng, Xiaotong
Wang, Yuanhang
Zhao, Lizhi
Zhao, Lei
Wang, Xiayan
Guo, Guangsheng
Pu, Qiaosheng
author_sort Bian, Lei
collection PubMed
description Photochemical stability of 5,12-dihydrobenzo[b]phenazine (DHBP) was investigated with LEDs with central emission wavelengths in a range of 365 to 595 nm. Photochemical conversion of DHBP to benzo[b]phenazine (BP) was observed with wavelengths upto 516 nm. Light of 490 and 516 nm is not absorbed by DHBP, but photoactivated autocatalytic oxidation of DHBP to BP with these wavelengths was confirmed. The reaction rate is in a range of 111–208 μg min(−1) with these LEDs. The mechanism of the reaction was examined and the experimental results exclude the intermolecular interaction such as the Förster resonance energy transfer, the intermolecular charge transfer, the photoinduced electron transfer and the formation of an exciplex. The formation of the reactive oxygen species was verified with electron paramagnetic resonance, which indicates its potential in the synthesis. When sunlight was used as the light source, the oxidation rate of 1 mg mL(−1) DHBP was 393 μg min(−1). Same autocatalytic oxidation was also observed on similar compounds and it can be used for producing metal-free organic substances for semiconductors.
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spelling pubmed-90503382022-04-29 Wavelength selective photoactivated autocatalytic oxidation of 5,12-dihydrobenzo[b]phenazine and its application in metal-free synthesis Bian, Lei Ma, Jie Feng, Xiaotong Wang, Yuanhang Zhao, Lizhi Zhao, Lei Wang, Xiayan Guo, Guangsheng Pu, Qiaosheng RSC Adv Chemistry Photochemical stability of 5,12-dihydrobenzo[b]phenazine (DHBP) was investigated with LEDs with central emission wavelengths in a range of 365 to 595 nm. Photochemical conversion of DHBP to benzo[b]phenazine (BP) was observed with wavelengths upto 516 nm. Light of 490 and 516 nm is not absorbed by DHBP, but photoactivated autocatalytic oxidation of DHBP to BP with these wavelengths was confirmed. The reaction rate is in a range of 111–208 μg min(−1) with these LEDs. The mechanism of the reaction was examined and the experimental results exclude the intermolecular interaction such as the Förster resonance energy transfer, the intermolecular charge transfer, the photoinduced electron transfer and the formation of an exciplex. The formation of the reactive oxygen species was verified with electron paramagnetic resonance, which indicates its potential in the synthesis. When sunlight was used as the light source, the oxidation rate of 1 mg mL(−1) DHBP was 393 μg min(−1). Same autocatalytic oxidation was also observed on similar compounds and it can be used for producing metal-free organic substances for semiconductors. The Royal Society of Chemistry 2020-03-09 /pmc/articles/PMC9050338/ /pubmed/35498597 http://dx.doi.org/10.1039/d0ra01495h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Bian, Lei
Ma, Jie
Feng, Xiaotong
Wang, Yuanhang
Zhao, Lizhi
Zhao, Lei
Wang, Xiayan
Guo, Guangsheng
Pu, Qiaosheng
Wavelength selective photoactivated autocatalytic oxidation of 5,12-dihydrobenzo[b]phenazine and its application in metal-free synthesis
title Wavelength selective photoactivated autocatalytic oxidation of 5,12-dihydrobenzo[b]phenazine and its application in metal-free synthesis
title_full Wavelength selective photoactivated autocatalytic oxidation of 5,12-dihydrobenzo[b]phenazine and its application in metal-free synthesis
title_fullStr Wavelength selective photoactivated autocatalytic oxidation of 5,12-dihydrobenzo[b]phenazine and its application in metal-free synthesis
title_full_unstemmed Wavelength selective photoactivated autocatalytic oxidation of 5,12-dihydrobenzo[b]phenazine and its application in metal-free synthesis
title_short Wavelength selective photoactivated autocatalytic oxidation of 5,12-dihydrobenzo[b]phenazine and its application in metal-free synthesis
title_sort wavelength selective photoactivated autocatalytic oxidation of 5,12-dihydrobenzo[b]phenazine and its application in metal-free synthesis
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9050338/
https://www.ncbi.nlm.nih.gov/pubmed/35498597
http://dx.doi.org/10.1039/d0ra01495h
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