In this work, five 3,6,11-trisubstituted-dibenzo[a,c]phenazine (2–6) derivatives were synthesized by employing Palladium-catalyzed Suzuki–Miyaura ‘C–C bond’ coupling reaction and characterized. Absorption spectra of 2–6 show the formation of charge-transfer complexes. Dyes exhibit blue-green fluorescence with emission maxima 434–506 nm in various solvents and neat solid film. To elucidate AIE phenomenon, photophysical properties of dye 2 and 3 in different THF/water mixture were studied. The HOMO and LUMO energy level were found in the range of − 6.38 to − 6.82 eV and − 3.67 to − 3.75 eV with an electrochemical bandgap of 2.71–3.08 eV. The HOMO and LUMO distribution in molecules were further studied by DFT/TD–DFT calculations. Herein, characteristic blue emission, comparable energy levels with n-type materials, and good thermal stability of derivatives make them a potential candidate for their application in optoelectronics.

Graphic abstract

中文翻译：

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用于有机电子学的 Suzuki 偶联吩嗪衍生物调制光电化学性质的研究

在这项工作中，五3,6,11三取代二苯并[ A，C ]吩嗪（2 - 6）衍生物通过使用钯催化的铃木-宫浦“C-C键”偶联反应和表征合成。2-6 的吸收光谱显示了电荷转移复合物的形成。染料在各种溶剂和纯固体薄膜中表现出蓝绿色荧光，最大发射波长为 434-506 nm。阐明 AIE 现象，染料2和3 的光物理性质在不同的 THF/水混合物中进行了研究。发现 HOMO 和 LUMO 能级在 - 6.38 至 - 6.82 eV 和 - 3.67 至 - 3.75 eV 的范围内，电化学带隙为 2.71-3.08 eV。通过 DFT/TD-DFT 计算进一步研究了分子中的 HOMO 和 LUMO 分布。在此，特征性的蓝光发射、与 n 型材料相当的能级以及衍生物良好的热稳定性使它们成为其在光电子学中应用的潜在候选者。

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