Synthesis and Application of Fluorescent Probe Containing Barbitone Unit

doi:10.6023/cjoc201904001

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2980-2984.DOI: 10.6023/cjoc201904001 Previous Articles Next Articles

Special Issue: 荧光探针-生物传感合辑；有机超分子化学合辑

NOTES

含巴比妥结构荧光探针的合成及其应用研究

刘钰^a, 汤永星^c, 罗月阳^c, 朱叶婷^c, 杨进^c, 魏欣雨^c, 刘雄^c, 赵云辉^a^b^c^*()

a 河南工业大学小麦和玉米深加工国家工程实验室郑州 450001
b 中国科学院上海有机化学研究所天然产物有机合成化学重点实验室上海 200032
c 湖南科技大学化学化工学院精细聚合物可控制备及功能应用湖南省重点实验室湘潭 411201

收稿日期:2019-04-01 修回日期:2019-05-05 发布日期:2019-05-21
通讯作者: 赵云辉 E-mail:zhao_yunhui@163.com
基金资助:
河南工业大学小麦和玉米深加工国家工程实验室开放课题(No. NL2018006)

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

Received:2019-04-01 Revised:2019-05-05 Published:2019-05-21
Contact: Zhao, Yunhui E-mail:zhao_yunhui@163.com
Supported by:
Project supported by the Open Project of the National Engineering Laboratory for Wheat & Corn Further Processing, Henan University of Technology(No. NL2018006)

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 Hg ²⁺ ion.

Key words: fluorescent probe, mercury ion, barbitone, excited-state intramolecular proton transfer (ESIPT)

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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.

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Fig. & Tab. 6

Scheme 1. Synthetic route for probe

Figure 1. UV-visible, fluorescence spectra of probe in MeCN (a) UV-visible spectra of 5; (b) UV-visible spectra of probe; (c) fluorescence spectra of 5; (d) fluorescence spectra of probe

Figure 2. Effect of MeCN concentration (VMeCN/Vwater=9/1, 8/2, 7/3, 6/4, 5/5, 4/6, 3/7, 2/8, 1/9, from up to down) on fluorescence intensity of probe (10 μmol?L-1)

Figure 3. (a) Fluorescent emission changes of probe (10 μmol L-1) in the presence of increasing amounts of Hg2+ (0, 2.0, 4.0, 9.0, 10.0, 15.0, 20.0 μmol?L-1, from up to down) in 50% MeCN-H2O (V/V), and (b) the linear relationship between the relative fluorescent intensities (?F/F0) and concentration of Hg2+

Figure 4. Fluorescent emission changes of probe (10 μmol L-1) upon addition of various cations (10 μmol?L-1) in 50% H2O- MeCN solution (a) and fluorescence spectra of probe (10 μmol?L-1) in the presence of Hg2+ (10 μmol?L-1) and other metal ions (10 μmol?L-1) (b)

Figure 5. Fluorescent emission of probe (10 μmol?L-1) and the system of probe (10 μmol?L-1) mixed with NaOH (10 μmol?L-1)

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含巴比妥结构荧光探针的合成及其应用研究

Synthesis and Application of Fluorescent Probe Containing Barbitone Unit

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