2, 3‐Di(thiophen‐2‐yl)quinoxaline Amine Derivatives: Yellow‐Blue Fluorescent Materials for Applications in Organic Electronics. Issue 34 (9th September 2019)

• Record Type: Journal Article
• Authors: Mahadik, Suraj S.; Chacko, Sajeev; Kamble, Rajesh M.
• Is Part Of: ChemistrySelect. Volume 4:Issue 34(2019)
• Page Start: 10021
• Page End: 10032
• Publication Date: 2019-09-09
• Subjects: 2, 3-di(thiophen-2-yl)quinoxaline amine derivatives -- Intramolecular charge transfer (ICT) transition -- D–A architecture -- yellow–blue emission -- Aggregation induced emission (AIE) -- ambipolar materials; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201902109
• Languages: English
• ISSNs: 2365-6549

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, compound2, 3 and9 exhibit aggregation induced emission in THF:water system due to the formation of nanoaggregates. Electrochemical properties of2–10 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 (Eg ) 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. Abstract : Donor–Acceptor (D–A) based 2, 3‐di(thiophen‐2‐yl)quinoxaline Amine derivatives with ICT feature are synthesized and studied. Dyes emit in blue to yellow region in solution as well as in solid film. Aggregation Induced Emission (AIE) characteristic possessed by some molecules attributed towards nanoaggregate formation. The HOMO and LUMO energy level of these molecules are comparable with reported ambipolar materials and thus promises the use of these derivatives as solid state emissive and ambipolar materials in optoelectronic devices.