CN112442358B - Benzothiazole type mercury ion fluorescent probe - Google Patents

Benzothiazole type mercury ion fluorescent probe Download PDF

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CN112442358B
CN112442358B CN201910826032.XA CN201910826032A CN112442358B CN 112442358 B CN112442358 B CN 112442358B CN 201910826032 A CN201910826032 A CN 201910826032A CN 112442358 B CN112442358 B CN 112442358B
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fluorescent probe
mercury
mercury ion
ion fluorescent
benzothiazole
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CN112442358A (en
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杨绍祥
田红玉
刘永国
孙宝国
武小明
王皓
李雅楠
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Beijing Technology and Business University
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1011—Condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur

Abstract

The invention discloses a benzothiazole mercury ion fluorescent probe, which has the following specific chemical structural formula:

Description

Benzothiazole type mercury ion fluorescent probe
Technical Field
The invention relates to a benzothiazole mercury ion fluorescent probe and application thereof in detection of mercury ions.
Background
Mercury ion (Hg)2+) Is widely present in the food chain and in the ecological environment. Has strong toxicity, and can cause brain and liver damage after inhalation, contact or mistaken administration. Hg is a mercury vapor2+Can be converted into methyl mercury and dimethyl mercury, the methyl mercury is more toxic than mercury ions and is easy to be absorbed by human body, and it is a disease of methyl mercury poisoning. The existing analytical methods for detecting mercury mainly comprise a dithizone colorimetric method, an inductively coupled plasma mass spectrometry method, an atomic fluorescence spectrometry method, a cold atomic absorption spectrometry method, an inductively coupled plasma emission spectrometry method and the like.
The organic small-molecule fluorescent probe detection method has the advantages of rapid detection, simple and convenient operation, high sensitivity and the like, thereby arousing high attention of researchers, developing a bifunctional fluorescent probe for measuring the content of mercury ions and having important research significance.
Disclosure of Invention
The invention aims to provide a benzothiazole-type mercury ion fluorescent probe which is suitable for detecting mercury ions in water.
More specifically, the invention relates to a benzothiazole mercury ion fluorescent probe, which is represented by the following formula:
Figure BSA0000189384000000011
drawings
FIG. 1 shows the fluorescence intensity of the fluorescent probe (10. mu.M) of the present invention in a dimethylsulfoxide/water (v/v. equal to 3: 1) solution with the addition of mercury ions at different concentrations. Embedding a graph: concentration of mercury ions.
FIG. 2 is a standard curve of fluorescence intensity of the fluorescent probe of the present invention (10. mu.M) as a function of mercury ion concentration in dimethylsulfoxide/water (v/v. equal to 3: 1).
FIG. 3 shows the change of the luminous intensity of the fluorescent probe test paper after the fluorescent probe test paper is dipped in mercury ion solutions (0, 2, 4, 6, 8, 10 μ M) with different concentrations under a 365nm ultraviolet lamp.
Detailed Description
Example 1 preparation of benzothiazole-type Mercury ion fluorescent Probe
The synthetic route is shown as the following formula:
Figure BSA0000189384000000021
compound 1(0.47g, 2.70mmol), compound 2(0.50g, 1.80mmol) were added to a 100mL three-necked flask, dichloromethane (15mL) was added thereto, N-diisopropylethylamine (0.75mL) was added dropwise with stirring, and the mixture was stirred at room temperature for 10 hours, and then subjected to column chromatography to give compound 3 as a white solid.
The product is characterized by nuclear magnetic hydrogen spectrum and nuclear magnetic carbon spectrum.
1H NMR(300MHz，DMSO)，δ(ppm)：8.61(s，1H)，8.27(dd，J＝8.6，1.7Hz，1H)，8.13(d，J＝8.0Hz，1H)，8.06(d，J＝8.9Hz，1H)，7.99-7.93(m，2H)，7.72(d，J＝2.1Hz，1H)，7.55-7.40(m，5H)，7.35(dd，J＝10.6，4.2Hz，1H)，7.27(d，J＝1.1Hz，1H).13C NMR(75MHz，DMSO)，δ(ppm)：193.59，166.60，153.16，152.55，151.12，134.10，133.94，130.65，130.46，129.60，128.75，128.72，128.70，127.77，126.41，125.92，125.50，124.46，124.41，122.30，121.26，120.81，120.79，120.68，118.18.
EXAMPLE 2 preparation of fluorescent Probe test paper
The filter paper is cut into square test paper with the size of 1cm multiplied by 1cm, and the square test paper is soaked in 1mM of the fluorescent probe solution (DMSO solvent) to obtain the fluorescent probe test paper.
The change of the fluorescence intensity of the fluorescent probe of the invention along with the mercury ions is shown in figure 1, a standard curve of the fluorescence intensity of the fluorescent probe (10 mu M) along with the change of the mercury ion concentration can be made according to the change, the standard curve is shown in figure 2, and the fluorescent probe of the invention can be used for the quantitative detection of the mercury ions through the establishment of the standard curve.
Mercury ions with different concentrations were dropped onto the prepared test paper, and the change of the luminescence intensity of the test paper is shown in fig. 3. With the increase of the concentration of mercury ions, the luminous intensity of the fluorescent probe test paper is gradually enhanced.

Claims (1)

1. A benzothiazole type mercury ion fluorescent probe has a specific chemical structural formula as follows:
Figure FSA0000189383990000011
CN201910826032.XA 2019-09-03 2019-09-03 Benzothiazole type mercury ion fluorescent probe Active CN112442358B (en)

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CN115368316A (en) * 2021-05-19 2022-11-22 北京工商大学 Naphthalene ring tyrosinase fluorescent probe

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105419788A (en) * 2015-12-25 2016-03-23 济南大学 Small-molecular fluorescent probe for recognizing H2S, preparation method and application thereof
CN107298664A (en) * 2017-07-11 2017-10-27 济南大学 A kind of colorimetric fluorescence probe for analyzing mercury ion, preparation method and application
CN107337654A (en) * 2017-07-11 2017-11-10 济南大学 A kind of fluorescence probe for analyzing mercury ion, preparation method and application

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105419788A (en) * 2015-12-25 2016-03-23 济南大学 Small-molecular fluorescent probe for recognizing H2S, preparation method and application thereof
CN107298664A (en) * 2017-07-11 2017-10-27 济南大学 A kind of colorimetric fluorescence probe for analyzing mercury ion, preparation method and application
CN107337654A (en) * 2017-07-11 2017-11-10 济南大学 A kind of fluorescence probe for analyzing mercury ion, preparation method and application

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
A carbonothioate-based highly selective fluorescent probe with a large Stokes shift for detection of Hg2+;Jing Xu等;《Luminescence》;20181231;第33卷;219-224 *

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