Fluorescent probe for detecting mercury ions as well as preparation method and use method thereof

A fluorescent probe, mercury ion technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of unfavorable and accurate detection, quantitative detection of samples that are difficult to contain mercury ions, detection limit, etc. Application, easy operation, low cost effect

Inactive Publication Date: 2019-11-22
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, probes based on thioacetal or thioamide as probe reporter groups (see review Mahato, P.; Saha, S.; Das, P.; Agarwalla H.; Das, Amitava. RSC Adv., 2014,4,36140–36174.) are vulnerable to common coexisting ions in the system such as Ag + , Cu 2+ etc., which is not conducive to its accurate detection in the complex aqueous phase system
In addition, the detection limit of current mercury ion fluorescent probes is relatively high, and it is difficult to quantitatively detect trace or even extremely trace amounts of mercury ion samples.

Method used

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  • Fluorescent probe for detecting mercury ions as well as preparation method and use method thereof
  • Fluorescent probe for detecting mercury ions as well as preparation method and use method thereof
  • Fluorescent probe for detecting mercury ions as well as preparation method and use method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1, the synthesis of compound NMS1

[0039] Synthesis of N-n-butyl-3-(2'-bromoethyl)-oxyphthalimide (4)

[0040] 1.32g N-n-butyl-3-hydroxyphthalimide (1) (6.03mmol), 0.54mL allyl bromide (2) (6.03mmol), and 1.2g potassium carbonate (3) ( 9.03mmol) was dissolved in 50mL acetone, and after reflux stirring for 12 hours, 1.4g of compound N-n-butyl-3-(2'-bromoethyl)-oxyphthalimide (4) was obtained, producing The rate is 92%.

[0041] 1 H NMR (400MHz, Chloroform-d) δ7.62 (dd, J = 8.4, 7.3Hz, 1H), 7.43 (d, J = 7.3Hz, 1H), 7.18 (d, J = 8.4Hz, 1H), 6.09 (ddt, J=17.2,10.2,5.0Hz,1H),5.54(dd,J=17.3,1.4Hz,1H),5.36(dd,J=10.6,1.4Hz,1H),4.79(dt,J=4.9 ,1.5Hz,2H),3.66(t,J=7.2Hz,2H),1.66(q,J=7.4Hz,2H),1.36(dq,J=14.7,7.4Hz,2H),0.94(t,J =7.4Hz, 3H).

[0042] Synthesis of Compound N-n-Butyl-3-Hydroxy-4-allylphthalimide (5)

[0043] Add 1.5g of N-n-butyl-3-(2'-bromoethyl)-oxyphthalimide (4) (5.8mmol) to 4mL o-dichlorobenzene, microwave at 200 degrees After reacting for 1 hou...

Embodiment 2

[0045] Embodiment 2, the color response of compound NMS1 to mercury ion

[0046] A test mother solution of dimethyl sulfoxide (DMSO) of the fluorescent probe NMS1 for detecting mercury ions according to the present invention with a concentration of 1 mM was prepared for use. Measure 10 μL of this mother solution and add it dropwise to a phosphate buffer solution with a certain concentration of mercury ions, and use the corresponding phosphate buffer solution to adjust the volume to 10 mL, so that in the test solution, the concentration of the probe is 1.0 μM, and the concentration of mercury ions is 10.0 μM for color response testing. like figure 2 and 3 As shown, after the mercury ion aqueous solution was added, the color of the solution was observed to change from light yellow to colorless, and the fluorescence of the solution also changed from almost green fluorescence to blue fluorescence, indicating that the probe NMS1 has an intuitive color development for mercury ion...

Embodiment 3

[0047] Embodiment 3, the ultraviolet titration detection of different concentrations of mercury ions to compound NMS1

[0048] A test mother solution of dimethyl sulfoxide (DMSO) of the fluorescent probe NMS1 for detecting mercury ions according to the present invention with a concentration of 1 mM was prepared for use. Measure 10 μL of this mother solution and add it dropwise to phosphate buffer with different concentrations of mercury ions, and use the corresponding phosphate buffer to make up to 10 mL, so that in the test solution, the concentration of the probe is 1.0 μM, and the concentration of mercury ions is 0-40.0μM for absorption spectrum test. The ultraviolet absorption curves in each system were obtained, and the standard curves of absorbance and mercury ion concentration were established. like Figure 4 As shown, with the increase of mercury ion concentration, the absorbance at 514nm decreases gradually and the absorbance at 427nm increases gradually, and their ...

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PUM

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Abstract

The invention discloses a fluorescent probe for detecting mercury ions as well as a preparation method and a use method of the fluorescent probe. 3-hydroxyphthalimide is used to construct a classicalexcited state intramolecular proton transfer (ESIPT) system, and a propenyl group is introduced to the 4-site. The probe itself has a classic ESIPT effect and emits green fluorescence at a long wave,but in the presence of mercury ions, the mercury ions promote an intramolecular cyclization reaction of 3-hydroxyl, so that the ESIPT effect of the probe is inhibited, and probe molecules emit strongblue fluorescence. The 'ratio' type mercury ion probe based on N-n-butyl phthalimide dye has good response to a mercury ion solution, can realize sensitive quantitative detection of trace mercury ionsin a sample, and has the advantages of simplicity and convenience in operation, low cost, sensitive response, easiness in popularization and application and the like.

Description

technical field [0001] The invention belongs to the field of organic small molecule fluorescent probes, and in particular relates to a 3-hydroxyphthalimide derivative used as a mercury ion fluorescent probe, a preparation method and a use method thereof. Background technique [0002] Mercury is a heavy metal with severe physiological toxicity. Mercury and its derivatives are widely distributed in air, water and soil through processes such as volcanic eruption, fuel combustion, metallurgy, battery, and electronic industry. Elemental mercury and mercury ions can be converted into methylmercury by microorganisms, enter the food chain through various channels, accumulate in the organism and finally enter the human body, causing great damage to the human brain and central nervous system. , can seriously cause language and memory impairment, and even death. In recent years, with the frequent application of mercury in industrial production, the environmental pollution caused by it...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48C09K11/06G01N21/64
CPCC07D209/48C09K11/06C09K2211/1029G01N21/643G01N2021/6417
Inventor 韩益丰杨斌英黄静
Owner ZHEJIANG SCI-TECH UNIV
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