CN115594856A - Preparation method and application of ratiometric fluorescent probe - Google Patents
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Abstract
The invention relates to a preparation method of a ratiometric fluorescent probe, which comprises the following steps: TCPP, copper nitrate and fluorescein isothiocyanate are used as raw materials to carry out two-step solvothermal reaction, thus obtaining the fluorescent material. The fluorescent probe disclosed by the invention has the fluorescence of fluorescein FITC, the fluorescence intensity of FITC changes in a small range after the fluorescent probe reacts with hydrogen sulfide, the fluorescence of porphyrin TCPP is rapidly enhanced, the maximum emission wavelength is 650nm (lambda ex =420 nm), and the fluorescent probe has an excellent detection effect.
Description
Technical Field
The invention belongs to the technical field of chemical analysis and detection, and particularly relates to a preparation method and application of a ratiometric fluorescent probe.
Background
The information in this background section is only for enhancement of understanding of the general background of the invention and is not necessarily to be construed as an admission or any form of suggestion that this information forms the prior art that is already known to a person of ordinary skill in the art.
Hydrogen sulfide is highly corrosive and irritant, has great harm to human bodies, and is urgently detected effectively. The traditional detection methods of hydrogen sulfide include absorption spectroscopy, electrochemical methods, gas chromatography, sulfur precipitation methods and the like, and the methods are complex in pretreatment process of detection standard samples and generally damage the samples, so that the application of the methods in the aspect of hydrogen sulfide detection is limited. The fluorescence probe method can visually reflect the existence of ions through the change of fluorescence intensity, has little destructiveness to a sample, but the fluorescence probe in the prior art needs longer response time for the detection of hydrogen sulfide, has complex synthesis process and low sensitivity, has certain limitation on the detection range, is limited by field equipment in use, cannot be produced on a large scale, has poor stability, and influences the detection effect by the fluorescence probe stored for a short time.
Disclosure of Invention
In order to overcome the problems, the invention designs the ratiometric fluorescent probe which can rapidly and sensitively detect the hydrogen sulfide and has the advantages of low detection limit, high sensitivity, small using amount and wide detection range.
Based on the research results, the present disclosure provides the following technical solutions:
in a first aspect of the present disclosure, a method for preparing a ratiometric fluorescent probe is provided, which includes: TCPP, copper nitrate and fluorescein isothiocyanate are used as raw materials, and two-step solvothermal reaction is carried out to obtain the fluorescent dye.
In a second aspect of the present disclosure, a ratiometric fluorescent probe prepared by the above preparation method is provided.
In a third aspect of the invention, the ratiometric fluorescent probes described above are provided for use in the identification and detection of hydrogen sulfide molecules.
In a fourth aspect of the present invention, a method for rapidly detecting a concentration of hydrogen sulfide is provided, which includes: and adding the fluorescent probe into the solution to be detected, uniformly mixing, detecting the fluorescent response, obtaining the fluorescence intensity ratio, and calculating the concentration of hydrogen sulfide to obtain the fluorescent probe.
One or more specific embodiments of the present disclosure achieve at least the following technical effects:
(1) The invention adopts a two-step solvothermal method, and practices prove that the structures of the fluorescent probes prepared by the one-step solvothermal method and the two-step solvothermal method have certain difference, so that the sensitivity, stability, detection range and response time in the aspect of hydrogen sulfide detection are different, the FITC peak of the product prepared by the one-step solvothermal method is weak, and the FITC in the two-step method is combined on the basis of the MOF generated in the first step, so that the combination is more stable, and the fluorescence of the FITC is stronger. The invention discovers that the fluorescent probe prepared by the two-step solvothermal method has the advantages of high sensitivity, good stability, short response time and wide detection range.
(2) The MOF material Cu-TCPP (FITC) is synthesized by a two-step solvothermal method, and porphyrin TCPP in the MOF material is transferred to metal ion Cu due to electron transfer 2+ The above (LMCT effect) causes fluorescence quenching. The material can recognize and combine hydrogen sulfide molecules, and then the fluorescence is recovered as a response signal. The technical method has the advantages of high detection speed, high sensitivity, simple operation, low cost and the like.
(3) The synthesis time of the porphyrin-based MOF is short, the raw materials are cheap and easy to obtain, and the dosage is very small. The porphyrin ligand in the material determines the fluorescence property of the material to be outstanding. The self fluorescence of the MOF probe formed by modification can be almost completely masked, and the fluorescence intensity is rapidly enhanced after the MOF probe reacts with hydrogen sulfide for several seconds, and the enhancement amplitude is large. The MOF material has the advantages of low detection limit (3.2 mu M), high sensitivity, small dosage (10 mu g/mL), wide detection range (5-400 mu M) and strong ratiometric fluorescence anti-interference performance.
(4) The stability study of the fluorescent probe shows that the material does not influence the detection of the probe on hydrogen sulfide after being stored for 150 days, and has excellent stability.
(5) The method has the advantages of simple operation method, low cost, universality and easy large-scale generation.
Drawings
The accompanying drawings, which are included to provide a further understanding of the disclosure, illustrate embodiments of the disclosure and together with the description serve to explain the disclosure and are not to limit the disclosure.
FIG. 1 is a diagram of the synthesis and sensing mechanism of Cu-TCPP (FITC) prepared in example 1;
FIG. 2 is a UV spectrum of each material of example 1, wherein (1) the UV spectrum of FITC, (2) the UV spectrum of TCPP, and (3) the UV spectrum of Cu-TCPP (FITC); (4) fluorescence spectra of the two-step synthesis method and the one-step synthesis method.
FIG. 3 is a graph showing the fluorescence spectra (1), the fluorescence intensity ratio and the hydrogen sulfide concentration in different hydrogen sulfide concentrations of Cu-TCPP (FITC) prepared in example 1 as a linear relationship (2).
Detailed Description
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the disclosure. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of example embodiments according to the present disclosure. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof, unless the context clearly indicates otherwise.
As introduced in the background art, the existing fluorescent probe needs longer response time for detecting hydrogen sulfide, has complex synthesis process, low sensitivity and a certain limitation on detection range, is limited by site equipment in use, and cannot be produced in a large scale. Therefore, the invention provides a preparation method of the ratiometric fluorescent probe, and the prepared fluorescent probe MOF for detecting hydrogen sulfide has the advantages of large fluorescence enhancement amplitude, high sensitivity, low detection limit, small usage amount, strong ratiometric fluorescence anti-interference performance and the like.
In a first aspect of the present disclosure, a method for preparing a ratiometric fluorescent probe is provided, which includes: TCPP, copper nitrate and fluorescein isothiocyanate are used as raw materials to carry out two-step solvothermal reaction, thus obtaining the fluorescent material.
In one exemplary embodiment, the two solvothermal reaction process is: TCPP and copper nitrate are subjected to a first solvothermal reaction, and then FITC is added for a second solvothermal reaction; further, the specific conditions of the first solvothermal step are as follows: the heating time is 85-100 ℃, the heating time is 3-4.5h, preferably, the heating time is 90 ℃, and the heating time is 4h; the specific solvothermal conditions of the second step are as follows: stirring and reacting at 30-50 ℃ for 20-28h, preferably at 35 ℃ for 24h.
In one exemplary embodiment, the mass ratio of TCPP, copper nitrate and fluorescein isothiocyanate is: (1.5-2.6) mg, (5.4-7.5) mg, (3.5-5.8) mg, preferably 2mg.
In a typical embodiment, the specific steps of using TCPP, copper nitrate and fluorescein isothiocyanate as raw materials are as follows: TCPP is dissolved in N, N-dimethylformamide, copper nitrate is dissolved in water, benzoic acid is added after mixing, heating and stirring are carried out, and FITC is added subsequently.
In a typical embodiment, the ratio of TCPP to N, N-dimethylformamide is (1.5-2.6) mg (8-15) ml, preferably 2mg; the ratio of the copper nitrate to the water is (5.4-7.5) mg, (0.6-1.4) ml, preferably 6.3mg; the mass of the benzoic acid is 7-12mg, preferably 10mg.
In a typical embodiment, the reaction solution after the first solvent heating and stirring process is further subjected to cooling, centrifugation and washing, wherein the centrifugation speed is 10000r/min, and the reaction solution is washed 3-5 times by ethanol.
In a typical embodiment, the wash product is added to ethanol, followed by addition of an ethanol solution of sodium hydroxide, followed by addition of FITC, followed by homogeneous mixing. Further, the mass of the FITC is 3.5-5.8mg, and the volume of the ethanol is 2.5-5.5ml, preferably 4ml; the concentration of the sodium hydroxide ethanol solution is 8-12mM, the volume is 0.2-0.6ml, and preferably, the concentration of the sodium hydroxide solution is 10mM, and the volume is 0.4ml.
In a typical embodiment, the Cu-TCPP (FITC) is obtained after cooling, washing and drying after the second solvothermal reaction, and further, the Cu-TCPP is washed for 5 to 6 times by ethanol and dried for 10 to 12 hours in vacuum.
In a second aspect of the present disclosure, a ratiometric fluorescent probe prepared by the above preparation method is provided.
The fluorescent probe disclosed by the invention has the fluorescence of fluorescein FITC, the fluorescence intensity of FITC changes in a small range after the fluorescent probe reacts with hydrogen sulfide, the fluorescence of porphyrin TCPP is rapidly enhanced, the maximum emission wavelength is 650nm (lambda ex =420 nm), and the fluorescent probe has an excellent detection effect.
In a third aspect of the invention, the application of the ratiometric fluorescent probe in the identification and detection of hydrogen sulfide molecules is provided, and further, the application is to use the fluorescent probe in an aqueous system, an organic solvent system or an organism for the identification and detection of hydrogen sulfide molecules.
In a fourth aspect of the present invention, a method for rapidly detecting a concentration of hydrogen sulfide is provided, which includes: adding a fluorescent probe into the solution to be detected, uniformly mixing, detecting the fluorescent response, obtaining the fluorescence intensity ratio, and calculating the concentration of hydrogen sulfide to obtain the fluorescent probe; further, after a fluorescent probe solution is added into a solution to be detected, the fluorescence intensity is detected, wherein the probe solution is an ethanol solution of Cu-TCPP (FITC), and the solution to be detected is a solution prepared by adding hydrogen sulfide into HEPES buffer solution; further, the final concentration of the Cu-TCPP (FITC) is 10 mu g/mL, the excitation wavelength is 420nm, the emission wavelengths are selected to be 525nm and 650nm, and the content range of hydrogen sulfide is 5-400 mu M.
Further, according to the ratio of the measured 650nm fluorescence intensity to the measured 525nm fluorescence intensity, a corresponding relation between the concentration of hydrogen sulfide and the ratio of the fluorescence intensity is established.
In a typical embodiment, the buffer solution has a pH of 7.2 and a concentration of 0.1M; the volume of the solution to be detected is 2ml; further, the mixture is stirred uniformly in an oscillating mode.
In order to make the technical solutions of the present disclosure more clearly understood by those skilled in the art, the technical solutions of the present disclosure will be described in detail below with reference to specific examples and comparative examples.
Example 1
As shown in FIG. 1, the preparation process of Cu-TCPP (FITC) is as follows:
(1) 2mg of TCPP was dissolved in 12ml of N, N-Dimethylformamide (DMF), 6.3mg of copper nitrate was dissolved in 1ml of H 2 O, 10mg of benzoic acid was added thereto, and the mixture was heated and stirred at 90 ℃ for 4 hours.
(2) The reaction solution cooled to room temperature was centrifuged (rotation speed 10000 r/min) and washed with ethanol 3 times.
(3) The product obtained in (2) was added to ethanol (4 mL) and an ethanol solution of sodium hydroxide (10 mM,0.4 mL), FITC (5 mg) was added, and the mixture was stirred at 35 ℃ for 24 hours.
(4) Cool to room temperature and wash with ethanol 5 times. After drying in vacuo for 10h, cu-TCPP (FITC) was obtained.
The MOF probe Cu-TCPP (FITC) prepared in example 1 was subjected to structural analysis using ultraviolet spectroscopy. As shown in FIG. 2 (3), it can be seen from FIG. 2 (3) that the MOF has porphyrin characteristic peaks at 419.4nm and 544 nm. Only 419nm of Sore band in MOF confirms that porphyrin is uniformly distributed in MOF, no molecular level dimer is generated, the red shift of the Sore band relative to 415nm TCPP porphyrin peak and the appearance of 544nm new Q band and the disappearance of 4 original Q bands between 500nm and 700nm confirm that the porphyrin center is combined with copper ions. In addition, the presence of fluorescein FITC in the material Cu-TCPP (FITC) was also confirmed including the high absorbance peak between 200nm and 250nm in MOF. As can be seen from FIG. 2 (4), the peak of FITC of the product prepared by the one-step solvothermal method is very weak, while FITC is combined on the basis that MOF is generated in the first step in the two-step method, so that the combination is more stable, and FITC has stronger fluorescence.
Example 2
(1) 1.5mg of TCPP was dissolved in 15ml of N, N-Dimethylformamide (DMF), 5.7mg of copper nitrate was dissolved in 1.2ml of H 2 O, after mixing the two, 8mg of benzoic acid was added, and the mixture was heated and stirred at 100 ℃ for 3 hours.
(2) The reaction solution cooled to room temperature was centrifuged (rotation speed 10000 r/min) and washed with ethanol 3 times.
(3) The product obtained in (2) was added to ethanol (3 mL) and an ethanol solution of sodium hydroxide (12mM, 0.2mL), FITC (4 mg) was added, and the mixture was stirred at 40 ℃ for 20h.
(4) Cool to room temperature and wash with ethanol 5 times. After drying in vacuo for 10h, cu-TCPP (FITC) was obtained.
Example 3
(1) 2.5mg of TCPP was dissolved in 10ml of N, N-Dimethylformamide (DMF), and 7.2mg of copper nitrate was dissolved in 0.8ml of H 2 O, 12mg of benzoic acid was added thereto, and the mixture was heated at 85 ℃ with stirring for 4.5 hours.
(2) The reaction solution cooled to room temperature was centrifuged (rotation speed 10000 r/min) and washed with ethanol 3 times.
(3) The product obtained in (2) was added to ethanol (5 mL) and an ethanol solution of sodium hydroxide (8 mM,0.6 mL), FITC (5.5 mg) was added, and the mixture was stirred at 50 ℃ for 24 hours.
(4) Cooled to room temperature and washed 5 times with ethanol. After drying in vacuo for 10h, cu-TCPP (FITC) was obtained.
Example 4
The Cu-TCPP (FITC) probe prepared in the example 1 is dispersed in ethanol in an ultrasonic mode for standby application, the concentration of the probe solution is 1mg/mL, hydrogen sulfide is added into HEPES buffer solution to prepare a solution to be tested, the concentration of the hydrogen sulfide is 5-400 mu M, the pH value of the buffer solution is 7.2, and the concentration of the buffer solution is 0.1M. And adding 2mL of the solution to be detected into 20 mu L of probe solution, oscillating for 5min at normal temperature, transferring to a quartz cuvette, and measuring the fluorescence spectrum of 600-800 nm under the excitation wavelength of 420 nm.
The detection result is shown in (1) in fig. 3, after the probe is added into a buffer solution of low-concentration hydrogen sulfide, weak fluorescence can be seen under a 365nm ultraviolet lamp, because a small amount of hydrogen sulfide is combined with copper ions at the center of porphyrin, the transfer of metal charges by a ligand is prevented, and the fluorescence is weakly recovered. When the concentration of hydrogen sulfide is higher, copper sulfide precipitation is generated by further combining metal copper ions, the LMCT effect is inhibited, and further fluorescence is enhanced violently.
The fluorescent probe of the invention shows high sensitivity to the detection of hydrogen sulfide. The fluorescence intensity of the probe solution increases with increasing hydrogen sulfide concentration. At a hydrogen sulfide concentration of about 400. Mu.M, the fluorescence intensity peaked. In the range of 0-400 mu M hydrogen sulfide concentration, the fluorescence intensity ratio of the probe solution has a good linear relation with the hydrogen sulfide concentration. The detection limit of the fluorescent probe to the liquid to be detected is 3.2 mu M.
As the concentration of the hydrogen sulfide in the detection solution is increased continuously, the fluorescence intensity of the solution is increased continuously, and the fluorescence intensity reaches a peak value at the concentration of the hydrogen sulfide of about 400 mu M. The ratio of the hydrogen sulfide concentration to the fluorescence intensities at 650nm and 525nm is well linear in the range of 0 to 400. Mu.M hydrogen sulfide concentration (FIG. 3 (2)), and the linear equation is y =0.02233x-0.42082 (R =0.02233 x-0.42082) 2 = 0.993), linear range 5-400 μ M. The lowest detection limit was 3.2. Mu.M. The MOF material Cu-TCPP (FITC) is low in lower limit of fluorescence detection of hydrogen sulfide, wide in detection range and high in application value.
Although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications may be made to the embodiments described above, or equivalents may be substituted for elements thereof. 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 (10)
1. A method for preparing a ratiometric fluorescent probe, comprising: TCPP, copper nitrate and fluorescein isothiocyanate are used as raw materials to carry out two-step solvothermal reaction, thus obtaining the fluorescent material.
2. The preparation method according to claim 1, wherein the two solvothermal reaction processes are as follows: TCPP and copper nitrate are subjected to a first solvothermal reaction, and then FITC is added for a second solvothermal reaction; further, the specific conditions of the first solvothermal step are as follows: the heating time is 85-100 ℃ and 3-4.5h, preferably, the heating time is 90 ℃ and 4h; the specific solvothermal conditions of the second step are as follows: stirring and reacting at 30-50 ℃ for 20-28h, preferably at 35 ℃ for 24h.
3. The preparation method of claim 1, wherein the steps of using TCPP, cupric nitrate and fluorescein isothiocyanate as raw materials are as follows: dissolving TCPP in N, N-dimethylformamide, dissolving copper nitrate in water, mixing, adding benzoic acid, heating, stirring, and adding FITC;
further, the ratio of TCPP to N, N-dimethylformamide is (1.5-2.6) mg (8-15) ml, preferably 2mg; the ratio of the copper nitrate to the water is (5.4-7.5) mg, (0.6-1.4) ml, preferably 6.3mg; the mass of the benzoic acid is 7-12mg, preferably 10mg.
4. The preparation method according to claim 1, wherein the reaction solution after the first solvothermal heating and stirring is further subjected to cooling, centrifugation and washing; further, adding the washing product into ethanol, then adding an ethanol solution of sodium hydroxide, then adding FITC, and then uniformly mixing; further, the mass of the FITC is 3.5-5.8mg, and the volume of the ethanol is 2.5-5.5ml, preferably 4ml; the concentration of the sodium hydroxide ethanol solution is 8-12mM, the volume is 0.2-0.6ml, and the preferred concentration of the sodium hydroxide solution is 10mM, and the volume is 0.4ml.
5. The preparation method according to claim 1, wherein the Cu-TCPP (FITC) is obtained after cooling, washing and drying after the second solvothermal reaction, and further, the Cu-TCPP is washed for 5 to 6 times by ethanol and dried for 10 to 12 hours in vacuum.
6. A ratiometric fluorescent probe prepared by the method of any one of claims 1 to 5.
7. The use of the ratiometric fluorescent probe of claim 6 to identify and detect hydrogen sulfide molecules, further wherein the use is in an aqueous system, an organic solvent system, or an organism.
8. A method for rapidly detecting the concentration of hydrogen sulfide is characterized by comprising the following steps: adding the ratiometric fluorescent probe of claim 6 into a solution to be detected, uniformly mixing, detecting fluorescence response, obtaining a fluorescence intensity ratio, and calculating the concentration of hydrogen sulfide to obtain the ratiometric fluorescent probe; and further, after adding a fluorescent probe solution into a solution to be detected, detecting the fluorescence intensity, wherein the probe solution is an ethanol solution of Cu-TCPP (FITC), and the solution to be detected is a solution prepared by adding hydrogen sulfide into HEPES buffer solution.
9. The method for rapidly detecting the concentration of hydrogen sulfide as claimed in claim 8, wherein the final concentration of Cu-TCPP (FITC) is 10 μ g/mL, the excitation wavelength is 420nm, the emission wavelength is selected from 525nm and 650nm, and the content of hydrogen sulfide is in the range of 5-400 μ M.
10. The method for rapidly detecting the concentration of hydrogen sulfide as claimed in claim 8, wherein the corresponding relationship between the concentration of hydrogen sulfide and the ratio of fluorescence intensity is established according to the ratio of the measured fluorescence intensities at 650nm and 525 nm.
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