Citation: Gao-Bin ZHANG, Qi-Han JI, Fang-Jie CHEN, Jian-Li YAN, Yu-Jie YANG, Jia-Le CHEN. Design, synthesis, and application of triphenylamine-based organoboron complexes with dual-state emission property[J]. Chinese Journal of Inorganic Chemistry, ;2023, 39(8): 1545-1552. doi: 10.11862/CJIC.2023.087 shu

Design, synthesis, and application of triphenylamine-based organoboron complexes with dual-state emission property

School of Material Science and Engineering, Henan Polytechnic University, Jiaozuo, Henan 454003, China

Corresponding author: Gao-Bin ZHANG, gbzhang@hpu.edu.cn
Received Date: 14 January 2023
Revised Date: 23 March 2023

Figures(8)

A novel tri-branched structure organoboron complex based on triphenylamine (TPAB) was designed and synthesized by Suzuki coupling reaction, condensation reaction, and complexation reaction using tris(4-bromophenyl)amine, 4-aminophenyl boronic acid pinacol ester, 4-(diethylamino)salicylaldehyde and boron trifluoride etherate. The structures of the compounds were characterized by ¹H and ¹³C NMR. The photophysical properties of TPAB in solution and solid state were investigated by UV-Vis absorption and fluorescence spectra. TPAB was a dual-state emission active compound that showed strong fluorescence in both solution and solid state. The absorption peak of TPAB in tetrahydrofuran solution was located at 417 nm and the emission peak was located at 548 nm with a fluorescence quantum yield of 40.49% and a fluorescence lifetime of 1.72 ns. The fluorescence emission peak of the TPAB solid was located at 582 nm with a fluorescence quantum yield of 11.43% and a fluorescence lifetime of 0.72 ns. In addition, the fluorescence property of the compound was stable and was not affected by pH, metal ions, amino acids, and pressure. Based on the excellent fluorescence property, TPAB was applied for cell imaging that performed bright fluorescence in HepG2 cells under one- and two-photon excitation.
- dual-state emission,
- organoboron complex,
- triphenylamine,
- cell imaging
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