Citation: Fu-Sheng BIE, Ai-Shan REN, Hua-Qin XU, Jin-Hu WANG, Xue-Jing LIU, Dong-Jian ZHU. Fluorescent Probe Based on Carbazole-N, S-Heterocrown Ether: Synthesis and Properties of Ag⁺ Detection[J]. Chinese Journal of Inorganic Chemistry, ;2022, 38(2): 237-243. doi: 10.11862/CJIC.2022.013 shu

Fluorescent Probe Based on Carbazole-N, S-Heterocrown Ether: Synthesis and Properties of Ag⁺ Detection

1.
Engineering and Technology Institute of LuNan Coal Chemical Engineering, Zaozhuang University, Zaozhuang, Shandong 277160, China
2.
College of Food and Bioengineering, Hezhou University, Hezhou, Guangxi 542899, China

Corresponding author: Fu-Sheng BIE, fsbie@uzz.edu.cn Dong-Jian ZHU, zhdj1983@126.com
Received Date: 10 July 2021
Revised Date: 19 October 2021

Figures(6)

A new fluorescent probe L containing heterocrown ether group was designed and synthesized from t-butyl bis(2-chloroethyl)carbamate, 2, 2'-(ethane-1, 2-diylbis(oxy))diethanethiol, and N-ethyl carbazole. The structure of L was characterized by ¹H NMR, ¹³C NMR, and high-resolution mass spectrometry. The selectivity of probe L with Ag⁺ was investigated by fluorescence spectroscopy in water/ethanol solvent (4:1, V/V). All the results showed that the binding ratio for probe L to Ag⁺ was 1:1. The binding constant K_a was calculated to be 2.01×10⁵ L·mol^-1 and the detection limit was 4.13 μmol·L^-1. The results also showed that probe L could be used to detection of Ag⁺ in the river and other environmental water samples.
- carbazole,
- heterocrown ether,
- fluorescent probe,
- silver ion
1. [1]
  Qi L, Yan Z, Huo Y, Hai X M, Zhang Z Q. MnO₂ Nanosheet-Assisted Ligand-DNA Interaction-Based Fluorescence Polarization Biosensor for the Detection of Ag⁺ Ions[J]. Biosens. Bioelectron., 2017,87:566-571. doi: 10.1016/j.bios.2016.08.093
2. [2]
  SUN J F, HUANG S L, GUO X P. Research on the Appropriate Concentration of Silver Ion in Antibacterial Agents[J]. Journal of Pharmaceutical Research, 2017,36(9):516-518.
3. [3]
  El-Shekheby H A, Mangood A H, Hamza S M, Al-Kady A S, Ebeid E M. A Highly Efficient and Selective Turn-On Fluorescent Sensor for Hg²⁺, Ag⁺ and Ag Nanoparticles Based on a Coumarin Dithioate Derivative[J]. Luminescence, 2014,29(2):158-167. doi: 10.1002/bio.2521
4. [4]
  Saptarshi S R, Duschl A, Lopata A L. Interaction of Nanoparticles with Proteins: Relation to Bio-reactivity of the Nanoparticle[J]. J. Nanobiotechnol., 2013,1126. doi: 10.1186/1477-3155-11-26
5. [5]
  Li Y F, Chen C Y, Li B, Sun J, Wang J X, Gao Y X, Zhao Y L, Chai Z F. Elimination Efficiency of Different Reagents for the Memory Effect of Mercury Using ICP-MS[J]. J. Anal. At. Spectrom., 2006,21:94-96. doi: 10.1039/B511367A
6. [6]
  Karunasagar D, Arunachalam J, Gangadharan S. Development of a 'Collect and Punch'Cold Vapour Inductively Coupled Plasma Mass Spectrometric Method for the Direct Determination of Mercury at Nanograms per Litre Levels[J]. J. Anal. At. Spectrom., 1998,13:679-682. doi: 10.1039/A802132E
7. [7]
  Zanganeh A R, Amini M K. A Potentiometric and Voltammetric Sensor Based on Polypyrrole Film with Electrochemically Induced Recognition Sites for Detection of Silver Ion[J]. Electrochim. Acta, 2007,52:3822-3830. doi: 10.1016/j.electacta.2006.10.055
8. [8]
  Czarnik A W. Supramolecular Chemistry, Fluorescence, and Sensing. ACS Symposium Series: Vol. 538. Washington DC: American Chemical Society, 1993: 1-9
9. [9]
  LI L Q, MENG L P. Recent Progress in Fluorescent Sensor for Silver Ion Based on Small Organic Molecule[J]. Guangzhou Chemical Industry, 2013,41(12):24-26. doi: 10.3969/j.issn.1001-9677.2013.12.009
10. [10]
  ZHANG X, YU X G, LI C Y, LIAO H G, TAN Y, LIU H L, TONG M L, LI J R, WANG X Z. Development of a Furan-Derived Hexaazatriphenlene (HAT) Sensor with Fluorescent"Turn-Off"Feature for Selective Ag⁺ Recognition[J]. Journal of Chemical Engineering of Chinese Universities, 2021,35(4):697-701. doi: 10.3969/j.issn.1003-9015.2021.04.015
11. [11]
  Wang H H, Xue L, Jiang H. Ratiometric Fluorescent Sensor for Silver Ion and Its Resultant Complex for Iodide Anion in Aqueous Solution[J]. Org. Lett., 2011,13(15):3844-3847. doi: 10.1021/ol2013632
12. [12]
  YIN K, YU Z, LUO Z L, LI Y, REN J. The Synthesis and Properties of a Coumarin Based Chemosensor for Silver Ion[J]. Journal of Hubei University (Natural Science Edition), 2015,37(2):154-158.
13. [13]
  ZHOU W, WU A B. Synthesis and Properties of Pyrimidine Naphthalimide-Based Ag⁺ Fluorescent Probes[J]. Chemical Reagents, 2020,42(6):694-698.
14. [14]
  FU D Y, YUAN W J, WANG W. Synthesis and Performance of a New Fluorescent Probe for Ag⁺ Recognition[J]. Chemical World, 2020,61(3):171-175.
15. [15]
  Han Q X, Liu X, Wang X C, Song Y Y, Yang L N, Li J, Qiang T T. Photoactivated Fluorescence-Based Analysis for the Facilitative and Selective Detection of Silver(Ⅰ) in Aqueous Solutions[J]. Dyes Pigm., 2021,184108793. doi: 10.1016/j.dyepig.2020.108793
16. [16]
  Senkuytu E, Ecik E, Cosut B. Bodipy Decorated Triazine Chemosensors for Ag⁺ Ions with High Selectivity and Sensitivity[J]. J. Lumin., 2018,203:639-645. doi: 10.1016/j.jlumin.2018.06.075
17. [17]
  Saiyasombata W, Kiatisevi S. Bis-BODIPY Linked-Triazole Based on Catechol Core for Selective Dual Detection of Ag⁺ and Hg²⁺[J]. RSC Adv., 2021,11:3703-3712. doi: 10.1039/D0RA09686E
18. [18]
  Zhao F, Hu Y, Li Q, Hu S L. A New Carbazole-Based Fluorescence Sensor for High Selective Detection of Copper in Aqueous Solutions[J]. Heterocycles, 2017,94(3):515-522. doi: 10.3987/COM-17-13645
19. [19]
  Steed J W, Atwood J L. Supramolecular Chemistry. 2nd ed. Chichester: John Wiley&Sons, Ltd., 2009: 114
20. [20]
  GAO R M, LIU H G. Discussion of Concept of Detection of Limit[J]. Chin. J. Anal. Chem., 1993,21(10):1232-1236.
21. [21]
  The National Environmental Protection Agency of People's Republic of China, The State Bureau of Quality and Technical Supervision of People's Republic of China. Intgrated Wastwater Discharge Standard: GB 8978—1996. Beijing: China Standard Press, 1996.
22. [22]
  Zhang Y Y, Chen X Z, Liu J J, Gao G, Zhang X Y, Hou S C, Wang H M. A Highly Selective and Sensitive Fluorescent Chemosensor for Distinguishing Cadmium(Ⅱ) from Zinc(Ⅱ) Based on Amide Tautomerization[J]. New J. Chem., 2018,42:19245-19251.
23. [23]
  Wang H H, Xue L, Qian Y Y, Jiang H. Novel Ratiometric Fluorescent Sensor for Silver Ions[J]. Org. Lett., 2010,12:292-295.
24. [24]
  Sherwood P, de Vries A H, Guest M F, Schreckenbach G C, Catlow R A, French S A, Billeter S. QUASI: A General Purpose Implementation of the QM/MM Approach and Its Application to Problems in Catalysis.[J]. J. Mol. Struct.-THEOCHEM, 2003,632:1-28.
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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

Fluorescent Probe Based on Carbazole-N, S-Heterocrown Ether: Synthesis and Properties of Ag+ Detection

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

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通讯作者: 陈斌, bchen63@163.com

Fluorescent Probe Based on Carbazole-N, S-Heterocrown Ether: Synthesis and Properties of Ag⁺ Detection