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
1. [1]
  Zhang H, Liu X, Gong Y, Yu T, Zhao Y. Synthesis and characterization of SFX-based coumarin derivatives for OLEDs[J]. Dyes Pigm., 2021,185108969. doi: 10.1016/j.dyepig.2020.108969
2. [2]
  TANG Z Y, GUO H Q, XIAO J, CHEN Z J, XIAO L X. Recent advances on electronic transport materials in OLEDs[J]. Chin. J. Lumin., 2023,44(1):26-36.
3. [3]
  Nie Y X, Wang P L, Liang Z H, Ma Q, Su X G. Rational fabrication of a smart electrochemiluminescent sensor: Synergistic effect of a self- luminous Faraday cage and biomimetic magnetic vesicles[J]. Anal. Chem., 2021,93(20):7508-7515. doi: 10.1021/acs.analchem.1c00814
4. [4]
  Sohrabi H, Javanbakht S, Oroojalian F, Rouhani F, Shaabani A, Majidi M R, Hashemzaei M, Hanifehpour Y, Mokhtarzadeh A, Morsali A. Nanoscale metal-organic frameworks: recent developments in synthesis, modifications and bioimaging applications[J]. Chemosphere, 2021,281130717. doi: 10.1016/j.chemosphere.2021.130717
5. [5]
  Luo J D, Xie Z L, Lam J W Y, Cheng L, Chen H Y, Qiu C F, Kwok H S, Zhan X W, Liu Y Q, Zhu D B, Tang B Z. Aggregation-induced emission of 1-methyl-1, 2, 3, 4, 5-pentaphenylsilole[J]. Chem. Commun., 2001(18):1740-1741. doi: 10.1039/b105159h
6. [6]
  HAN P B, XU H, AN Z F, CAI Z Y, CAI Z X, CHAO H, CHEN B, CHEN M, CHEN Y, CHI Z G, DAI S T, DING D, DONG Y P, GAO Z Y, GUAN W J, HE Z K, HU J J, HU R, HU Y X, HUANG Q Y, KANG M M, LI D X, LI J S, LI S Z, LI W L, LI Z, LIN X L, LIU H Y, LIU P Y, LOU X D, LV C, MA D G, OU H L, OUYANG J, PENG Q, QIAN J, QIN A J, QU J M, SHI J B, SHUAI Z G, SUN L H, TIAN R, TIAN W J, TONG B, WANG H L, WANG D, WANG H, WANG T, WANG X, WANG Y C, WU S Z, XIA F, XIE Y J, XIONG K, XU B, YAN D P, YANG H B, YANG Q Z, YANG Z Y, YUAN L Z, YUAN W Z, ZANG S Q, ZENG F, ZENG J J, ZENG Z, ZHANG G Q, ZHANG X Y, ZHANG X P, ZHANG Y, ZHANG Y F, ZHANG Z J, ZHAO J, ZHAO Z, ZHAO Z H, ZHAO Z J, TANG B Z. Aggregation-induced emission[J]. Prog. Chem., 2022,34(1):1-130.
7. [7]
  Zhao Z, Zhang H K, Lam J W Y, Tang B Z. Aggregation-induced emission: new vistas at the aggregate level[J]. Angew. Chem. Int. Ed., 2020,59:9888-9907. doi: 10.1002/anie.201916729
8. [8]
  GUI Y X, CHEN K Y, LUO W S, TAN Y H, YAN D Y, WANG D, TANG B Z. Near-infrared-Ⅱ AIE probes for biomedical applications[J]. Chin. J. Lumin, 2023,44(2):356-373.
9. [9]
  Belmonte-Vázquez J L, Amador-Sánchez Y A, Rodríguez-Cortés L A, Rodríguez-Molina B. Dual-state emission (DSE) in organic fluorophores: design and applications[J]. Chem. Mater, 2021,33(18):7160-7184. doi: 10.1021/acs.chemmater.1c02460
10. [10]
  Yin Y N, Ding A X, Yang L M, Kong L, Yang J X. Fusing rigid planar units to engineer twisting molecules as dual-state emitters[J]. Mater. Chem. Front., 2022,6(10):1261-1268. doi: 10.1039/D2QM00067A
11. [11]
  Zhang H Y, Yang H Y, Zhang M, Lin H, Tao S L, Zheng C J, Zhang X H. A novel orange-red thermally activated delayed fluorescence emitter with high molecular rigidity and planarity realizing 32.5% external quantum efficiency in organic light-emitting diodes[J]. Mater. Horiz., 2022,9(9):2425-2432. doi: 10.1039/D2MH00639A
12. [12]
  Nijegorodov N, Luhanga P V C, Nkoma J S, Winkoun D P. The influence of planarity, rigidity and internal heavy atom upon fluorescence parameters and the intersystem crossing rate constant in molecules with the biphenyl basis[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2006,64(1):1-5. doi: 10.1016/j.saa.2005.06.032
13. [13]
  Li H K, Li B S, Tang B Z. Molecular design, circularly polarized luminescence, and helical self-assembly of chiral aggregation- induced emission molecules[J]. Chem.-Asian J., 2019,14(6):674-688. doi: 10.1002/asia.201801469
14. [14]
  Qiu Q Q, Xu P F, Zhu Y J, Yu J R, Wei M R, Xi W B, Feng H, Chen J R, Qian Z S. Rational design of dual-state emission luminogens with solvatochromism by combining a partially shared donor- acceptor pattern and twisted structures[J]. Chem.-Eur. J., 2019,25(70):15983-15987. doi: 10.1002/chem.201903857
15. [15]
  Behera S K, Park S Y, Gierschner J. Dual emission: Classes, mechanisms, and conditions[J]. Angew. Chem. Int. Ed., 2021,60:22624-22638. doi: 10.1002/anie.202009789
16. [16]
  Rodríguez-Cortés L A, Navarro-Huerta A, Rodríguez-Molina B. One molecule to light it all: The era of dual-state emission[J]. Matter, 2021,4(8):2622-2624. doi: 10.1016/j.matt.2021.06.023
17. [17]
  Ni Y Y, Zhang S S, He X, Huang J Y, Kong L, Yang J Y, Yang J X. Dual-state emission difluoroboron derivatives for selective detection of picric acid and reversible acid/base fluorescence switching[J]. Anal. Methods, 2021,13(25):2830-2835. doi: 10.1039/D1AY00477H
18. [18]
  Jing T T, Yan L F. pH-responsive dye with dual-state emission in both visible and near infrared regions[J]. Sci. China Chem., 2018,61(7):863-870. doi: 10.1007/s11426-017-9221-6
19. [19]
  Huang Z, Tang F, Ding A X, He F, Duan R H, Huang J Y, Kong L, Yang J X. D-A-D structured triphenylamine fluorophore with bright dual-state emission for reversible mechanofluorochromism and trace water detection[J]. Mol. Syst. Des. Eng., 2022,7(8):963-968. doi: 10.1039/D2ME00053A
20. [20]
  LU H B, WU S J, ZHANG C, QIU L Z, YANG J X. Synthesis and photoluminescence property of α-cyanostilbene derivatives molecules[J]. Chin. J. Lumin, 2015,36(9):983-988.
21. [21]
  ZHAO C H, ZHAO Y H, LIN J M. Optoelectronic materials of organoboron π-conjugated systems[J]. Prog. Chem, 2009,21(12):2605-2612.
22. [22]
  QIN Y Y, XU W J, HU C Y, LIU S J, ZHAO Q. Four-coordinated organoboron compounds with π-conjugated N, C-chelate ligand and their optoelectronic applications[J]. Chinese J. Inorg. Chem, 2017,33(10):1705-1721.
23. [23]
  Prates J L B, Pavan A R, Dos Santos J L. Boron in medicinal and organic chemistry[J]. Curr. Org. Chem., 2021,25(16):1853-1867. doi: 10.2174/1385272825666210625120209
24. [24]
  Kataria M, Kim Y, Chau H D, Kwon N Y, Hong Y J, Kim T, Ko J, Son M K, Bang J, Park S, Kim H I, Lee K, Choi D H. Solvent mediated thermodynamically favorable helical supramolecular self-assembly: Recognition behavior towards achiral and chiral analytes[J]. J. Mater. Chem. C, 2022,1010679. doi: 10.1039/D2TC01113A
25. [25]
  Gong Y, Guo X M, Wang S F, Su H M, Xia A D, He Q G, Bai F L. Photophysical properties of photoactive molecules with conjugated push-pull structures[J]. J. Phys. Chem. A, 2007,111(26):5806-5812. doi: 10.1021/jp0705323
26. [26]
  Seo J, Kim J, Park S Y. Strong solvatochromic fluorescence from the intramolecular charge-transfer state created by excited-state intramolecular proton transfer[J]. J. Am. Chem. Soc., 2004,126(36):11154-11155. doi: 10.1021/ja047815i
27. [27]
  Zhang C L, Liu M S, Liu S X, Yang H, Zhao Q, Liu Z P, He W J. Phosphorescence lifetime imaging of labile Zn²⁺ in mitochondria via a phosphorescent Iridium? complex[J]. Inorg. Chem., 2018,57:10625-10632. doi: 10.1021/acs.inorgchem.8b01272
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