Premium
Preparation and Electrochemical Behavior of Quinoxaline‐Bridged Diphenylamines
Author(s) -
Hayashi Hideki,
Tsuda Erika,
Koizumi Takeaki
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202101087
Subject(s) - quinoxaline , diphenylamine , solvatochromism , moiety , chemistry , fluorescence , electrochemistry , condensation , polymer chemistry , medicinal chemistry , combinatorial chemistry , photochemistry , organic chemistry , molecule , electrode , physics , quantum mechanics , thermodynamics
N ‐Phenylindroquinoxalines ( PhIQ s), 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. PhIQ s showed fluorescent solvatochromism. PhIQ s 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 3‐positions 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.