Citation: Yonghui ZHOU, Rujun HUANG, Dongchao YAO, Aiwei ZHANG, Yuhang SUN, Zhujun CHEN, Baisong ZHU, Youxuan ZHENG. Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives[J]. Chinese Journal of Inorganic Chemistry, ;2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373 shu

Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives

1.
School of Chemistry and Materials Science, Nanjing University of Information Science & Technology, Nanjing 210044, China
2.
Nanjing Iron and Steel Co., Ltd., Nanjing 210035, China
3.
State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China

Corresponding author: Yonghui ZHOU, 002083@nuist.edu.cn Youxuan ZHENG, yxzheng@nju.edu.cn
Received Date: 9 October 2023
Revised Date: 23 February 2024

Figures(9)

Four nitrogen heterocyclic fluorescent materials F1 - F4 with electron donor - acceptor structures were synthesized based on quinoxaline and pyridinopyrazine derivatives, which were constructed by the condensation reaction of α-diketone with o-phenylenediamine and pyridine diamine. Their photophysical properties were studied in detail. By testing of the fluorescence lifetimes and low-temperature fluorescence/phosphorescence spectra of F1-F4, combined with density functional theory calculations, it can be concluded that all four molecules are fluorescent small materials. Compounds F1-F4 showed photoluminescence spectra with peaks at 529, 464, 568, and 507 nm, respectively, with photoluminescence quantum efficiencies (PLQYs) of up to 98.2% in toluene. Additionally, positive solvatochromism was recorded from the emission spectra of four compounds in solvents with different polarities, further confirming their intramolecular charge transfer nature. Furthermore, the lifetimes of four compounds were 12.21, 2.61, 9.76, and 6.03 ns, respectively. To further explore the functionalized applications of these fluorescent molecules, they were doped as luminescent materials in organic light- emitting diodes (DF1 - DF4). Among them, devices DF1 and DF3 achieved maximum current efficiencies of 13.38 and 11.98 cd·A^-1 and maximum external quantum efficiencies of 4.8% and 4.5% with low-efficiency roll-off, which are related to the high PLQYs of molecules F1 and F3.
- fuorescent molecule,
- electron donor-acceptor,
- quinoxaline,
- pyridinopyrazine,
- organic light-emitting diode
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