Synthsis of Diphenylphthalide Derivatives and Their Properties

概要

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As heat-sensitive blue-color formers, derivatives of diphenylphthalide were synthesized by the introduction of substituens on the phenyl ring of Crystal Violet Lactone (CVL), and the effect of the substituents on their visible absorption spectra in acid solution was investigated.<BR>Phenylphthalides were prepared first by the condensation of aldehydes with m-dimethylaminobenzoic acid. The phenylphthalides were oxidized with sodium m-nitrobenzenesulfonate to give benzoylbenzoic acids. Then variously substituted diphenylphthalides were obtained by the condensation of the benzoylbenzoic acids with anilines in acetic anhydride.<BR>All these diphenylphthalides were colored in 95% acetic acid or in zinc 3, 5-bis (1-phenylethyl) salicylate (SAZN) -benzene solution. Their molar absorption coefficient were greater in SAZNbenzene than acetic acid. The effect of the substituents on their visible absorption spectra was observed clearly when a methyl group was substituted to ortho position of the phenyl ring, which gave bathochromic shifts from CVL without affecting the absorbance. Especially two methyl groups on ortho position of the phenyl ring gave the largest bathochromic shifts more than 20 nm.
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