Progresses in Reactive Fluorescent Probes with Fused Aggregation- Induced Emission (AIE) and Excited State Intramolecular Proton Transfer (ESIPT) Structures

doi:10.6023/cjoc202112009

Abstract

Reactive fluorescent probes with the features of excited state intramolecular proton transfer (ESIPT) and aggregation-induced emission (AIE) have been widely used in the detection of various anions, metal cations and biomolecules in recent years, because they have some advantages including good biocompatibility, good sensing performance, a large Stokes shift, and as well high fluorescence quantum efficiency. The progress in reactive fluorescent probes that are structural simple and have the combined structures of AIE and ESIPT is briefly summarized, and the probes are divided into several types such as benzothiazole, salicylaldehyde Schiff base, hydrazine dihydrazone, chalcone fluorophore, etc. The related researches are discussed and prospected.

Key words: excited state intramolecular proton transfer (ESIPT), aggregation-induced emission (AIE), fluorescent probe, reaction-based recognition

Cite this article

Yuetian Guo, Yongxin Pan, Lijun Tang. Progresses in Reactive Fluorescent Probes with Fused Aggregation- Induced Emission (AIE) and Excited State Intramolecular Proton Transfer (ESIPT) Structures[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1640-1650.

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Fig. & Tab. 23

Figure 1. Schematic representation of the four-level energy cycle of the ESIPT process

Scheme 1. Reaction of probe 1 with H2S

Scheme 2. Reaction of probe 2 with Hg2+

Scheme 3. Reaction of probe 3 with GUS

Scheme 4. Synthesis of probe 4 and its detection mechanism for Cys

Scheme 5. Reversible reaction of probe 5 with Cu2+ and PPi

Scheme 6. Reaction of probe 6 with Zn2+

Scheme 7. Reaction of probe 7 with H+

Scheme 8. Reaction of probe 8 with Zn2+

Scheme 9. Reaction of probe 9 with esterase

Scheme 10. Reactions of probe 10 with N2H4 and ClO–

Scheme 11. Reaction of probe 11 with Pd0

Scheme 12. Reaction mechanism of probe 12 and Cys

Scheme 13. Reaction mechanism of probe 13 and Cys

Scheme 14. The detection mechanism of probe 15 for β-lactamase

Scheme 15. Reaction of probe 16 with ONOO–

Scheme 16. Reaction of probe 17 with ALP

Scheme 17. Reaction mechanism of probe 18 and 19 with H2O2

Scheme 18. Reaction of probe 20 with NTR

Scheme 19. Reaction of probe 21 with Cys/GSH/Hcy

Scheme 20. Reaction mechanism of probe 22 with H2O2

Scheme 21. Reaction of probe 23 with superoxide anion

Scheme 22. Reaction mechanism of probe 24 with Zn2+

References 59

[1]	Xu, Z.; Wang, Y.; Wang, Y.; Li, J.; Luo, W.; Wu, W.; Fan, Y. Spectrochim. Acta, Part A 2019, 212, 146.
[2]	Liao, Z.; Zheng, J.; Tan, H.; Zheng, X.; Jin, L. RSC Adv. 2016, 6, 33798. doi: 10.1039/C6RA01030J
[3]	Samanta, S.; P. D.; Ramesh, A.; Das, G. Chem. Commun. 2016, 52, 10381. doi: 10.1039/C6CC03910C
[4]	Visscher, A.; Bachmann, S.; Schnegelsberg, C.; Teuteberg, T.; Mata, R.; Stalke, D. Dalton Trans. 2016, 45, 5689. doi: 10.1039/c6dt00557h pmid: 26928871
[5]	Shi, W.; Chen, Y.; Chen, X.; Xie, Z.; Hui, Y. J. Lumin. 2016, 174, 56.
[6]	Hu, F.; Huang, Y.; Zhang, G.; Zhao, R.; Zhang, D. Tetrahedron Lett. 2014, 55, 1471. doi: 10.1016/j.tetlet.2014.01.056
[7]	Che, W.; Zhang, L.; Li, Y.; Zhu, D.; Xie, Z.; Li, G.; Zhang, P.; Su, Z.; Dou, C.; Tang, B. Anal. Chem. 2019, 91, 3467. doi: 10.1021/acs.analchem.8b05024
[8]	Weller, A.; Elektrochem, Z. Ber. Bunsen-Ges. 1956, 60, 1144.
[9]	Knibbe, H.; Dieter Rehm, D.; Weller, A. Ber. Bunsen-Ges. 1968, 72, 125.
[10]	Massue, J.; Felouat, A.; Curtil, M.; Vérité, P. M.; Jacquemin, D.; Ulrich, G. Dyes Pigm. 2019, 160, 915. doi: 10.1016/j.dyepig.2018.09.014
[11]	Lampkin, B.; Monteiro, C.; Powers, E.; Bouc, P.; Kelly, J.; VanVeller, B. Org. Biomol. Chem. 2019, 17, 1076. doi: 10.1039/c8ob02673d pmid: 30534794
[12]	Niu, Y.; Wang, R.; Shao, P.; Wang, Y.; Zhang, Y. Chemistry 2018, 24, 16670.
[13]	Munch, M.; Curtil, M.; Vérité, P.; Jacquemin, D.; Massue, J.; Ulrich, G. Eur. J. Org. Chem. 2018, 5, 1134
[14]	Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Chem. Commun. 2001, 18, 1740.
[15]	Xu, B.; Chi, Z.; Yang, Z.; Chen, J.; Deng, S.; Li, H.; Li, X.; Zhang, Y.; Xu, N.; Xu, J. J. Mater. Chem. 2010, 20, 4135.
[16]	Li, X.; Chi, Z.; Xu, B.; Li, H.; Zhang, X.; Zhou, W.; Zhang, Y.; Liu, S.; Xu, J. J. Fluoresc. 2011, 21, 1969. doi: 10.1007/s10895-011-0896-1
[17]	Ma, C.; Xu, B.; Xie, G.; He, J.; Zhou, X.; Peng, B.; Jiang, L.; Xu, B.; Tian, W.; Chi, Z.; Liu, S.; Zhang, Y.; Xu, J. Chem. Commun. 2014, 50, 7374. doi: 10.1039/C4CC01012D
[18]	Gu, X.; Yao, J.; Zhang, G.; Zhang, C.; Yan, Y.; Zhao, Y.; Zhang, D. Chem. Asian J. 2013, 8, 2362. doi: 10.1002/asia.201300451
[19]	La, D.; Bhosale, S.; Jones, L.; Bhosale, S. ACS Appl. Mater. Interfaces 2018, 10, 12189. doi: 10.1021/acsami.7b12320
[20]	Mei, J.; Huang, Y.; Tian, H. ACS Appl. Mater. Interfaces 2018, 10, 12217. doi: 10.1021/acsami.7b14343
[21]	Mei, J.; Leung, N. L.; Kwok, R. T.; Lam, J. W.; Tang, B. Z. Chem. Rev. 2015, 115, 11718. doi: 10.1021/acs.chemrev.5b00263 pmid: 26492387
[22]	La, D.; Bhosale, S.; Jones, L. ACS Appl. Mater. Interfaces 2018, 10, 12189. doi: 10.1021/acsami.7b12320
[23]	Liang, J.; Tang, B.; Liu, B. Chem. Soc. Rev. 2015, 10, 2798.
[24]	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. doi: 10.1002/anie.202005785
[25]	Zhang, J.; Wang, Q.; Guo, Z.; Zhang, S.; Yan, C.; Tian, H.; Zhu, W. Adv. Funct. Mater. 2019, 29, 1808153. doi: 10.1002/adfm.201808153
[26]	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. doi: 10.1039/C7SC01400G
[27]	Zhang, J. D.; Liu, A. C.; Chen, J.; Yuan, G. H.; Jin, H. F. Prog. Chem. 2020, 32, 594. (in Chinese)
	( 张继东, 刘阿晨, 陈娇, 袁光辉, 金华峰, 化学进展, 2020, 32, 594.) doi: 10.7536/PC190819
[28]	Chen, L.; D. W.; Lim, C.; Kim, D. Chem. Commun. 2017, 53, 4791. doi: 10.1039/C7CC01695F
[29]	Huang, J.; Li, T.; Liu, R.; Zhang, R.; Wang, Q.; Li, N.; Gu, Y.; Wang, P. Sens. Actuators, B 2017, 248, 257.
[30]	Liu, Y.; Nie, J.; Niu, J.; Wang, W.; Lin, W. J. Mater. Chem. B 2018, 6, 1973 doi: 10.1039/C8TB00075A
[31]	Chen, Q.; Zhang, Y.; Du, W.; Wang, Y.; Huang, Y.; Yang, Q.; Zhang, Q. J. Mater. Chem. B 2017, 5, 7736. doi: 10.1039/C7TB02076G
[32]	Zhang, P.; Nie, X.; Gao, M.; Zeng, F.; Qin, A.; Wu, S.; Tang, B. Mater. Chem. Front. 2017, 1, 838. doi: 10.1039/C6QM00223D
[33]	Sen Gupta, A.; Paul, K.; Luxami, V. Sens. Actuators, B 2017, 246, 653.
[34]	Hu, Z.; Zhang, H.; Chen, Y.; Wang, Q.; Elsegood, M.; Teat, S.; Feng, X.; Islam, M.; Wu, F.; Tang, B. Dyes Pigm. 2020, 175, 108175. doi: 10.1016/j.dyepig.2019.108175
[35]	Xie, Y.; Yan, L.; Tang, Y.; Tang, M.; Wang, S.; Bi, L.; Sun, W.; Li, J. J. Fluoresc. 2019, 29, 399. doi: 10.1007/s10895-019-02348-6 pmid: 30680508
[36]	Yan, L.; Li, R.; Wang, Z.; Qi, Z. RSC Adv. 2016, 6, 63874. doi: 10.1039/C6RA09920C
[37]	Wang, X.; Y. H.; W. L.; C. L.; W. Z.; Y. Z.; Feng, X. Anal. Methods 2017, 9, 1872. doi: 10.1039/C7AY00167C
[38]	Chen, K.; Han, B. C.; Ji, S. X.; Sun, J.; Gao, Z. Z.; Hou, X. F. Acta Chim. Sinica 2019, 77, 365. (in Chinese) doi: 10.6023/A18120484
	( 陈凯, 韩百川, 嵇思鑫, 孙瑾, 高振忠, 侯贤锋, 化学学报, 2019, 77, 365.) doi: 10.6023/A18120484
[39]	Bai, L.; Feng, W.; Feng, G. Dyes Pigm. 2019, 163, 483. doi: 10.1016/j.dyepig.2018.12.013
[40]	Xu, D.; Tang, L.; Tian, M.; He, P.; Yan, X. Tetrahedron Lett. 2017, 58, 3654. doi: 10.1016/j.tetlet.2017.08.016
[41]	Wei, X.; Wu, Q.; Feng, Y.; Chen, M.; Zhang, S.; Chen, M.; Zhang, J.; Yang, G.; Ding, Y.; Yang, X.; Ye, Q.; Zhang, Y.; Gu, Q.; Wang, J.; Wu, S.; Pang, R.; Li, Y. Sens. Actuators, B 2019, 304, 127242.
[42]	Feng, B.; Liu, Y.; Huang, S.; Huang, X.; Huang, L.; Liu, M.; Wu, J.; Du, T.; Wang, S.; Feng, X.; Zeng, W. Sens. Actuators, B 2020, 325, 128786.
[43]	Tang, L.; Xia, J.; Zhong, K.; Tang, Y.; Gao, X.; Li, J. Dyes Pigm. 2020, 178, 108379. doi: 10.1016/j.dyepig.2020.108379
[44]	Naha, S.; Velmathi, S. Microchem. J. 2020, 153, 104499. doi: 10.1016/j.microc.2019.104499
[45]	Qin, J.; Wang, B.; Yang, Z.; Yu, K. Sens. Actuators, B 2016, 224, 892.
[46]	Wang, Q.; Chen, Q.; Li, C.; Lai, Q.; Zou, F.; Liang, F.; Jiang, G.; Wang, J. Microchem. J. 2020, 153, 104503. doi: 10.1016/j.microc.2019.104503
[47]	Xu, D.; Liu, M.; Zou, H.; Tian, J.; Huang, H.; Wan, Q.; Dai, Y.; Wen, Y.; Zhang, X.; Wei, Y. Talanta 2017, 174, 803. doi: 10.1016/j.talanta.2017.07.010
[48]	Liu, H.; X. W.; Yu Xiang, Y.; Tong, A. Anal. Methods 2015, 7, 5028. doi: 10.1039/C5AY00653H
[49]	Cui, L.; Baek, Y.; Lee, S.; Kwon, N.; Yoon, J. Mater. Chem. C 2016, 4, 2909 doi: 10.1039/C5TC03272E
[50]	Leung, C.; Wang, Z.; Zhao, E.; Hong, Y.; Chen, S.; Kwok, R. T.; Leung, A. C.; Wen, R.; Li, B.; Lam, J. W.; Tang, B. Z. Adv. Healthcare Mater. 2016, 5, 427. doi: 10.1002/adhm.201500674
[51]	Peng, L.; Xiao, L.; Ding, Y.; Xiang, Y.; Tong, A. J. Mater. Chem. B 2018, 6, 3922. doi: 10.1039/c8tb00414e pmid: 32254320
[52]	Shen, Y.; Li, M.; Yang, M.; Zhang, Y.; Li, H.; Zhang, X. Spectrochim. Acta, Part A 2019, 222, 117230.
[53]	Jin, X.; Di, X.; Huang, H.; Liu, J.; Sun, X.; Zhang, X.; Zhu, H. RSC Adv. 2015, 5, 87306. doi: 10.1039/C5RA16614D
[54]	Zhu, K.; Qin, T.; Zhao, C.; Luo, Z.; Huang, Y.; Liu, B.; Wang, L. Sens. Actuators, B 2018, 276, 397.
[55]	Dai, F.; Zhao, M.; Yang, F.; Wang, T.; Wang, C. Dyes Pigm. 2020, 183, 108627. doi: 10.1016/j.dyepig.2020.108627
[56]	Czernel, G.; Budziak, I.; Oniszczuk, A.; Karcz, D.; Pustula, K.; Gorecki, A.; Matwijczuk, A.; Gladyszewska, B.; Gagos, M.; Niewiadomy, A.; Matwijczuk, A. Molecules 2020, 25, 4168. doi: 10.3390/molecules25184168
[57]	Dwivedi, B. K.; Singh, V. D.; Paitandi, R. P.; Pandey, D. S. ChemPhysChem 2018, 19, 2672. doi: 10.1002/cphc.201800579
[58]	Long, R.; Tang, C.; Xu, J.; Li, T.; Tong, C.; Guo, Y.; Shi, S.; Wang, D. Chem. Commun. 2019, 55, 10912. doi: 10.1039/C9CC05212G
[59]	Singhal, D.; Althagafi, I.; Kumar, A.; Yadav, S.; Prasad, A. K.; Pratap, R. New J. Chem. 2020, 44, 12019. doi: 10.1039/D0NJ02236E

聚集诱导发光(AIE)和激发态分子内质子转移(ESIPT)结构融合的反应型荧光探针的研究进展