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2,3‐Di(thiophen‐2‐yl)quinoxaline Amine Derivatives: Yellow‐Blue Fluorescent Materials for Applications in Organic Electronics
ChemistrySelect ( IF 1.9 ) Pub Date : 2019-09-09 , DOI: 10.1002/slct.201902109
Suraj S. Mahadik 1 , Sajeev Chacko 2 , Rajesh M. Kamble 1
Affiliation  

In this work, we have designed and synthesized new donor–acceptor (D–A) type, 2,3‐di(thiophen‐2‐yl)quinoxaline based amine derivatives (210). 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 (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.

中文翻译:

2,3-二(噻吩-2-基)喹喔啉胺衍生物:黄蓝色荧光材料,用于有机电子

在这项工作中,我们设计并合成了新的供体-受体(d-A)型,2,3-二(噻吩-2-基)喹喔啉基胺衍生物(2 - 10)。这些化合物分别包含二芳基/杂环胺链段和喹喔啉核心作为电子给体和受体。通过标准光谱技术对合成的分子进行了充分表征。所有化合物的吸收光谱显示分子内电荷转移(ICT)跃迁在390至461 nm范围内。染料在各自的ICT吸收最大值下激发时,在黄蓝色区域发射,发射最大值在465至566 nm之间。此外,化合物239由于形成了纳米聚集体,因此在THF:水系统中表现出聚集诱导的发射。通过循环伏安法研究了2-10的电化学性质。发现HOMO和LUMO的能级分别为–4.90至–5.70 eV和–3.10至–3.36 eV,电化学带隙(E g)为1.72至2.48 eV。分子显示出良好的热稳定性。还通过使用DFT和TD-DFT计算进行了理论研究。基于光物理和电化学性质,这些衍生物可用作光电器件中的固态发射极和双极性电荷传输材料。
更新日期:2019-09-09
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