Syntheses and Properties of Diphenylaminophthalide Derivatives

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  • NAGAO Yukinori
    Department of Industrial Chemistry, Faculty of Science and Technology, Science University of Tokyo
  • TACHIKAWA Masashi
    Department of Industrial Chemistry, Faculty of Science and Technology, Science University of Tokyo
  • KOZAWA Kozo
    Department of Industrial Chemistry, Faculty of Science and Technology, Science University of Tokyo

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Other Title
  • ジフェニルアミノフタリド誘導体の合成と性質
  • ジフェニルアミノフタリド ユウドウタイ ノ ゴウセイ ト セイシツ

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Abstract

Diphenylaminophthalide derivatives were synthesized and their properties as color formers were investigated. Condensation of benzoyl benzoic acids and diphenylamines in acetic anhydride and pyridine afforded the diphenylaminophthalide derivatives having substituents of 4-R2 and 4-R3 in diphenylamino moiety and of 2-X in 3-phenyl moiety.<BR>The diphenylaminophthalides were colored red to reddish violet in acidic solvent. The visible absorption spectra were measured for the investigation of the substituent effect. R2 and R3 substituents gave a bathochromic shift of the λmax in the order of diethylamino>>dimethylamono>>methoxy>>H. X substituent provided a hypsochromic shift of λmax in the order of ethoxy>>hydroxy>>methyl. Therefore the bathochromic shift increased with incresing electron donating ability of R2 and R3 substituents, and the hypsochromic shift increased with incresing electron-donating ability of X substituent. PPP-MO calculation also gave a reasonable explanation for the substituent effect.

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