REVIEWS

Progress in Design, Synthesis and Application of Triphenylamine-Based Fluorescent Probes

  • Sihong Chen ,
  • Qi Chen ,
  • Shihe Luo ,
  • Xiying Cao ,
  • Guoxian Yang ,
  • Xiaoqing Zeng ,
  • Zhaoyang Wang
Expand
  • a Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, School of Chemistry, South China Normal University, Guangzhou 510006
    b Key Lab of Functional Molecular Engineering of Guangdong Province in SCUT, Guangzhou 510640
* Corresponding authors. E-mail: ;

Received date: 2020-09-05

  Revised date: 2020-09-29

  Online published: 2020-10-22

Supported by

Scientific Special Project of Guangzhou Science and Technology(201607010251); Science and Technology Project of Guangdong Province(2017A010103016); Open Fund of the Key Laboratory of Functional Molecular Engineering of Guangdong Province(2017kf01)

Abstract

The triphenylamine fluorophore with propeller-structure can be used not only as a strong electron donor, but also as a potential aggregation-induced emission (AIE) framework. At the same time, triphenylamine derivatives with different substituted groups (e.g. formyl, amino, halogen, boronic acid group, alkynyl) can easily be modified for further functionalization by simple reactions, such as condensation and metal coupling reaction. Thus, the functional triphenylamine derivatives are widely applied in the molecular design of solar cells, fluorescent dyes, solid-state luminescent materials and fluorescent probes. According to the detected analytes, such as cations, anions, and neutral small molecules, the triphenylamine-based fluorescent probes reported in the past five years are divided into three types. And on the viewpoint of their structures and performances, the new progress on the molecular design, synthesis and detecting application is reviewed. The developing potential of triphenylamine-based fluorescent probes is also envisioned, and the AIE-type probes with the properties of near-infrared and high photoluminescence quantum yield should be highlighted in the future.

Cite this article

Sihong Chen , Qi Chen , Shihe Luo , Xiying Cao , Guoxian Yang , Xiaoqing Zeng , Zhaoyang Wang . Progress in Design, Synthesis and Application of Triphenylamine-Based Fluorescent Probes[J]. Chinese Journal of Organic Chemistry, 2021 , 41(3) : 919 -933 . DOI: 10.6023/cjoc202009012

References

[1]
Murakami, T. N.; Koumura, N. Adv. Energy Mater. 2019, 9, 1802967.
[2]
Rodriguez-Seco, C.; Mendez, M.; Roldan-Carmona, C.; Pudi, R.; Nazeeruddin, M. K.; Palomares, E. J. Angew. Chem., Int. Ed. 2020, 13, 5303.
[3]
Li, Y. Y.; Liu, S. J.; Ni, H. W.; Zhang, H. K.; Zhang, H. Q.; Chuah, C.; Ma, C.; Wong, K. S.; Lam, J. W. Y.; Kwok, R. T. K.; Qian, J.; Lu, X. F.; Tang, B. Z. Angew. Chem., Int. Ed. 2020, 59, 12822.
[4]
Xu, W. H.; Wang, D.; Tang, B. Z. Angew. Chem., Int. Ed. 2021, DOI: 10.1002/anie.202005899.
[5]
Jiang, M. J.; Gu, X. G.; Lam, J. W. Y.; Zhang, Y. L.; Kwok, R. T. K.; Wong, K. S.; Tang, B. Z. Chem. Sci. 2017, 8, 5440.
[6]
Shen, P.; Hua, J. Y.; Jin, H. D.; Du, J. Y.; Liu, C. L.; Yang, W.; Gao, Q. Y.; Luo, H. J.; Liu, Y.; Yang, C. Y. Sens. Actuators, B 2017, 247, 587.
[7]
Li, Y.; Gu, Z. Y.; He, T.; Yuan, X. C.; Zhang, Y. Y.; Xu, Z.; Qiu, H. Y.; Zhang, Q.; Yin, S. C. Dyes Pigm. 2020, 173, 107969.
[8]
Yang, X. D.; Chen, X. L.; Lu, X. D.; Yan, C. G.; Xu, Y. K.; Hang, X. D.; Qu, J. Q.; Liu, R. Y. J. Mater. Chem. C 2016, 4, 383.
[9]
Xia, Y.; Zhang, H. H.; Zhu, X. J.; Zhang, G. J.; Yang, X. Y.; Li, F.; Zhang, X. J.; Fang, M.; Yu, J. H.; Zhou, H. P. Dyes Pigm. 2018, 155, 159.
[10]
Abdurahman, A.; Wang, L.; Zhang, Z. X.; Feng, Y. T.; Zhao, Y. H.; Zhang, M. Dyes Pigm. 2020, 174, 108050.
[11]
Cai, W. N.; Xiao, T. D.; Niu, H. J.; Bai, X. D.; Zhang, Y. H.; Wang, C.; Wang, W.; Qi, H. Sens. Actuators, B 2017, 252, 330.
[12]
Wu, X. M.; Mao, Y.; Wang, D. Y.; Huang, Q.; Yin, Q. X.; Zheng, M.; Hu, Q. H.; Wang, H. Q. Sens. Actuators, B 2020, 307, 127681.
[13]
Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecule Recognition, American Chemical Society, Washington, DC, 1993.
[14]
Pang, C.-M.; Luo, S.-H.; Jiang, K.; Wang, B.-W.; Chen, S.-H.; Wang, N.; Wang, Z.-Y. Dyes Pigm. 2019, 170, 107651.
[15]
Li, H.; Zhang, R. L.; Li, C. X.; Huang, B.; Yu, T. T.; Huang, X. D.; Zhang, X. J.; Li, F.; Zhou, H. P.; Tian, Y. P. Org. Biomol. Chem. 2017, 15, 598.
[16]
Gao, Z.-Y.; Zhang, C.-J.; Zhang, X.; Xing, S.; Yao, J.-S.; Qiao, C.-D.; Liu, W.-L. Appl. Sci. 2019, 9, 577.
[17]
Mu, Y.-L.; Zhang, C.-J.; Gao, Z.-L.; Zhang, X.; Lu, Q.; Yao, J.-S.; Xing, S. Synth. Met. 2020, 262, 116334.
[18]
Gan, X. P.; Li, W.; Li, C. X.; Wu, Z. C.; Liu, D.; Huang, B.; Zhou, H. P.; Tian, Y. P. Sens. Actuators, B 2017, 239, 642.
[19]
Zhang, H. H.; Wei, Z. Y.; Xia, Y.; Fang, M.; Zhu, W. J.; Yang, X. Y.; Li, F.; Tian, Y. P.; Zhang, X. J.; Zhou, H. P. Spectrochim. Acta, Part A 2018, 196, 256.
[20]
Li, W.; Gan, X. P.; Liu, D.; Tian, X. H.; Yu, J. H.; Tian, Y. P.; Wu, J. Y.; Zhou, H. P. RSC Adv. 2016, 6, 44599.
[21]
Shi, F.; Cui, S. Q.; Liu, H. L.; Pu, S. Z. Dyes Pigm. 2020, 173, 107914.
[22]
Chen, H.; Yang, P.; Li, Y. H.; Zhang, L. L.; Ding, F.; He, X. J.; Shen, J. L. Spectrochim. Acta, Part A 2020, 224, 117384.
[23]
Jiang, K.; Wu, Y.-C.; Wu, H.-Q.; Li, S.-L.; Luo, S.-H.; Wang, Z.-Y. J. Photochem. Photobiol., A 2018, 350, 52.
[24]
Huang, Q. X.; Peng, Z. X.; Xie, X. R.; Tang, Z. F.; Lei, M. ChemistrySelect 2019, 4, 13490.
[25]
Pan, C. Q.; Wang, K.; Ji, S. M.; Wang, H. Q.; Li, Z. Z.; He, H. H.; Huo, Y. P. RSC Adv. 2017, 7, 36007.
[26]
Zhang, Z. X.; Li, F.; He, C. Y.; Ma, H. W.; Feng, Y. T.; Zhang, Y. N.; Zhang, M. Sens. Actuators, B 2018, 255, 1878.
[27]
Jiang, K.; Chen, S.-H.; Luo, S.-H.; Pang, C.-M.; Wu, X.-Y.; Wang, Z.-Y. Dyes Pigm. 2019, 167, 164.
[28]
Wei, W. G.; Jin, Y.; Han, T.; Du, B.; Zhi, X. J.; Wei, C. J.; Yuan, S. C. Aust. J. Chem. 2018, 77, 890.
[29]
Liu, B.; Tan, Y. H.; Hu, Q. H.; Wang, Y. Y.; Wu, X. M.; Huang, Q. X.; Zhang, W. F.; Zheng, M.; Wang, H. Q. Chem. Pap. 2019, 73, 3123.
[30]
Shi, W.; Zhao, S. Y.; Su, Y.; Hui, Y. H.; Xie, Z. F. New J. Chem. 2016, 40, 7814.
[31]
Zhang, Q. S.; Li, Y. H.; Zuo, H. J.; Wang, C. Y.; Shen, Y. J. J. Photochem. Photobiol., A 2017, 332, 293.
[32]
Zhang, Q. S.; Zhang, J.; Zuo, H. J.; Wang, C. Y.; Shen, Y. J. Tetrahedron 2017, 73, 2824.
[33]
Xiao, H. B.; Zhang, Y. Z.; Zhang, W.; Li, S. Z.; Tan, J. J.; Han, Z. Y. Mater. Chem. Phys. 2017, 192, 268.
[34]
Xiao, H. B.; Zhang, Y. Z.; Li, S. Z.; Zhang, W.; Han, Z. Y.; Tan, J. J.; Zhang, S. Y.; Du, J. Y. Sens. Actuators, B 2016, 236, 233.
[35]
Wu, Y.-C.; Jiang, K.; Luo, S.-H.; Cao, L.; Wu, H.-Q.; Wang, Z.-Y. Spectrochim. Acta, Part A 2019, 206, 632.
[36]
Xiao, H. B.; Zhang, Y. Z.; Zhang, W.; Li, S. Z.; Xu, R. H. Sens. Actuators, B 2016, 233, 469.
[37]
Jiang, Y.-B.; Gao, C.; Zhang, X.; Yao, J.-S.; Liu, Q.-Z.; Cai, X.-X. J. Mol. Struct. 2018, 1163, 33.
[38]
Pal, S.; Roy, D.; Bar, N.; Chowdhury, S.; Chowdhury, P. Polymer 2020, 191, 122292.
[39]
Wang, X. N.; Zuo, Y. J.; Zhang, Y.; Yang, T. X.; Lin, W. Y. Analyst 2019, 144, 5373.
[40]
Thanzeel, F. Y.; Sripada, A.; Wolf, C. J. Am. Chem. Soc. 2019, 141, 16382.
[41]
Pang, C.-M.; Chen, S.-H.; Cao, X.-Y.; Zhang, J.-R.; Xiao, Y.; Li, X.-D.; Luo, S.-H.; Wang, Z.-Y. J. Photochem. Photobiol., A 2020, 403, 112835.
[42]
Chen, S.-H.; Pang, C.-M.; Chen, X.-Y.; Yan, Z.-H.; Huang, S.-M.; Li, X.-D.; Zhong, Y.-T.; Wang, Z.-Y. Chin. J. Org. Chem. 2019, 39, 1846. (in Chinese)
[42]
(陈思鸿, 庞楚明, 陈孝云, 严智浩, 黄诗敏, 李香弟, 钟雅婷, 汪朝阳, 有机化学, 2019, 39, 1846.).
[43]
Erdemir, S.; Malkondu, S. Sens. Actuators, B 2013, 188, 1225.
[44]
Li, W.; Tian, X. H.; Huang, B.; Li, H. J.; Zhao, X. Y.; Gao, S.; Zheng, J.; Zhang, X. Z.; Zhou, H. P.; Tian, Y. P.; Wu, J. Biosens. Bioelectron. 2016, 77, 530.
[45]
Shen, B. X.; Qian, Y. ChemistrySelect 2017, 2, 2406.
[46]
Kundu, A.; Anthony, S. P. Spectrochim. Acta, Part A 2018, 189, 342.
[47]
Wang, L.; Yang, X. D.; Chen, X. L.; Zhou, Y. P.; Lu, X. D.; Yan, C. G.; Xu, Y. K.; Liu, R. Y.; Qu, J. Q. Mater. Sci. Eng., C 2017, 72, 551.
[48]
Mathivanan, M.; Tharmalingam, B.; Mani, K. S.; Thiagarajan, V.; Murugesapandian, B. Spectrochim. Acta, Part A 2020, 234, 118235.
[49]
Zhang, X.; Sun, P.; Li, F.; Li, H.; Zhou, H. P.; Wang, H.; Zhang, B. W.; Pan, Z. W.; Tian, Y. P.; Zhang, X. J. Sens. Actuators, B 2018, 255, 366.
[50]
Shen, B.-X.; Qian, Y. J. Mater. Chem. B 2016, 4, 7549.
[51]
Erdemir, S. Sens. Actuators, B 2019, 290, 558.
[52]
Sathiyan, G.; Chatterjee, S.; Sen, P.; Garg, A.; Gupta, R. K.; Singh, A. ChemistrySelect 2019, 4, 11718.
[53]
Thamaraiselvi, P.; Duraipandy, N.; Kiran, M. S.; Easwaramoorthi, S. ACS Sustainable Chem. Eng. 2019, 7, 9865.
[54]
Wu, Y.-C.; You, J.-Y.; Jiang, K.; Xie, J.-C.; Li, S.-L.; Cao, D. R.; Wang, Z.-Y. Dyes Pigm. 2017, 140, 47.
[55]
Wu, Y.-C.; Huo, J.-P.; Cao, L.; Ding, S.; Wang, L.-Y.; Cao, D. R.; Wang, Z.-Y. Sens. Actuators, B 2016, 237, 865.
[56]
Beneto, A. J.; Siva, A. Photochem. Photobiol. Sci. 2017, 16, 255.
[57]
Tamilarasan, D.; Suhasini, R.; Thiagarajan, V.; Balamurugan, R. Eur. J. Org. Chem. 2020,993.
[58]
Ozdemir, A.; Erdemir, S. J. Photochem. Photobiol., A 2020, 390, 112328.
[59]
Li, Q. Y.; Wang, Z. C.; Song, W. W.; Ma, H. L.; Dong, J. Y.; Quan, Y. Y.; Ye, X. X.; Huang, Z.-S. Dyes Pigm. 2019, 161, 389.
[60]
Zheng, Z.-H.; Li, Z.-K.; Song, L.-J.; Wang, Q.-W.; Huang, Q.-F.; Yang, L. Sensors 2017, 17, 405.
[61]
Zhang, Q. S.; Zhang, J.; Zuo, H. J.; Wang, C. Y.; Shen, Y. J. Tetrahedron 2016, 72, 1244.
[62]
Yang, C. J.; Wang, X. C.; Xu, Z. G.; Wang, M. F. Sens. Actuators, B 2017, 245, 845.
[63]
Liu, Y. J.; Qiu, D. L.; Pan, H.; Li, M. N.; Chen, H. B.; Li, H. M. J. Photochem. Photobiol., A 2018, 364, 151.
[64]
Zhang, H.-M.; Wu, Y.-C.; You, J.-Y.; Cao, L.; Ding, S.; Jiang, K.; Wang, Z.-Y. Chin. J. Org. Chem. 2016, 36, 2559. (in Chinese)
[64]
(张惠敏, 吴彦城, 尤嘉宜, 曹梁, 丁沙, 蒋凯, 汪朝阳, 有机化学, 2016, 36, 2559.)
[65]
Ponnuvel, K.; Padmini, V. J. Lumin. 2016, 169, 289.
[66]
Che, W. L.; Li, G. F.; Zhang, J. X.; Geng, Y.; Xie, Z. G.; Zhu, D. X.; Su, Z. M. J. Photochem. Photobiol., A 2018, 358, 274.
[67]
Zhang, D. S.; Liu, A. K.; Ji, R. X.; Dong, J.; Ge, Y. Q. Anal. Chim. Acta 2019, 1055, 133.
[68]
Cheng, X. H.; He, P.; Zhong, Z. C.; Liang, G. J. Luminescence 2016, 31, 1372.
[69]
Liu, K. Y.; Chen, Y. L.; Sun, H.; Wang, S. J.; Kong, F. G. J. Mater. Chem. B 2018, 6, 7060.
[70]
Wang, L. Y.; Li, L. Q.; Cao, D. R. Sens. Actuators, B 2017, 241, 1224.
[71]
Jiang, Y. H.; Zhang, S.; Wang, B. X.; Qian, T.; Jin, C.; Wu, S. S.; Shen, J. Tetrahedron 2018, 74, 5733.
[72]
Xu, C.; Qian, Y.; Qi, Z.-Q.; Lu, C.-G.; Cui, Y.-P. New J. Chem. 2018, 42, 6910.
[73]
Xu, X.-X.; Qian, Y. Spectrochim. Acta, Part A 2017, 183, 356.
[74]
Xu, X.-X.; Qian, Y. New J. Chem. 2017, 41, 9607.
[75]
Wang, T.; Shah, I.; Yang, Z. M.; Yin, W. D.; Zhang, S. X.; Yang, Y.; Yin, P.; Ma, H. C. Anal. Chem. 2020, 92, 2824.
[76]
Ma, H. C.; Yang, M. Y.; Zhang, S. X.; Yin, P.; Wang, T.; Yang, Y.; Lei, Z. Q.; Ma, Y. C.; Qin, Y. F.; Yang, Z. M. Analyst 2019, 144, 536.
[77]
Cao, L.; Xiong, J.-F.; Wu, Y.-C.; Ding, S.; Li, M.-B.; Xie, F.; Ma, Z.-H.; Wang, Z.-Y. Chin. J. Org. Chem. 2016, 36, 2053. (in Chinese)
[77]
(曹梁, 熊金锋, 吴彦城, 丁沙, 李铭冰, 谢芬, 马志晗, 汪朝阳, 有机化学, 2016, 36, 2053.).
[78]
Wang, B.-W.; Jiang, K.; Li, J.-X.; Luo, S.-H.; Wang, Z.-Y.; Jiang, H.-F. Angew. Chem., Int. Ed. 2020, 59, 2338.
[79]
Chen, S.-H.; Jiang, K.; Lin, J. Y.; Yang, K.; Cao, X.-Y.; Luo, X.-Y.; Wang, Z.-Y. J. Mater. Chem. C 2020, 8, 8257.
[80]
Ma, H. W.; Li, F.; Li, P.; Wang, H. L.; Zhang, M.; Zhang, G.; Baumgarten, M.; Mullen, K. Adv. Funct. Mater. 2016, 26, 2025.
[81]
Ji, N.-N.; Shi, Z.-Q.; Hu, H.-L.; Zheng, H.-G. Dalton Trans. 2018, 47, 7222.
[82]
Xiong, J.-F.; Li, J.-X.; Mo, G.-Z.; Huo, J.-P.; Liu, J.-Y.; Chen, X.-Y.; Wang, Z.-Y. J. Org. Chem. 2014, 79, 11619.
[83]
Wu, Y.-C.; Luo, S.-H.; Cao, L.; Jiang, K.; Wang, L.-Y.; Xie, J.-C.; Wang, Z.-Y. Anal. Chim. Acta 2017, 976, 74.
[84]
Jiang, K.; Luo, S.-H.; Pang, C.-M.; Wang, B.-W.; Wu, H.-Q.; Wang, Z.-Y. Dyes Pigm. 2019, 162, 367.
[85]
Sathiyan, G.; Balasubramaniam, B.; Ranjan, S.; Chatterjee, S.; Sen, P.; Garg, A.; Gupta, R. K.; Singh, A. Mater. Today Chem. 2019, 12, 178.
[86]
Wu, H. T.; Tao, F. R.; Cui, Y. Z.; Guo, L. Mater. Chem. Phys. 2020, 240, 122141.
[87]
Doan, B. K.; Tran, T. V. T.; Nguyen, T. H.; Luu, T. H.; Nguyen, L. T. T; Van, T. P.; Nguyen, V. M.; Nguyen, H. J. Photochem. Photobiol., A 2020, 394, 112496.
[88]
Chang, Z.-F.; Jing, L.-M.; Liu, Y.-Y.; Liu, J.-J.; Ye, Y.-C.; Zhao, Y.-S.; Wang, J.-L. J. Mater. Chem. C 2016, 4, 8407.
[89]
Wang, N.; Arulkumar, M.; Chen, X.-Y.; Wang, B.-W.; Chen, S.-H.; Yao, C.; Wang, Z.-Y. Chin. J. Org. Chem. 2019, 39, 2771. (in Chinese)
[89]
(王能, Mani, Arulkumar, 陈孝云, 王柏文, 陈思鸿, 姚辰, 汪朝阳, 有机化学, 2019, 39, 2771.)
[90]
Chen, S.-H.; Jiang, K.; Xiao, Y.; Cao, X.-Y.; Arulkumar, M.; Wang, Z.-Y. Dyes Pigm. 2020, 175, 108157.
[91]
Verbitskiy, E. V.; Kvashnin, Y. A.; Baranova, A. A.; Khokhlov, K. O.; Chuvashov, R. D.; Schapov, I. E.; Yakovleva, Y. A.; Zhilina, E. F.; Shchepochkin, A. V.; Makarova, N. I.; Vetrova, E. V.; Metelitsa, A. V.; Rusinov, G. L.; Chupakhin, O. N.; Charushin, V. N. Dyes Pigm. 2020, 178, 108344.
[92]
Zhang, W. J.; Yin, C. X.; Zhang, Y. B.; Chao, J. B.; Huo, F. J. Sens. Actuators, B 2016, 233, 307.
[93]
Bu, L. L.; Chen, J. Q.; Wei, X. D.; Li, X.; Agren, H.; Xie, Y. S. Dyes Pigm. 2017, 136, 724.
[94]
Xia, Y.; Zhang, H. H.; Zhu, X. J.; Fang, M.; Yang, M. D.; Zhang, Q.; Li, X. W.; Zhou, H. P.; Yang, X. Y.; Tian, Y. P. Dyes Pigm. 2019, 163, 441.
[95]
Sun, J. J.; Cao, J.; Cheng, H. L.; Wang, J. C.; Wang, S. X. Chem. Res. Chin. Univ. 2019, 35, 990.
[96]
Duan, Y. K.; Ding, G.; Yao, M. Y.; Wang, Q.; Guo, H.; Wang, X. C.; Zhang, Y. F.; Li, J. Y.; Li, X. J.; Qin, X. Z. Spectrochim. Acta, Part A 2020, 236, 118348.
[97]
Jiang, N.; Wang, B.; Liu, T.; Liu, Q. Y.; Wei, Q.; Xing, Y. J.; Zheng, G. X. Anal. Methods 2019, 11, 232.
[98]
Xu, L. F.; Ni, L.; Sun, L. H.; Zeng, F.; Wu, S. Z. Analyst 2019, 144, 6570.
[99]
Li, Q. Y.; Wang, Z. C.; Zhao, M.; Hong, Y. P.; Jin, Q. W.; Yao, S. Y.; Zheng, C. L.; Quan, Y.-Y.; Ye, X. X.; Huang, Z.-S. Sens. Actuators, B 2019, 298, 126898.
[100]
Ma, H. C.; Qi, C. X.; Cao, H. Y.; Zhang, Z. W.; Yang, Z. M.; Zhang, B.; Chen, C.; Lei, Z. Q. Chem.-Asian J. 2016, 11, 58.
[101]
Aich, K.; Das, S.; Gharami, S.; Patra, L.; Mondal, T. K. New J. Chem. 2017, 41, 12562.
[102]
Wu, Y.; Jin, P. W.; Gu, K. Z.; Shi, C. X.; Guo, Z. Q.; Yu, Z.-Q.; Zhu, W.-H. Chem. Commun. 2019, 55, 4087.
[103]
Wang, X. C.; Ding, G.; Duan, Y. K.; Zhu, Y. J.; Zhu, G. S.; Wang, M.; Li, X. J.; Zhang, Y. F.; Qin, X. Z.; Hung, C.-H. Talanta 2020, 217, 121029.
[104]
Wang, Z.-Y.; Chen, S.-H.; Jiang, K.CN 111039892, 2020.
[105]
Han, M. K.; Chen, M.; Ebendorff-Heidepriem, H.; Fang, C.; Qin, A. J.; Zhang, H.; Tang, B. Z.; Tang, Y. H.; Ruan, Y. L. RSC Adv. 2016, 6, 82186.
[106]
Wu, Z. H.; Fu, X. B.; Wang, Y. Sens. Actuators, B 2017, 245, 406.
Outlines

/