多価アルデヒド類による定量法の研究 (第4報)

2-フェニルフタルイミジン類のケイ光能

抄録

Phenylphthalimidines, possessing substituents like hydroxyl, methoxyl, chlorine, bromine, iodine, sulfonilamide, carboxyl, and nitro group in the phenyl ring, and 2-(1-naphthyl) phthalimidine and 2-(2-naphthyl) phthalimidine were prepared and their fluorescence ability was examined. Fluorescence of 2-phenylphthalimidines requires the conjugation of phthalimidine ring and phenyl group, and there is a great contribution of ionic resonance structure. Extension of the conjugate system increases fluorescence ability while interference of planar configuration by steric hindrance decreased or completely inhibited fluorescence. This fluorescence ability is affected by the electronic character of the substituent in the phenyl ring; increased electron-donating nature of the substituent resulted in the red shift of the maximum wave length and decrease in fluorescence intensity, while increased electron-accepting nature of the substituent resulted in the blue shift of the maximum wave length and increase in fluorescence intensity. Introduction of a nitro group completely inhibited fluorescence ability of 2-phenylphthalimidine.