Citation: Liu Yu, Tang Yongxing, Luo Yueyang, Zhu Yeting, Yang Jin, Wei Xinyu, Liu Xiong, Zhao Yunhui. Synthesis and Application of Fluorescent Probe Containing Barbitone Unit[J]. Chinese Journal of Organic Chemistry, ;2019, 39(10): 2980-2984. doi: 10.6023/cjoc201904001 shu

Synthesis and Application of Fluorescent Probe Containing Barbitone Unit

Liu Yu ^a ,
Tang Yongxing ^c ,
Luo Yueyang ^c ,
Zhu Yeting ^c ,
Yang Jin ^c ,
Wei Xinyu ^c ,
Liu Xiong ^c ,
Zhao Yunhui ^a,b,c,,

a.
National Engineering Laboratory for Wheat & Corn Further Processing, Henan University of Technology, Zhengzhou 450001
b.
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c.
Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201

Corresponding author: Zhao Yunhui, zhao_yunhui@163.com
Received Date: 1 April 2019
Revised Date: 5 May 2019
Available Online: 21 October 2019
Fund Project: Project supported by the Open Project of the National Engineering Laboratory for Wheat & Corn Further Processing, Henan University of Technology (No. NL2018006)the Open Project of the National Engineering Laboratory for Wheat & Corn Further Processing, Henan University of Technology NL2018006

Figures(6)

Mercury ion pollution has serious harmful impact on the ecological environment and human health. It is of great significance to develop a probe with high selectivity and sensitivity that could be applied to the detection of mercury ion in water environment. In this paper, a novel excited-state intramolecular proton transfer (ESIPT) fluorescent probe containing barbitone unit was designed and synthesized from salicylaldehyde. Mechanism studies showed that mercury ions and probes formed a structure similar to "(thymine)T-Hg-T" which has high selectivity in determining mercury ions. The calibration curve indicated that there was a good linear correlation between the relative fluorescent intensities over the concentration range of 4~20 μmol·L^-1 of Hg²⁺ ion.
- fluorescent probe,
- mercury ion,
- barbitone,
- excited-state intramolecular proton transfer (ESIPT)
1. [1]
  Choi, M. G.; Im, H. G.; Noh, J. H.; Ryu, D. H.; Chang, S. K. Sens. Actuators, B 2013, 177, 583. doi: 10.1016/j.snb.2012.11.090
2. [2]
  Zhang, D.; Su, J. H.; Ma, S.; Tian, H. Tetrahedron 2008, 64, 8515. doi: 10.1016/j.tet.2008.05.048
3. [3]
  Zalups, R.K.; Ahmad, S. J. Am. Soc. Nephrol. 2004, 15, 2023. doi: 10.1097/01.ASN.0000135115.63412.A9
4. [4]
  Silbergeld, E. K.; Silva, I. A.; Nyland, J. F. Toxicol. Appl. Pharmacol. 2005, 207, 282. doi: 10.1016/j.taap.2004.11.035
5. [5]
  Tseng, C. M.; Diego, A. D.; Martin, O. F.; Amouroux, D.; Donard, O. F. J. Anal. At. Spectrom. 1997, 12, 743. doi: 10.1039/a700956i
6. [6]
  Chen, F.; Li, Y.; Li, B.; Sun, J.; Wang, X.; Gao, X. J. Anal. At. Spectrom. 2006, 21, 94. doi: 10.1039/B511367A
7. [7]
  Qian G. S.; Zhao, W.; Xu, J. J. Tao, H. Y. Acta Chim. Sinica 2017, 75, 1097(in Chinese). doi: 10.11862/CJIC.2017.152
8. [8]
  Nolan, E. M.; Lippard, S. J. Chem. Rev. 2008, 108, 3443. doi: 10.1021/cr068000q
9. [9]
  Xuan, F.; Luo, X.; Hsing, I. M. Anal. Chem. 2013, 85, 4586. doi: 10.1021/ac400228q
10. [10]
  Li, Y.; Shi, W.; Ma, J.; Wang, X.; Kong, X.; Zhang, Y.; Feng, L.; Hui, Y.; Xie, Z. J. Photochem. Photobiol., A 2017, 338, 1.
11. [11]
  Feng, L.; Shi, W.; Ma, J.; Chen, Y.; Fan, K.; Hui, Y.; Xie, Z. Sens. Actuators, B 2016, 237, 563. doi: 10.1016/j.snb.2016.06.129
12. [12]
  Lin, H.; Shi, W.; Tian, Y.; Ma, F.; Xu, L.; Ma, J.; Hui, Y.; Xie, Z. J. Lumin. 2015, 157, 280. doi: 10.1016/j.jlumin.2014.09.004
13. [13]
  Kim, H. N.; Ren, W. X.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2012, 41, 3210. doi: 10.1039/C1CS15245A
14. [14]
  Wang, H.; Zhang, P.; Chen, J.; Li, Y.; Yu, M.; Long, Y.; Yi, P. Sens. Actuators, B 2017, 242, 818. doi: 10.1016/j.snb.2016.09.177
15. [15]
  Fan, Y.; Long, Y. F.; Li, Y. F. Anal. Chim. Acta 2009, 653, 207. doi: 10.1016/j.aca.2009.09.017
16. [16]
  Zhu, J. H.; Fan, X. T.; Jiang, P.; Cao, Q. Y. Chin. J. Org. Chem. 2017, 37, 185(in Chinese).
17. [17]
  Shiraishi, Y.; Sumiya, S.; Hirat, T. Org. Biomol. Chem. 2010, 8, 1310. doi: 10.1039/b924015b
18. [18]
  Zhang, Y.; Wang, Q.; Li, W.; Zhang, J.; Xia, M. H.; Chen, S. M.; Chen, X. M. Chin. J. Org. Chem. 2014, 34, 403(in Chinese).
19. [19]
  Yang, Y. K.; Yook, K. J.; Tae, J. A. J. Am. Chem. Soc. 2005, 127, 16760. doi: 10.1021/ja054855t
20. [20]
  Chen, J.; Li, Y.; Zhong, W.; Wang, H.; Zhang, P.; Jiang. J. Anal. Methods 2016, 8, 1964. doi: 10.1039/C5AY03281D
21. [21]
  Zhang, D.; Li, M.; Jiang, Y.; Wang, C.; Wang, Z.; Ye, Y.; Zhao, Y. Dyes Pigm. 2013, 99, 607. doi: 10.1016/j.dyepig.2013.06.021
22. [22]
  Wang, C.; Zhang, D.; Huang, X.; Ding, P.; Wang, Z.; Zhao, Y.; Ye, Y. Sens. Actuators, B 2014, 198, 33. doi: 10.1016/j.snb.2014.03.032
23. [23]
  Ma, S.; Li, L.; She, M.; Mo, Y.; Zhang, S.; Liu, P.; Li, J. Chin. Chem. Lett. 2017, 28, 2014. doi: 10.1016/j.cclet.2017.09.027
24. [24]
  Song, J.; Huai, M.; Wang, C.; Xu, Z.; Zhao, Y.; Ye, Y. Spectrochim. Acta, Part A 2015, 139, 549. doi: 10.1016/j.saa.2014.12.073
25. [25]
  Yang, L.; Su, Y.; Geng, Y.; Xiong, H.; Han, J.; Fang, Q.; Song, X. Org. Biomol. Chem. 2018, 16, 5036. doi: 10.1039/C8OB00831K
26. [26]
  Zhang, P. P.; Chen, S.; Kang, Y. F.; Long, Y. F. Spectrochim. Acta, Part A 2012, 99, 347. doi: 10.1016/j.saa.2012.08.044
27. [27]
  Zhao, Y.-H.; Luo, Y.; Wang, H.; Guo, T.; Zhou, H.; Tan, H.; Zhou, Z.; Long, Y.; Tang, Z. ChemistrySelect 2018, 3, 1521. doi: 10.1002/slct.201702603
28. [28]
  Zhao, Y.-H.; Li, Y.; Long, Y.; Zhou, Z.; Tang, Z.; Deng, K.; Zhang, S. Tetrahedron Lett. 2017, 58, 1351. doi: 10.1016/j.tetlet.2017.02.066
29. [29]
  Zhao, Y.-H.; Luo, Y.; Wang, H.; Wei, H.; Guo, T.; Tan, H.; Yuan, L.; Zhang, X.-B. Anal. Chim. Acta 2019, 1065, 134. doi: 10.1016/j.aca.2019.03.029
30. [30]
  Zhao, Y.-H.; Luo, Y.; Guo, T.; Tang, Z.; Zhou, Z. ChemistrySelect 2019, 4, 5195. doi: 10.1002/slct.201900976
31. [31]
  Tanaka, Y.; Oda, S.; Yamaguchi, H.; Kondo, Y.; Kojima, C.; Ono, A. J. Am. Chem. Soc. 2007, 129, 244. doi: 10.1021/ja065552h
32. [32]
  Hou, P.; Long, Y.; Zhao, J.; Wang, J.; Zhou, F. Spectrochim. Acta, Part A 2012, 86, 76. doi: 10.1016/j.saa.2011.10.005
33. [33]
  Sfrazzetto, G. T.; Millesi, S.; Pappalardo, A.; Tomaselli, G. A.; Ballistreri, F. P.; Toscano, R. M.; Fragalà, I.; Gulino, A. Chem.-Eur. J. 2017, 23, 1576. doi: 10.1002/chem.201602292
34. [34]
  He, X.; Wu, Y.; Jin, W.; Wang, X.; Wu, C.; Shang, Y. Appl. Organomet. Chem. 2018, 32, e4284. doi: 10.1002/aoc.4284
1. [1]
  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
2. [2]
  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
3. [3]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
4. [4]
  Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
5. [5]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
6. [6]
  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
7. [7]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
8. [8]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
9. [9]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
10. [10]
  Zhifeng CAI , Ying WU , Yanan LI , Guiyu MENG , Tianyu MIAO , Yihao ZHANG . Effective detection of malachite green by folic acid stabilized silver nanoclusters. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 983-993. doi: 10.11862/CJIC.20240394
11. [11]
  Wei GAO , Meiqi SONG , Xuan REN , Jianliang BAI , Jing SU , Jianlong MA , Zhijun WANG . A self-calibrating fluorescent probe for the selective detection and bioimaging of HClO. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1173-1182. doi: 10.11862/CJIC.20250112
12. [12]
  Lei ZHANG , Cheng HE , Yang JIAO . An azo-based fluorescent probe for the detection of hypoxic tumor cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1162-1172. doi: 10.11862/CJIC.20250081
13. [13]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
14. [14]
  Pingping LU , Shuguang ZHANG , Peipei ZHANG , Aiyun NI . Preparation of zinc sulfate open frameworks based probe materials and detection of Pb²⁺ and Fe³⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 959-968. doi: 10.11862/CJIC.20240411
15. [15]
  Qingjun PAN , Zhongliang GONG , Yuwu ZHONG . Advances in modulation of the excited states of photofunctional iron complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 45-58. doi: 10.11862/CJIC.20240365
16. [16]
  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
17. [17]
  Qi Wang , Yicong Gao , Feng Lu , Quli Fan . Preparation and Performance Characterization of the Second Near-Infrared Phototheranostic Probe: A New Design and Teaching Practice of Polymer Chemistry Comprehensive Experiment. University Chemistry, 2024, 39(11): 342-349. doi: 10.12461/PKU.DXHX202404141
18. [18]
  Xiaoli Sun , Xiang Wu , Li Gan , Wenming Wan . Barbier Polymerization: A New Teaching Case for Step-Growth Polymerization. University Chemistry, 2025, 40(4): 113-118. doi: 10.12461/PKU.DXHX202406102
19. [19]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
20. [20]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1821)
HTML views(189)

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