UV Photolysis of 1,4-Diaminobenzene in a Low-Temperature Argon Matrix to 2,5-Cyclohexadiene-1,4-diimine via 4-Aminoanilino Radical

UV Photolysis of 1,4-Diaminobenzene in a Low-Temperature Argon Matrix to 2,5-Cyclohexadiene-1,4-diimine via 4-Aminoanilino Radical

UV photolysis of 1,4-diaminobenzene isolated in a low-temperature argon matrix has been investigated by Fourier transform infrared spectroscopy with the aid of the density-functional-theory calculation. Infrared bands of an intermediate produced from 1,4-diaminobenzene upon UV irradiation (λ < 35...

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Veröffentlicht in:The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2003-08, Vol.107 (34), p.6725-6730
Hauptverfasser: Akai, Nobuyuki, Kudoh, Satoshi, Nakata, Munetaka
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Kudoh, Satoshi
Nakata, Munetaka
description UV photolysis of 1,4-diaminobenzene isolated in a low-temperature argon matrix has been investigated by Fourier transform infrared spectroscopy with the aid of the density-functional-theory calculation. Infrared bands of an intermediate produced from 1,4-diaminobenzene upon UV irradiation (λ < 350 nm) are assigned to a semiquinone-type radical, 4-aminoanilino radical. A final product produced from the 4-aminoanilino radical upon shorter-wavelength irradiation (λ < 310 nm) is assigned as 2,5-cyclohexadiene-1,4-diimine. Optimized structures of 1,4-diaminobenzene, 4-aminoanilino radical, and 2,5-cyclohexadiene-1,4-diimine are compared with one another, resulting in changes of the π-conjugated system similar to those of the hydroquinone and 1,4-benzoquinone system. In addition, trans − cis isomerization of 2,5-cyclohexadiene-1,4-diimine upon UV irradiation is observed in photoequilibrium, where the cis/trans population ratio depends on the irradiation wavelength.
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title UV Photolysis of 1,4-Diaminobenzene in a Low-Temperature Argon Matrix to 2,5-Cyclohexadiene-1,4-diimine via 4-Aminoanilino Radical
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