A series of donor–acceptor-based 6H-indolo[2,3-b]quinoxaline amine derivatives were synthesized with different donor amines. The impact of the different donor moieties on 6H-indolo[2,3-b]quinoxaline was systematically examined by absorption-emission spectroscopy, cyclic voltammetry and theoretical studies. The photophysical properties of these molecules, such as intramolecular charge transfer transitions (400 to 462 nm) and emission (491 to 600 nm), were influenced by the nature of the peripheral amines. Further, the solid-state emission demonstrated by some of the dyes aroused our interest in performing photophysical studies on the aggregation-induced emission phenomenon; these dyes showed nanoparticle formation in THF/H₂O solvent mixtures. Varying the strength of the peripheral amines in the derivatives also tuned the electrochemical data, with lower band gaps (1.56 to 2.21 eV) and comparable HOMO–LUMO energy levels with reported ambipolar materials. The donor–acceptor architectures and HOMO–LUMO energies were further rationalized using DFT/TDDFT calculations. Thus, the opto-electrochemical studies and high thermal stability of these molecules indicate their potential application as solid-state emissive, ambipolar materials in optoelectronic devices.

中文翻译：

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供体取代基对6 H-吲哚并[2,3- b ]喹喔啉胺衍生物的光电化学性能的影响†

用不同的供体胺合成了一系列基于供体-受体的6 H-吲哚并[2,3- b ]喹喔啉胺衍生物。通过吸收-发射光谱法，循环伏安法和理论研究系统地考察了不同供体基团对6 H-吲哚并[2,3- b ]喹喔啉的影响。这些分子的光物理性质，例如分子内的电荷转移跃迁（400至462 nm）和发射（491至600 nm），受外围胺类性质的影响。此外，某些染料显示的固态发射引起了我们对聚集诱导发射现象进行光物理研究的兴趣。这些染料在THF / H中显示出纳米颗粒的形成₂ O溶剂混合物。改变衍生物中外围胺的强度还可以调节电化学数据，具有较低的带隙（1.56至2.21 eV），并且具有与报道的双极性材料相当的HOMO-LUMO能级。使用DFT / TDDFT计算进一步合理化了供体-受体结构和HOMO-LUMO能量。因此，这些分子的光电化学研究和高热稳定性表明它们作为固态发射双极性材料在光电器件中的潜在应用。