三苯胺衍生物的合成及其基于聚集诱导发光(AIE)机理对汞离子“OFF-ON”荧光识别
收稿日期: 2022-06-22
修回日期: 2022-08-01
网络出版日期: 2022-09-02
基金资助
国家自然科学基金(22278038); 国家自然科学基金(32201948); 辽宁省自然科学基金(2020-MS-289); 辽宁省自然科学基金(20180551195); 农业农村部水产品质量安全控制重点实验室基金(2021C001); 辽宁省教育厅基本科研(LJKMZ20221480); 辽宁省教育厅基本科研(LJKQZ2021135)
Synthesis of Triphenylamine Derivative and Its Recognition for Hg2+ with “OFF-ON” Fluorescence Response Based on Aggregation-Induced Emission (AIE) Mechanism
Received date: 2022-06-22
Revised date: 2022-08-01
Online published: 2022-09-02
Supported by
National Natural Science Foundation of China(22278038); National Natural Science Foundation of China(32201948); Natural Science Foundation of Liaoning Province(2020-MS-289); Natural Science Foundation of Liaoning Province(20180551195); Fund of Key Laboratory of Control of Quality and Safety for Aquatic Products, Ministry of Agriculture and Rural Affairs(2021C001); Scientific Research Fund of Liaoning Provincial Education Department(LJKMZ20221480); Scientific Research Fund of Liaoning Provincial Education Department(LJKQZ2021135)
汞离子(Hg2+)作为一种环境污染物不能被生物降解, 而且还会通过食物链积累, 对人体造成损害, 因此, 开发简单、有效检测Hg2+方法具有重要意义. 通过简单的两步反应合成了新颖的三苯胺衍生物Tbia, 该探针在羟乙基哌嗪乙硫磺酸(HEPES)溶液中可与Hg2+发生特异性反应, 释放出具有聚集诱导发光(AIE)特性的前体化合物, 从而实现对 Hg2+荧光“OFF-ON”识别. Tbia对Hg2+具有良好的选择性和灵敏度, 较宽的pH适用范围, 检测限仅为63 nmol/L. 此外, Tbia可被制成隐形墨水有望用于防伪包装, 利用负载Tbia的试纸可定性或粗定量检测Hg2+, Tbia还能检测真实水样中的Hg2+, 并可对活细胞中的Hg2+进行荧光成像.
关键词： 荧光探针; 聚集诱导发光(AIE); 识别; 汞离子; 多重应用
李阳阳 , 孙小飞 , 胡晓玲 , 任源远 , 钟克利 , 燕小梅 , 汤立军 . 三苯胺衍生物的合成及其基于聚集诱导发光(AIE)机理对汞离子“OFF-ON”荧光识别[J]. 有机化学, 2023 , 43(1) : 320 -325 . DOI: 10.6023/cjoc202206043
As an environmental pollutant, mercury ion (Hg2+) cannot be biodegraded, and will accumulate through the food chain and cause damage to human body. Therefore, it is of great significance to develop a simple and effective method for detecting Hg2+. In this paper, a novel triphenylamine derivative Tbia was synthesized by a simple two-step reaction. Tbia can react with Hg2+ specifically in hydroxyethylpiperazine ethane sulfonic acid (HEPES) solution and release the precursor compound with aggregation-induced emission (AIE) properties, which realized recognition of Hg2+ with “off-on” response. Tbia has good selectivity and sensitivity for Hg2+, a wide range of pH, and the detection limit of 63 nmol/L. In addition, Tbia can be prepared into invisible ink and is expected to be used in packaging of anti-counterfeiting. The test paper loaded with Tbia can be used for qualitative or roughly quantitative detection of Hg2+, and Tbia can detect Hg2+ in real water samples as well as image of Hg2+ in living cells.
| [1] | He, Y.; Sun, X.; Yan, X.; Li, Y.; Zhong, K.; Tang, L. J. Mater. Chem. C 2022, 10, 9009. |
| [2] | Driscoll, C. T.; Mason, R. P.; Chan, H. M.; Jacob, D. J.; Pirrone, N. Environ. Sci. Technol. 2013, 47, 4967. |
| [3] | Sarkar, A.; Chakraborty, S.; Lohar, S.; Ahmmed, E.; Saha, N. C.; Mandal, S. K.; Dhara, K.; Chattopadhyay, P. Chem. Res. Toxicol. 2019, 32, 1144. |
| [4] | Tang, A.; Chen, Z.; Deng, D.; Liu, G.; Tu, Y.; Pu, S. RSC Adv. 2019, 9, 11865. |
| [5] | Liu, X.; Liu, X.; Tao, M.; Zhang, W. J. Mater. Chem. A 2015, 3, 13254. |
| [6] | Luo, W.; Jiang, H.; Zhang, K.; Liu, W.; Tang, X.; Dou, W.; Ju, Z.; Li, Z.; Liu, W. J. Mater. Chem. B 2015, 3, 3459. |
| [7] | Gupta, S.; Milton, M. D. New J. Chem. 2018, 42, 2838. |
| [8] | Fang, W.; Zhang, G.; Chen, J.; Kong, L.; Yang, L.; Bi, H.; Yang, J. Sens. Actuators, B 2016, 229, 338. |
| [9] | Yang, L.; Su, Y.; Geng, Y.; Xiong, H.; Han, J.; Fang, Q.; Song, X. Org. Biomol. Chem. 2018, 16, 5036. |
| [10] | Gao, T.; Huang, X.; Huang, S.; Dong, J.; Yuan, K.; Feng, X.; Liu, T.; Yu, K.; Zeng, W. J. Agric. Food. Chem. 2019, 67, 2377. |
| [11] | Li, Y.; Chen, C.; Li, B.; Sun, J.; Wang, J.; Gao, Y.; Zhao, Y.; Chai, Z. J. Anal. At. Spectrom. 2006, 21, 94. |
| [12] | Tseng, C. M.; De Diego, A.; Martin, F. M.; Amouroux, D.; Donard, O. F. X. J. Anal. At. Spectrom. 1997, 12, 743. |
| [13] | Tian, M.; Wang, C.; Ma, Q.; Bai, Y.; Sun, J.; Ding, C. ACS Omega 2020, 5, 18176. |
| [14] | Tang, L.; Yu, H.; Zhong, K.; Gao, X.; Li, J. RSC Adv. 2019, 9, 23316. |
| [15] | Zhong, K.; Yao, Y.; Sun, X.; Wang, Y.; Tang, L.; Li, X.; Zhang, J.; Yan, X.; Li, J. J. Agric. Food. Chem. 2022, 70, 5159. |
| [16] | Wu, D.; Chen, L.; Lee, W.; Ko, G.; Yin, J.; Yoon, J. Coord. Chem. Rev. 2018, 354, 74. |
| [17] | Zhong, K.; Hu, X.; Zhou, S.; Liu, X.; Gao, X.; Tang, L.; Yan, X. J. Agric. Food. Chem. 2021, 69, 4628. |
| [18] | Pan, Y.; Ban, L.; Li, J.; Liu, M.; Tang, L.; Yan, X. Dyes Pigm. 2022, 203, 110305. |
| [19] | Arivazhagan, C.; Borthakur, R.; Ghosh, S. Organometallics 2015, 34, 1147. |
| [20] | Xu, D.; Tang, L.; Tian, M.; He, P.; Yan, X. Tetrahedron Lett. 2017, 58, 3654. |
| [21] | Li, G.; Gao, G.; Cheng, J.; Chen, X.; Zhao, Y.; Ye, Y. Luminescence 2016, 31, 992. |
| [22] | Guo, Y.; An, J.; Tang, H.; Peng, M.; Suzenet, F. Mater. Res. Bull. 2015, 63, 155. |
| [23] | Hu, D.; Liao, S.; Chen, X.; Du, J.; Dawood, K.; Chauhan, S.; Gao, C.; Li, W. Bull. Korean Chem. Soc. 2020, 41, 686. |
| [24] | Wang, J.; Niu, Q.; Hu, T.; Li, T.; Wei, T. J. Photochem. Photobiol., A 2019, 384, 112036. |
| [25] | Tang, L.; Zhou, L.; Yan, X.; Zhong, K.; Gao, X.; Li, J. J. Photochem. Photobiol., A 2020, 387, 112160. |
| [26] | Huang, L.; Yang, Z.; Zhou, Z.; Li, Y.; Tang, S.; Xiao, W.; Hu, M.; Peng, C.; Chen, Y.; Gu, B.; Li, H. Dyes Pigm. 2019, 163, 118. |
| [27] | Liu, Y.-Y.; Naha, S.; Thirumalaivasan, N.; Velmathi, S.; Wu, S.-P. Sens. Actuators, B 2018, 277, 673. |
| [28] | Gao, Y.; Ma, T.; Ou, Z.; Cai, W.; Yang, G.; Li, Y.; Xu, M.; Li, Q. Talanta 2018, 178, 663. |
| [29] | Huang, S.; Gao, T.; Bi, A.; Cao, X.; Feng, B.; Liu, M.; Du, T.; Feng, X.; Zeng, W. Dyes Pigm. 2020, 172, 107830. |
| [30] | Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Chem. Commun. 2009, 4332. |
| [31] | Hong, Y.; Lam, J. W.; Tang, B. Z. Chem. Soc. Rev. 2011, 40, 5361. |
| [32] | Ozturk, S.; Atilgan, S. Tetrahedron Lett. 2014, 55, 70. |
| [33] | Xu, D.; Tang, L.; Tian, M.; He, P.; Yan, X. Tetrahedron Lett. 2017, 58, 3654. |
| [34] | Hu, D.; Liao, S.; Chen, X.; Du, J.; Dawood, K.; Chauhan, S.; Gao, C.; Li, W. Bull. Korean Chem. Soc. 2020, 41, 686. |
| [35] | Liu, B.; Liu, J.; He, J.; Zhang, J.; Zhou, H.; Gao, C. Chem. Phys. 2020, 539, 110944. |
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