一种基于香豆素骨架的荧光化学传感器于水溶液中实现对Al3+和焦磷酸根(PPi)的连续识别
收稿日期: 2020-10-06
修回日期: 2020-10-28
网络出版日期: 2020-11-12
基金资助
山西省基础应用研究(201801D221087); 山西农业大学科技创新(2020BQ18); 山西省优秀博士来晋工作奖励(SXYBKY2019046); 山西省高等学校创新(2020L0140)
A Fluorescent Chemosensor Based on Coumarin for Squential Recognition of Al3+ and Pyrophosphate (PPi) in Aqueous Solution
Received date: 2020-10-06
Revised date: 2020-10-28
Online published: 2020-11-12
Supported by
Applied Basic Research Programs of Shanxi Province(201801D221087); Science and Technology Innovation Project of Shanxi Agricultural University(2020BQ18); Shanxi Excellent Doctor Grant Award(SXYBKY2019046); Science and Technology Innovation Project of Colleges and Universities(2020L0140)
合成了一种新型的荧光化学传感器(E)-N'-(3-((双(吡啶-2-亚甲基)氨基)甲基)-2-羟基-5-甲基亚苄基)-7-(二乙氨基)-2-氧代-2H-色烯-3-甲酰肼(1), 并通过1H NMR、13C NMR和ESI-MS对其结构进行表征, 利用紫外/荧光分光光度法研究了传感器1的传感性能. 结果表明: 传感器1于水中对Al3+表现出明显的荧光增强响应, 而配合物1-Al3+对PPi表现出明显的荧光淬灭响应. 传感器1对Al3+和焦磷酸根(PPi)的检测限分别为0.26和0.1 μmol/L, 配位比均为1∶1. 配位机理通过荧光滴定、核磁滴定和高分辨质谱进行了证实, 另外传感器 1的有效测试pH范围是2~10, 且循环响应测试可达4次.
孟宪娇 , 赵晋忠 , 张永坡 , 李志春 , 袁长春 , 马文兵 . 一种基于香豆素骨架的荧光化学传感器于水溶液中实现对Al3+和焦磷酸根(PPi)的连续识别[J]. 有机化学, 2021 , 41(3) : 1161 -1167 . DOI: 10.6023/cjoc202010007
A novel fluorescent chemosensor (E)-N'-(3-((bis(pyridin-2-ylmethyl)amino)methyl)-2-hydroxy-5-methylbenzyl- idene)-7-(diethylamino)-2-oxo-2H-chromene-3-carbohydrazide (1) has been synthesized and showed an obviously “off-on-off” fluorescence response toward Al 3+ and pyrophosphate (PPi) in aqueous solution. The detection limits of sensor 1 were 0.26 μmol/L to Al 3+ and 0.1 μmol/L to PPi, and the binding stoichiometry was 1∶1. In addition, the binding mechanism was further confirmed by fluorescence titration, nuclear magnetic titration and ESI-MS. The effective determination pH range for Al 3+ and PPi was from 2 to 10, and the cycle response test could reach 4 times.
Key words: coumarin; fluorescent chemosensor; Al3+; PPi; sequential recognition
[1] | Zhong, K. L.; Zhou, L. L.; Deng, L. L.; Tang, L. J.; Gao, X.; Liu, X. Y.; Yan, X. M. Chin. J. Org. Chem. 2020, 40, 1251. (in Chinese) |
[1] | (钟克利, 周璐璐, 邓隆隆, 汤立军, 高雪, 刘秀英, 燕小梅, 有机化学, 2020, 40, 1251.) |
[2] | Kim, S.; Noh, J. Y.; Kim, K. Y.; Kim, J. H.; Kang, H. K.; Nam, S. W.; Kim, S. H.; Park, S.; Kim, C.; Kim, J. Inorg. Chem. 2012, 51, 3597. |
[3] | Wang, B.; Xing, W.; Zhao, Y.; Deng, X. Environ. Toxicol. Pharmacol. 2010, 29, 308. |
[4] | Bothra, S.; Upadhyay, Y.; Kumar, R.; Sahoo, S. K. Spectrochim. Acta, Part A 2017, 174, 1. |
[5] | Wang, F.; Xu, Y. L.; Aderinto, S. O.; Peng, H. P.; Zhang, H.; Wu, H. L. J. Photochem. Photobiol., A 2017, 332, 273. |
[6] | Shree, G. J.; Sivaraman, G.; Siva, A.; Chellappa, D. Dyes Pigm. 2019, 163, 204. |
[7] | Peng, H. N.; Han, Y. J.; Lin, N.; Liu, H. H. Opt. Mater. 2019, 95, 109210. |
[8] | Zhu, Y. L.; Gong, X. S.; Li, Z. P.; Zhao, X.; Liu, Z. Q.; Cao, D. X.; Guan, R. F. Spectrochim. Acta, Part A 2019, 219, 202. |
[9] | Fan, L.; Qin, J. C.; Li, C. R.; Yang, Z. Y. Spectrochim. Acta, Part A 2019, 218, 342. |
[10] | Nikfar, Z.; Shariatinia, Z. J. Mol. Graphics Modell. 2017, 76, 86. |
[11] | Taha, A.; Akram, M.; Jawad, Z.; Alshemary, A. Z.; Hussain, R. Mater. Sci. Eng., C 2017, 80, 93. |
[12] | Zhao, L.; Cao, X. D.; Zheng, W.; Scott, J. W.; Sharma, B. K.; Chen, X. ACS Sustainable Chem. Eng. 2016, 4, 1630. |
[13] | Tang, Y. F.; Wang, X. Y.; Yang, Y. C.; Gao, B.; Wan, Y. S.; Li, Y. C.; Chen, D. D. J. Agric. Food Chem. 2017, 65, 5879. |
[14] | Slaughter, G.; Sunday, J.; Stevens, B. Mater. Chem. Phys. 2015, 163, 245. |
[15] | Hu, Y.; Yang, J.; Jia, R.; Ding, Y.; Li, S.; Huang, H. Bioprocess Biosyst. Eng. 2014, 37, 1617. |
[16] | Strianese, M.; Milione, S.; Maranzana, A.; Grassi, A.; Pellecchia, C. Chem. Commun. 2012, 48, 11419. |
[17] | Ronaghi, M.; Karamohamed, S.; Pettersson, B.; Uhlén, M.; Nyrén, P. Anal. Biochem. 1996, 242, 84. |
[18] | Zhang, J.; She, M.; Li, J.; Wang, C.; Wang, S.; Liu, P.; Zhang, S. Y.; Li, J. L. Sens. Actuators, B 2018, 270, 362. |
[19] | Aragoni, M. C.; Arca, M.; Bencini, A.; Caltagirone, C.; Garau, A.; Isaia, F.; Light, M. E.; Lippolis, V.; Lodeiro, C.; Mameli, M.; Montis, R.; Mostallino, M. C.; Pintusa, A.; Puccioni, S. Dalton Trans. 2013, 42, 14516. |
[20] | Meng, X. J.; Zhao, J. Z.; Ma, W. B. Chin. J. Org. Chem. 2020, 40, 276. (in Chinese) |
[20] | (孟宪娇, 赵晋忠, 马文兵, 有机化学, 2020, 40, 276.) |
[21] | Fu, J. X.; Chang, Y. X.; Li, B.; Wang, X. H.; Xie, X. M.; Xu, K. X. Spectrochim. Acta, Part A 2020, 225, 117493. |
[22] | Tang, L. J.; Xia, J. Y.; Zhong, K. L.; Tang, Y. W.; Gao, X.; Li, J. R. Dyes Pigm. 2020, 178, 108379. |
[23] | Zhong, K. L.; Guo, B. F.; Sun, X. H.; Zhou, X.; Zhang, Q.; Tang, L. J.; Zhang, X. R. Chin. J. Org. Chem. 2017, 37, 2002. (in Chinese) |
[23] | (钟克利, 郭宝峰, 孙笑寒, 周雪, 张强, 汤立军, 张行荣, 有机化学, 2017, 37, 2002.) |
[24] | Fu, J. X.; Li, B.; Mei, H. H.; Chang, Y. X.; Xu, K. X. Spectrochim. Acta, Part A 2020, 227, 117678. |
[25] | Li, F. J.; Bian, Y. J.; Chen, Z. X.; Tang, L. J.; Zhong, K. L.; Hou, S. H. Chem. Bull. 2019, 82, 743. (in Chinese) |
[25] | (李方霁, 边延江, 陈志新, 汤立军, 钟克利, 侯淑华, 化学通报, 2019, 82, 743.) |
[26] | Geng, F. H.; Zou, C. P.; Liu, J. H.; Zhang, Q. C.; Guo, X. Y.; Fan, Y. C.; Yu, H. D.; Yang, S.; Liu, Z. P.; Li, L. Anal. Chim. Acta 2019, 1076, 131. |
[27] | Zhu, Y.; Gong, X.; Li, Z.; Zhao, X.; Liu, Z.; Cao, D.; Guan, R. Spectrochim. Acta, Part A 2019, 219, 202. |
[28] | Suresh, S.; Bhuvanesh, N.; Prabhu, J.; Thamilselvan, A.; Kannan, K.; Nandhakumar, R. K. V. R. J. Photochem. Photobiol., A 2018, 359, 172. |
[29] | Yang, S. J.; Feng, W. Y.; Feng, G. Q. Anal. Chim. Acta 2018, 1034, 119. |
[30] | Wang, Y.; Hou, X. F.; Li, Z. S.; Zhou, Q. H.; Lei, M. M.; Hu, S. S.; Wu, X. P.; Li, C. M.; Xu, Z. H.; Wang, Y. Anal. Methods 2018, 10, 5790. |
[31] | Meng, X. J.; Li, S. L.; Ma, W. B.; Wang, J. L.; Hu, Z. Y.; Cao, D. L. Dyes Pigm. 2018, 154, 194. |
[32] | Meng, X. J.; Cao, D. L.; Hu, Z. Y.; Han, X. H.; Li, Z. C.; Liang, D.; Ma, W. B. Tetrahedron Lett. 2018, 59, 4299. |
[33] | Chen, Y.; Bi, K. Y.; Hao, R. T.; Xie, P.; Huang, L. N.; Wang, Y. M.; Zhang, J. F.; Xu, R.; Wu, X. H. Chin. J. Org. Chem. 2020, 40, 511. (in Chinese) |
[33] | (陈宇, 毕克英, 郝瑞亭, 谢萍, 黄丽娜, 王玉敏, 张俊峰, 徐锐, 吴相华, 有机化学, 2020, 40, 511.) |
[34] | Meng, X. J.; Cao, D. L.; Hu, Z. Y.; Han, X. H.; Li, Z. C.; Ma, W. B. RSC Adv. 2018, 8, 33947. |
[35] | Li, S. L.; Cao, D. L.; Meng, X. J.; Hu, Z. Y.; Li, Z. C.; Yuan, C. C.; Zhou, T.; Han, X. H.; Ma, W. B. Spectrochim. Acta, Part A 2020, 230, 118022. |
[36] | Li, S. L.; Cao, D. L.; Meng, X. J.; Hu, Z. Y.; Li, Z. C.; Yuan, C. C.; Zhou, T.; Han, X. H. Ma W. B. J. Photochem. Photobiol., A 2020, 392, 112427. |
[37] | Xu, Y.; Wang, H.; Zhao, J.; Yang, X.; Pei, M.; Zhang, G.; Zhang, Y. New J. Chem. 2019, 43, 14320. |
[38] | Xu, Y.; Wang, H.; Zhao, J.; Yang, X.; Pei, M.; Zhang, G.; Zhang, Y.; Lin, L. J. Photochem. Photobiol., A 2019, 383, 112026. |
[39] | Xing, Z. T.; Wang, H. C.; Cheng, Y. X.; James, T. D.; Zhu, C. J. Chem.-Asian J. 2011, 6, 3054. |
[40] | Dutta, A.; Biswas, S.; Escuer, A.; Dolai, M.; Ghosh, S.; Ali, M. ChemPlusChem 2015, 80, 1440. |
[41] | Zhu, G. H.; Huang, Y.; Lu, L. X.; Wang, C.; Sun, T. M.; Tang, Y. F.; Wang, M.; Shan, D. D.; Wen, S. J.; Zhu, J. L. Spectrochim. Acta, Part A 2019, 210, 105. |
[42] | Kumar, V.; Kumar, P.; Kumar, S.; Singhal, D.; Gupta, R. Inorg. Chem. 2019, 58, 10364. |
/
〈 |
|
〉 |