Citation: Huang Qing, Qu Wenjuan, Chen Jie, Lin Qi, Yao Hong, Zhang Youming, Wei Taibao. A Reaction Type Colorimetric and Fluorescence Chemosensor Based on Coumarin Derivatives Design for Detecting Cyanide Ion and Its Application[J]. Chinese Journal of Organic Chemistry, ;2018, 38(3): 629-635. doi: 10.6023/cjoc201709040 shu

A Reaction Type Colorimetric and Fluorescence Chemosensor Based on Coumarin Derivatives Design for Detecting Cyanide Ion and Its Application

Huang Qing ^a,b ,
Qu Wenjuan ^a ,
Chen Jie ^c ,
Lin Qi ^a ,
Yao Hong ^a ,
Zhang Youming ^a ,
Wei Taibao ^a,,

a.
Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education; Key Laboratory of Polymer Materials of Gansu Province; College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
b.
School of Pharmacy, Ningxia Medical University, Yinchuan 750006
c.
Lanzhou City University, Lanzhou 730070

Corresponding author: Wei Taibao, weitaibao@126.com
Received Date: 25 September 2017
Revised Date: 31 October 2017
Available Online: 17 March 2017
Fund Project: the National Natural Science Foundation of China 21661028the National Natural Science Foundation of China 21262032the National Natural Science Foundation of China 21662031the National Natural Science Foundation of China 21574104Project supported by the National Natural Science Foundation of China (Nos. 21662031, 21661028, 21574104, 21262032)

Figures(9)

A novel CN^- chemosensor based N-4-pyridylcoumarin-3-carboxamide derivative Q1 was designed and synthesized. The recognition performance of sensor Q1 for ten different anions was studied by UV and fluorescence spectroscopy. When anions such as CN^-, F^-, Cl^-, Br^-, I^-, AcO^-, H₂PO₄^-, HSO₄^-, ClO₄^- and SCN^- were added to the mixed solution (DMSO/H₂O, V:V=9:1), addition of CN^- could increase the absorption peak of Q1 at 304 nm, and the corresponding fluorescence produced a strong emission peak at 431 nm. Q1 solution with CN^- emitted strong blue fluorescent that can be easily observed by naked eyes. The color changed (from colorless to faint yellow) and the "Turn-On" fluorescence behavior suggested that Q1 could detect CN^- by dual-channel. Happily, the fluorescent limit of detection (LOD) is 1.44×10^-8 mol/L, was lower than the specified content by World Health Organization (WHO) in drinking water. Based on all the experimental facts, we speculated that the possible identification mechanism was that the addition reaction took place between Q1 and CN^-, and it can also be confirmed by density functional theory (DFT). This result can be applied to the detection of CN^- in cherry kernel.
- coumarin derivatives,
- dual-channel,
- cyanide ions,
- food sample application
1. [1]
  Zamecnik, J.; Tam, J. J. Anal. Toxicol. 1987, 11, 47. doi: 10.1093/jat/11.1.47
2. [2]
  Anderson, R. A.; Harland, W. A. Med. Sci. Law. 1982, 22, 35. doi: 10.1177/002580248202200106
3. [3]
  Suzuki, T.; Hioki, A.; Kurahashi, M. Anal. Chim. Acta 2003, 476, 159. doi: 10.1016/S0003-2670(02)01362-4
4. [4]
  Christison, T. T.; Rohrer, J. S.; J. Chromatogr., A 2007, 1155, 31. doi: 10.1016/j.chroma.2007.02.083
5. [5]
  Surleva, A. R.; Nikolova, V. D.; Neshkova, M. T. Anal. Chim. Acta 2007, 583, 174. doi: 10.1016/j.aca.2006.09.044
6. [6]
  Yen, S.; Wang, C.-T.; Wang, J.-S. Chem. Eng. Commun. 1991, 109, 167. doi: 10.1080/00986449108910979
7. [7]
  Bhalla, V.; Singh, H.; Kumar, M. Dalton Trans. 2012, 41, 11413. doi: 10.1039/c2dt31244a
8. [8]
  Chattaraj, S.; Das, A. K. Analyst 1991, 116, 739. doi: 10.1039/an9911600739
9. [9]
  Zhang, Y.-M.; Shi, B.-B.; Zang, P.; Huo, J. Q.; Chen, P.; Lin, Q.; Liu, J.; Wei, T.-B. Sci. China, Chem. 2013, 56, 612. doi: 10.1007/s11426-012-4798-0
10. [10]
  Lin, Q.; Liu, X.; Chen, P.; Wei, T.-B.; Zhang, Y.-M. Prog. Chem. 2013, 25, 2131(in Chinese).
11. [11]
  Li, W.-T.; Qu, W-J.; Zhang, H.-L.; Li, X.; Lin, Q.; Yao, H.; Zhang, Y.-M.; Wei, T.-B. Chin. J. Org. Chem. 2017, 37, 754(in Chinese).
12. [12]
  Li, X.; Lin, Q.; Qu, W-J.; Li, Q.; Chen, X.-B.; Li, W.-T.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. Chin. J. Org. Chem. 2017, 37, 889(in Chinese).
13. [13]
  Lin, Q.; Fu, Y.-P.; Chen, P.; Wei, T.-B.; Zhang, Y.-M. Dyes Pigm. 2013, 96, 1. doi: 10.1016/j.dyepig.2012.06.023
14. [14]
  Zhang, Y.-M.; Lin, Q.; Wei, T.-B.; Li, Y.; Qin, X.-P. Chem. Commun. 2009, 40, 6074.
15. [15]
  Lin, Q.; Wei, T.-B.; Yao, H.; Zhang, Y.-M. Acta Chim. Sinica 2007, 65, 159(in Chinese).
16. [16]
  Lee, K. H.; Chai, H. B.; Tamez, P. A. Phytochemistry 2003, 64, 535. doi: 10.1016/S0031-9422(03)00243-7
17. [17]
  Pai, N. R.; Vishwasrao, S.; Wankhede, K. J. Chem. Pharm. Res. 2012, 4, 4946.
18. [18]
  Kudo, E.; Taura, M.; Matsuda, K.; Shimamoto, M.; Kariya, R.; Goto, H.; Hattori, S.; Kimura, S.; Okada, S. Bioorg. Med. Chem. Lett. 2013, 23, 606. doi: 10.1016/j.bmcl.2012.12.034
19. [19]
  Jung, J. C.; Kin, J.; Park, O. S. Synth. Commun. 2001, 31, 1195. doi: 10.1081/SCC-100104003
20. [20]
  Anand, P.; Singh, B.; Singh, N. Bioorg. Med. Chem. 2012, 20, 1175. doi: 10.1016/j.bmc.2011.12.042
21. [21]
  Kobayashi, H.; Ogawa, M.; Alford, R.; Choyke, P. L.; Urano, Y. Chem. Rev. 2010, 110, 2620. doi: 10.1021/cr900263j
22. [22]
  Huang, X.-H.; Zhang, G.-X.; Zhang, D.-Q. Acta Chim. Sinica 2012, 70, 2133(in Chinese).
23. [23]
  Ma, W.-H.; Xia, W.; Xu, Q.; Han, H.-Y.; Song, B.; Sun, L.-W.; Liang, C.-H. Acta Chim. Sinica 2012, 70, 917(in Chinese). doi: 10.3866/PKU.WHXB201201172
24. [24]
  Liu, G.; Cao, H.-Y.; Shao, J. Chin. J. Org. Chem. 2011, 31, 1678(in Chinese).
25. [25]
  Roy, N.; Dutta, A.; Mondal, P.; Paul, P. C.; Takhellambam, S. S. Sens. Actuators, B 2016, 236, 719. doi: 10.1016/j.snb.2016.06.061
26. [26]
  Hu, J.-H.; Sun, Y.; Qi, J.; Li, Q.; Wei, T.-B. Spectrochim. Acta, Part A 2017, 175, 125. doi: 10.1016/j.saa.2016.12.009
27. [27]
  Zhang, P.; Zhang, Y.-M.; Lin, Q.; Yao, H.; Wei, T.-B. Chin. J. Org. Chem. 2014, 34, 1300(in Chinese).
28. [28]
  Hossain, S. M.; Singh, K.; Lakma, A.; Pradhan, R. N.; Singh, A. K. Sens. Actuators, B 2017, 239, 1109.. doi: 10.1016/j.snb.2016.08.093
29. [29]
  Gao, Y.; Liu, H.-M.; Li, P.; Liu, Q.-L.; Wang, W.; Zhao, B. Tetrahedron Lett. 2017, 58, 2193. doi: 10.1016/j.tetlet.2017.04.054
30. [30]
  Wang, S.-J.; Li, C.-W.; Li, J.; Chen, B.; Guo, Y. Acta Chim. Sinica 2017, 75, 383(in Chinese).
31. [31]
  Ma, L.-L.; Leng, T.-H.; Wang, K.; Wang, C.-Y.; Shen, Y.-J.; Zhu, W.-H. Tetrahedron 2017, 73, 1306. doi: 10.1016/j.tet.2017.01.034
32. [32]
  Hu, J.-H.; Li, J.-B.; Qi, J.; Sun, Y. N. J. Chem. 2015, 39, 4041.
33. [33]
  Saha, S.; Ghosh, A.; Mahato, P.; Mishra, S.; Mishra, S. K.; Suresh, E.; Das, S.; Das, A. Org. Lett. 2010, 12, 3406. doi: 10.1021/ol101281x
34. [34]
  Kumari, N.; Jha, S.; Bhattacharya, S. J. Org. Chem. 2011, 76, 8215. doi: 10.1021/jo201290a
35. [35]
  Lin, Q.; Chen, P.; Fu, Y.-P.; Zhang, Y.-M.; Shi, B.-B.; Zhang, P.; Wei, T.-B. Chin. Chem. Lett. 2013, 24, 699. doi: 10.1016/j.cclet.2013.05.005
36. [36]
  Li, W.-T.; Qu, W.-J.; Zhu, X.; Li, Q.; Zhang, H.-L.; Yao, H.; Lin, Q.; Zhang, Y.-M.; Wei, T.-B. Sci. China Chem. 2017, 60, 1.
37. [37]
  Lin, Q.; Chen, P.; Liu, J.; Fu, Y.-P.; Zhang, Y.-M.; Wei, T.-B. Dyes Pigm. 2013, 98, 100. doi: 10.1016/j.dyepig.2013.01.024
38. [38]
  Zhu, X.; Lin, Q.; Lou, J.-C.; Lu, T.-T.; Zhang, Y.-M.; Wei, T.-B. New J. Chem. 2015, 39, 7206. doi: 10.1039/C5NJ01158B
39. [39]
  Leng, Y.-L.; Zhang, J.-H.; Li, Q.; Zhang, Y.-M.; Lin, Q.; Yao, H.; Wei, T.-B. New J. Chem. 2016, 40, 8607. doi: 10.1039/C6NJ00181E
40. [40]
  Wang, L.-Y.; Ye, D.-C.; Cao, D.-R. J. South China Univ. Technol. 2012, 40, 46(in Chinese).
41. [41]
  Li, Q.; Zhang, J. H.; Cai, Y., Qu.; W. J.; Gao, G. Y.; Lin, Q.; Yao, H.; Zhang, Y.-M.; Wei, T.-B. Tetrahedron 2015, 71, 857. doi: 10.1016/j.tet.2014.12.047
1. [1]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
2. [2]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
3. [3]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
4. [4]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
5. [5]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
6. [6]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
7. [7]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
8. [8]
  Yang Xia , Kangyan Zhang , Heng Yang , Lijuan Shi , Qun Yi . 构建双通道路径增强iCOF/Bi₂O₃ S型异质结在纯水体系中光催化合成H₂O₂性能. Acta Physico-Chimica Sinica, 2024, 40(11): 2407012-. doi: 10.3866/PKU.WHXB202407012
9. [9]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
10. [10]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
11. [11]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
12. [12]
  Xiaochen Zhang , Fei Yu , Jie Ma . 多角度数理模拟在电容去离子中的前沿应用. Acta Physico-Chimica Sinica, 2024, 40(11): 2311026-. doi: 10.3866/PKU.WHXB202311026
13. [13]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
14. [14]
  . . Chinese Journal of Inorganic Chemistry, 2024, 40(12): 0-0.
15. [15]
  Chun-Lin Sun , Yaole Jiang , Yu Chen , Rongjing Guo , Yongwen Shen , Xinping Hui , Baoxin Zhang , Xiaobo Pan . Construction, Performance Testing, and Practical Applications of a Home-Made Open Fluorescence Spectrometer. University Chemistry, 2024, 39(5): 287-295. doi: 10.3866/PKU.DXHX202311096
16. [16]
  Ping Ye , Lingshuang Qin , Mengyao He , Fangfang Wu , Zengye Chen , Mingxing Liang , Libo Deng . 荷叶衍生多孔碳的零电荷电位调节实现废水中电化学捕集镉离子. Acta Physico-Chimica Sinica, 2025, 41(3): 2311032-. doi: 10.3866/PKU.WHXB202311032
17. [17]
  Siyu Zhang , Kunhong Gu , Bing'an Lu , Junwei Han , Jiang Zhou . Hydrometallurgical Processes on Recycling of Spent Lithium-lon Battery Cathode: Advances and Applications in Sustainable Technologies. Acta Physico-Chimica Sinica, 2024, 40(10): 2309028-. doi: 10.3866/PKU.WHXB202309028
18. [18]
  Qi Li , Pingan Li , Zetong Liu , Jiahui Zhang , Hao Zhang , Weilai Yu , Xianluo Hu . Fabricating Micro/Nanostructured Separators and Electrode Materials by Coaxial Electrospinning for Lithium-Ion Batteries: From Fundamentals to Applications. Acta Physico-Chimica Sinica, 2024, 40(10): 2311030-. doi: 10.3866/PKU.WHXB202311030
19. [19]
  Zhaoxuan ZHU , Lixin WANG , Xiaoning TANG , Long LI , Yan SHI , Jiaojing SHAO . Application of poly(vinyl alcohol) conductive hydrogel electrolytes in zinc ion batteries. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 893-902. doi: 10.11862/CJIC.20240368
20. [20]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423

Get Citation

PDF

XML

Metrics

PDF Downloads(13)
Abstract views(1256)
HTML views(188)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142