CN112724057B - Anion fluorescent probe, preparation method and application thereof - Google Patents
Anion fluorescent probe, preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an anion fluorescent probe, a preparation method and application thereof, and the anion fluorescent probe is prepared by mixing 1- (4-amino) phenyl-1, 2, 2-triphenylethylene and a phenyl isothiocyanate derivative for condensation reaction. The fluorescent probe is selective for anions and allows for quantitative analysis of the identified anions.
Description
Technical Field
The invention relates to a fluorescent probe, a preparation method and application thereof, in particular to an anion fluorescent probe, a preparation method and application thereof.
Background
In nature, anions participate extensively in chemical reactions and biological processes. Taking fluorine ions (F-) as an example, a proper amount of F-ions have the effect of preventing dental caries and tooth demineralization in the case of bone loosening. However, excessive F-ion will cause no harm to human body, for example, children often use fluorine-containing toothpaste to develop "fluorosis", and excessive F-ion in drinking water will cause fluorosis and even cancer. The world health organization requires that the content of F-ions in drinking water should not exceed 1.5 mg/L. In recent years, a series of methods for detecting anions have been developed, including electrochemical analysis, chromatographic analysis, chemical analysis, and the like. The fluorescent sensor has the characteristics of high sensitivity, simple and convenient operation and easily obtained raw materials, and further becomes a hotspot for researching anion identification.
Over the last decade, a series of anionic fluorescence sensors have been investigated. In 1995, M.H Noir and b.dureault developed a fluorescence sensor that recognizes ions by fluorescence quenching; in 1999, Hongzhi Xie et al synthesized a fluorescent sensor containing a urea structure, which could be used to identify H2PO 4-and HSO 4-ions; in 2005, Eun Jin Cho et al developed a fluorescent sensor that specifically recognizes F-ions; in 2013, Soham Samanta et al developed a fluorescence sensor with aggregation-induced emission phenomenon, in the structure, thiourea was connected with Schiff base to recognize not only F-ions but also Zn2+、Al3+、Cu2+Ions. To date, a series of structures such as ureas, pyrroles, indoles, imidazoles, calixarenes, furans, and the like have been developed for anionic fluorescence sensors.
In 1954, Forster and Kasper found that fluorescent compounds have a concentration quenching effect. Most fluorescent dyes have aggregation-induced fluorescence quenching-phenomenon (ACQ). Due to the ACQ effect, the development of the traditional organic fluorescent dye in practical application is greatly limited. In 2001, the professor group of professors of down's loyalty found that silacyclopentadiene derivatives did not fluoresce in dilute solutions, while compounds fluoresced strongly in the aggregated state, a phenomenon known as aggregation-induced emission (AIE). Further research shows that the structure of the AIE effect is connected with a plurality of ACQ fluorescent groups to have the AIE property, and accordingly, a fluorescence sensor with the AIE effect can be developed.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to provide an anion fluorescent probe for identification and quantitative analysis.
The invention also aims to provide a preparation method of the anion fluorescent probe.
The last purpose of the invention is to provide the application of the ion fluorescent probe.
The technical scheme is as follows: the invention relates to an anionic fluorescent probe with a general formula (1):
in the formula (I), the compound is shown in the specification,
r represents a side chain, and is methyl, trifluoromethyl, nitro or hydrogen atom.
Further, the anionic fluorescent probe having the general formula (1) is any one of the following:
the preparation method of the anion fluorescent probe with the general formula (1) is characterized in that:
the reaction is shown below:
the 1- (4-amino) phenyl-1, 2, 2-triphenylethylene and phenyl isothiocyanate derivatives are mixed and subjected to condensation reaction to obtain the anion fluorescent probe with the general formula (1).
Furthermore, the molar ratio of the 1- (4-amino) phenyl-1, 2, 2-triphenylethylene to the phenyl isothiocyanate derivative is 1: 2.0-3.0.
Further, the 1- (4-amino) phenyl-1, 2, 2-triphenylethylene was completely dissolved in the redistilled tetrahydrofuran before being mixed.
Further, the reaction solvent is one or a combination of more of an amide solvent, a ketone solvent, a nitrile solvent, a sulfoxide solvent, dichloromethane, tetrahydrofuran or ethanol.
Further, the reaction temperature is the reflux temperature of the solvent.
Further, the condensation reaction product is subjected to reduced pressure distillation, water washing, drying, reduced pressure and column chromatography.
Further, the column chromatography solvent is a mixed solution of ethyl acetate and petroleum ether.
The use of the anionic fluorescent probe with the general formula (1) in anion recognition.
Has the advantages that: the invention can identify anions and quantitatively analyze the identified anions, and provides a method for identifying and quantifying the anions by using a fluorescent probe.
Drawings
FIG. 1 is a fluorescent emission curve of the fluorescent probe TC2 in a mixed solution of dimethyl sulfoxide and water according to the invention;
FIG. 2 is a graph showing the UV absorption curves of the fluorescent probe TC2 for different anion identifications according to the present invention;
FIG. 3 shows the UV absorption values of the fluorescent probe TC2 for different anion recognition at a wavelength of 450 nm;
FIG. 4 shows the identification of fluorescent probe TC2 of the present invention at a wavelength of 450nm for different concentrations F-Ultraviolet absorption value of (a);
FIG. 5 shows fluorescent probes TC2 and F according to the present invention-Job's plot of (1).
Detailed Description
Example 1
Compound TC1 is of the formula:
preparation of 1- (4-amino) phenyl-1, 2, 2-triphenylethylene is shown below
(1) Synthesis of tetraphenylethylene
Adding 7.66g (0.117mol) of zinc powder into 40ml of redistilled tetrahydrofuran, carrying out ice bath, and stirring for 10-15 min under the protection of argon. 5.0ml (0.045mol) of titanium tetrachloride was slowly added dropwise to the above solution, and heated under reflux for 2 hours. 5.46g (0.03mol) of benzophenone was dissolved in 10ml of tetrahydrofuran and slowly added dropwise to the above reaction solution. The reaction was heated to reflux for 12 h. After the reaction is finished, the reaction is quenched by saturated sodium bicarbonate, and the pH is adjusted to be alkalescent. Extracting with dichloromethane for three times, combining organic phases, washing with water twice, drying with anhydrous sodium sulfate, and evaporating to dryness under reduced pressure. And (4) carrying out column chromatography separation on the crude product to obtain white solid tetraphenylethylene.
(2) Synthesis of 1- (4-nitro) phenyl-1, 2, 2-triphenylethylene
2.0g (6.02mmol) of tetraphenylethylene are dissolved in 20ml of dichloromethane, stirred in an ice bath and 1.2ml of glacial acetic acid are slowly added. 1.0ml of concentrated nitric acid was added slowly over 30min and the reaction was monitored by TLC. After the reaction, 50ml of water was added, washed with water three times, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. And carrying out column chromatography separation on the crude product to obtain yellow solid 1- (4-nitro) phenyl-1, 2, 2-triphenylethylene.
(3) Synthesis of 1- (4-amino) phenyl-1, 2, 2-triphenylethylene
1.2g (3.18mmol) of 1- (4-nitro) phenyl-1, 2, 2-triphenylethylene and 100mg of 10% palladium on charcoal were dissolved in 50ml of ethanol and stirred for 15 min. 5.4ml of 85% hydrazine hydrate was added thereto, and the mixture was refluxed overnight. After the reaction, dichloromethane was added for dilution, and the mixture was filtered through celite, washed with water three times, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. And (3) carrying out column chromatography separation on the crude product to obtain a yellow solid 1- (4-amino) phenyl-1, 2, 2-triphenylethylene.
(4) Synthesis of p-nitrophenylisothiocyanate
0.690g (5mmol) of p-nitroaniline and 1.122g (10mmol) of 1, 4-diazabicyclo [2.2.2] octane were dissolved in 40ml of redistilled tetrahydrofuran, and 3.0ml (50mmol) of carbon disulfide was added dropwise under the protection of argon, and the mixture was stirred at room temperature overnight. After the reaction, 1.622g (10mmol) of ferric trichloride was dissolved in 20ml of water to prepare an aqueous ferric trichloride solution, which was added to the above reaction solution and stirred for 1 hour. After stirring, extracting with ethyl acetate for three times, combining organic phases, washing with water twice, drying with anhydrous sodium sulfate, and evaporating to dryness under reduced pressure. And carrying out column chromatography separation on the crude product to obtain white solid p-nitrophenylisothiocyanate.
(5) 1.04g (3mmol) of 1- (4-amino) phenyl-1, 2, 2-triphenylethylene was dissolved in 20ml of methylene chloride, and 0.270g (2mmol) of phenylisothiocyanate was added thereto. The reaction was stirred at room temperature for 12h to terminate the reaction. The solvent was distilled off under reduced pressure, dissolved in 20ml of methylene chloride, washed twice with water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. Crude column chromatography gave the yellow compound TC1(0.900g, 93.4% yield).
1H NMR(300MHz，DMSO)δ(ppm)：10.30-10.20(d，2H)，7.70-7.30(m，23H)，7.00 (t，1H)。
Example 2
Compound TC2 has the formula
The preparation method is the same as example 1, except that in (4), p-nitroaniline is used as a raw material to carry out a reaction, in (5), tetrahydrofuran is used as a reaction solvent, and the rest of the synthesis steps are unchanged, so that the compound TC2 serving as a final product is obtained, and the yield is 20.7%.
1H NMR(300MHz，DMSO)δ(ppm)：10.33-10.20(d，2H)，8.20-8.17(d，2H)，7.78-7.75 (d，2H)，7.33-7.31(d，2H)，7.17-7.10(m，9H)，7.01-6.92(m，8H)。
Example 3
Compound TC3 has the formula
The preparation method was the same as example 1, except that p-trifluoromethylaniline was used as a raw material in (4) and ethanol was used as a reaction solvent in (5), and the remaining synthesis steps were unchanged, to obtain the final product compound TC3 in a yield of 43%.
1H NMR(300MHz，DMSO)δ(ppm)：1H NMR(300MHz，DMSO)δ(ppm)： 10.30-10.20(d，2H)，8.20-8.17(d，2H)，7.78-7.75(d，2H)，7.33-7.31(d，2H)，7.17-7.10(m， 9H)，7.01-6.92(m，8H)。
Example 4
Compound TC4 has the formula
The preparation method is the same as example 1, except that p-methylaniline is used as a raw material in the step (4) for reaction, dichloromethane is used as a reaction solvent in the step (5), and the rest of the synthesis steps are unchanged, so that the compound TC4 serving as a final product is obtained with the yield of 82%.
1H NMR(300MHz，DMSO)δ(ppm)：1H NMR(300MHz，DMSO)δ(ppm)： 10.33-10.20(d，2H)，8.20-8.17(d，2H)，7.78-7.75(d，2H)，7.33-7.31(d，2H)，7.17-7.10(m， 9H)，7.01-6.92(m，8H)，2.30(t，3H)。
Example 5: and (4) relevant performance test:
AIE Property testing
Compound TC2 AIE property test solution was prepared as an example: compound TC224.3mg was weighed out accurately, placed in a 10ml EP tube and 8.836ml tetrahydrofuran was added using a pipette gunThe solution is prepared into 5.0 × 10-3And taking the mol/L solution as a solution to be detected. Respectively putting 50 μ l of the solution into 11 EP tubes of 5.0ml, respectively adding 4.0, 3.6, 3.2, 2.8, 2.4, 2.0, 1.6, 1.2, 0.8 and 0.4ml of tetrahydrofuran solution, then adding deionized water until the total liquid volume in each glass bottle is 4.0ml, oscillating the glass bottles to uniformly mix the solutions to obtain a mixed solution with water content of 0%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90% and 100%, respectively, wherein the solution concentration is 5.0 × 10-5And (3) mol/L, and finally pouring the mixed solutions into quartz cuvettes respectively for fluorescence spectrum test.
2. Ion identification
2.1 preparation of Ionic solutions to be tested
Configuration 4.0 × 10-2And (3) the to-be-detected solution of acetate ions, fluoride ions, chloride ions, bromide ions, iodide ions, hypochlorite ions, nitrate ions and dihydrogen phosphate ions in mol/L.
Taking acetate ions as an example: 51.6mg of tetrabutylammonium acetate is accurately weighed, placed in a 10ml EP tube, and 8.556ml of DMSO solution is added by a pipette to prepare 4.0X 10-2And taking the mol/L solution as a solution to be detected.
2.2 preparation of ion-selective recognition solution by Compounds
Preparing a concentration fluorescent probe solution, adding an ion solution to be detected, and respectively detecting an ultraviolet absorption spectrum and a fluorescence emission spectrum in dimethyl sulfoxide or a mixed solution of dimethyl sulfoxide and water.
Taking TC2 as an example: 40. mu.l of TC2 test solution were placed in two quartz cuvettes (thickness of quartz cuvette 1cm), 4ml of dimethyl sulfoxide and 4: 1 dimethyl sulfoxide/water solution were added to prepare a solution with a concentration of 5X 10-5Adding 40 mul of ion solution to be tested into mol/L sample to be tested by using a pipette, shaking up and standing to prepare solution capable of testing ultraviolet absorption spectrum and fluorescence emission spectrum of probe solution of different ion pairs.
AIE Property test results
FIG. 1, TC2 (5X 10) as the volume fraction of water changes-5mol/L) in dimethyl sulfoxide-water mixed solutionThe curve of the change in medium fluorescence (. lamda.ex. 300nm, ex/em slits 15/15nm) shows that significant fluorescence is produced at water ratios greater than 50%. Indicating that the compound has an AIE effect.
4. Ion selective recognition results
Taking TC2 as an example:
FIG. 2 shows the concentration of 5X 10-5The mol/L fluorescent probe TC2 is added to the solution with the concentration of 10-4And (3) the absorption peak intensity of the probe solution at 360nm is continuously reduced by mol/L of anions, the absorption degree of an original and unobvious absorption peak at 450nm is continuously increased, and the absorption peaks are red-shifted when acetate ions and perchlorate ions are added.
FIG. 3 shows that the fluorescent probe TC2 is used for identifying the absorption values of ultraviolet absorption curves at 450nm for different anions, wherein 1 is acetate ion, 2 is fluoride ion, 3 is chloride ion, 4 is bromide ion, 5 is iodide ion, 6 is perchlorate ion, 7 is dihydrogen phosphate ion, and 8 is nitrate ion. The results show that acetate ions and perchlorate ions are the strongest correspondingly, and fluorine ions and nitrate ions indicate that the fluorescent probe has an anion recognition effect.
FIG. 4 shows the concentration of 2.5X 10 at a wavelength of 450nm-5Performing linear regression on the ultraviolet absorption curves of the mol/L fluorescent probe TC2 for different equivalent weights (EQ) of fluoride ions and the absorption value with the equivalent weight of 0-2 to obtain a linear fitting equation as follows: 0.1373x-0.0643, correlation coefficient R2＝0.993；
FIG. 5 Job's plot of fluorescent probe TC2 and fluoride ion shows that TC2 and fluoride ion act at a ratio of 7: 13.
Claims (10)
1. An anionic fluorescent probe having the general formula (1):
in the formula (I), the compound is shown in the specification,
r represents a side chain, and is methyl, trifluoromethyl, nitro or hydrogen atom.
2. The anionic fluorescent probe of claim 1 having the general formula (1) being any one of the following:
3. the method for preparing an anionic fluorescent probe having the general formula (1) as set forth in claim 1, wherein:
the reaction is shown below:
mixing 1- (4-amino) phenyl-1, 2, 2-triphenylethylene and a phenyl isothiocyanate derivative for condensation reaction to obtain the compound.
4. The method for preparing an anionic fluorescent probe having the general formula (1) according to claim 3, wherein: the molar ratio of the 1- (4-amino) phenyl-1, 2, 2-triphenylethylene to the phenyl isothiocyanate derivative is 1: 2.0-3.0.
5. The method for preparing an anionic fluorescent probe having the general formula (1) according to claim 3, wherein: the 1- (4-amino) phenyl-1, 2, 2-triphenylethylene was completely dissolved in the redistilled tetrahydrofuran before mixing.
6. The method for preparing an anionic fluorescent probe having the general formula (1) according to claim 3, wherein: the reaction solvent is one or a composition of more of amide solvents, ketone solvents, nitrile solvents, sulfoxide solvents, dichloromethane, tetrahydrofuran or ethanol.
7. The method for preparing an anionic fluorescent probe having the general formula (1) according to claim 3 or 6, characterized in that: the reaction temperature is the reflux temperature of the solvent.
8. The method for preparing an anionic fluorescent probe having the general formula (1) according to claim 3, wherein: and carrying out reduced pressure distillation, water washing, drying, reduced pressure and column chromatography on the condensation reaction product.
9. The method for preparing an anionic fluorescent probe having the general formula (1) according to claim 8, wherein: the column chromatography solvent is a mixed solution of ethyl acetate and petroleum ether.
10. Use of the anionic fluorescent probe of the general formula (1) as defined in claim 1 for anion recognition.
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