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Hydrogen Atom Abstraction and Electron Transfer of Triplet 2,3-Dihalo-1,4-Naphthoquinones Studied By the Cidep Technique and Laser Flash Photolysis

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Investigations using CIDEP techniques showed that an H-atom abstraction from phenol and the electron transfer from 1,2,4,5-tetramethoxybenzene to photoexcited 2,3-dibromo-1,4-naphthoquinone (DBNQ) and 2,3-dichloro-1,4-naphthoquinone (DCNQ) in the polar media originated from their triplet states. Nanosecond laser photolysis at 355 nm was carried out to determine the absorption spectra and coefficients of the corresponding triplet states, semiquinone, and anion radicals for a quantitative investigation of the mechanisms involved in the H-atom abstraction and the electron transfer. The steric hindrance of the substituted groups was indifferent to H-atom abstraction. The electronic structures of triplet DBNQ and DCNQ at 295 K were both revealed to be the mixed states of 3(n,π*) with a 3(π,π*) character.

Affiliations: 1: Department of Chemistry, Gunma University, Kiryu, Gunma 376, Japan; 2: Institute for Chemical Reaction Science, Tohoku University, Katahira, Aobaku, Sendai 980-77, Japan


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