N-Phenylindroquinoxalines (PhIQs), which have a bridged diphenylamine structure, were synthesized and their physical and chemical properties were investigated. Syntheses of the materials were carried out by dehydration condensation between 4,5-disubstituted-1,2-phenylenediamine derivatives and N-phenylisatin. PhIQs showed fluorescent solvatochromism. PhIQs contain a diphenylamine moiety, but exhibit n-type properties due to the introduction of an electronegative quinoxaline unit. Introduction of substituents at the 2-and 3positions of PhIQ can regulate the reduction-oxidation potentials of the compound. The first reduction potential and fluorescent λ max vs. Hammett's σ p value has a good linear correlation.
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