Unusual Oxidative Dealkylation Strategy toward Functionalized Phenalenones as Singlet Oxygen Photosensitizers and Photophysical Studies
Author
dc.contributor.author
De Bonfils, Paul
Author
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Verron, Elise
Author
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Sandoval Altamirano, Catalina
Author
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Jaque Olmedo, Pablo
Author
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Moreau, Xavier
Author
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Gunther Sapunar, Germán
Author
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Nun, Pierrick
Author
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Coeffard, Vincent
Admission date
dc.date.accessioned
2020-11-11T22:17:50Z
Available date
dc.date.available
2020-11-11T22:17:50Z
Publication date
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2020
Cita de ítem
dc.identifier.citation
J. Org. Chem. 2020, 85, 10603−10616
es_ES
Identifier
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10.1021/acs.joc.0c01140
Identifier
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https://repositorio.uchile.cl/handle/2250/177667
Abstract
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A series of functionalized 6-alkoxy phenalenones was prepared through an unprecedented oxidative dealkylation of readily available phenalene precursors. The starting phenalenes were efficiently synthesized via an aminocatalyzed annulation/O-alkylation strategy starting from simple substrates. The spectroscopic properties of some phenalenones were investigated in different solvents. Introducing an alkoxy substituent at the 6-position onto the phenalenone framework results in a red shift of the absorption. The synthesized phenalenones exhibit low fluorescence quantum yields, and the fluorescence decay was studied in different solvents, highlighting the presence of several lifetimes. The singlet oxygen (O-1(2)) photosensitizing propensity of some phenalenones was investigated, and the results showed the striking importance of the phenalenone molecular structure in generating singlet oxygen with high yields. The ability of phenalenones to generate singlet oxygen was then harnessed in three photooxygenation reactions: anthracene oxidation, oxy-functionalization of citronellol through the Schenck-ene reaction, and photooxidation of a diene.
es_ES
Patrocinador
dc.description.sponsorship
French National Research Agency (ANR)
ANR-18-CE07-0013-01
French National Research Agency (ANR)
Universite de Nantes
Centre National de la Recherche Scientifique (CNRS)
FONDEQUIP
EQM160099