徳島大学 教育・研究者情報データベース(EDB)

1. 徳島大学.工学研究科.エコシステム工学専攻.資源循環工学講座(〜2014年3月31日)

1. (英) Suzuki Itsuko

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2. (英) Tanaka Ryoko

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3. (英) Yamaguchi Akinori

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4. (英) Maki Shin-ichiro

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5. 三澤 弘明([北海道大学])

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6. (英) Tokumaru Katsumi

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7. (英) Nakagaki Ryoichi

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8. (英) Sakuragi Hirochika

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(英) Behavior of Biradicals Generated from a Norrish Type-I Reaction of 2,2-Diphenylcycloalkanones. Chain-Length Dependence and Magnetic Field Effects

(英) The reaction course of acyl-diphenylmethyl biradicals (α-oxo-ω,ω-diphenyl-α,ω-alkanediyl biradicals), O=C↑-(CH2)n-2-C↑Ph2 (3BR-n), generated from the Norrish type-I reaction of 2,2-diphenylcycloalkanones (CK-n) with various ring sizes in methanol, is switched from intramolecular disproportionation (n = 6, 7), giving a diphenylalkenal, to acyl-phenyl recombination (n ≥ 9), affording a cyclophane derivative. The behavior of 3BR-9 derived from CK-9 was studied in detail; the photolysis of CK-9 afforded an open-chain and a cyclic decarbonylation product together with an unsaturated aldehyde and a 4-methylene-2,5-cyclohexadienyl ketone (a pre-cyclophane). The photolysis of this ketone gave the same products that arose from the photolysis of CK-9, presenting the possibility that the decarbonylation products and a part of the aldehyde are formed as secondary products during irradiation. The magnetic field dependence of the lifetimes of 3BR-n (n = 12 and 13) generated from CK-12 and 13, respectively, was measured in methanol by means of a pulsed-laser excitation technique. The rate constants for intersystem crossing showed a maximum at a relatively low field strength, which decreased with increasing the field strength to level off to an asymptotic value at > 1.5 kG. The results show that the role of hyperfine coupling in intersystem crossing is less important in these systems, presumably because of the presence of a carbonyl oxygen and the absence of a hydrogen atom at the radical center.