Determinations with polyaldehydes. IV. Fluorescence of 2-phenylphthalimidines was written by Amano, Tameyuki;Sakano, Toshiyuki;Mizukami, Satoshi. And the article was included in Yakugaku Zasshi in 1965.Application of 5388-42-1 This article mentions the following:
Following I are synthesized and their fluorescence ability examined Thus, a mixture of 536 mg. ο-phthalaldehyde and 436 mg. ο-aminophenol is kept for 3 weeks in 100 ml. Et2O, 90 ml. solvent removed, the precipitated mass dissolved in C6H6, chromatographed on 12 Al2O3, and eluted with C6H6 to give 44 mg. I (R = ο-OH), needles, m. 166.5° (C6H6-Et2O). Similarly are prepared the following I (R and m.p. given): m-OH, 202-3° (MeOH); p-OH, 221-3° (MeOH); m-OMe, 130-1° (MeOH); p-OMe, 139° (MeOH); m-Me, 145° (Et2O); p-Me, 139-40° (C6H6); ο-Cl, 172-3° (EtOH); m-Cl, 185.5° (MeOH); p-Cl, 184-5° (dioxane); m-Br, 186-7° (dioxane-MeOH); p-Br, 183° (dioxane); m-I, 171° (dioxane); p-I, 200-1° (dioxane); ο-CO2H, 248-50° (MeOH); m-CO2H, 282-3° (dioxane); p-CO2H, <300° (EtOH-dioxane); ο-NO2, 164° (dioxane); m-NO2, 237-8° (dioxane); p-NO2, 236° (dioxane) (yellow); 2′,3′-benzo, 194-5° (C6H6); 3′,4′-benzo, 188-9° (C6H6). Fluorescence of I requires the conjugation of phthalimidine ring and Ph group, and there is a great contribution of ionic resonance structure. Extension of the conjugated system increased 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 Ph 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 NO2 group completely inhibited fluorescence ability of 2-phenylphthalimidine. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application of 5388-42-1).
2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Application of 5388-42-1
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles