Solvent effects on the photoamination of 1-amino-2,4-dibromoanthraquinone. II. Dual mode of the photoamination in ethanol via the S1(1CT) and T1(3CT) states.

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概要

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• The photoamination of 1-amino-2,4-dibromoanthraquinone (<B>1</B>) by butylamine in ethanol was investigated. The reaction was accelerated under an air atmosphere (<I>Φ</I><SUB>air</SUB>=1.7×10<SUP>−3</SUP>, <I>Φ</I><SUB>N<SUB>2</SUB></SUB>=2.3×10<SUP>4</SUP>, where [butylamine]=5.00×10<SUP>−2</SUP> mol/dm<SUP>3</SUP>). A detailed kinetic study indicated that, under nitrogen, the photoamination proceeded <I>via</I> the T<SUB>1</SUB>(<SUP>3</SUP>CT) state populated by the intersystem crossing from the S<SUB>1</SUB>(<SUP>1</SUP>CT) state, while under air it proceeded <I>via</I> both the T<SUB>1</SUB>(<SUP>3</SUP>CT) and the S<SUB>1</SUB>(<SUP>1</SUP>CT) states. The latter pathway under air included an interaction between the S<SUB>1</SUB>(<SUP>1</SUP>CT) state and oxygen to form an exciplex or a collisional complex such as [AQ<SUP>δ+</SUP>···O<SUB>2</SUB><SUP>δ−</SUP>]. The deactivation constant from the T<SUB>1</SUB>(<SUP>3</SUP>CT) of <B>1</B> in ethanol was revealed to be one order of magnitude smaller than that in benzene and one order magnitude larger than that of 1-aminoanthraquinone in benzene. These results were discuessd in relation to the energy diagram in the excited state and the intramolecular heavy-atom effect of bromine in <B>1</B>.

• 公益社団法人 日本化学会の論文

著者

• Inoue Haruo

  Department Of Applied Chemistry Graduate Course Of Engineering Tokyo Metropolitan University

• Shinoda Tsutomu

  Organic Division Tokyo Metropolitan Industrial Technology Center

• Hida Mitsuhiko

  Department of Industrial Chemistry, Faculty of Engineering, Tokyo Metropolitan University

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