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
1. [1]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
2. [2]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
3. [3]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
4. [4]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
5. [5]
  Linfang ZHANG , Wenzhu YIN , Gui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405
6. [6]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
7. [7]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
8. [8]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
9. [9]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
10. [10]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
11. [11]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
12. [12]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
13. [13]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
14. [14]
  Qingjun PAN , Zhongliang GONG , Yuwu ZHONG . Advances in modulation of the excited states of photofunctional iron complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 45-58. doi: 10.11862/CJIC.20240365
15. [15]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
16. [16]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
17. [17]
  Jinfeng Chu , Yicheng Wang , Ji Qi , Yulin Liu , Yan Li , Lan Jin , Lei He , Yufei Song . Comprehensive Chemical Experiment Design: Convenient Preparation and Characterization of an Oxygen-Bridged Trinuclear Iron(III) Complex. University Chemistry, 2024, 39(7): 299-306. doi: 10.3866/PKU.DXHX202310105
18. [18]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
19. [19]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
20. [20]
  Jin Yan , Chengxia Tong , Yajie Li , Yue Gu , Xuejian Qu , Shigang Wei , Wanchun Zhu , Yupeng Guo . Construction of a “Dual Support, Triple Integration” Chemical Safety Practical Education System. University Chemistry, 2024, 39(7): 69-75. doi: 10.12461/PKU.DXHX202405008

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(2427)
HTML views(211)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142