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Selective photocatalytic aerobic bromination with hydrogen bromide via an electron-transfer state of 9-mesityl-10-methylacridinium ion†

Title
Selective photocatalytic aerobic bromination with hydrogen bromide via an electron-transfer state of 9-mesityl-10-methylacridinium ion†
Authors
Ohkubo K.Mizushima K.Iwataa R.Fukuzumi S.
Ewha Authors
Shunichi Fukuzumi
SCOPUS Author ID
Shunichi Fukuzumiscopus
Issue Date
2011
Journal Title
Chemical Science
ISSN
2041-6520JCR Link
Citation
vol. 2, no. 4, pp. 715 - 722
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Photocatalytic bromination of aromatic hydrocarbons by molecular oxygen with hydrogen bromide occurs efficiently to produce monobrominated products selectively using 9-mesityl-10- methylacridinium ion (Acr +-Mes) as a photocatalyst under visible light irradiation. Both the product yield and selectivity for the bromination of 1,3,5-trimethoxybenzene were 100% with a quantum yield of 4.8%. The photocatalytic turnover number is 900 based on the initial concentration of Acr +-Mes. The reactive radical intermediates involved in the photocatalytic cycle have been successfully detected by laser flash photolysis measurements. The photocatalytic bromination is initiated by photoinduced electron transfer from the mesitylene moiety to the singlet excited state of acridinium ion, which results in formation of the electron-transfer state of Acr +-Mes (Acrc .-Mesc .+), followed by electron transfer from aromatic hydrocarbons to the mesitylene radical cation moiety and electron transfer from the acridinyl radical moiety to O 2. The resulting radical cations of aromatic hydrocarbons react with Br - to produce the corresponding monobrominated products selectively. © The Royal Society of Chemistry 2011.
DOI
10.1039/c0sc00535e
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자연과학대학 > 화학·나노과학전공 > Journal papers
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