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
收稿日期: 2021-12-04
修回日期: 2022-01-23
网络出版日期: 2022-02-18
基金资助
国家自然科学基金(21878023); 国家自然科学基金(U1608222); 辽宁省特聘教授支持计划资助项目.
Progresses in Reactive Fluorescent Probes with Fused Aggregation- Induced Emission (AIE) and Excited State Intramolecular Proton Transfer (ESIPT) Structures
Received date: 2021-12-04
Revised date: 2022-01-23
Online published: 2022-02-18
Supported by
National Natural Science Foundation of China(21878023); National Natural Science Foundation of China(U1608222); Program for Distinguished Professor of Liaoning Province.
兼具激发态分子内质子转移(ESIPT)和聚集诱导发光(AIE)性质的反应型荧光探针, 因其具有较好的生物相容性、良好的传感性能、较大的斯托克斯位移以及较高的荧光量子效率等优点, 在近几年来被广泛应用于检测各种阴离子、金属阳离子和生物分子中. 简要总结了结构简单, 既是AIE结构模块又是ESIPT结构模块的苯并噻唑、水杨醛席夫碱、肼二腙、查尔酮荧光团等反应型荧光探针的研究进展, 并对相关研究进行了总结和展望.
关键词： 激发态分子内质子转移(ESIPT); 聚集诱导发光(AIE); 荧光探针; 反应型识别
郭钺甜 , 潘永鑫 , 汤立军 . 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[J]. 有机化学, 2022 , 42(6) : 1640 -1650 . DOI: 10.6023/cjoc202112009
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.
| [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. |
| [3] | Samanta, S.; P. D.; Ramesh, A.; Das, G. Chem. Commun. 2016, 52, 10381. |
| [4] | Visscher, A.; Bachmann, S.; Schnegelsberg, C.; Teuteberg, T.; Mata, R.; Stalke, D. Dalton Trans. 2016, 45, 5689. |
| [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. |
| [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. |
| [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. |
| [11] | Lampkin, B.; Monteiro, C.; Powers, E.; Bouc, P.; Kelly, J.; VanVeller, B. Org. Biomol. Chem. 2019, 17, 1076. |
| [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. |
| [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. |
| [18] | Gu, X.; Yao, J.; Zhang, G.; Zhang, C.; Yan, Y.; Zhao, Y.; Zhang, D. Chem. Asian J. 2013, 8, 2362. |
| [19] | La, D.; Bhosale, S.; Jones, L.; Bhosale, S. ACS Appl. Mater. Interfaces 2018, 10, 12189. |
| [20] | Mei, J.; Huang, Y.; Tian, H. ACS Appl. Mater. Interfaces 2018, 10, 12217. |
| [21] | Mei, J.; Leung, N. L.; Kwok, R. T.; Lam, J. W.; Tang, B. Z. Chem. Rev. 2015, 115, 11718. |
| [22] | La, D.; Bhosale, S.; Jones, L. ACS Appl. Mater. Interfaces 2018, 10, 12189. |
| [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. |
| [25] | Zhang, J.; Wang, Q.; Guo, Z.; Zhang, S.; Yan, C.; Tian, H.; Zhu, W. Adv. Funct. Mater. 2019, 29, 1808153. |
| [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. |
| [27] | Zhang, J. D.; Liu, A. C.; Chen, J.; Yuan, G. H.; Jin, H. F. Prog. Chem. 2020, 32, 594. (in Chinese) |
| [27] | ( 张继东, 刘阿晨, 陈娇, 袁光辉, 金华峰, 化学进展, 2020, 32, 594.) |
| [28] | Chen, L.; D. W.; Lim, C.; Kim, D. Chem. Commun. 2017, 53, 4791. |
| [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 |
| [31] | Chen, Q.; Zhang, Y.; Du, W.; Wang, Y.; Huang, Y.; Yang, Q.; Zhang, Q. J. Mater. Chem. B 2017, 5, 7736. |
| [32] | Zhang, P.; Nie, X.; Gao, M.; Zeng, F.; Qin, A.; Wu, S.; Tang, B. Mater. Chem. Front. 2017, 1, 838. |
| [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. |
| [35] | Xie, Y.; Yan, L.; Tang, Y.; Tang, M.; Wang, S.; Bi, L.; Sun, W.; Li, J. J. Fluoresc. 2019, 29, 399. |
| [36] | Yan, L.; Li, R.; Wang, Z.; Qi, Z. RSC Adv. 2016, 6, 63874. |
| [37] | Wang, X.; Y. H.; W. L.; C. L.; W. Z.; Y. Z.; Feng, X. Anal. Methods 2017, 9, 1872. |
| [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) |
| [38] | ( 陈凯, 韩百川, 嵇思鑫, 孙瑾, 高振忠, 侯贤锋, 化学学报, 2019, 77, 365.) |
| [39] | Bai, L.; Feng, W.; Feng, G. Dyes Pigm. 2019, 163, 483. |
| [40] | Xu, D.; Tang, L.; Tian, M.; He, P.; Yan, X. Tetrahedron Lett. 2017, 58, 3654. |
| [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. |
| [44] | Naha, S.; Velmathi, S. Microchem. J. 2020, 153, 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. |
| [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. |
| [48] | Liu, H.; X. W.; Yu Xiang, Y.; Tong, A. Anal. Methods 2015, 7, 5028. |
| [49] | Cui, L.; Baek, Y.; Lee, S.; Kwon, N.; Yoon, J. Mater. Chem. C 2016, 4, 2909 |
| [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. |
| [51] | Peng, L.; Xiao, L.; Ding, Y.; Xiang, Y.; Tong, A. J. Mater. Chem. B 2018, 6, 3922. |
| [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. |
| [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. |
| [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. |
| [57] | Dwivedi, B. K.; Singh, V. D.; Paitandi, R. P.; Pandey, D. S. ChemPhysChem 2018, 19, 2672. |
| [58] | Long, R.; Tang, C.; Xu, J.; Li, T.; Tong, C.; Guo, Y.; Shi, S.; Wang, D. Chem. Commun. 2019, 55, 10912. |
| [59] | Singhal, D.; Althagafi, I.; Kumar, A.; Yadav, S.; Prasad, A. K.; Pratap, R. New J. Chem. 2020, 44, 12019. |
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