CN109678891B - Palladium ion fluorescent probe compound and preparation method and application thereof - Google Patents
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Abstract
The invention discloses a palladium ion fluorescent probe combinationThe product and its preparation method are provided. The preparation method of the compound comprises the following steps: dissolving rhodamine B in an organic solvent to react with ethylenediamine to obtain rhodamine amide; adding 5-amino-4, 6-dichloropyrimidine and 1-naphthylamine into an organic solvent, and reacting to obtain 6-chloro-N4- (Naphthalen-1-yl) pyrimidine-4, 5-diamines, reacting 6-chloro-N4Dissolving the- (naphthalene-1-yl) pyrimidine-4, 5-diamine, acetic acid, polyphosphoric acid and dodecyl trimethyl ammonium chloride in phosphorus oxychloride, and reacting to obtain 6-chloro-8-methyl-9- (naphthalene-1-yl) -9H-purine; adding rhodamine amide, 6-chlorine-8-methyl-9- (naphthalene-1-yl) -9H-purine and sodium bicarbonate into an organic solvent, and reacting to obtain the palladium ion fluorescent probe compound. The palladium ion fluorescent probe compound has high sensitivity and strong anti-interference performance, and can be widely used for detecting palladium ions.
Description
Technical Field
The invention belongs to the technical field of fluorescent probes for metal ion detection, and particularly relates to a palladium ion fluorescent probe compound and a preparation method and application thereof.
Technical Field
Palladium (Pd) is one of the most important platinum group elements and plays a crucial role due to its wide application in many catalytic reactions and industrial applications. Due to its inertness, biocompatibility and versatility as a catalyst, it is widely used in organic synthesis, drug design and pharmaceuticals, such as fuel cells, crowns, medical devices, catalytic converters, etc. A certain amount of palladium may remain as an impurity in the final product and may have a negative impact on our health. After a certain amount of palladium is taken by a human body, the palladium can be combined with biological macromolecules in the human body, such as protein, DNA, RNA and the like, so that the normal metabolism of the human body is interfered. Therefore, the method is particularly important for detecting palladium ions in natural environment and organisms.
Currently, the commonly used method for detecting palladium ion (Pd)2+) Including atomic absorption spectroscopy, inductively coupled plasma atomic emission spectroscopy, inductively coupled plasma mass spectrometry, and X-ray fluorescence, however, all of these methods require complex and expensive instruments, complex sample preparation, stringent experimental conditions, and professional and experienced operators; in contrast, fluorescence assays can avoid the disadvantages of these conventional methods in trace analysis and detection while maintaining high selectivity and accuracy.
The rhodamine B fluorescent dye is a fluorescent substance with excellent performance, has good photostability, high fluorescence quantum yield and high extinction coefficient, and has excitation and emission wavelengths in a visible light region, so that the rhodamine B fluorescent dye has a stable synthetic structure, good selectivity and high sensitivity, and has very important significance and research value for a rhodamine B fluorescent probe capable of detecting palladium ions in a water phase system.
Nevertheless, many of the reported palladium ion fluorescent probes still have the problems of poor water solubility, complex synthesis steps, poor selectivity, harsh test conditions, and the like.
Disclosure of Invention
Based on the above, one of the purposes of the present invention is to provide a palladium ion fluorescent probe compound.
The specific technical scheme is as follows:
a palladium ion fluorescent probe compound, which has the following structural general formula I:
the invention also aims to provide a preparation method of the palladium ion fluorescent probe compound. The synthetic route is shown as the following figure:
wherein, formula IIThe intermediate is rhodamine amide, and the intermediate of the formula IV is 6-chlorine-N4- (naphthalene-1-yl) pyrimidine-4, 5-diamine, wherein the intermediate in the formula III is 6-chlorine-8-methyl-9- (naphthalene-1-yl) -9H-purine, and the compound in the formula I is the palladium ion fluorescent probe compound.
The other technical scheme is as follows:
a preparation method of a palladium ion fluorescent probe compound comprises the following steps:
(1) preparation of intermediate of formula II (rhodamine amide)
Dissolving rhodamine B in an organic solvent, preheating for 10-30min, adding ethylenediamine, carrying out reflux reaction at 78-80 ℃ for 15-18 h, cooling, evaporating at 45-55 ℃ to remove the organic solvent, extracting a reaction system with dichloromethane and water, collecting an organic phase, adding desiccant anhydrous sodium sulfate, filtering, evaporating to remove the solvent in filtrate, and carrying out column chromatography separation by using eluent methanol/dichloromethane to obtain an intermediate shown in a formula II;
(2) preparation of intermediate of formula III (6-chloro-8-methyl-9- (naphthalen-1-yl) -9H-purine)
Adding 5-amino-4, 6-dichloropyrimidine and 1-naphthylamine into an organic solvent, adding concentrated hydrochloric acid after complete dissolution, carrying out reflux reaction for 24-26 h at 78-80 ℃, cooling, removing the solvent under reduced pressure, dissolving with NaOH with the concentration of 1M, extracting with ethyl acetate, evaporating to remove ethyl acetate at 45-55 ℃, recrystallizing with methanol and water, and drying at 45-55 ℃ to obtain an intermediate of the formula IV;
dissolving the intermediate shown in the formula IV, acetic acid, polyphosphoric acid and dodecyl trimethyl ammonium chloride in phosphorus oxychloride, refluxing for 20-36 h at 78-80 ℃, cooling reactants to room temperature, evaporating the solvent at 68-72 ℃, adding an ice water mixture into a reaction system under an ice water bath at 0-5 ℃, filtering, washing with water, and drying at 45-55 ℃ to obtain an intermediate shown in the formula III;
(3) preparation of Palladium ion fluorescent Probe Compound
Dissolving the intermediate of the formula III in the step (2) in an organic solvent, adding sodium bicarbonate and the intermediate of the formula II in the step (1), refluxing for 20-36 h at 78-80 ℃, cooling, filtering, removing the organic solvent, and performing column chromatography separation by using an eluent methanol/dichloromethane to obtain a light yellow product, namely the palladium ion fluorescent probe compound.
Preferably, the organic solvent in steps (1) - (3) is ethanol.
Preferably, the molar ratio of the rhodamine B to the ethylenediamine in the step (1) is 4-5: 40-50.
Preferably, the molar ratio of the 5-amino-4, 6-dichloropyrimidine in the step (2), the 1-naphthylamine, the concentrated hydrochloric acid and the NaOH is 28-32: 56-64: 45-55.
Preferably, the volume ratio of methanol to water for recrystallization in the step (2) is VMethanol:VWater (W)＝95～105∶475～525。
Preferably, the molar ratio of the intermediate of formula IV in the step (2), acetic acid, polyphosphoric acid and dodecyl trimethyl ammonium chloride is 18.1-18.9: 96-100: 73-76: 0.09-0.11.
Preferably, the volume ratio of the eluent in the steps (1) and (2) is VMethanol:VMethylene dichloride1: 95-105; the volume ratio of the eluent in the step (3) is VMethanol:VMethylene dichloride＝1:140～160。
Preferably, the molar ratio of the intermediate of formula II, the intermediate of formula III and sodium bicarbonate in the step (3) is 3.2-3.6: 16-18.
The invention also aims to provide application of the palladium ion fluorescent probe compound.
The specific technical scheme is as follows:
an application of the palladium ion fluorescent probe compound in palladium ion detection.
Preferably, the palladium ion fluorescent probe compound is used as a fluorescent probe of a palladium ion detection substance.
The invention has the following beneficial effects:
the invention synthesizes the palladium ion (Pd) based on rhodamine B by using rhodamine B as a fluorescent group, ethylenediamine as a connecting group and 6-chlorine-8-methyl-9- (naphthalene-1-yl) -9H-purine as an identification group2+) A fluorescent probe compound. The method has the advantages of simple synthesis steps, easily obtained raw materials, convenient preparation, and easy storage of the obtained product, which is solid powder; is made ofThe prepared palladium ion fluorescent probe compound has specific recognition on palladium ions, high sensitivity and strong anti-interference capability on other metal ions, can be used for manufacturing the palladium ion fluorescent probe, is widely used for palladium ion detection in the fields of biochemistry, environmental science, medicine and the like, and has wide application prospect.
Description of the drawings:
FIG. 1 shows the palladium ion (Pd) added to the palladium ion fluorescent probe compound of example 22+) Front and back ultraviolet absorption spectrograms;
FIG. 2 shows the palladium ion (Pd) added to the palladium ion fluorescent probe compound of example 22+) Front and back fluorescence spectra;
FIG. 3 shows the palladium ion (Pd) pair of the palladium ion fluorescent probe compound in the ethanol solution in example 22+) Wherein the abscissa is fluorescence emission wavelength (nm) and the ordinate is fluorescence intensity, and each curve in the graph represents a fluorescence spectrum with an increase in palladium ion concentration, respectively;
FIG. 4 is a graph of the fluorescence response of the palladium ion fluorescent probe compound in example 2 in ethanol solution for selective interfering detection of different metal ions, wherein the abscissa is different metal ions and the ordinate is fluorescence intensity;
FIG. 5 shows the compound of the fluorescent probe for palladium ion and palladium ion (Pd) in example 22+) A Job-plot of the complex ratio;
FIG. 6 shows NMR of the fluorescent probe compound for Pd ion in example 21H-NMR spectrum.
FIG. 7 shows NMR of the fluorescent probe compound for Pd ion in example 213C-NMR spectrum.
FIG. 8 is a mass spectrum of a palladium ion fluorescent probe compound in example 2.
Detailed Description
In order that the nature of the invention may be better understood, reference will now be made to the following examples.
The reagents used in the examples were either commercially available, analytically pure or chemically pure.
Example 1
(1) Preparation of rhodamine amides
Adding ethanol (30mL) and rhodamine B (2g, 4.5mmol) into a 100mL round-bottom flask, preheating for 20min, adding ethylenediamine (3.0mL, 44.98mmol), carrying out reflux reaction at 78-80 ℃ for 15-18 h, cooling, distilling off the ethanol at 50 ℃, extracting a reaction system with 200mL dichloromethane and 50mL water, collecting an organic phase, adding 5g desiccant anhydrous sodium sulfate, filtering to obtain a filtrate, distilling off the solvent in the filtrate at 50 ℃ to obtain a crude product, and using an eluent methanol/dichloromethane (volume ratio is V/dichloromethane) (volume ratio is V)Methanol:VMethylene dichloride1: 100) and carrying out column chromatography separation to obtain rhodamine amide.
(2) Preparation of 6-chloro-8-methyl-9- (naphthalen-1-yl) -9H-purine
Adding 5-amino-4, 6-dichloropyrimidine (5g, 30mmol) and 1-naphthylamine (8.584g, 60mmol) into a 100mL round-bottom flask, dissolving in ethanol (50mL), adding concentrated hydrochloric acid (5mL, 60mmol) after complete dissolution, refluxing at 78-80 ℃ for 24-26 h, cooling, removing the solvent under reduced pressure, adding NaOH (1M, 50mL) for dissolution, extracting with 400mL ethyl acetate, evaporating at 50 ℃ to remove ethyl acetate, recrystallizing with methanol and water (volume ratio V)Methanol:VWater (W)100: 500), filtering, drying at 50 ℃ to obtain light purple solid, namely 6-chloro-N4- (naphthalen-1-yl) pyrimidine-4, 5-diamine.
To a 100mL round bottom flask was added acetic acid (5.882g, 98mmol), polyphosphoric acid (25g, 74mmol), dodecyltrimethylammonium chloride (0.5g, 0.1mmol), 6-chloro-N4Dissolving (naphthalene-1-yl) pyrimidine-4, 5-diamine (5g, 18.5mmol) in phosphorus oxychloride (60mL, with the concentration of 98%), refluxing at 78-80 ℃ for 20-36 h, cooling the reaction to room temperature, evaporating the solvent at 70 ℃, adding 90mL of ice-water mixture into the reaction system at 0-5 ℃ in an ice-water bath, filtering, washing the solid with 100mL of water, drying at 50 ℃ to obtain a yellow solid, and eluting with methanol/dichloromethane (the volume ratio is V/dichloromethane) (the volume ratio is V// V// V// V// V// V/and then/and the mixture is/and then adding and then to obtain the mixture, and then adding the mixture to obtain the mixture and then adding the mixture to obtain the mixture and then adding the mixture and then the mixture to the mixture and then adding the mixture to the mixture and then the mixture to obtain the mixture and the mixture of theMethanol:VMethylene dichloride1: 100) to obtain 6-chloro-8-methyl-9- (naphthalene-1-yl) -9H-purine.
(3) Preparation of Palladium ion fluorescent Probe Compound
6-chloro-8-methyl-9- (naphthalen-1-yl) -9H-purine (1g, 3.4mmol) was added to a 100mL round-bottomed flask, dissolved in 20mL ethanol,adding rhodamine amide (1.54g, 3.4mmol) and sodium bicarbonate (1.43g, 17mmol), refluxing at 78-80 deg.C for 20-36 h, cooling, filtering the solid in the flask to obtain filtrate, removing organic solvent from the filtrate, and eluting with methanol/dichloromethane (volume ratio of V)Methanol:VMethylene dichloride1: 150) to obtain a light yellow product, namely the palladium ion fluorescent probe compound.
Example 2
The tests were performed using the palladium ion fluorescent probe compounds described in example 1.
And (3) dissolving the palladium ion fluorescent probe compound in an ethanol solution, wherein the concentration is 20 mu M, the concentration of other metal ions is 100 mu M, and testing by using a fluorescence spectrometer and an ultraviolet spectrophotometer.
As shown in FIG. 1, the ultraviolet change spectrum before and after palladium ions are added to the palladium ion fluorescent probe compound of the invention, the probe compound itself has no ultraviolet absorption peak at 550-580nm, and a new absorption peak appears at 562nm after the probe compound molecules are complexed with the palladium ions.
As shown in FIG. 2, the fluorescence change spectrum before and after the palladium ion is added to the palladium ion fluorescent probe compound of the present invention shows that the probe itself does not absorb in the ethanol solution, but strong fluorescence is generated at 584nm with the addition of the palladium ion.
As shown in FIG. 3, which is a plot of fluorescence increment of the reaction of the palladium ion fluorescent probe compound of the present invention with palladium ions versus palladium ion concentration, when 0-100. mu.M of palladium ions is added to the palladium ion fluorescent probe compound of the present invention containing 20. mu.M of palladium ions, the fluorescence intensity increases with the increase of palladium ion concentration.
As shown in fig. 4, which is a bar graph of fluorescence intensity of the palladium ion fluorescent probe compound of the present invention after reacting with palladium ions in the presence of different interfering metal ions, the result shows that the presence of other metal ions does not significantly interfere with the palladium ion identification of the palladium ion fluorescent probe compound of the present invention.
As shown in FIG. 5, in order that the total concentration of the palladium ion fluorescent probe compound and palladium ions of the present invention is 100. mu.M, the difference between the fluorescence intensity at 584nm and the autofluorescence of the palladium ion fluorescent probe compound at this concentration was obtained by changing the concentration ratio of the two (the amount ratio of the palladium ion fluorescent probe compound to the palladium ion substance was 1:9, 2: 8, 3: 7, 4: 6, 5: 5, 6: 4, 7: 3, 8: 2, 9: 1 in this order), and the ratio of the ion to the total concentration was plotted. From this figure, it can be seen that when the ratio of palladium ions is 0.5, the ordinate reaches the maximum value, and it can be determined that the palladium ion fluorescent probe compound and the palladium ions are mainly combined in a 1: 1 form to form a stable complex.
FIG. 6 shows the palladium ion fluorescent probe compound of the present invention1An H-NMR spectrum of the mixture is shown,1H NMR(400MHz,DMSO-d6)δ8.18(d,J＝8.1Hz,1H),8.12(d,J＝8.2Hz,1H),7.90(s,1H),7.85–7.81(m,1H),7.71(dd,J＝8.3,7.3Hz,1H),7.65–7.57(m,3H),7.55–7.45(m,3H),7.08–6.98(m,2H)6.42–6.34(m,6H),3.30(q,J＝7.0Hz,10H),2.19(s,3H),1.24(s,1H),1.06(t,J＝7.0Hz,12H)。
FIG. 7 shows a palladium ion fluorescent probe compound of the present invention13A C-NMR spectrum of the mixture is shown,13C NMR(101MHz,DMSO-d6)δ167.94,154.20,153.98,153.22,152.44,134.32,133.20,131.16,130.73,130.25,128.81,128.18,127.25,126.23,124.10,122.80,122.42,108.60,97.81,64.79,44.12,14.18,12.85。
FIG. 8 shows a mass spectrum of the palladium ion fluorescent probe compound of the present invention, MS (ESI) M/z: 743.3[ M + H ]]+. In an ethanol system, palladium ions can react with lactam group carbonyl oxygen in the palladium ion fluorescent probe compound and nitrogen on purine, so that a lactam ring is induced to generate ring opening reaction, strong fluorescence is generated, an absorption peak is generated at 562nm, the color of a solution is changed from colorless to purple pink, the fluorescence at 584nm is also obviously enhanced, the fluorescence intensity and the palladium ion concentration show excellent linear relation in a certain range, the linear range of quantitatively detecting the palladium ions is 0-40 mu M, and the complex constant of fluorescent probe molecules and the palladium ions is 1.15 multiplied by 104M-1. The lowest detection limit of the probe to palladium ions is 4.95 multiplied by 10 according to linear fitting-8M。
Claims (9)
1. A palladium ion fluorescent probe compound is characterized by having the following structural general formula (I):
2. the method for preparing the palladium ion fluorescent probe compound according to claim 1, characterized by comprising the following steps:
(1) preparation of intermediates of formula II
Dissolving rhodamine B in an organic solvent, preheating for 10-30min, adding ethylenediamine, carrying out reflux reaction at 78-80 ℃ for 15-18 h, cooling, evaporating at 45-55 ℃ to remove the organic solvent, extracting a reaction system with dichloromethane and water, collecting an organic phase, adding desiccant anhydrous sodium sulfate, filtering, evaporating to remove the solvent in filtrate, and carrying out column chromatography separation by using eluent methanol/dichloromethane to obtain an intermediate shown in a formula II;
(2) preparation of intermediates of formula III
Adding 5-amino-4, 6-dichloropyrimidine and 1-naphthylamine into an organic solvent, adding concentrated hydrochloric acid after complete dissolution, carrying out reflux reaction for 24-26 h at 78-80 ℃, cooling, removing the solvent under reduced pressure, dissolving with NaOH with the concentration of 1M, extracting with ethyl acetate, evaporating to remove ethyl acetate at 45-55 ℃, recrystallizing with methanol and water, and drying at 45-55 ℃ to obtain an intermediate of the formula IV;
dissolving the intermediate shown in the formula IV, acetic acid, polyphosphoric acid and dodecyl trimethyl ammonium chloride in phosphorus oxychloride, refluxing for 20-36 h at 78-80 ℃, cooling reactants to room temperature, evaporating the solvent at 68-72 ℃, adding an ice water mixture into a reaction system under an ice water bath at 0-5 ℃, filtering, washing with water, and drying at 45-55 ℃ to obtain an intermediate shown in the formula III;
(3) preparation of Palladium ion fluorescent Probe Compound
Dissolving the intermediate of the formula III in the step (2) in an organic solvent, adding sodium bicarbonate and the intermediate of the formula II in the step (1), refluxing for 20-36 h at 78-80 ℃, cooling, filtering, removing the organic solvent, and performing column chromatography separation by using an eluent methanol/dichloromethane to obtain a light yellow product, namely the palladium ion fluorescent probe compound.
3. The method for preparing a palladium ion fluorescent probe compound according to claim 2, wherein the organic solvent in steps (1) to (3) is ethanol.
4. The method for preparing the palladium ion fluorescent probe compound according to claim 2, wherein the molar ratio of rhodamine B and ethylenediamine in the step (1) is 4-5: 40-50.
5. The method for preparing a palladium ion fluorescent probe compound according to claim 2, wherein the molar ratio of the 5-amino-4, 6-dichloropyrimidine, the 1-naphthylamine, the concentrated hydrochloric acid and the NaOH in the step (2) is 28-32: 56-64: 45-55.
6. The method for preparing a palladium ion fluorescent probe compound according to claim 2, wherein the volume ratio of methanol to water for recrystallization in the step (2) is VMethanol:VWater (W)＝95～105∶475～525。
7. The method for preparing a palladium ion fluorescent probe compound according to claim 2, wherein the molar ratio of the intermediate of formula IV in the step (2), acetic acid, polyphosphoric acid and dodecyl trimethyl ammonium chloride is 18.1-18.9: 96-100: 73-76: 0.09-0.11.
8. The method for preparing a palladium ion fluorescent probe compound according to claim 2, wherein the volume ratio of the eluent in the step (1) is VMethanol:VMethylene dichloride1: 95-105; the volume ratio of the eluent in the step (3) is VMethanol:VMethylene dichloride＝1:140～160。
9. The method for preparing a palladium ion fluorescent probe compound according to claim 2, wherein the molar ratio of the intermediate of formula II, the intermediate of formula III and sodium bicarbonate in step (3) is 3.2-3.6: 16-18.
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