Linear Conjugated Systems Bearing Aromatie Terminal Groups. XI. Syntheses and Electronic Spectra of α,ω-Diphenanthrylpolyenes
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概要
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The syntheses of α,ω-di(2-phenanthryl)-, di(3-phenanthryl)-, and di(9-phenanthryl)polyenes (I<I><SUB>n</SUB></I>, I<I><SUB>n</SUB></I>′, and I<I><SUB>n</SUB></I>″, <I>n</I>=1–6) by means of the Wittig reaction are described. Formylphenanthrenes (II, II′, II″), phenanthrylpropenals (III′, III″), phenanthrylpentadienals (IV, IV′, IV″) and muconaldehyde (VIII) were used as carbonyl components in the reaction. Phenanthrylmethyl-, phenanthrylpropenyl- and phenanthrylpentadienyltriphenylphosphonium bromides and l,4-bis(triphenylphosphonium)-2-butene dibromide were converted into phosphoranes (V, V′, V″, VI, VI′, VII″, IX, IX′, IX″, VII) by a reaction with phenyllithium. The reaction of carbonyl components with phosphoranes with a proper combination yielded diphenanthrylpolyenes (I<I><SUB>n</SUB></I>, I<I><SUB>n</SUB></I>′, I<I><SUB>n</SUB></I>″). 2- and 3-Phenanthryl derivatives (I<I><SUB>n</SUB></I> and I<I><SUB>n</SUB></I>′) exhibited electronic spectra with well-defined vibartional fine structure, whereas 9-phenanthryl derivative (I<I><SUB>n</SUB></I>″) showed broad and structureless absorption curves. It was found that the plots of the longest-wavelength maxima (λ<SUB>max</SUB>) of I<I><SUB>n</SUB></I> and I<I><SUB>n</SUB></I>′ against <I>n</I><SUP>0.6</SUP> and <I>n</I><SUP>0.8</SUP> give excellent straight lines which can be given by the empirical formulas:<BR>I<I><SUB>n</SUB></I>:λ<SUB>max</SUB>=57.9<I><SUB>n</SUB></I><SUP>0.6</SUP>+303 nm (in tetrahydrofuran)<BR>I<I><SUB>n</SUB></I>′:λ<SUB>max</SUB>=30.3<I><SUB>n</SUB></I><SUP>0.8</SUP>+348 nm (in tetrahydrofuran)
- 公益社団法人 日本化学会の論文
著者
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Akiyama Shuzo
Department of Applied Physics and Chemistry, Fukui University of Technology
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Nakagawa Masazumi
Department of Chemistry Faculty of Science Osaka University
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Akiyama Shuzo
Department of Chemistry, Faculty of Science, Osaka University
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Yasuhara Akio
Department of Chemistry, Faculty of Science, Osaka University
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Takeuchi Yasuhira
Department of Chemistry, Faculty of Science, Osaka University
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