Preparation and Electrochemical Behavior of Quinoxaline‐Bridged Diphenylamines

Abstract

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.

Preparation, Electrochemical Behavior, and Reactivity of Bis(N‐Boc type Indroquinoxaline) Derivatives

“…Indroquinoxaline derivatives without the bromo group ( IQ s) were also prepared to compare the physical and chemical properties. BrIQ−H s were prepared by dehydration condensation between bromoisatin and 1,2‐phenylenediamine as prepared procedure [9,11] . BrIQ−H s were obtained as yellow powder.…”

“…BrIQÀ Hs were prepared by dehydration condensation between bromoisatin and 1,2-phenylenediamine as prepared procedure. [9,11] BrIQÀ Hs were obtained as yellow powder. Then, NH of BrIQÀ H was converted to N-Boc (Boc = t-butoxycarbonyl) by the reported method.…”

“…Additionally, we also prepared quinoxaline N-phenylindoloquinoxaline (IQÀ Ph) derivatives, which have a quinoxaline unitbridged diphenylamine structure, and their properties were investigated [9] as shown in Scheme 1. Indoloquinoxaline derivatives have been studied in not only biological and medical applications, [10][11][12] but also in electronic applications.…”