Abstract
Directly linked donor and acceptor arenes, such as phenanthrene/naphthalene/biphenyl and 1,3-dicyanobenzene were found to work as photoredox catalysts in the photoreactions of indene, 2,3-dimethyl-2-butene, and 4-methoxyphenylacetic acid. The new stable organic photocatalyst forms an intramolecular exciplex (excited complex) when irradiated in a polar solvent and shows redox catalyst activity, even at low concentrations. To the best of our knowledge, this is the first example of an intramolecular exciplex working as a redox catalyst.
Highlights
Photoinduced electron transfer (PET) promoted reactions are a powerful and environmentally friendly tool for the construction of complex organic molecules [1,2,3,4,5] and polymers [6,7] that cannot be prepared by other methods
1b–e, bearing naphthyl biphenyl units. These results that for other catalysts bearing naphthyl and biphenyland units. These results indicated thatindicated the rotation of the aryl-aryl rotation of the aryl-aryl σ-bonds in is not completely restricted by the cyano substituents and σ-bonds in 1 is not completely restricted by the cyano substituents and that π-π interactions that interactions exist donor acceptor arene within 1
Photoinduced decarboxylation of carboxylic acids using the Phen/DCB system has been established as a powerful method for the generation of alkyl radicals that can react with a variety of radical acceptors to provide the respective products in high yields [10,11,12,13,14,15]
Summary
Photoinduced electron transfer (PET) promoted reactions are a powerful and environmentally friendly tool for the construction of complex organic molecules [1,2,3,4,5] and polymers [6,7] that cannot be prepared by other methods. The Fukuzumi photocatalyst, in particularan electron donor–acceptor-linked dyad (9-mesityl-10-methylacridinium ion, Acr+ -Mes)acts as an efficient organic photoredox catalyst due to the long-lived electron-transfer state formed upon irradiation. This state can efficiently oxidize and reduce organic molecules to produce the corresponding radical cations and radical anions, respectively. New type of organic photoredox catalyst discussed in this work
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