CN109678891A - A kind of palladium ion fluorescent probe compounds and its preparation method and application - Google Patents
A kind of palladium ion fluorescent probe compounds and its preparation method and application Download PDFInfo
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Abstract
The invention discloses a kind of palladium ion fluorescent probe compounds and preparation method thereof.The compound the preparation method comprises the following steps: rhodamine B is dissolved in organic solvent and reacting ethylenediamine, obtain rhodamine amide；Organic solvent is added in 5- amino -4,6- dichloro pyrimidine, naphthalidine, reaction obtains the chloro- N of 6-4(naphthalene -1- base) pyrimidine -4,5- diamines, by the chloro- N of 6-4(naphthalene -1- base) pyrimidine -4,5- diamines, acetic acid, polyphosphoric acids, dodecyl trimethyl ammonium chloride are dissolved in phosphorus oxychloride, and reaction obtains the chloro- 8- methyl -9- of 6- (naphthalene -1- base) -9H- purine；Organic solvent is added in rhodamine amide, the chloro- 8- methyl -9- of 6- (naphthalene -1- base) -9H- purine, sodium bicarbonate, reaction obtains the palladium ion fluorescent probe compounds.Palladium ion fluorescent probe compounds high sensitivity of the invention, strong interference immunity, can be widely used for the detection of palladium ion.
Description
Technical field
The invention belongs to the fluorescent probe technique fields of metal ion detection, and in particular to a kind of palladium ion fluorescence probe
Close object and its preparation method and application.
Technical background
Palladium (Pd) is one of most important platinum family element, due to its answering in many catalysis reactions and industrial application extensively
With playing a crucial role.Due to its inertia, biocompatibility and as the multifunctionality of catalyst, it is widely used in
Organic synthesis, drug design and drug, such as fuel cell, corona, medical instrument, catalyst.A certain amount of palladium may
Adverse effect may be caused to our health in the final product by staying as impurity.After human body takes in a certain amount of palladium, palladium meeting
With in human body protein, in conjunction with the large biological molecules such as DNA, RNA, interfere the eubolism of human body.Therefore to natural environment and
Palladium ion detection is particularly important in organism.
Currently used detection palladium ion (Pd2+) method include atomic absorption spectrum, inductively coupled plasma body atom
Emission spectrum, inductivity coupled plasma mass spectrometry and x-ray fluorescence, however, all these methods require complicated and expensive instrument
Device, complicated sample preparation, stringent experiment condition, and profession and veteran operator；In contrast, fluorescence is surveyed
Surely can be to avoid these conventional methods the trace analysis and context of detection the shortcomings that, while keeping highly selective and accuracy.
Rhodamine B fluorescent dye is a kind of fluorescent material haveing excellent performance, and has good light stability, fluorescence quantum yield
High, extinction coefficient height, excitation and launch wavelength are in visible light region, therefore composite structure is stable, the good, sensitivity of selectivity
The rhodamine B fluorescence probe of height, the detectable palladium ion that can be used in aqueous phase system has very important significance and grinds
Study carefully value.
Nevertheless, many reported palladium ion fluorescence probes still have, poorly water-soluble, synthesis step are complicated, select
The problems such as property is poor, test condition is harsh.
Summary of the invention
Based on this, an object of the present invention is to provide a kind of palladium ion fluorescent probe compounds.
Specific technical solution is as follows:
A kind of palladium ion fluorescent probe compounds, the compound have the following structure general formula I:
The second object of the present invention is to provide a kind of preparation method of above-mentioned palladium ion fluorescent probe compounds.It synthesizes road
Line is as shown below:
Wherein, II intermediate of formula is rhodamine amide, and IV intermediate of formula is the chloro- N of 6-4(naphthalene -1- base) pyrimidine -4,5- two
Amine, III intermediate of formula are the chloro- 8- methyl -9- of 6- (naphthalene -1- base) -9H- purine, and type I compound is palladium ion of the present invention
Fluorescent probe compounds.
Another technical solution is as follows:
A kind of preparation method of palladium ion fluorescent probe compounds, comprising the following steps:
(1) II intermediate of preparation formula (rhodamine amide)
Rhodamine B is dissolved in organic solvent, preheating 10-30min, addition ethylenediamine, 78~80 DEG C of back flow reactions 15~
18h, cooling, 45~55 DEG C are evaporated off organic solvent, and reaction system methylene chloride and water are extracted, and collect organic phase, are added dry
Drying prescription anhydrous sodium sulfate filters and is evaporated off the solvent in filtrate, carries out column chromatography for separation using eluant, eluent ethanol/methylene and obtains
To II intermediate of formula；
(2) III intermediate of preparation formula (the chloro- 8- methyl -9- of 6- (naphthalene -1- base) -9H- purine)
5- amino -4,6- dichloro pyrimidine, naphthalidine are added in organic solvent, are added concentrated hydrochloric acid after being completely dissolved, 78
~80 DEG C of 24~26h of back flow reaction, it is cooling, solvent is removed under reduced pressure, is dissolved with the NaOH that concentration is 1M, is then extracted with ethyl acetate
It takes, 45~55 DEG C are evaporated off ethyl acetate, are recrystallized with methanol and water, and 45~55 DEG C of drying obtain IV intermediate of formula；
IV intermediate of formula, acetic acid, polyphosphoric acids, dodecyl trimethyl ammonium chloride are dissolved in phosphorus oxychloride, 78
~80 DEG C of 20~36h of reflux, after reactant is cooled to room temperature, 68~72 DEG C are evaporated off solvent, to anti-under 0~5 DEG C of ice-water bath
It answers and mixture of ice and water is added in system, filter, washing, 45~55 DEG C of drying obtain III intermediate of formula；
(3) palladium ion fluorescent probe compounds are prepared
After III intermediate of formula in step (2) is dissolved in organic solvent, in the formula II in addition sodium bicarbonate, step (1)
Mesosome, 78~80 DEG C of 20~36h of reflux are cooling, and filtering removes organic solvent, carry out column using eluant, eluent ethanol/methylene
Chromatography obtains light yellow product, i.e., the described palladium ion fluorescent probe compounds.
Preferably, organic solvent described in step (1)-(3) is ethyl alcohol.
Preferably, step (1) rhodamine B, ethylenediamine molar ratio be 4~5: 40~50.
Preferably, step (2) 5- amino -4,6- dichloro pyrimidine, naphthalidine, concentrated hydrochloric acid, NaOH molar ratio be 28
~32: 56~64: 56~64: 45~55.
Preferably, the volume ratio of step (2) recrystallization in methanol and water is VMethanol:VWater=95~105: 475~525.
Preferably, step (2) IV intermediate of formula, acetic acid, polyphosphoric acids, dodecyl trimethyl ammonium chloride mole
Than being 18.1~18.9: 96~100: 73~76: 0.09~0.11.
Preferably, step (1) and the volume ratio of (2) described eluant, eluent are VMethanol:VMethylene chloride=1:95~105；Step (3) institute
The volume ratio for stating eluant, eluent is VMethanol:VMethylene chloride=1:140~160.
Preferably, step (3) II intermediate of formula, III intermediate of formula, sodium bicarbonate molar ratio be 3.2~3.6:
3.2~3.6: 16~18.
The third object of the present invention is to provide the application of above-mentioned palladium ion fluorescent probe compounds.
Specific technical solution is as follows:
A kind of application of palladium ion fluorescent probe compounds in palladium ion detection.
Preferably, the fluorescence probe of substance is detected using the palladium ion fluorescent probe compounds as palladium ion.
The invention has the following advantages:
For the present invention using rhodamine B as fluorophor, ethylenediamine is linking group, the chloro- 8- methyl -9- of 6- (naphthalene -1- base) -
9H- purine is that recognition group has synthesized a kind of palladium ion (Pd based on rhodamine B2+) fluorescent probe compounds.This method synthesis
Step is simple, and raw material is easy to get, and convenient for preparation, products obtained therefrom is solid powder, is easy to store；Prepared palladium ion fluorescence probe
Compound has the identification of specificity to palladium ion, and high sensitivity can be used for making to the strong antijamming capability of other metal ions
Make palladium ion fluorescence probe, is widely used in the palladium ion detection in the fields such as biochemistry, environmental science, medicine, has extensive
Application prospect.
Detailed description of the invention:
Fig. 1 is that palladium ion (Pd is added in palladium ion fluorescent probe compounds in embodiment 22+) before and after ultra-violet absorption spectrum
Figure；
Fig. 2 is that palladium ion (Pd is added in palladium ion fluorescent probe compounds in embodiment 22+) before and after fluorescence spectra；
Fig. 3 is for palladium ion fluorescent probe compounds in embodiment 2 to palladium ion (Pd in ethanol solution2+) fluorescence spectrum
Response diagram, wherein abscissa is fluorescence emission wavelengths (nm), and ordinate is fluorescence intensity, and every curve is respectively represented with palladium in figure
The increased fluorescence spectrum of ion concentration；
Fig. 4 is that palladium ion fluorescent probe compounds are dry to different Metal Ion Selective Electrodes in ethanol solution in embodiment 2
The fluorescence response figure of immunity detection, wherein abscissa is different metal ions, and ordinate is fluorescence intensity；
Fig. 5 is palladium ion fluorescent probe compounds and palladium ion (Pd in embodiment 22+) the Job-plot curve of ratio is complexed；
Fig. 6 is the nuclear magnetic resonance of palladium ion fluorescent probe compounds in embodiment 21H-NMR spectrum.
Fig. 7 is the nuclear magnetic resonance of palladium ion fluorescent probe compounds in embodiment 213C-NMR spectrogram.
Fig. 8 is the mass spectrogram of palladium ion fluorescent probe compounds in embodiment 2.
Specific embodiment
To better understand the essence of the present invention, the invention will be further elaborated combined with specific embodiments below.
Reagent employed in embodiment is that commercially available analysis is pure or chemical pure.
Embodiment 1
(1) rhodamine amide is prepared
Ethyl alcohol (30mL), rhodamine B (2g, 4.5mmol) are added into 100mL round-bottomed flask, preheats 20min, second is added
Diamines (3.0mL, 44.98mmol), 78~80 DEG C of 15~18h of back flow reaction, cooling, 50 DEG C are evaporated off ethyl alcohol, and reaction system is used
200mL methylene chloride and the extraction of 50mL water, collect organic phase, 5g desiccant anhydrous sodium sulfate are added, filters to get filtrate, 50 DEG C of steamings
Except the solvent in filtrate obtains crude product, eluant, eluent ethanol/methylene (volume ratio V is usedMethanol:VMethylene chloride=1: 100) carrying out
Column chromatography for separation obtains rhodamine amide.
(2) the chloro- 8- methyl -9- of 6- (naphthalene -1- base) -9H- purine is prepared
5- amino -4,6- dichloro pyrimidine (5g, 30mmol) is added into 100mL round-bottomed flask, naphthalidine (8.584g,
60mmol), it is dissolved in ethyl alcohol (50mL), concentrated hydrochloric acid (5mL, 60mmol) is added after being completely dissolved, 78~80 DEG C of back flow reactions 24
~26h, it is cooling, solvent is removed under reduced pressure, NaOH (1M, 50mL) dissolution is added, is extracted with 400mL ethyl acetate, 50 DEG C are evaporated off second
Acetoacetic ester recrystallizes (volume ratio V with methanol and waterMethanol:VWater=100: 500), it is solid to obtain lilac for filtering, 50 DEG C of drying
The chloro- N of body, i.e. 6-4(naphthalene -1- base) pyrimidine -4,5- diamines.
Acetic acid (5.882g, 98mmol), polyphosphoric acids (25g, 74mmol), dodecane are added into 100mL round-bottomed flask
Base trimethyl ammonium chloride (0.5g, 0.1mmol), the chloro- N of 6-4(naphthalene -1- base) pyrimidine -4,5- diamines (5g, 18.5mmol) is dissolved in
Phosphorus oxychloride (60mL, concentration 98%), 78~80 DEG C of 20~36h of reflux, the reaction is cooled to after room temperature, 70 DEG C be evaporated off it is molten
Agent, under 0~5 DEG C of ice-water bath into reaction system be added 90mL mixture of ice and water, filter and with 100mL water washing solid, 50
DEG C yellow solid is dried to obtain, uses eluant, eluent ethanol/methylene (volume ratio VMethanol:VMethylene chloride=1: 100) carrying out column chromatography
The isolated chloro- 8- methyl -9- of 6- (naphthalene -1- base) -9H- purine.
(3) palladium ion fluorescent probe compounds are prepared
The chloro- 8- methyl -9- of 6- (naphthalene -1- base) -9H- purine (1g, 3.4mmol) is added into 100mL round-bottomed flask, uses
20mL ethyl alcohol dissolution after, be added rhodamine amide (1.54g, 3.4mmol), sodium bicarbonate (1.43g, 17mmol), 78~80 DEG C
Flow back 20~36h, cooling, and the solid in flask is filtered to get filtrate, and removes organic solvent in filtrate, using eluant, eluent methanol/
Methylene chloride (volume ratio VMethanol:VMethylene chloride=1: 150) carrying out column chromatography for separation, obtain light yellow product, i.e. palladium ion fluorescence
Probe compound.
Embodiment 2
It is tested using palladium ion fluorescent probe compounds described in embodiment 1.
The palladium ion fluorescent probe compounds are dissolved in ethanol solution, concentration is 20 μM, other concentration of metal ions
It is 100 μM, is tested with Fluorescence Spectrometer and ultraviolet specrophotometer.
Such as Fig. 1, the ultraviolet variation map before and after palladium ion, probe are added for palladium ion fluorescent probe compounds of the invention
After compound no ultraviolet absorption peak at 550-580nm itself, probe compound molecule and palladium ion complexing, in 562nm
There is new absorption peak in place.
Such as Fig. 2, the change in fluorescence map before and after palladium ion is added for palladium ion fluorescent probe compounds of the invention, as a result
Showing the probe, itself is without absorption in ethanol solution, but with the addition of palladium ion, the strong fluorescence of the place 584nm generation.
Such as Fig. 3, the fluorescence increment reacted for palladium ion fluorescent probe compounds of the invention with palladium ion is dense to palladium ion
It writes music line, when 0-100 μM of palladium ion being added in 20 μM of Xiang Hanyou of palladium ion fluorescent probe compounds of the present invention, fluorescence intensity
Increase with palladium ion concentration and constantly enhances.
Such as Fig. 4, be palladium ion fluorescent probe compounds of the invention in the presence of disturbance metal ion with
Fluorescence intensity histogram after palladium ion reaction, the results showed that, palladium ion fluorescence of the present invention is visited in the presence of other metal ions
Needle compound identification palladium ion is without significantly interfering with.
It is 100 μM for the concentration summation of palladium ion fluorescent probe compounds and palladium ion of the invention, by changing such as Fig. 5
Become both concentration ratio (palladium ion fluorescent probe compounds and palladium ion the mass ratio of the material are followed successively by 1: 9,2: 8,3: 7,4: 6,5:
5,6: 4,7: 3,8: 2,9: 1) obtaining palladium ion fluorescent probe compounds autofluorescence under the fluorescence intensity and the concentration at 584nm
The difference of intensity accounts for the scale of total concentration with ion.By this figure it is found that vertical when palladium ion proportion is 0.5 sit
Mark reaches peak, can determine that palladium ion fluorescent probe compounds to be formed surely with mainly being combined in the form of 1: 1 between palladium ion
Fixed complex compound.
It is palladium ion fluorescent probe compounds of the invention such as Fig. 61H-NMR spectrum,1H NMR(400MHz,DMSO-
D6) δ 8.18 (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).
It is palladium ion fluorescent probe compounds of the invention such as Fig. 713C-NMR spectrogram,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。
It is the mass spectrogram of palladium ion fluorescent probe compounds of the invention, MS (ESI) m/z: 743.3 [M+H] such as Fig. 8+。
In ethanol system, palladium ion can be with the lactams group ketonic oxygen and purine in palladium ion fluorescent probe compounds of the invention
On nitrogen effect, thus induce lactam nucleus occur ring-opening reaction, generate hyperfluorescence, and 562nm at generation absorption peak, solution
Color becomes purple pink colour from colourless, while the fluorescence at 584nm is significantly enhanced, and fluorescence intensity and palladium ion concentration exist
Excellent linear relationship is presented in a certain range, the range of linearity of quantitative detection palladium ion is 0-40 μM, fluorescent probe molecule with
Palladium ion complexation constant is 1.15 × 104M-1.By linear fit obtain probe to the minimum detectability of palladium ion be 4.95 ×
10-8M。
Claims (10)
1. a kind of palladium ion fluorescent probe compounds, which is characterized in that the compound has the following structure general formula (I):
2. a kind of preparation method of palladium ion fluorescent probe compounds according to claim 1, which is characterized in that including with
Lower step:
(1) II intermediate of preparation formula
Rhodamine B is dissolved in organic solvent, preheating 10-30min, addition ethylenediamine, 78~80 DEG C of 15~18h of back flow reaction,
Cooling, 45~55 DEG C are evaporated off organic solvent, and reaction system methylene chloride and water are extracted, and collect organic phase, and desiccant is added
Anhydrous sodium sulfate filters and is evaporated off the solvent in filtrate, carries out column chromatography for separation using eluant, eluent ethanol/methylene and obtains formula
II intermediate；
(2) III intermediate of preparation formula
5- amino -4,6- dichloro pyrimidine, naphthalidine are added in organic solvent, are added concentrated hydrochloric acid after being completely dissolved, 78~80
DEG C 24~26h of back flow reaction, it is cooling, solvent is removed under reduced pressure, is dissolved with the NaOH that concentration is 1M, is then extracted with ethyl acetate,
45~55 DEG C are evaporated off ethyl acetate, are recrystallized with methanol and water, and 45~55 DEG C of drying obtain IV intermediate of formula；
IV intermediate of formula, acetic acid, polyphosphoric acids, dodecyl trimethyl ammonium chloride are dissolved in phosphorus oxychloride, 78~80
DEG C reflux 20~36h, after reactant is cooled to room temperature, 68~72 DEG C are evaporated off solvent, to reactant under 0~5 DEG C of ice-water bath
Mixture of ice and water is added in system, filters, washing, 45~55 DEG C of drying obtain III intermediate of formula；
(3) palladium ion fluorescent probe compounds are prepared
After III intermediate of formula in step (2) is dissolved in organic solvent, sodium bicarbonate, II intermediate of formula in step (1) is added,
78~80 DEG C of 20~36h of reflux, cooling, filtering removes organic solvent, carries out column chromatography using eluant, eluent ethanol/methylene
Separation, obtains light yellow product, i.e., the described palladium ion fluorescent probe compounds.
3. a kind of preparation method of palladium ion fluorescent probe compounds according to claim 2, which is characterized in that step
(1) organic solvent described in-(3) is ethyl alcohol.
4. a kind of preparation method of palladium ion fluorescent probe compounds according to claim 2, which is characterized in that step
(1) rhodamine B, ethylenediamine molar ratio be 4~5: 40~50.
5. a kind of preparation method of palladium ion fluorescent probe compounds according to claim 2, which is characterized in that step
(2) the 5- amino -4,6- dichloro pyrimidine, naphthalidine, concentrated hydrochloric acid, NaOH molar ratio be 28~32: 56~64: 56~64:
45~55.
6. a kind of preparation method of palladium ion fluorescent probe compounds according to claim 2, which is characterized in that step
(2) volume ratio of the recrystallization in methanol and water is VMethanol:VWater=95~105: 475~525.
7. a kind of preparation method of palladium ion fluorescent probe compounds according to claim 2, which is characterized in that step
(2) IV intermediate of formula, acetic acid, polyphosphoric acids, dodecyl trimethyl ammonium chloride molar ratio be 18.1~18.9: 96~
100: 73~76: 0.09~0.11.
8. a kind of preparation method of palladium ion fluorescent probe compounds according to claim 2, which is characterized in that step
(1) and the volume ratio of (2) described eluant, eluent is VMethanol:VMethylene chloride=1:95~105；The volume ratio of step (3) described eluant, eluent is
VMethanol:VMethylene chloride=1:140~160.
9. a kind of preparation method of palladium ion fluorescent probe compounds according to claim 2, which is characterized in that step
(3) II intermediate of formula, III intermediate of formula, sodium bicarbonate molar ratio be 3.2~3.6: 3.2~3.6: 16~18.
10. application of the palladium ion fluorescent probe compounds described in claim 1 in palladium ion detection.
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| CN110498803A (en) * | 2019-09-06 | 2019-11-26 | 山东师范大学 | A kind of compound and the preparation method and application thereof based on hydrazide structure in rhodamine |
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| CN112094270A (en) * | 2020-08-28 | 2020-12-18 | 江苏科技大学 | Purine parent-based cadmium ion detection fluorescent probe and preparation method and application thereof |
| CN112110922A (en) * | 2020-08-28 | 2020-12-22 | 江苏科技大学 | Purine matrix-based aluminum ion detection fluorescent probe and preparation method and application thereof |
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| CN114507213A (en) * | 2022-03-03 | 2022-05-17 | 河北师范大学 | Fluorescent compound, fluorescent probe, fluorescent visual test paper, and preparation method and application thereof |
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