Photocatalytic reduction of phenacyl halides by 9,10-dihydro-10-methylacridine. Control between the reductive and oxidative quenching pathways of tris(bipyridine)ruthenium complex utilizing an acid catalysis

Journal Article · Thu Jan 25 04:00:00 EST 1990 · Journal of Physical Chemistry; (USA)

DOI:https://doi.org/10.1021/j100365a039· OSTI ID:6652258

Fukuzumi, Shunichi; Mochizuki, Seiji; Tanaka, Toshio ^[1]

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1. Osaka Univ. (Japan)

The photoreductions of phenacyl halide derivatives (YC{sub 6}H{sub 4}COCH{sub 2}X (X = Br, Cl; Y = p-CN, p-Br, H, p-Me, p-MeO)) by 9,10-dihydro-10-methylacridine (AcrH{sub 2}) in both the absence and presence of perchloric acid in acetonitrile proceed efficiently under irradiation of visible light of {lambda} = 450 nm at 298 K with (Ru(bpy){sub 3}){sup 2+} (bpy = 2,2{prime}-bipyridine) as a photocatalyst to yield 10-methylacridinium ion (AcrH{sup +}) and the corresponding acetophenone derivatives. The dependences of the quantum yields for the (Ru(bpy){sub 3}){sup 2+}-sensitized photoreduction of phenacyl halides by AcrH{sub 2} on the HClO{sub 4} concentration have been examined. The reductive and oxidative quenching of the excited state (Ru(bpy){sub 3}){sup 2+}* by AcrH{sub 2} and phenacyl halides in the absence and presence of HClO{sub 4} have also been studied, respectively. The results indicate that the reaction in the absence of HClO{sub 4} proceeds via the reductive quenching of (Ru(bpy){sub 3}){sup 2+} by AcrH{sub 2}, followed by the reduction of phenacyl halides by (Ru(bpy){sub 3}){sup +}, while the reaction in the strongly acidic media proceeds via the oxidative quenching of (Ru(bpy){sub 3}){sup 2+} by phenacyl halides, followed by the oxidation of AcrH{sub 2} by (Ru(bpy){sub 3}){sup 3+}.

• OSTI ID: 6652258
• Journal Information: Journal of Physical Chemistry; (USA), Journal Name: Journal of Physical Chemistry; (USA) Vol. 94:2; ISSN 0022-3654; ISSN JPCHA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400500* -- Photochemistry
ARYL RADICALS
CATALYSTS
CHEMICAL REACTIONS
COMPLEXES
DATA
DATA ANALYSIS
ELECTRON TRANSFER
EXPERIMENTAL DATA
HALIDES
HALOGEN COMPOUNDS
INFORMATION
MEASURING INSTRUMENTS
MEASURING METHODS
NUMERICAL DATA
PHENYL RADICALS
PHOTOCHEMICAL REACTIONS
QUENCHING
RADICALS
REDUCTION
RUTHENIUM COMPLEXES
TRANSITION ELEMENT COMPLEXES