CN109574921B - Fluorescent probe for detecting acetate ions and preparation method and use method thereof - Google Patents
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Abstract
The invention discloses a fluorescent probe for detecting acetate ions, a preparation method and a use method thereof, belonging to the field of fluorescent probe compounds and preparation thereof, wherein the molecular formula of the fluorescent probe is as follows: c12H14N3OPF6Quinoline is used as a raw material and is prepared through alkylation and anion exchange, the synthesis is simple and convenient, the reaction conditions are mild, the prepared fluorescent probe has stable optical performance and high synthesis yield, can be used as a ratiometric fluorescent recognition probe for detecting the concentration of acetate, has high sensitivity, wide detection range and good selectivity, and is suitable for detecting the acetate in the fields of biochemistry, environmental chemistry and the like.
Description
Technical Field
The invention relates to a fluorescent probe and a preparation method and a using method thereof, in particular to a fluorescent probe for detecting acetate ions and a preparation method and a using method thereof, belonging to the field of molecular probes for ion detection.
Background
Anions play an important role in many chemical and biological processes and, therefore, in recent years, the identification and detection of anions has received widespread attention. Among them, the identification and detection of acetate is particularly important. The acetate plays a role in regulating and stabilizing the acidity of the hemodialysis solution in clinical dialysis, and the acidity of the hemodialysis solution can not meet the requirement due to the fact that the content of the acetate is too low, so that Ca in the dialysate cannot meet the requirement2+And HCO3 -Reaction takes place and CaCO is formed3Precipitation, which in turn damages the dialysis machine; if the content is too high, the metabolic capability of the body is exceeded, and adverse reactions such as nausea, tiredness, muscle spasm and the like are caused. At the same time, byThe rate of oxidation to acetate is considered an indicator of organic decomposition in marine sediments. Currently, acetate ions in water, environmental, biological and food samples are mainly determined by different methods such as ion chromatography, selective electrode method, liquid membrane sensor, flow injection analysis system, etc. These methods are time consuming, involve multiple sample manipulations, require extensive basic equipment and expertise, and are not well suited to analyzing large numbers of samples. The chemical sensor can overcome the defects, has the advantages of good selectivity, high sensitivity, convenience, rapidness, low cost and the like, and is designed and synthesized by chemical researchers in a large scale. The chemical sensors reported to date that can be used to identify acetate are mainly: hydrogen bond type receptors such as amides, pyrroles, ureas and thioureas, ionic hydrogen bond receptors such as imidazoles, lewis acid type receptors and photonic crystal hydrogel type receptors. The acylhydrazone compounds containing selenazole designed and synthesized by Zhanglu and the like can realize fluorescence recognition on acetate in DMSO solution [ Zhanglu, Liyizheng, Lijin pool and the like, the synthesis of two novel 1, 3-selenazole acylhydrazones and the characteristic fluorescence recognition on acetate ions, application chemistry, 2018,35(2):197-]The synthesized double hydrogen bond donor compound designed by Vincent E.Zwicker et al can recognize acetate by color change (yellow → red) [ V E Zwicker, K K Y Yuen, D G Smith, et al. Deltamides and Croconamides: Expanding the Range of Dual H-bonds for Selective inhibition recognition. chem. Eur. J.,2018,24:1140-]. The fluorescent probe materials are synthesized, the synthesis raw materials have complex structures and more steps, and meanwhile, when acetate is identified, anions with stronger alkalinity such as: f-、H2PO4 -And thus the application range is limited.
Disclosure of Invention
In view of the above, the invention provides a fluorescent probe for detecting acetate ions, a preparation method and a use method thereof, which have the advantages of high sensitivity, wide detection range and good selectivity and are suitable for detecting acetate ions in the fields of biochemistry, environmental chemistry and the like.
In order to achieve the purpose, the invention adopts the following technical scheme:
a kind ofA fluorescent probe for detecting acetate ions is used for a fluorescent spectrometer to detect the acetate ions, and has the molecular formula: c12H14N3OPF6The structural formula is as follows:
the fluorescent probe has stable optical performance, can be used as a ratiometric fluorescent recognition probe for detecting the concentration of the acetate, has high sensitivity, wide detection range and good selectivity, and is suitable for detecting the acetate in the fields of biochemistry, environmental chemistry and the like.
The invention also provides a preparation method of the fluorescent probe for detecting acetate ions, and the reaction formula is
The method specifically comprises the following steps:
(1) under the protection of inert gas, dropwise adding an absolute ethanol solution of 2-chloroethyl urea with the concentration of 0.25-1.2 mol/L into an absolute ethanol solution of quinoline with the concentration of 0.2-1 mol/L, uniformly mixing, heating and refluxing at 80-85 ℃ for 12-72 h, cooling to 20-25 ℃, freezing, filtering, washing with diethyl ether, and performing vacuum drying to obtain an intermediate (compound II) for later use;
(2) and dissolving the intermediate in dichloromethane, uniformly mixing, washing for 3-5 times by using a saturated aqueous solution of ammonium hexafluorophosphate, collecting an organic layer, drying by using anhydrous sodium sulfate, filtering, and performing rotary evaporation to obtain the fluorescent probe (compound I).
The fluorescent probe compound I is prepared by taking quinoline as a raw material through alkylation and anion exchange, and is simple and convenient to synthesize and mild in reaction conditions.
Further, the dropwise adding operation in the step (1) is that the molar ratio of the 2-chloroethylurea to the quinoline dropwise added into the mixed solution is 1.05-1.2: 1.
The method has the further beneficial effects that the feeding molar ratio is set according to the reaction mechanism so as to ensure that the reaction is fully carried out, reduce the generation of byproducts and improve the reaction purity.
Further, the freezing temperature in the step (1) is-18 to-20 ℃, and the time is 5 to 10 hours.
The further beneficial effect of adopting the above is that the freezing at the temperature can ensure the complete precipitation of the intermediate and the yield of the intermediate, so that the reaction can be fully carried out.
Further, the intermediate in step (2) is dissolved in dichloromethane in an amount such that the concentration of the intermediate added to dichloromethane is: 0.005-0.05 mol/L.
Further, the use amount of the saturated aqueous solution of ammonium hexafluorophosphate in the step (2) is as follows: the volume ratio of the saturated aqueous solution of ammonium hexafluorophosphate to dichloromethane is 1-1.5: 1.
The method has the further beneficial effects that the fluorescent probe of the reaction final product can be generated to the maximum extent by using the intermediate under the dosage, so that the generation of by-products is reduced, and the cost can be controlled.
The invention also provides a using method of the fluorescent probe for detecting acetate ions, which comprises the following steps:
(1) the prepared concentration is 5 multiplied by 10-6Adding acetonitrile solution of fluorescent probe at mol/L into the solution with concentration of 5 × 10 by using a microsyringe-4A mol/L acetonitrile solution of tetrabutylammonium acetate to ensure the molar concentration of acetate ions and the fluorescent probe [ G]/[H]The ratio is an integer between 0 and 50(0, 1, 2, 3, 4 and 5 … … 50), the fluorescence intensity of acetate ions at different concentrations is measured by a fluorescence spectrometer, a standard curve is made, and the functional relation between the fluorescence intensity and the acetate ion concentration is determined;
(2) the concentration is 5X 10-6Adding the acetonitrile solution of the fluorescent probe of mol/L into the acetonitrile solution of the sample to be detected and recording the fluorescence intensity of the solution;
(3) and determining the concentration of the acetate in the solution to be detected according to the functional relation between the fluorescence intensity and the concentration of the acetate ions.
Wherein, the fluorescence intensity measuring conditions are that the excitation wavelength is 356nm, the slit width is 10nm, and the scanning ranges are respectively 360-700 nm.
Further, the method for determining the functional relationship between the fluorescence intensity and the acetate ion concentration in the step (2) is to perform nonlinear fitting by using a least square method, and the equation is as follows:
Ι＝Ι0+(Ιlim-Ι0)/2CH{CH+CG+1/K-[(CH+CG+1/K)2-4CHCG]1/2}
wherein, CHAs acceptor concentration, CGFor the concentration of added anions, K is the binding constant, I0And I is the fluorescence intensity of the free acceptor and the acceptor after addition of the anion, respectively.
Drawings
FIG. 1 is a graph showing the results of the change in the fluorescence intensity of acetonitrile solution of the fluorescent probe prepared in examples 1 to 3 of the present invention depending on the type of anion added;
FIG. 2 is a graph showing the results of the change in the fluorescence intensity of acetonitrile solution of the fluorescent probe prepared in examples 1 to 3 of the present invention depending on the concentration of acetate added;
FIG. 3 is a graph showing the results of fluorescence intensity at the maximum emission wavelength of acetonitrile solution of the fluorescent probes prepared in examples 1 to 3 of the present invention as a function of acetate concentration.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Preparation of fluorescent probes
Under the protection of nitrogen, quinoline (1.29g, 10mmol) and absolute ethyl alcohol (10mL) are sequentially added into a 100mL two-neck flask provided with a reflux condenser tube and a stirrer, a solution of 2-chloroethyl urea (1.35g, 11mmol) in absolute ethyl alcohol (20mL) is slowly added dropwise for about 1h, the mixture is refluxed for 72h, cooled to room temperature, frozen at-18 ℃ for 5h, white solid is separated out, filtered, washed with diethyl ether for 3 times and then dried in vacuum to obtain an intermediate, and the yield is 74%.
The intermediate (1.51g, 6mmol) was dissolved in dichloromethane (30mL), washed with saturated aqueous solution of ammonium hexafluorophosphate (3X 20mL), the organic layer was collected, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to give the fluorescent probe in 66% yield.
Example 2
Preparation of fluorescent probes
Under the protection of nitrogen, quinoline (0.645g, 5mmol) and absolute ethyl alcohol (10mL) are sequentially added into a 500mL two-neck flask provided with a reflux condenser tube and a stirrer, a solution of 2-chloroethyl urea (0.675g, 5.5mmol) in absolute ethyl alcohol (10mL) is slowly added dropwise, the dropwise addition is finished after about 0.5h, the mixture is refluxed for 48h, cooled to room temperature, frozen at-18 ℃ for 10h, a white solid is separated out, filtered, washed with diethyl ether for 3 times and dried in vacuum, and an intermediate is obtained with the yield of 88%.
The intermediate (0.76g, 3mmol) was dissolved in dichloromethane (20mL), washed with saturated aqueous solution of ammonium hexafluorophosphate (3X 20mL), the organic layer was collected, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to give the fluorescent probe in a yield of 72%.
Example 3
Preparation of fluorescent probes
Under the protection of nitrogen, quinoline (2.58g, 20mmol) and absolute ethyl alcohol (30mL) are sequentially added into a 500mL two-neck flask provided with a reflux condenser tube and a stirrer, an absolute ethyl alcohol (20mL) solution of 2-chloroethyl urea (2.58g, 21mmol) is slowly added dropwise, the dropwise addition is finished for about 2h, the reflux is carried out for 48h, the mixture is cooled to the room temperature, the mixture is frozen at-18 ℃ for 8h, white solid is separated out, the white solid is filtered, the mixture is washed with ethyl ether for 3 times and then dried in vacuum, and an intermediate is obtained, wherein the yield is 92%.
The intermediate (2.52g, 10mmol) was dissolved in dichloromethane (40mL), washed with saturated aqueous solution of ammonium hexafluorophosphate (3X 20mL), the organic layer was collected, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to give the fluorescent probe in 66% yield.
Performance characterization
The performance of the fluorescent probes prepared in examples 1-3 was characterized, and the items and results were as follows:
the results of the hydrogen nuclear magnetic resonance spectrum are as follows:1H NMR(DMSO-d6,400MHz)，δ：3.57-3.61(m,2H)，5.07(t,J＝5.2Hz,2H)，5.58(s,2H)，6.17(t,J＝5.2Hz,1H)，8.05(t,J＝7.2Hz,1H)，8.15-8.19(m,1H)，8.28(t,J＝8.0Hz,1H)，8.47(d,J＝8.0Hz,1H)，8.69(d,J＝9.2Hz,1H)，9.27(d,J＝8.4Hz,1H)，9.32(d,J＝5.6Hz,1H)。
the results of nuclear magnetic resonance carbon spectrum are as follows:13C NMR(DMSO–d6,100MHz)：39.44，58.21，119.36，122.30，130.16，130.21，131.07，135.93，138.52，147.96，150.29，159.05。
elemental analysis: c12H14F6N3OP, found (calculated),%: c39.89 (39.90); h3.95 (3.91); n11.59 (11.63).
The mass spectrometry results were as follows: ESI-MS, m/z: 261.11[ I-PF6 -]+。
The fluorescent probes prepared in examples 1 to 3 were dissolved in acetonitrile at a concentration of 6X 10-6mol/L, the addition concentration is 5 multiplied by 10-4Testing the fluorescence emission spectrum of different anion (fluoride ion, dihydrogen phosphate, acetate, bromide, hydrogen sulfate, chlorate, iodide, chloride and nitrate) solutions in mol/L, wherein the change condition of the fluorescence emission spectrum is shown in figure 1, the abscissa is wavelength, and the ordinate is fluorescence intensity;
the fluorescent probes prepared in examples 1 to 3 were dissolved in acetonitrile at a concentration of 6X 10-6Adding acetate solutions with different concentrations into the solution at mol/L, and testing the fluorescence emission spectrum of the solution, wherein the change condition of the fluorescence emission spectrum is shown in figure 2, the abscissa is the wavelength, and the ordinate is the fluorescence intensity;
the results of fig. 1 and fig. 2 show that when 356nm light is used as excitation light and the slit width is 10nm, the fluorescent probe has two strong fluorescence emission peaks at 398nm and 419nm, and a weaker fluorescence emission peak at 439nm, when acetate is added, the fluorescence emission peak intensity of the fluorescent molecular probe I is obviously enhanced, and simultaneously, under the irradiation of an ultraviolet lamp, the fluorescent probe shows blue fluorescence and is not affected by anions such as fluoride ion, dihydrogen phosphate, bromide ion, hydrogen sulfate, chlorate, iodide ion, chloride ion, nitrate, and the like, which indicates that the fluorescent probe of the present invention has good selectivity for acetate.
3mL of acetonitrile solution of the fluorescent probe (concentration: 6X 10) was added to the cuvette-6mol/L), then dropwise adding the mixture into the mixture with the concentration of 5X 10-3mol/L of AcO-Acetonitrile solution, scanning under 356nm exciting light, slit width 10nm, fluorescence peak intensity change delta I at 419nm419As ordinate, AcO-Concentration is plotted on the abscissa and non-linear fit is performed by the following equation, as shown in figure 3,
Ι＝Ι0+(Ιlim-Ι0)/2CH{CH+CG+1/K-[(CH+CG+1/K)2-4CHCG]1/2}
wherein, CHAs acceptor concentration, CGFor the concentration of added anions, K is the binding constant, I0And I is the fluorescence intensity of the free acceptor and the acceptor after addition of the anion, respectively.
The result shows that the synthesized fluorescent probe has good response capability to acetate, can avoid the interference of common anions, can be used as a colorimetric and fluorescent probe for selectively detecting acetate ions, and has wide application prospect.
Claims (6)
1. The utility model provides a detect fluorescence probe of acetate ion which characterized in that, fluorescence probe is used for fluorescence spectrometer to detect acetate ion, and the molecular formula is: c12H14N3OPF6The structural formula is as follows:
2. the method for preparing the fluorescent probe for detecting acetate ions, which is described in claim 1, is characterized by comprising the following steps:
(1) under the protection of inert gas, dropwise adding the anhydrous ethanol solution of 2-chloroethyl urea into the anhydrous ethanol solution of quinoline, uniformly mixing, heating and refluxing, cooling, freezing, filtering, washing with diethyl ether, and then drying in vacuum to obtain an intermediate for later use; the concentration of the absolute ethanol solution of the 2-chloroethyl urea is 0.25-1.2 mol/L; the concentration of the anhydrous ethanol solution of quinoline is 0.2-1 mol/L; the dropwise adding operation is that the mol ratio of the 2-chloroethyl urea to the quinoline which are dropwise added into the mixed solution is 1.05-1.2: 1,
(2) and dissolving the intermediate in dichloromethane, uniformly mixing, washing for 3-5 times by using a saturated aqueous solution of ammonium hexafluorophosphate, wherein the volume ratio of the saturated aqueous solution of ammonium hexafluorophosphate to the dichloromethane is 1-1.5: 1, collecting an organic layer, drying by using anhydrous sodium sulfate, filtering, and performing rotary evaporation to obtain the fluorescent probe.
3. The method for preparing the fluorescent probe for detecting acetate ions according to claim 2, wherein the heating reflux temperature in the step (1) is 80-85 ℃ and the time is 12-72 hours; the cooling is to be carried out to 20-25 ℃; the freezing temperature is-18 to-20 ℃, and the time is 5 to 10 hours.
4. The method for preparing a fluorescent probe for detecting acetate ions according to claim 2, wherein the intermediate is dissolved in dichloromethane in the step (2) in such an amount that the concentration of the intermediate added to dichloromethane is: 0.005-0.05 mol/L.
5. The method for using the fluorescent probe for detecting acetate ions, according to claim 1, is characterized by comprising the following steps:
(1) preparing acetonitrile solution of a fluorescent probe, adding the acetonitrile solution of tetrabutylammonium acetate by using a micro-injector to ensure that the molar concentration ratio of acetate ions to the fluorescent probe is an integer between 0 and 50 in sequence, measuring the fluorescence intensity of the acetate ions at different concentrations by using a fluorescence spectrometer, making a standard curve, and determining the functional relation between the fluorescence intensity and the acetate ion concentration, wherein the fluorescence is fluorescenceThe light intensity measurement conditions are that the excitation wavelength is 356nm, the slit width is 10nm, and the scanning ranges are respectively 360-700 nm; the concentration of acetonitrile solution of the fluorescent probe is 5X 10-6mol/L, the concentration of the acetonitrile solution of tetrabutylammonium acetate is 5 multiplied by 10-4mol/L；
(2) Adding the acetonitrile solution of the fluorescent probe into the acetonitrile solution of the sample to be detected and recording the fluorescence intensity of the solution;
(3) and determining the concentration of the acetate in the solution to be detected according to the functional relation between the fluorescence intensity and the concentration of the acetate ions.
6. The method of claim 5, wherein the step (3) of determining the fluorescence intensity as a function of acetate ion concentration is a non-linear fit using least squares.
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| Ionic liquids containing the urea moiety for recognition of halides and complex anions;DONG ZhiYun et al.,;《Chin Sci Bull》;20120229;第57卷(第5期);第473-478页 * |
| 含脲苯并咪唑鎓类离子液体的合成及阴离子识别性能;董智云等;《高等学校化学学报》;20121031;第33卷(第10期);第2256页摘要和Scheme 1,第2259页第2-3段和图5 * |
| 脲类受体对阴离子的结合、识别和分离;魏梅莹等;《高等学校化学学报》;20110930;第32卷(第9期);第1939页第1段,倒数第2段和第1940页第1段 * |
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