2,3‐Di(thiophen‐2‐yl)quinoxaline Amine Derivatives: Yellow‐Blue Fluorescent Materials for Applications in Organic Electronics

Abstract

Abstract In this work, we have designed and synthesized new donor–acceptor (D–A) type, 2,3‐di(thiophen‐2‐yl)quinoxaline based amine derivatives ( 2 – 10 ). These compounds contain diaryl/heterocyclic amine segment and quinoxaline core as an electron donor and acceptor respectively. The synthesized molecules were fully characterized by standard spectroscopic techniques. Absorption spectra of all compounds showed intramolecular charge transfer (ICT) transition in the range of 390 to 461 nm. Dyes emit in yellow–blue region with emission maxima within 465 to 566 nm on excitation at their respective ICT absorption maxima. Moreover, compound 2 , 3 and 9 exhibit aggregation induced emission in THF:water system due to the formation of nanoaggregates. Electrochemical properties of 2–10 were studied by cyclic voltammetry. The HOMO and LUMO energy level were found in the range of –4.90 to –5.70 eV and –3.10 to –3.36 eV respectively, with an electrochemical band gap (E g ) from 1.72 to 2.48 eV. Molecules showed good thermal stability. Theoretical studies were also carried out by using DFT and TD–DFT calculation. Based on photophysical and electrochemical properties these derivatives could be used as solid state emitter and ambipolar charge transport materials in optoelectronic devices.