一种基于二氰基异佛尔酮的近红外汞离子荧光探针的合成与应用

引用本文: 杜婉晴, 宋文琦, 梁天宇, 孙小飞, 汤立军, 钟克利. 一种基于二氰基异佛尔酮的近红外汞离子荧光探针的合成与应用[J]. 分析化学, 2023, 51(3): 421-428. doi: 10.19756/j.issn.0253-3820.221583 shu

Citation: DU Wan-Qing, SONG Wen-Qi, LIANG Tian-Yu, SUN Xiao-Fei, TANG Li-Jun, ZHONG Ke-Li. Synthesis and Application of Near Infrared Mercury (Ⅱ) Fluorescent Probe Based on Dicyanoisophorone[J]. Chinese Journal of Analytical Chemistry, 2023, 51(3): 421-428. doi: 10.19756/j.issn.0253-3820.221583 shu

一种基于二氰基异佛尔酮的近红外汞离子荧光探针的合成与应用

杜婉晴 ^1, ,
宋文琦 ^1, ,
梁天宇 ^1, ,
孙小飞 ^2, ,
汤立军 ^1, ,
钟克利 ^{1,
,}

1.
渤海大学化学与材料工程学院, 锦州 121013;
2.
渤海大学食品科学与工程学院, 锦州 121013

通讯作者: 钟克利,E-mail:zhongkeli2000@bhu.edu.cn

基金项目:
国家自然科学基金项目(Nos.22278038,32201948)、辽宁省教育厅基本科研项目(Nos.LJKMZ20221480,LJKQZ2021135)和辽宁特聘教授支持计划项目资助。

摘要: 以二氰基异佛尔酮和4-二乙氨基水杨醛为原料,通过两步反应合成了一种具有近红外发射(675 nm)的荧光探针SAM-S,并对其结构进行了表征。此探针在甲醇/4-羟乙基哌嗪乙磺酸(HEPES)(1:1,V/V,pH=7.4)溶液中表现出弱荧光,加入Hg²⁺后荧光显著增强,基于此建立了检测Hg²⁺的新方法。本方法具有选择性好、抗干扰能力强、检出限低(0.49 μmol/L)等优点。采用此探针检测湖水和自来水中Hg²⁺的含量,加标回收率在99.9%~104.8%之间。探针SAM-S可制作成荧光墨水,有望用于商标包装;由于SAM-S的毒性较低,因此可用于活细胞中Hg²⁺的荧光成像。

关键词:

English

Synthesis and Application of Near Infrared Mercury (Ⅱ) Fluorescent Probe Based on Dicyanoisophorone

1.
College of Chemistry and Chemical Engineering, Bohai University, Jinzhou 121013, China;
2.
College of Food Science and Technology, Bohai University, Jinzhou 121013, China

Corresponding author: ZHONG Ke-Li, zhongkeli2000@bhu.edu.cn

Received Date: 25 November 2022
Revised Date: 18 January 2023
Fund Project:
Supported by the National Natural Science Foundation of China (Nos. 22278038, 32201948), the Scientific Research Fund of Liaoning Provincial Education Department (Nos. LJKMZ20221480, LJKQZ2021135) and the Program for Distinguished Professor of Liaoning Province.

Abstract: A novel fluorescence probe SAM-S with near infrared emission (675 nm) was synthesized by a two-step reaction using dicyanoisophorone and 4-diethylaminosalicylaldehyde as raw materials. The probe showed a weak fluorescence in CH₃OH/HEPES buffer (1∶1, V/V, pH = 7.4) solution, and the fluorescence was significantly enhanced only after adding Hg²⁺. Therefore, a new method for detecting Hg²⁺ was established. SAM-S for detection of Hg²⁺ possessed many advantages such as good selectivity, strong anti-interference ability, and low detection limit (0.49 μmol/L). The content of Hg²⁺ in lake water and tap water was determined by this method, and the recoveries were between 99.9% and 104.8%. In addition, the probe SAM-S could be produced into fluorescent ink, which was expected to be used for trademark packaging. Meanwhile, because of the low toxicity of SAM-S, probe SAM-S could perform fluorescence imaging of Hg²⁺ in living cells.

Key words:

1. [1]
  GAO Q, JIAO Y, HE C, DUAN C. Molecules, 2019, 24(12):2268.GAO Q, JIAO Y, HE C, DUAN C. Molecules, 2019, 24(12):2268.
2. [2]
  JIAO X, LIU C, HE S, ZHAO L, ZENG X. Dyes Pigm., 2019, 160:86-92.JIAO X, LIU C, HE S, ZHAO L, ZENG X. Dyes Pigm., 2019, 160:86-92.
3. [3]
  GONG J, LIU C, JIAO X, HE S, ZHAO L, ZENG X. Org. Biomol. Chem., 2020, 18(27):5238-5244.GONG J, LIU C, JIAO X, HE S, ZHAO L, ZENG X. Org. Biomol. Chem., 2020, 18(27):5238-5244.
4. [4]
  DING Y, PAN Y, HAN Y. Ind. Eng. Chem. Res., 2019, 58(19):7786-7793.DING Y, PAN Y, HAN Y. Ind. Eng. Chem. Res., 2019, 58(19):7786-7793.
5. [5]
  LI S, HUANG D, WAN J, YAN S, JIANG J, XIAO H. Sens. Actuators, B, 2018, 275:101-109.LI S, HUANG D, WAN J, YAN S, JIANG J, XIAO H. Sens. Actuators, B, 2018, 275:101-109.
6. [6]
  LI Y, QI S, XIA C, XU Y, DUAN G, GE Y. Anal. Chim. Acta, 2019, 1077:243-248.LI Y, QI S, XIA C, XU Y, DUAN G, GE Y. Anal. Chim. Acta, 2019, 1077:243-248.
7. [7]
  CHEN H, CHEN J, JIN X, WEI D. J. Hazard. Mater., 2009, 172(2-3):1282-1287.CHEN H, CHEN J, JIN X, WEI D. J. Hazard. Mater., 2009, 172(2-3):1282-1287.
8. [8]
  WANG M, FENG W, SHI J, ZHANG F, WANG B, ZHU M, LI B, ZHAO Y, CHAI Z. Talanta, 2007, 71(5):2034-2039.WANG M, FENG W, SHI J, ZHANG F, WANG B, ZHU M, LI B, ZHAO Y, CHAI Z. Talanta, 2007, 71(5):2034-2039.
9. [9]
  TANG L, TIAN M, CHEN H, YAN X, ZHONG K, BIAN Y. Dyes Pigm., 2018, 158:482-489.TANG L, TIAN M, CHEN H, YAN X, ZHONG K, BIAN Y. Dyes Pigm., 2018, 158:482-489.
10. [10]
  DUAN Q, ZHU H, LIU C, YUAN R, FANG Z, WANG Z, JIA P, LI Z, SHENG W, ZHU B. Analyst, 2019, 144(4):1426-1432.DUAN Q, ZHU H, LIU C, YUAN R, FANG Z, WANG Z, JIA P, LI Z, SHENG W, ZHU B. Analyst, 2019, 144(4):1426-1432.
11. [11]
  TIAN L, SUN X, ZHOU L, ZHONG K, LI S, YAN X, TANG L. Food Chem., 2023, 401:135031.TIAN L, SUN X, ZHOU L, ZHONG K, LI S, YAN X, TANG L. Food Chem., 2023, 401:135031.
12. [12]
  WU D, CHEN L, LEE W, KO G, YIN J, YOON J. Coord. Chem. Rev., 2018, 354:74-97.WU D, CHEN L, LEE W, KO G, YIN J, YOON J. Coord. Chem. Rev., 2018, 354:74-97.
13. [13]
  ZHONG K, HU X, ZHOU S, LIU X, GAO X, TANG L, YAN X. J. Agric. Food Chem., 2021, 69(16):4628-4634.ZHONG K, HU X, ZHOU S, LIU X, GAO X, TANG L, YAN X. J. Agric. Food Chem., 2021, 69(16):4628-4634.
14. [14]
  PAN Y, BAN L, LI J, LIU M, TANG L, YAN X. Dyes Pigm., 2022, 203:110305.PAN Y, BAN L, LI J, LIU M, TANG L, YAN X. Dyes Pigm., 2022, 203:110305.
15. [15]
  HE Y, SUN X, YAN X, LI Y, ZHONG K, TANG L. J. Mater. Chem. C, 2022, 10(23):9009-9016.HE Y, SUN X, YAN X, LI Y, ZHONG K, TANG L. J. Mater. Chem. C, 2022, 10(23):9009-9016.
16. [16]
  LI G, GAO G, CHENG J, CHEN X, ZHAO Y, YE Y. Luminescence, 2016, 31(4):992-996.LI G, GAO G, CHENG J, CHEN X, ZHAO Y, YE Y. Luminescence, 2016, 31(4):992-996.
17. [17]
  GUO Y, AN J, TANG H, PENG M, SUZENET F. Mater. Res. Bull., 2015, 63:155-163.GUO Y, AN J, TANG H, PENG M, SUZENET F. Mater. Res. Bull., 2015, 63:155-163.
18. [18]
  WANG J, NIU Q, HU T, LI T, WEI T. J. Photochem. Photobiol., A, 2019, 384:112036.WANG J, NIU Q, HU T, LI T, WEI T. J. Photochem. Photobiol., A, 2019, 384:112036.
19. [19]
  ZHONG K, ZHOU X, HOU R, ZHOU P, HOU S, BIAN Y, ZHANG G, TANG L, SHANG X. RSC Adv., 2014, 4(32):16612.ZHONG K, ZHOU X, HOU R, ZHOU P, HOU S, BIAN Y, ZHANG G, TANG L, SHANG X. RSC Adv., 2014, 4(32):16612.
20. [20]
  YAN Z, YUEN M F, HU L, SUN P, LEE C S. RSC Adv., 2014, 4(89):48373-48388.YAN Z, YUEN M F, HU L, SUN P, LEE C S. RSC Adv., 2014, 4(89):48373-48388.
21. [21]
  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, 163:118-125.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, 163:118-125.
22. [22]
  LIU Y, NAHA S, THIRUMALAIVASAN N, VELMATHI S, WU S P. Sens. Actuators, B, 2018, 277:673-678.LIU Y, NAHA S, THIRUMALAIVASAN N, VELMATHI S, WU S P. Sens. Actuators, B, 2018, 277:673-678.
23. [23]
  LIU B, LIU J, HE J, ZHANG J, ZHOU H, GAO C. Chem. Phys., 2020, 539:110944.LIU B, LIU J, HE J, ZHANG J, ZHOU H, GAO C. Chem. Phys., 2020, 539:110944.
24. [24]
  GAO Y, MA T, OU Z, CAI W, YANG G, LI Y, XU M, LI Q. Talanta, 2018, 178:663-669.GAO Y, MA T, OU Z, CAI W, YANG G, LI Y, XU M, LI Q. Talanta, 2018, 178:663-669.
25. [25]
  LI Q, HU Y, HOU H N, YANG W N, HU S L. Inorg. Chim. Acta, 2018, 471:705-708.LI Q, HU Y, HOU H N, YANG W N, HU S L. Inorg. Chim. Acta, 2018, 471:705-708.
26. [26]
  XU J, XU Z, WANG Z, LIU C, ZHU B, WANG X, WANG K, WANG J, SANG G. Luminescence, 2018, 33(1):219-224.XU J, XU Z, WANG Z, LIU C, ZHU B, WANG X, WANG K, WANG J, SANG G. Luminescence, 2018, 33(1):219-224.
27. [27]
  TIAN Q Q, ZHAO Z G, SHI Z C. Inorg. Chim. Acta, 2021, 521:120349.TIAN Q Q, ZHAO Z G, SHI Z C. Inorg. Chim. Acta, 2021, 521:120349.
28. [28]
  LI X, DUAN Q, YU Y, WANG K, ZHU H, ZHANG X, LIU C, JIA P, LI Z, SHENG W, ZHU B. Luminescence, 2020, 35(6):941-946.LI X, DUAN Q, YU Y, WANG K, ZHU H, ZHANG X, LIU C, JIA P, LI Z, SHENG W, ZHU B. Luminescence, 2020, 35(6):941-946.
29. [29]
  YUAN G, LV H, LIU H, HE H, SUN Q, ZHANG X, WANG S. Dyes Pigm., 2020, 183:108674.YUAN G, LV H, LIU H, HE H, SUN Q, ZHANG X, WANG S. Dyes Pigm., 2020, 183:108674.
30. [30]
  TANG L, ZHOU L, YAN X, ZHONG K, GAO X, LI J. J. Photochem. Photobiol., A, 2020, 387:112160.TANG L, ZHOU L, YAN X, ZHONG K, GAO X, LI J. J. Photochem. Photobiol., A, 2020, 387:112160.
31. [31]
  SHU W, WANG Y, WU L, WANG Z, DUAN Q, GAO Y, LIU C, ZHU B, YAN L. Ind. Eng. Chem. Res., 2016, 55(32):8713-8718.SHU W, WANG Y, WU L, WANG Z, DUAN Q, GAO Y, LIU C, ZHU B, YAN L. Ind. Eng. Chem. Res., 2016, 55(32):8713-8718.
32. [32]
  DUAN Q, LV X, LIU C, GENG Z, ZHANG F, SHENG W, WANG Z, JIA P, LI Z, ZHU H, ZHU B. Ind. Eng. Chem. Res., 2019, 58(1):11-17.DUAN Q, LV X, LIU C, GENG Z, ZHANG F, SHENG W, WANG Z, JIA P, LI Z, ZHU H, ZHU B. Ind. Eng. Chem. Res., 2019, 58(1):11-17.
33. [33]
  LI Y, SUN X, ZHOU L, TIAN L, ZHONG K, ZHANG J, YAN X, TANG L. J. Agric. Food Chem., 2022, 70(35):10899-10906.LI Y, SUN X, ZHOU L, TIAN L, ZHONG K, ZHANG J, YAN X, TANG L. J. Agric. Food Chem., 2022, 70(35):10899-10906.
34. [34]
  ZHONG K, ZHOU S, YAN X, LI X, HOU S, CHENG L, GAO X, LI Y, TANG L. Dyes Pigm., 2020, 174:108049.ZHONG K, ZHOU S, YAN X, LI X, HOU S, CHENG L, GAO X, LI Y, TANG L. Dyes Pigm., 2020, 174:108049.
35. [35]
  PAN X T, LI Q, XU Y Y, HU S L. J. Chem. Res., 2020, 44(5-6):349-353.PAN X T, LI Q, XU Y Y, HU S L. J. Chem. Res., 2020, 44(5-6):349-353.
36. [36]
  GB/T 5749-2022. Standards of Drinking Water Quality. National Standards of the People's Republic of China. 生活饮用水标准. 中华人民共和国国家标准. GB/T 5749-2022.

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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

一种基于二氰基异佛尔酮的近红外汞离子荧光探针的合成与应用

通讯作者: 钟克利,E-mail:zhongkeli2000@bhu.edu.cn

English

Synthesis and Application of Near Infrared Mercury (Ⅱ) Fluorescent Probe Based on Dicyanoisophorone

Corresponding author: ZHONG Ke-Li, zhongkeli2000@bhu.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

一种基于二氰基异佛尔酮的近红外汞离子荧光探针的合成与应用

通讯作者: 钟克利,E-mail:zhongkeli2000@bhu.edu.cn

English

Synthesis and Application of Near Infrared Mercury (Ⅱ) Fluorescent Probe Based on Dicyanoisophorone

Corresponding author: ZHONG Ke-Li, zhongkeli2000@bhu.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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