双态发光三苯胺基有机硼配合物的设计、合成与应用

以三(4-溴苯)胺、4-氨基苯硼酸频哪醇酯、4-二乙氨基水杨醛和三氟化硼乙醚溶液为原料,经过Suzuki偶联反应、缩合反应和配位反应,设计、合成了一种新型三枝结构的三苯胺有机硼配合物(TPAB),使用 ¹H和 ¹³C NMR对 TPAB的结构进行了表征,通过紫外可见吸收光谱和荧光发射光谱详细研究了TPAB溶液和固体态的光物理性能以及不同的外部条件对其发光性能的影响。发现 TPAB溶液和固体态都具有较强的荧光发射,在四氢呋喃溶液中的吸收峰位于 417 nm,发射峰位于 548 nm,荧光量子产率为 40.49%,荧光寿命为 1.72 ns;TPAB 固体的荧光发射峰位于 582 nm,荧光量子产率为 11.43%,荧光寿命为 0.72ns,表明TPAB具有优良的双光发光性能。此外,TPAB具有良好的发光稳定性,不受pH、金属离子、氨基酸和压力的影响。基于化合物优异的发光性能,将其应用于荧光细胞成像,在肝癌细胞(HepG2)中表现出良好的单光子和双光子荧光成像效果。

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

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 oneand two-photon excitation.