CN112358486A - Detection of Pb in acidic aqueous solutions2+Fluorescent probe for ions and preparation method thereof - Google Patents

Detection of Pb in acidic aqueous solutions2+Fluorescent probe for ions and preparation method thereof Download PDF

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CN112358486A
CN112358486A CN202011310937.0A CN202011310937A CN112358486A CN 112358486 A CN112358486 A CN 112358486A CN 202011310937 A CN202011310937 A CN 202011310937A CN 112358486 A CN112358486 A CN 112358486A
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黄月金
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Abstract

The invention relates to the detection of Pb in acidic aqueous solutions2+Ionic fluorescent probe and preparation method thereof, and the fluorescent probe can detect Pb in environment with pH value of 1-62+Ion and Pb2+The ion pair probe is fluorescence enhanced. The fluorescent probe is directed to Pb2+The ion recognition has good selectivity, strong specificity and strong anti-interference capability, and can directly detect Pb in acidic aqueous solution2+The ions can be directly applied to the detection of industrial wastewater, and the wastewater does not need to be further treated, so the method has strong applicability.

Description

Detection of Pb in acidic aqueous solutions2+Fluorescent probe for ions and preparation method thereof
Technical Field
The invention belongs to the field of ion detection, and particularly relates to rapid detection of Pb in an acid environment2+An ionic fluorescent probe and a preparation method thereof.
Background
Lead ion Pb2+Is a common environmental pollutant, has strong toxicity and very little Pb2+Serious damage can be done to the brain and central nervous system. Pb entering the environment2+Not easy to degrade and easy to accumulate and pollute the air, water source and soil. Conventional Pb2+The detection methods, such as atomic absorption spectroscopy, inductively coupled plasma emission spectroscopy and electrochemical voltammetry, have higher sensitivity, but have the defects of complicated sample pretreatment or expensive instruments and the like. Therefore, development of low-cost, rapid, sensitive Pb2+A new detection method for realizing the detection of Pb in the environment2+The rapid detection and the real-time monitoring have important practical significance.
The fluorescent probe has the characteristics of good selectivity, simplicity, rapidness, high sensitivity and no need of expensive instruments, and is widely applied to detection of various metal ions. At present, Pb is available2+Fluorescent probes, but currently Pb2+Fluorescent probes generally require detection in organic solvents, and environmental Pb is present2+Often in water, which greatly limits Pb2+Application of fluorescent probe. There are a few reports in the literature that Pb can be detected in water environments2+But all in a neutral environment, and the environment is Pb2+Especially Pb in wastewater2+Is acidic, the sample needs to be treated firstly, and the random sampling and random inspection of the sample cannot be realized, so the development of the method can carry out Pb in an acidic environment2+There is an urgent need for fluorescent probes for ion detection.
Disclosure of Invention
The invention aims to solve the technical problem of providing a method for quickly and highly sensitively detecting Pb in an acidic aqueous solution2+An ion fluorescence enhancement type probe and a preparation method thereof.
The technical scheme of the invention is as follows:
rapid and high-sensitivity detection of Pb in acidic aqueous solution2+The ion fluorescence enhancement type probe L has the following structural formula:
Figure BDA0002789799540000021
and a preparation method thereof, wherein the reaction formula is as follows:
the method comprises the following steps: reacting the compound 1 with monomethyl succinate in an organic solvent to obtain a compound 2.
Figure BDA0002789799540000022
Step two: hydrolyzing the compound 2 under the action of alkali to obtain a compound 3.
Figure BDA0002789799540000023
Step three: the compound 3 and the compound 4 are subjected to condensation reaction in an organic solvent to obtain a compound 5.
Figure BDA0002789799540000031
Step four: and hydrolyzing the compound 5 under the action of alkali to obtain the fluorescent probe L.
Figure BDA0002789799540000032
Further, the organic solvent in the first step and the third step is ethanol.
Further, the base in steps two and four is NaOH.
Rapid and high-sensitivity detection of Pb in acidic aqueous solution2+Application of ion fluorescence enhancement type probe.
Rapid and high-sensitivity detection of Pb in acidic aqueous solution2+The pH value of the acidic aqueous solution is between 1 and 6, preferably between 3 and 4.
Rapid and high-sensitivity detection of Pb in acidic aqueous solution2+The application of ion fluorescence enhancement type probe is that a fluorescence probe L is added into a detected water sample, the fluorescence emission intensity is measured under the excitation wavelength of 535nm, the fluorescence intensity is obviously enhanced at 598nm, and Pb is contained in the detected water sample2+Ions.
The invention has the beneficial effects that:
1. the fluorescent probes L are for Pb2+The ion recognition has good selectivity and strong specificity, and the fluorescent probes L and Pb have2+After the ion action, the fluorescence is enhanced, and the effect on Pb is realized2+The fluorescence of the ions is enhanced and recognized, the detection sensitivity is high, and the ions and other common metal ions such as Zn are mixed2+、Cu2+、Fe2+、Fe3+、Cd2+、Mn2+、Co2+、Ni2+、Cr3+、Ag+、Ba2+、Sr2+、Mg2+、Hg2+The action fluorescent signal is basically unchanged, the anti-interference capability is strong, and the method can be used for Pb2+And (4) identifying ions.
2. The fluorescent probes L are for Pb2+The ion identification can be carried out in aqueous solution without participation of organic solvent, so that the convenience, accuracy and application range of detection are increased.
3. The fluorescent probe L can be used for directly detecting Pb in acidic aqueous solution2+The ions can be directly applied to the detection of industrial wastewater, and the wastewater does not need to be further treated, so the method has strong applicability.
Drawings
FIG. 1 shows fluorescence spectra of a fluorescent probe L of the present invention added with different metal ions in an acidic aqueous solution;
FIG. 2 shows Pb in an acidic aqueous solution of the fluorescent probe L of the present invention2+The fluorescence titration spectrum of (a);
FIG. 3 shows the fluorescent probe L of the present invention at Pb2+And the change of fluorescence emission intensity in the presence of other metal ions, wherein the hollow column on the left side is Pb2+The fluorescence intensity of other ions is added, and the fluorescence intensity of the other ions is independently added in the solid column on the right.
Detailed Description
The invention is further illustrated by, but is not limited to, the following examples.
EXAMPLE 1 Synthesis of fluorescent Probe L
The method comprises the following steps: synthesis of Compound 2
Figure BDA0002789799540000041
Dissolving 200mg of compound 1 in ethanol, adding 100mg of monomethyl succinate and 155mg of DCC (1, 3-dicyclohexylcarbodiimide), stirring at room temperature for 4 hours, and performing column chromatography to obtain 232.7mg of compound 1Product 2, yield 93.1%. MS is 571.68(M + H)+)。
Step two: synthesis of Compound 3
Figure BDA0002789799540000042
Dissolving 200mg of Compound 2 in ethanol and water (5:1), adding 120mg NaOH, stirring at room temperature for 6 hr, evaporating solvent, washing with water, and drying to obtain 188.3mg of Compound 3 with yield of 96.5% and MS of 557.65(M + H)+)。
Step three: synthesis of Compound 5
Figure BDA0002789799540000051
150mg of Compound 3 was dissolved in ethanol, 75mg of Compound 4 and 70mg of DCC (1, 3-dicyclohexylcarbodiimide) were added thereto, and the mixture was stirred at room temperature for 10 hours, followed by column chromatography to give 174.2mg of Compound 5, which was 86.3% in yield. MS is 748.84(M + H)+)。
Step four: synthesis of fluorescent Probe L
Figure BDA0002789799540000052
Dissolving 100mg of compound 2 in a solution of ethanol and water (1:1), adding 53mg of NaOH, stirring at room temperature for 5 hours, evaporating the solvent, sequentially washing with the solution of ethanol and water (10:1) and diethyl ether, and drying to obtain 78.1mg of fluorescent probe L, wherein the yield is 79.6%, and the MS is 734.81(M + H)+)。
1H NMR(300MHz,DMSO-d6)δ1.13-1.15(t,12H)，2.51-2.56(m,4H)，3.39-3.41(m，8H)，4.36(t，4H)，6.13(s，2H)，6.19-6.84(m，4H)，7.25-7.83(m，6H)，8.0(bs，1H)，11.0(bs，1H)，11.8(bs，1H)。
Example 2 fluorescence spectroscopic measurement of fluorescent probe L:
preparing a fluorescence spectrum determination solution of a fluorescent probe L, and preparing 1.0 by taking deionized water as a solvent×10-3The solution of the fluorescent probe L in mol/L is then diluted to 1.0X 10 by acetic acid-sodium acetate buffer solution (10mmol/L, pH 3.8)- 5mol/L; 2mL of the solution was taken at a concentration of 1.0X 10-5The solution of the fluorescent probe L in mol/L was added to 100. mu.L of the solution of the fluorescent probe L in a concentration of 1.0X 10-3mol/L of various ions (Pb)2+、Zn2+、Cu2+、Fe2+、Fe3+、Cd2+、Mn2+、Co2+、Ni2+、Cr3+、Ag+、Ba2+、Sr2+、Mg2+、Hg2+) After shaking the solution, the fluorescence emission spectrum was measured at an excitation wavelength of λ 535nm (see fig. 1), and as a result, the fluorescence intensity of the fluorescent probe L was found to be weak; adding Pb2+Then, the fluorescence intensity of the fluorescent probe L significantly increases at 598nm (λ 535nm), and the change in fluorescence intensity is small when other ions are added.
Example 3 fluorescence spectrum titration experiment and determination of detection limits for fluorescent probe L:
2mL of the solution was taken at a concentration of 1.0X 10-5mol/L of fluorescent probe L in acetic acid-sodium acetate buffer solution (10mmol/L, pH 3.8), addition of different concentrations of metal ions was found to follow Pb2+The fluorescence intensity of the fluorescent probe L at 598nm is gradually enhanced when the concentration is increased, and when the concentration is Pb2+The concentration reached the highest value at 60 times the concentration of fluorescent probe L (FIG. 2), indicating that the highest saturation factor was reached. The ion concentration and the fluorescence intensity are in a good linear relationship. Wherein the fluorescent probes L are for Pb2+Has a detection limit of 2.8 × 10-8mol/L，R＝0.9982。
EXAMPLE 4 Pair Pb of fluorescent Probe L2+Selectivity and immunity to ion recognition:
2mL of the solution was taken at a concentration of 1.0X 10-5mol/L of fluorescent probe L in acetic acid-sodium acetate buffer solution (10mmol/L, pH 3.8), and then 100. mu.L of 1.0X 10-3mol/L of ionic Pb2+The solution was shaken up and the fluorescence emission spectrum was measured at an excitation wavelength of λ 535nm, which indicated the addition of other metal ions such as: zn2+、Cu2+、Fe2+、Fe3+、Cd2+、Mn2+、Co2+、Ni2+、Cr3+、Ag+、Ba2+、Sr2+、Mg2+、Hg2+The influence on the fluorescence emission and visible absorption intensity is small, which indicates that the fluorescent probe L has a small influence on Pb2+The identification has higher selectivity and better anti-interference capability (figure 3).
The above description is only exemplary of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (8)

1. Rapid and high-sensitivity detection of Pb in acidic aqueous solution2+The ion fluorescence enhancement type probe is characterized by having the following structural formula:
Figure FDA0002789799530000011
2. rapid and high-sensitivity detection of Pb in acidic aqueous solution2+The preparation method of the ion fluorescence enhanced probe is characterized by comprising the following reaction steps:
the method comprises the following steps: reacting the compound 1 with monomethyl succinate in an organic solvent to obtain a compound 2,
Figure FDA0002789799530000012
step two: hydrolyzing the compound 2 under the action of alkali to obtain a compound 3,
Figure FDA0002789799530000013
step three: the compound 3 and the compound 4 are subjected to condensation reaction in an organic solvent to obtain a compound 5,
Figure FDA0002789799530000021
step four: hydrolyzing the compound 5 under the action of alkali to obtain a fluorescent probe L,
Figure FDA0002789799530000022
3. pb according to claim 22+The preparation method of the ion fluorescence enhancement type probe is characterized in that the organic solvent in the first step and the third step is an alcohol solvent.
4. Pb according to claim 22+The preparation method of the ion fluorescence enhancement type probe is characterized in that the organic solvent in the first step and the third step is ethanol.
5. Pb according to claim 22+The preparation method of the ion fluorescence enhancement type probe is characterized in that the alkali in the second step and the fourth step is NaOH.
6. The fluorescent probe of claim 1 for rapid detection of Pb in acidic aqueous solutions2+Application of ions.
7. The fluorescent probe of claim 6 for rapid detection of Pb in acidic aqueous solution2+Use of ions, characterized in that the pH of an acidic aqueous solution is between 1 and 6.
8. The fluorescent probe of claim 6 for rapid detection of Pb in acidic aqueous solution2+Use of ions, characterized in that the pH of an acidic aqueous solution is 3-4.
CN202011310937.0A 2021-01-07 2021-01-07 Detection of Pb in acidic aqueous solutions2+Fluorescent probe for ions and preparation method thereof Pending CN112358486A (en)

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Citations (6)

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CN104087287A (en) * 2014-06-23 2014-10-08 昆山东大智汇技术咨询有限公司 Water-soluble polymer pH fluorescent probe PRAM and preparation method thereof
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US20200392148A1 (en) * 2019-06-12 2020-12-17 King Fahd University Of Petroleum And Minerals Chemosensor and a method of detecting palladium ions

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CN101914102A (en) * 2010-07-16 2010-12-15 中国科学院烟台海岸带研究所 Derivative L of rhodamine B, preparation thereof and use thereof
WO2015139263A1 (en) * 2014-03-20 2015-09-24 The Procter & Gamble Company Stannous fluorescent probe
CN104087287A (en) * 2014-06-23 2014-10-08 昆山东大智汇技术咨询有限公司 Water-soluble polymer pH fluorescent probe PRAM and preparation method thereof
CN107129503A (en) * 2017-05-06 2017-09-05 渤海大学 A kind of quick detection Cr in aqueous3+The preparation method and applications of the enhanced probe of ion fluorescence
CN110256452A (en) * 2019-05-10 2019-09-20 安徽工业大学 A kind of preparation and its application of 1- methyl piperazine rhodamine amide
US20200392148A1 (en) * 2019-06-12 2020-12-17 King Fahd University Of Petroleum And Minerals Chemosensor and a method of detecting palladium ions

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宿甜甜: "罗丹明类荧光探针用于环境Cu2+、Pb2+检测及机理研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 *

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Application publication date: 20210212