CN113004256B - Ratio type probe for detecting mercury ions and preparation method and application thereof - Google Patents
Ratio type probe for detecting mercury ions and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to a ratio type probe for detecting mercury ions and a preparation method and application thereof. Specifically, the invention provides a probe for detecting mercury ions, which is simple and convenient to operate and high in sensitivity. The name of the probe is 7-diethylamino-3- (3- (7-diethylamino) coumarinyl) -3-oxopropenyl quinoline-2-ketone, which is short for QCT-O. QCT-O is obtained by reacting 7-diethylamino-2-oxo-1, 2-dihydroquinoline-3-formaldehyde and 7-diethylamino coumarin-3-ethanone serving as raw materials under the action of a catalyst. The probe has the advantages of quick response to mercury ions, strong selectivity and high sensitivity. In the presence of mercury ions, the color of the probe solution changes from red to yellow (under sunlight) and from red fluorescence to blue-green fluorescence (under an ultraviolet lamp); and the absorption peak at 500nm disappears, and new absorption peaks appear at 380nm and 440 nm; the fluorescence intensity at 650nm wavelength is obviously changed, the absorption and emission response intensities are linearly changed with the mercury ion concentration, and the lowest detection limit is 2.62 multiplied by 10 ‑8 mol/L and 4.37X 10 ‑8 mol/L。
Description
Technical Field
The invention belongs to the technical field of organic synthesis and analysis detection, and particularly relates to a small molecular probe for detecting mercury ions, a preparation method thereof and application thereof in mercury ion detection.
Background
Mercury ion (Hg) 2+ ) The most stable inorganic mercury exists in natural water and is one of the common toxic heavy metal ions. It can accumulate in the organism and be transferred to the human body through the food chain. The micro mercury ions in the human body can directly damage important organs such as liver, heart and the like, and cause dysfunction and even death of the nervous system and the respiratory system. Meanwhile, the methylation product methyl mercury of mercury ion microorganisms can be converted into highly toxic organic mercury through a food chain. Therefore, the method can be used for quickly and accurately detecting the mercury ions and has important significance in the aspects of environmental monitoring, food safety, medical diagnosis and the like.
Compared with mercury ion detection methods such as atomic spectrometry, inductively coupled plasma mass spectrometry, inductively coupled plasma atomic emission spectrometry, capillary electrophoresis and the like, ultraviolet-visible absorption and fluorescence detection technologies have the advantages of high detection sensitivity, good selectivity, simplicity and convenience in use, capability of real-time monitoring and the like, and are widely concerned by people. One of the centers of the ultraviolet-visible absorption method and the fluorescence detection technology is a small molecule probe. At present, the reported probes for detecting mercury ions show good sensitivity and selectivity to mercury ions, but the probes also have the defects of long synthetic route, unsatisfactory detection and the like. Therefore, it is still necessary to develop a novel probe that can effectively overcome the above disadvantages.
Disclosure of Invention
Aiming at the technical problems, the invention provides a ratiometric probe for detecting mercury ions, which is 7-diethylaminocoumarin-3- (3- (7-diethylamino) coumarin group) -3-oxopropenylquinoline-2-ketone (named as QCT-O) and has the following specific structural formula:
the preparation method of the ratio type probe for detecting mercury ions is characterized by comprising the following steps: adding 7-diethylamino-2-oxo-1, 2-dihydroquinoline-3-formaldehyde, 7-diethylaminocoumarin-3-ethanone and a solvent into a reaction bottle, heating and stirring to dissolve solids, adding a catalyst, and stirring and refluxing; and after the reaction is finished, carrying out suction filtration and purification to obtain the ratio type probe for detecting mercury ions.
The molar ratio of 7-diethylamino-2-oxo-1, 2-dihydroquinoline-3-carbaldehyde to 7-diethylaminocoumarin-3-ethanone is 1:0.5 to 1.5, preferably 1: 1.
The solvent comprises any one of methanol, ethanol, n-propanol, isopropanol or butanol, preferably ethanol.
The catalyst is alkali, acid or a mixture of the acid and the alkali in any volume ratio.
The base comprises piperidine or pyridine or triethylamine, preferably piperidine; the acid is acetic acid; the volume ratio of acid to alkali in the acid-alkali mixture is 1: 0.5-3.
The alkali in the acid-base mixture is piperidine.
The invention also adopts the technical scheme that the ratio type probe for detecting the mercury ions is used for qualitatively identifying and quantitatively detecting the mercury ions Hg in the methanol water solution 2+ The use of the reagent of (1).
The application of QCT-O in qualitative identification is that a sample to be detected is added into a QCT-O solution or a prepared plate containing QCT-O, the mixture is uniformly mixed, and the color and brightness change of the sample is observed under natural light or an ultraviolet lamp.
The application of QCT-O in quantitatively detecting mercury ions is that a sample to be detected is added into a QCT-O solution, and the concentration of the mercury ions is detected by an ultraviolet-visible absorption spectrophotometry or a fluorescence spectrophotometry.
The invention has the beneficial effects that:
compared with the prior art, the invention has the following beneficial effects:
1. the structural units of the diethylaminoquinolinone and the diethylaminocoumarin in the small molecular probe have good ultraviolet-visible absorption and fluorescence effects, and after ketene connection, the conjugation degree of the molecules is increased, and the molecules are more sensitive to environmental changes.
2. The micromolecule is prepared by using an active aldehyde group in quinolinone serving as one raw material and coumarin ethyl ketone serving as the second raw material to perform aldol condensation reaction. The reaction has the characteristics of easily obtained raw materials, short synthetic route, mild reaction conditions, simple and convenient post-treatment, high yield and the like.
3. The probe molecule contains a plurality of nitrogen and oxygen heteroatoms, mercury ions act with the probe rapidly, the changes of the absorption spectrum and the fluorescence emission spectrum before and after the action are obvious, and the probe has the characteristics of rapid response, strong selectivity, high sensitivity and the like, and has good application prospects in qualitative and quantitative detection of the mercury ions.
Drawings
FIG. 1 is a QCT-O prepared in example 1 1 H-NMR spectrum.
FIG. 2 is a QCT-O prepared in example 1 13 C-NMR spectrum.
FIG. 3 shows UV-VIS absorption spectrum (A) and fluorescence emission spectrum (B) of QCT-O prepared in example 1 in the presence of different ions.
Fig. 4 is a uv-vis absorption spectrum (a) and a fluorescence emission spectrum (B) of the QCT-O prepared in example 1 for detecting mercury ions under different ion interferences.
Fig. 5 is a graph showing the uv-vis absorption spectrum (a) and the uv-vis absorption intensity of QCT-O prepared in example 1 in linear relationship with the change in mercury ion concentration (B).
FIG. 6 is a fluorescence emission spectrum (A) of QCT-O prepared in example 1 and a linear relationship between fluorescence emission intensity and mercury ion concentration (B).
FIG. 7 is a graph of fluorescence emission intensity versus time for the detection of mercury ions for QCT-O prepared in example 1.
FIG. 8 is a graph showing the relationship between fluorescence emission intensity and pH for detecting mercury ions for QCT-O prepared in example 1.
FIG. 9 is a graph of Job's plot of mercury ions detected by QCT-O prepared in example 1.
FIG. 10 is a qualitative detection of mercury ions of different concentrations in solution by thin layer chromatography silica gel plate.
Detailed Description
The invention is further illustrated by the following examples, but the scope of the invention as claimed is not limited to the scope of the examples.
Example 17-diethylamino-3- (3- (7-diethylamino) coumarinyl) -3-oxopropenylquinolin-2-one (QCT-O) 2.44g (10mmol) of 7-diethylamino-2-oxo-1, 2-dihydroquinoline-3-carbaldehyde were weighed into a 100mL two-necked flask, 2.60 g (10mmol) of 3-acetyl-7-diethylamino-coumarin and 50mL of ethanol were added, the mixture was dissolved by stirring, 1.0mL of acetic acid and 1.0mL of piperidine were added, the solution was dark reddish brown, the temperature was raised to 75 ℃ by heating, and the progress of the reaction was detected by TLC. After the reaction is completed, the reaction product is cooled to room temperature, red solid is separated out, and is filtered under reduced pressure and washed by methanol, so that 4.22g of red solid is obtained, and the yield is 87% m.p. and is 248.1-249.3 ℃. 1 H NMR(400MHz,DMSO-d 6 )δ11.43(s,1H),8.54(s,1H),8.22(s,1H),8.17 (d,J＝9.6Hz,1H),7.71(dd,J＝15.6,10.8Hz,2H),7.51(d,J＝9.2Hz,1H),6.80(d,J＝10.0Hz, 1H),6.69(d,J＝9.2Hz,1H),6.61(s,1H),6.48(s,1H),3.50(q,J＝6.4Hz,4H),3.42(q,J＝13.2 Hz,4H),1.15(t,J＝6.4Hz,12H). 13 C NMR(100MHz,DMSO-d 6 )δ186.40,161.88,160.21, 158.52,153.17,150.71,148.35,142.28,141.44,139.42,132.58,130.75,123.76,119.66,116.74, 110.44,109.42,108.34,96.35,94.20,44.88,44.63,12.95,12.84.
Example 1-1 gave 4.22g of a red solid in 87% yield m.p. 248.1-249.3 ℃. 1 H NMR(400MHz, DMSO-d 6 )δ11.43(s,1H),8.54(s,1H),8.22(s,1H),8.17(d,J＝9.6Hz,1H),7.71(dd,J＝15.6, 10.8Hz,2H),7.51(d,J＝9.2Hz,1H),6.80(d,J＝10.0Hz,1H),6.69(d,J＝9.2Hz,1H),6.61(s, 1H),6.48(s,1H),3.50(q,J＝6.4Hz,4H),3.42(q,J＝13.2Hz,4H),1.15(t,J＝6.4Hz,12H). 13 C NMR(100MHz,DMSO-d 6 )δ186.40,161.88,160.21,158.52,153.17,150.71,148.35,142.28, 141.44,139.42,132.58,130.75,123.76,119.66,116.74,110.44,109.42,108.34,96.35,94.20,44.88, 44.63,12.95,12.84.
EXAMPLE 2 preparation of test solutions
(1) Preparation procedure of stock solution:
the probe QCT-O is dissolved in DMF to prepare a stock solution of 1.0 mmol/L. The stock solution was diluted to 10. mu. mol/L in methanol/water (7:3, v/v) for spectroscopic measurements. The following spectral tests were all carried out in a methanol/water (7:3, v/v) system. The concentration of the metal ions was 10 mmol/L. Solutions of methanol/water (7:3, v/v) at different pH values were prepared and monitored using a Raymagnetic pH meter. After standing for 40 minutes, the ultraviolet absorption spectrum and the fluorescence emission spectrum (500nm is the excitation wavelength) were measured. And (4) preparing a blank test solution without adding the sample solution to be detected by the above operation.
(2) Selective experiments:
14 parts of 2mL methanol/water (7:3, v/v) solution are taken and added20 μ L of stock solution and different metal ions (Al) 3+ , Ca 2+ ,Cr 3+ ,Mn 2+ ,Fe 3+ ,Co 2+ ,Ni 2+ ,Cu 2+ ,Pb 2+ ,Zn 2+ ,Ag + ,Cd 2+ ,Ba 2+ ,K + ,Na + And Hg 2+ ) The ultraviolet absorption spectrum and the fluorescence emission spectrum were measured. When various analytes to be detected with the same concentration respectively act with QCT-O, in an ultraviolet absorption spectrum, blank test solution and QCT-O solution added with other analytes to be detected have absorption peaks at 500nm, and after mercury ions are added, the absorption peaks of the QCT-O solution at 500nm disappear, and new absorption peaks are generated at 380nm and 450 nm; in the fluorescence spectrum, the blank test solution and QCT-O solution added with other analytes to be detected have strong emission peaks at 650 nm; however, the fluorescence intensity of the QCT-O solution at 650nm was significantly reduced after the addition of mercury ions. This indicates that QCT-O has a high degree of specific selectivity for the detection of mercury ions, see figure 3.
(3) Effect of coexisting ions on mercury ion determination:
in order to further investigate the selectivity of QCT-O on mercury ion detection, the influence of the coexistence of the analyte to be detected and mercury ions on the ultraviolet absorption and fluorescence emission of the system is tried, and the analyte to be detected is respectively: al (Al) 3+ ,Ca 2+ ,Cr 3+ ,Mn 2+ ,Fe 3+ ,Co 2+ ,Ni 2 + ,Cu 2+ , Pb 2+ ,Zn 2+ ,Ag + ,Cd 2+ ,Ba 2+ ,K + ,Na + And Hg 2+ See fig. 4. When the mercury ions coexist with various analytes to be detected with the same concentration, the absorption value and the fluorescence intensity of the system are not changed greatly. This indicates that the other analytes to be detected have little interference with the detection of mercury ions.
(4) Titration experiment for detecting mercury ions:
in the ultraviolet absorption spectrum, a detected mercury ion concentration curve is obtained through linear fitting: y-0.2524 x +9.1169 (R) 2 0.9904, the concentration range of mercury ions is: 0 to 32.5 μ M); and (3) in the fluorescence emission spectrum, linearly fitting to obtain a detected mercury ion concentration curve: y-17.2785 x +844.018 (R) 2 ＝0.9914, the concentration range of mercury ions is as follows: 0-40 μ M); see fig. 5 and fig. 6 (concentration interval 5 μ M). The LOD of the uv-vis spectrophotometry QCT-O to mercury ions is calculated according to the lowest detection limit formula (LOD ═ 3 σ/b): 2.62X 10 -8 mol/L. The LOD of mercury ions by a fluorescence spectrophotometry QCT-O method is as follows: 4.37X 10 -8 mol/L。
(5) Dynamic experiment for detecting mercury ions:
the kinetic behavior of the reaction between QCT-O and mercury ions was studied by fluorescence spectroscopy as a function of time. As shown in FIG. 7, after addition of mercury ions to the QCT-O methanol/water (7:3, v/v) solution, the fluorescence intensity of QCT-O at 650nm quenched rapidly and was essentially stable within 5 minutes, with the reaction time extended to 40 minutes and the fluorescence intensity remained essentially unchanged. This phenomenon indicates that the binding reaction between QCT-O and mercury ions is rapid and complex stable. Therefore, the probe QCT-O can detect mercury ions in the solution in real time.
(6) Testing of fluorescence emission spectra of probes for pH changes:
and (3) adding 20 mu L of stock solution into 2mL of QCT-O solution with different pH values for spectrum test, and then adding 20 mu L of mercury ion solution for spectrum test. In both acidic and alkaline environments, QCT-O has influence on detection of mercury ions. QCT-O is more sensitive to mercury ion response in a neutral methanol/water (7:3, v/v) environment, see FIG. 8.
(7) QCT-O and mercury ion stoichiometry:
the stoichiometric relationship between QCT-O and mercury ions was determined by the method of equimolar variation (Job's Plot). The total concentration of QCT-O and mercury ions was kept constant at 10. mu.M. When the molar fraction of mercury ions was 0.5, the fluorescence intensity of probe QCT-O at 650nm reached a maximum (FIG. 9), indicating that the complex ratio of QCT-O and mercury ions was 1: 1.
Example 3 qualitative detection of Mercury ions of different concentrations in solution by thin layer chromatography silica gel plate
And immersing the silica gel thin-layer chromatography plate into 1.0mmol/L of QCT-O methanol solution, taking out after 1 minute, and volatilizing the solvent at room temperature to prepare the silica gel thin-layer chromatography detection plate containing QCT-O. Immersing the detection plate in mercury ion solutions with different concentrationsAnd taking out immediately, and observing the color change of the thin layer chromatography plate under natural light or a 365nm ultraviolet lamp after the solvent is volatilized. When the concentration of mercury ions is as low as 1X 10 -6 At mol/L, a noticeable color change was visible to the naked eye, as shown in FIG. 10.
Claims (8)
1. A ratiometric probe for detecting mercury ions is characterized in that the probe is 7-diethylaminocoumarin-3- (3- (7-diethylamino) coumarin group) -3-oxopropenylquinoline-2-ketone, and the specific structural formula is as follows:
2. the method of claim 1, comprising the steps of: adding 7-diethylamino-2-oxo-1, 2-dihydroquinoline-3-formaldehyde, 7-diethylaminocoumarin-3-ethanone and a solvent into a reaction bottle, heating and stirring to dissolve solids, adding a catalyst, and stirring and refluxing; and after the reaction is finished, carrying out suction filtration and purification to obtain the ratio type probe for detecting mercury ions.
3. The method for preparing a ratiometric probe for detecting mercury ions according to claim 2, wherein the molar ratio of 7-diethylamino-2-oxo-1, 2-dihydroquinoline-3-carbaldehyde to 7-diethylaminocoumarin-3-ethanone is 1: 0.5-1.5.
4. The method of claim 2, wherein the solvent is any one of methanol, ethanol, n-propanol, isopropanol or butanol.
5. The method for preparing a ratiometric probe for detecting mercury ions according to claim 2, wherein the catalyst is a base, or an acid, or a mixture of an acid and a base in any volume ratio.
6. The method for preparing a ratiometric probe for detecting mercury ions according to claim 5, wherein the base is piperidine or pyridine or triethylamine; the acid is acetic acid; the volume ratio of acid to alkali in the acid-alkali mixture is 1: 0.5-3.
7. The method of claim 6, wherein the base in the acid-base mixture is piperidine.
8. The ratiometric probe for detecting mercury ions according to claim 1, for qualitatively identifying and quantitatively detecting mercury ions in preparation of methanol aqueous solution 2+ The use of the reagent of (1).
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| CN103570678A (en) * | 2013-11-01 | 2014-02-12 | 山西大学 | 2-quinolinone compound and preparation method and application thereof |
| CN107417671A (en) * | 2017-05-19 | 2017-12-01 | 三峡大学 | A kind of coumarin derivative of the substitution containing quinoline and preparation method thereof and the application on Ratio-type pH fluorescence probes |
| CN110551498A (en) * | 2018-06-04 | 2019-12-10 | 南京大学 | Preparation and application of coumarin fluorescent probe for detecting Hg 2+ |
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| US5459276A (en) * | 1994-05-20 | 1995-10-17 | Molecular Probes, Inc. | Benzazolylcoumarin-based ion indicators for heavy metals |
| CN103570678A (en) * | 2013-11-01 | 2014-02-12 | 山西大学 | 2-quinolinone compound and preparation method and application thereof |
| CN107417671A (en) * | 2017-05-19 | 2017-12-01 | 三峡大学 | A kind of coumarin derivative of the substitution containing quinoline and preparation method thereof and the application on Ratio-type pH fluorescence probes |
| CN110551498A (en) * | 2018-06-04 | 2019-12-10 | 南京大学 | Preparation and application of coumarin fluorescent probe for detecting Hg 2+ |
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