CN115010675B - Quick detection I - Preparation method and application of ionic covalent organic framework fluorescent probe - Google Patents
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Abstract
Quick detection I ‑ 1,3, 5-trimethyl-phloroglucinol is dissolved in mesitylene, 2, 5-diaminobenzoic acid is dissolved in 1, 4-dioxane, the two solutions are uniformly mixed under ultrasonic condition, azobenzene is added into the mixed solution, acetic acid is used as a catalyst, and N is introduced after repeated freeze thawing 2 Degassing, reacting at 120deg.C for 3 days, centrifuging to remove solvent, grinding for 1 hr, adding into isopropanol, stirring for 1 hr under 365nm ultraviolet irradiation, and pulverizing with ultrasonic cell pulverizer for 3 hr to obtain covalent organic frame fluorescent probeThe advantages are that: the prepared covalent organic framework probe has small particle size, has good sensitivity and strong anti-interference capability, can be uniformly dispersed in solution, and has good anti-interference effect on I ‑ The identification of (c) can be performed in a solution system and is applicable to various pH conditions.
Description
Technical Field
The invention belongs to the field of iodine ion detection, and in particular relates to a rapid detection I - Preparation method and application of ionic covalent organic framework fluorescent probe.
Background
Iodine is an important trace element and plays a vital role in maintaining and regulating the stability of the intracellular environment of the human body. The lack or excess of iodine content can cause certain damage to the body and cause related thyroid diseases such as thyromegaly, hypothyroidism and hyperthyroidism, and iodide ion is also a key factor in controlling skeletal and brain developmental metabolism. As one of the micronutrients necessary for human growth, the development of an analytical method for iodide ions has important research significance. Heretofore, there are various analytical methods for detecting iodide ions, such as anion exchange chromatography, microfluidic flow injection, capillary electrophoresis, potentiometric titration, and the like. Although these methods can meet the requirements of measurement under certain conditions, there are obvious drawbacks such as relatively complex pretreatment of samples, relatively high test cost, and long detection time. Therefore, it is important to develop an analytical method for rapid and efficient detection of iodide ions. In recent years, fluorescence spectroscopy has received extensive attention from researchers due to its high sensitivity, good selectivity, simple operation, low cost, and the like.
The Covalent Organic Framework (COF) material is a novel porous material, and the COFs has the advantages of low density, large specific surface area, adjustable pore diameter, high stability and the like, so that the COFs has good application prospects in the aspects of gas storage, adsorption, photoelectricity, catalysis, chemical sensing and the like. They have unique advantages over traditional fluorescence sensors, such as open docking sites, permanent porosity, ultra low density, excellent thermal stability. However, most COF materials are prone to aggregate and precipitate in water and most organic solvents, which greatly affects the practical application of COF.
Disclosure of Invention
The invention aims to solve the technical problems of providing a preparation method and application of a covalent organic framework probe which has good sensitivity, strong anti-interference capability and can rapidly detect I-ions, wherein the prepared covalent organic framework probe has small particle size, can be uniformly dispersed in a solution and has the effect of detecting I - The identification of (2) can be performed in a solution system, andis suitable for various pH conditions to increase the application range of detection.
The technical scheme of the invention is as follows:
a preparation method of a rapid detection I-ion covalent organic framework probe has the following reaction formula:
the method comprises the following specific steps:
dissolving 1,3, 5-trimethyl-phloroglucinol in mesitylene to obtain a solution I, dissolving 2, 5-diaminobenzoic acid in 1, 4-dioxane to obtain a solution II, uniformly mixing the solution I and the solution II under ultrasonic conditions, wherein the molar ratio of the 1,3, 5-trimethyl-phloroglucinol to the 2, 5-diaminobenzoic acid is 1:1.5, adding azobenzene into the mixed solution, the molar ratio of the 1,3, 5-trimethyl-phloroglucinol to the azobenzene is 1:1.5, and taking acetic acid as a catalyst, and repeatedly freezing and thawing before introducing N 2 Degassing, reacting at 120deg.C for 3 days, centrifuging to remove solvent, grinding for 1 hr, adding into isopropanol, irradiating with 365nm ultraviolet ray while stirring for 1 hr, pulverizing with ultrasonic cell pulverizer for 3 hr, washing with dichloromethane, methanol and tetrahydrofuran for 3 times, centrifuging, and naturally air drying to obtain covalent organic frame fluorescent probe
Further, the concentration of the acetic acid is 6mol/L.
The covalent organic framework fluorescent probe is used for rapidly detecting I - Use in an ionic fluorescent probe.
Covalent organic framework fluorescent probe is in short-term test I - Use of an ionic fluorescent probe capable of selectively recognizing I - The solvent used for the ions is an aqueous tetrahydrofuran solution.
Further, the tetrahydrofuran aqueous solution is prepared by tetrahydrofuran and deionized water according to a volume ratio of 1:1.
Covalent organic framework fluorescent probe is in short-term test I - The application of the ionic fluorescent probe comprises the steps of adding a covalent organic framework fluorescent probe into tetrahydrofuran aqueous solution, and uniformly stirring to obtain a covalent organic framework fluorescent probe dispersion liquid with the concentration of 0.01 mg/mL-1 mg/mL; adding a covalent organic framework fluorescent probe dispersion liquid into a detection water sample, measuring the fluorescence emission intensity of the detection water sample at the excitation wavelength of lambda=230 nm, and weakening the fluorescence intensity at 317nm, wherein the detection sample contains I - Ions.
Further, the dispersion of the covalent organic framework fluorescent probe was 0.05mg/mL.
The invention has the beneficial effects that:
1) The fluorescent probe TpPa-COOH COF pair I - Has excellent selectivity and strong specificity, and fluorescent probes TpPa-COOH COF and I - After the action, the fluorescent light is weakened, and the I is realized - Has high detection sensitivity and other common anions such as F - ，Cl - ，Br - ，SCN - ，PO 4 3- ，S 2 O 3 2- ，H 2 PO 4 2- ，N 3- ，SO 3 2- ，SO 4 2- ，CH 3 COO - ，NO 2 - ，CO 3 2- ，HCO 3 2- ，S 2- ，CN - ，HSO 3 - The action fluorescent signal is basically unchanged, and the anti-interference capability is strong.
2) During synthesis, the covalent organic framework probe is prepared under the ultraviolet irradiation condition of azobenzene, and the configuration change of azobenzene under the ultraviolet irradiation condition promotes the COF dispersion of the probe to obtain particles with a diameter of hundreds of nanometers, and the particles are uniformly dispersed in a solution, so that stable dispersion liquid can be used for fluorescence detection.
3) The fluorescent probe TpPa-COOH COF has nanometer scale and is shown in C 2 H 5 OH/H 2 O (V: V=1:1) solution, THF/H 2 O (V: V=1:1) can be uniformly dispersed in the solution, and can realize the reaction of the solution in the solution systemI - And is suitable for various pH conditions, thereby increasing the detection accuracy and application range.
Drawings
FIG. 1 is a Fourier infrared spectrum of a fluorescent probe TpPa-COOH COF of the present invention;
FIG. 2 is a Raman spectrum of a fluorescent probe TpPa-COOH COF of the invention;
FIG. 3 is an X-ray photoelectron spectrum of a fluorescent probe TpPa-COOH COF of the present invention;
FIG. 4 is a scanning electron microscope SEM image of the fluorescent probe TpPa-COOH COF of the present invention;
FIG. 5 shows the fluorescent probe TpPa-COOH COF of the present invention in THF/H 2 Adding fluorescence spectra of different anions into the O (V: V=1:1) solution;
FIG. 6 shows that the fluorescent probe TpPa-COOH COF of the present invention is at I - And a plot of fluorescence emission intensity in the presence of other metal ions;
FIG. 7 shows the fluorescent probe TpPa-COOH COF of the present invention in THF/H 2 I in O (V: v=1:1) solution - Is a fluorescence titration spectrum of (2);
FIG. 8 shows the addition of TpPa-COOH COF of the fluorescent probe of the invention to I under different pH conditions - And (5) a change chart of fluorescence intensity before and after ions.
Detailed Description
The invention will be further illustrated by, but is not limited to, the following examples.
Example 1
Synthesis of covalent organic framework fluorescent probe TpPa-COOH COFThe reaction formula is as follows:
1,3, 5-Triacyl-phloroglucinol (Tp, 0.21g,1 mmol) was dissolved in 18mL of mesitylene, and 2, 5-diaminobenzoic acid (Pa-COOH, 0.23g,1.5 mmol) was dissolved in 18mL of 1, 4-dioxaneMixing the two solutions, performing ultrasonic dissolution, adding azobenzene (0.273 g,1.5 mmol) into the mixed solution, dropwise adding 6mL of 6M acetic acid as catalyst, freezing and thawing, and introducing N 2 Repeatedly degassing, reacting at 120deg.C for 3 days, centrifuging to remove solvent, grinding for 1 hr, adding into 500mL isopropanol, irradiating with 365nm ultraviolet ray while stirring for 1 hr, and pulverizing with ultrasonic cell pulverizer for 3 hr to make dispersion in solution more uniform; and after crushing, respectively cleaning with dichloromethane, methanol and tetrahydrofuran for three times, centrifuging, and airing at room temperature to obtain the brick red powder covalent organic framework fluorescent probe TpPa-COOH COF.
Basic data of the covalent organic framework fluorescent probe TpPa-COOH COF:
fourier transform Infrared Spectroscopy (FT-IR) at 1568cm -1 And 1200cm -1 Strong peaks are shown corresponding to c=c stretch and C-N stretch bands, respectively, in ketone form. Compared to the two monomers, tp, c=o stretch tape (1643 cm -1 ) And Pa-COOH (3300 cm) -1 ～3400cm -1 ) Disappeared, indicating that TpPa-COOH COF was successfully prepared (see fig. 1).
1392cm in Raman Spectroscopy -1 、1604cm -1 And 1667cm -1 The peak at which corresponds to the stretching vibration of the benzene ring and amine functions, respectively, at 1604cm -1 The raman band at corresponds to the c=c stretching vibration of the benzene ring in COF structure, 1667cm -1 The raman stretch signal at this point is related to c=o of the keto-enamine bond in the COF structure (see fig. 2).
The chemical structure of TpPa-COOH COF was further analyzed by X-ray photoelectron spectroscopy, and peaks of signals of C1s, N1s and O1s were found in XPS, thereby confirming the formation of novel compounds (see FIG. 3).
SEM images of scanning electron microscopy showed that the synthesized probe TpPa-COOH COF had a small particle size, as small as a few hundred nanometers (fig. 4).
Comparative example 1
1,3, 5-Triacyl phloroglucinol (Tp, 0.21g,1 mmol) was dissolved in 18mL of mesitylene, and 2, 5-diaminobenzeneFormic acid (Pa-COOH, 0.23g,1.5 mmol) is dissolved in 18mL of 1, 4-dioxane, the two solutions are mixed for ultrasonic dissolution, 6mL of acetic acid with the concentration of 6M is dropwise added as a catalyst, and the mixture is frozen and thawed before N is introduced 2 Repeatedly degassing, reacting for 3 days at 120 ℃, centrifuging to remove the solvent after the reaction is finished, grinding for 1 hour, adding into 500mL of isopropanol, stirring for 1 hour, and crushing for 3 hours by using an ultrasonic cell crusher to ensure that the solvent is dispersed more uniformly in the solution; and after crushing, respectively cleaning with dichloromethane, methanol and tetrahydrofuran for three times, centrifuging, and airing at room temperature to obtain the covalent organic framework compound. The covalent organic framework compound has larger particles, and the particle size is between a few micrometers and tens of micrometers.
1. Fluorescence spectrometry of fluorescent probe TpPa-COOH COF of example 1 of the present invention:
the fluorescent spectrometry solution of the fluorescent probe TpPa-COOH COF of the embodiment 1 is prepared, 50mg of the TpPa-COOH COF compound is accurately weighed, 5mL of secondary distilled water is used for dissolution, and an ultrasonic cell grinder is used for crushing for 1 hour after dissolution, so that the TpPa-COOH COF is uniformly dispersed in water, and 10mg/mL of fluorescent probe dispersion liquid for testing fluorescent property is obtained for standby.
2mL of a dispersion of the fluorescent probe TpPa-COOH COF diluted to a concentration of 0.05mg/mL was taken, and 20. Mu.L of each ion (F) was added at a concentration of 50mmol/L - ，Cl - ，Br - ，I - ，SCN - ，PO 4 3- ，S 2 O 3 2- ，H 2 PO 4 2- ，N 3- ，SO 3 2- ，SO 4 2- ，CH 3 COO - ，NO 2 - ，CO 3 2- ，HCO 3 2- ，S 2- ，CN - ，HSO 3 - ) The solution is shaken up, and then the fluorescence emission spectrum of the solution is measured at the excitation wavelength of lambda=230 nm (as shown in figure 5), and the result shows that the fluorescent probe TpPa-COOH COF has strong fluorescence at 317 nm; adding I - After that, the fluorescent probe TpPa-COOH COF was weakened in fluorescence intensity at 317nm, and other ions were not found to be similarAnd similarly vary.
2. Dispersion stability of the covalent organic framework fluorescent probes TpPa-COOH COF of example 1 and comparative example 1 of the present invention in aqueous tetrahydrofuran solution
(1) Dispersion stability in aqueous tetrahydrofuran solutions
THF/H of the fluorescent probe TpPa-COOH COF of example 1 of the present invention was prepared at a concentration of 2mL, 0.01mg/mL, 0.05mg/mL, 1mg/mL, respectively 2 O (V: V=1:1) dispersion, no precipitate was precipitated at the bottom of the flask after standing at room temperature for 7 days, indicating that the probe was stably dispersible in the tetrahydrofuran aqueous solution.
THF/H of the covalent organic framework compound of comparative example 1 of the present invention was prepared at a concentration of 0.01mg/mL, 0.05mg/mL, and 1mg/mL, respectively, 2mL 2 O (V: V=1:1) mixture, and after 24 hours, a large amount of sediment is precipitated at the bottom of the bottle.
(2) Dispersion stability in ethanol solution
C for preparing 2mL of the fluorescent probe TpPa-COOH COF of example 1 of the present invention at a concentration of 0.01mg/mL, 0.05mg/mL, 1mg/mL, respectively 2 H 5 OH/H 2 O (V: V=1:1) dispersion, no precipitate was precipitated at the bottom of the flask after standing at room temperature for 7 days, indicating that the probe was stably dispersible in ethanol solution.
Preparation of 2mL of the covalent organic framework Compound C of comparative example 1 of the present invention at a concentration of 0.01mg/mL, 0.05mg/mL, 1mg/mL, respectively 2 H 5 OH/H 2 O (V: V=1:1) mixture, and after 24 hours, a large amount of sediment is precipitated at the bottom of the bottle.
3. Pair I of fluorescent probes TpPa-COOH COF of example 1 of the invention - Selectivity and tamper resistance of ion recognition:
a2 mL concentration of THF/H of the fluorescent probe TpPa-COOH COF of example 1 of the present invention was taken at 0.05mg/mL 2 O (V: V=1:1) dispersion, then 20. Mu.L of ion I having a concentration of 50mmol/L was added, respectively - The solution was shaken and its fluorescence emission spectrum was measured at excitation wavelength of λ=230 nm, the results showing the addition of other anions such as: f (F) - ，Cl - ，Br - ，I - ，SCN - ，PO 4 3- ，S 2 O 3 2- ，H 2 PO 4 2- ，N 3- ，SO 3 2- ，SO 4 2- ，CH 3 COO - ，NO 2 - ，CO 3 2- ，HCO 3 2- ，S 2- ，CN - ，HSO 3 - Has little influence on fluorescence emission and visible absorption intensity, which indicates that the fluorescent probe TpPa-COOH COF has little influence on I - A higher selectivity and a better interference immunity were identified (fig. 6).
4. Fluorescence spectrum titration experiment of fluorescent probe TpPa-COOH COF and determination of detection limit:
a2 mL concentration of THF/H of the fluorescent probe TpPa-COOH COF of example 1 of the present invention was taken at 0.05mg/mL 2 O (V: v=1:1) dispersion, I at different concentrations was added - It can be found that following I - The concentration is increased, the fluorescent intensity of the fluorescent probe TpPa-COOH COF at 317nm is gradually weakened, when I - When the concentration was increased to 1.5. Mu.M, the fluorescence intensity was almost unchanged, indicating that saturation was reached at this time. The ion concentration and fluorescence intensity are in good linear relation. Wherein the probe TpPa-COOH COF pair I - The detection limit of (C) is 0.028 mu mol/L, R 2 >0.99 (FIG. 7).
5. The fluorescent probe TpPa-COOH COF has detection performance under different acid-base conditions:
a2 mL concentration of THF/H of the fluorescent probe TpPa-COOH COF of example 1 of the present invention was taken at 0.05mg/mL 2 O (V: V=1:1) dispersion liquid is added with HCl or NaOH to prepare different pH values respectively, and the fluorescent intensity of the probe TpPa-COOH COF is very high within the pH value range of 1-13; at the time of adding I - After that, the fluorescence intensity is remarkably reduced and relatively stable within the pH value range of 1-13. Experimental results show that in the pH range of 1-13, the probe TpPa-COOH COF can be used for detecting I - Has a better response (fig. 8).
The above is only a specific embodiment of the present invention, and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. Quick detection I - The preparation method of the ionic covalent organic framework fluorescent probe is characterized by comprising the following steps of:
the method comprises the following specific steps:
dissolving 1,3, 5-trimethyl-phloroglucinol in mesitylene to obtain a solution I, dissolving 2, 5-diaminobenzoic acid in 1, 4-dioxane to obtain a solution II, uniformly mixing the solution I and the solution II under ultrasonic conditions, wherein the molar ratio of the 1,3, 5-trimethyl-phloroglucinol to the 2, 5-diaminobenzoic acid is 1:1.5, adding azobenzene into the mixed solution, the molar ratio of the 1,3, 5-trimethyl-phloroglucinol to the azobenzene is 1:1.5, and taking acetic acid as a catalyst, and repeatedly freezing and thawing before introducing N 2 Degassing, reacting at 120deg.C for 3 days, centrifuging to remove solvent, grinding for 1 hr, adding into isopropanol, irradiating with 365nm ultraviolet rays while stirring for 1 hr, pulverizing with ultrasonic cell pulverizer for 3 hr, washing with dichloromethane, methanol and tetrahydrofuran for 3 times, centrifuging, and naturally air drying to obtain covalent organic frame fluorescent probe。
2. The rapid assay I of claim 1 - The preparation method of the ionic covalent organic framework fluorescent probe is characterized by comprising the following steps of: the concentration of the acetic acid is 6mol/L.
3. A covalent organic framework fluorescent probe as claimed in claim 1 for rapid detection of I - Application in ions.
4. The covalent organic framework fluorescent probe of claim 3 for rapid detection of I - The application in the ion is characterized in that: the covalent organic framework fluorescent probe is capable of selectively recognizing I - The solvent used for the ions is tetrahydrofuranAn aqueous solution.
5. The covalent organic framework fluorescent probe of claim 4 for rapid detection of I - The application in the ion is characterized in that: the tetrahydrofuran aqueous solution is prepared from tetrahydrofuran and deionized water according to a volume ratio of 1:1.
6. The covalent organic framework fluorescent probe of claim 5 for rapid detection of I - The application in the ion is characterized in that: adding the covalent organic framework fluorescent probe into the tetrahydrofuran aqueous solution, and uniformly stirring to obtain a covalent organic framework fluorescent probe dispersion liquid with the concentration of 0.01 mg/mL-1 mg/mL; adding a covalent organic framework fluorescent probe dispersion liquid into a detection water sample, measuring the fluorescence emission intensity of the detection water sample at the excitation wavelength of lambda=230 nm, and weakening the fluorescence intensity at 317nm, wherein the detection sample contains I - Ions.
7. The covalent organic framework fluorescent probe of claim 6 for rapid detection of I - The application in the ion is characterized in that: the concentration of the covalent organic framework fluorescent probe dispersion is 0.05mg/mL.
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| CN108276383A (en) * | 2018-02-10 | 2018-07-13 | 贵州大学 | A kind of fluorescence probe and preparation method thereof of identification iodide ion and recognition methods |
| AU2020103559A4 (en) * | 2020-01-13 | 2021-02-04 | Qilu University Of Technology | Ratiometric fluorescent probe for detecting hypochlorous acid, and preparation method and use thereof |
| CN113461887A (en) * | 2021-01-28 | 2021-10-01 | 渤海大学 | One-dimensional nanochannel self-supporting covalent organic framework membrane for salt difference power generation and application thereof |
| CN113929876A (en) * | 2021-10-22 | 2022-01-14 | 西北师范大学 | Covalent organic framework material with C = C double-bond fluorescent probe and synthetic method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108276383A (en) * | 2018-02-10 | 2018-07-13 | 贵州大学 | A kind of fluorescence probe and preparation method thereof of identification iodide ion and recognition methods |
| AU2020103559A4 (en) * | 2020-01-13 | 2021-02-04 | Qilu University Of Technology | Ratiometric fluorescent probe for detecting hypochlorous acid, and preparation method and use thereof |
| CN113461887A (en) * | 2021-01-28 | 2021-10-01 | 渤海大学 | One-dimensional nanochannel self-supporting covalent organic framework membrane for salt difference power generation and application thereof |
| CN113929876A (en) * | 2021-10-22 | 2022-01-14 | 西北师范大学 | Covalent organic framework material with C = C double-bond fluorescent probe and synthetic method and application thereof |
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| A Carboxyl-Functionalized Covalent Organic Framework Synthesized in a Deep Eutectic Solvent for Dye Adsorption;Bin Dong等;Chemistry-A European Journal;第27卷(第8期);2692-2698 * |
| 一种近红外发射荧光探针的合成及其荧光增强识别Hg2+;宋文琦等;化学通报;第84卷(第7期);726-731 * |
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