CN110128328A - A kind of fluorescence probe and preparation method thereof identifying molybdenum acid ion and recognition methods - Google Patents
A kind of fluorescence probe and preparation method thereof identifying molybdenum acid ion and recognition methods Download PDFInfo
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- CN110128328A CN110128328A CN201910512006.XA CN201910512006A CN110128328A CN 110128328 A CN110128328 A CN 110128328A CN 201910512006 A CN201910512006 A CN 201910512006A CN 110128328 A CN110128328 A CN 110128328A
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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Abstract
The invention discloses a kind of fluorescence probe for identifying molybdenum acid ion and preparation method thereof and recognition methods, the preparation method of the fluorescence probe is: (1) by 1,4- dibromine naphthalene, 4-vinylpyridine, palladium chloride, triphenylphosphine and potassium carbonate are added in triethylamine and mix, and mixture is sealed in N2In reaction under high pressure bottle under atmosphere, in 110-120 DEG C of reaction 24-36h, product methylene chloride and saturated salt solution is extracted, are then spin-dried for, with ethyl alcohol recrystallization, rear filtration drying obtains product A；(2) product A is dissolved in n,N-Dimethylformamide, 1- bromine normal octane is then added, is heated to 80-90 DEG C, react 20-24h, added ether and precipitated completely to it, filtered, with ether by washing of precipitate twice, drying obtains probe.The present invention is able to achieve the identification to molybdate, and has identification at low cost, easy to operate, as a result visually, high sensitivity and selective good feature.
Description
Technical field
The present invention relates to a kind of fluorescence probe and preparation method thereof and recognition methods, in particular to a kind of identification molybdate from
Fluorescence probe of son and preparation method thereof and recognition methods.
Background technique
Ammonium molybdate is mainly used for Smelting Ferromolybdenum and produces molybdenum trioxide, metal molybdenum powder as tungsten-molybdenum alloy, the raw material of molybdenum filament,
Followed by it is used as agricultural molydbenum fertilizer on a small quantity for making the catalyst of chemical industry, ammonium paramolybdate is a kind of trace-element fertilizer, can be promoted solid
Nitrogen can make nitrogen fixing capacity be increased to tens to hundred times the pulse families such as peanut, soya bean.Minute quantity is a variety of for medicine aspect
The component part of enzyme, the shortage of molybdenum will lead to the diseases such as saprodontia, kidney stone, Keshan disease, Kaschin-Beck disease, cancer of the esophagus, be mainly used for
The long-term patient for relying on intravenous hyperalimentation.
Therefore, the recognition methods for developing a kind of molybdate is of great significance to chemical industry, environmental and human health impacts.Fluorescence is visited
Needle is a kind of reagent that certain ion is identified by change in fluorescence, has highly selective, highly sensitive, inexpensive and result can
Depending on the characteristics of, and existing had not been reported at present for the fluorescence probe of the identification of molybdenum acid ion.
Summary of the invention
The object of the present invention is to provide a kind of fluorescence probe for identifying molybdenum acid ion and preparation method thereof and identification sides
Method.The present invention is able to achieve the identification to molybdate, and has identification at low cost, easy to operate, as a result visually, high sensitivity and choosing
The good feature of selecting property.
Technical solution of the present invention: a kind of fluorescence probe identifying molybdenum acid ion, the molecular formula of the fluorescence probe are as follows:
C40H52Br2N2, structural formula are as follows:
A kind of preparation method of the fluorescence probe of identification molybdenum acid ion above-mentioned, includes the following steps:
(1) 1,4- dibromine naphthalene, 4-vinylpyridine, palladium chloride, triphenylphosphine and potassium carbonate are added in triethylamine and are mixed
It closes, mixture is sealed in N2In reaction under high pressure bottle under atmosphere, in 110-120 DEG C of reaction 24-36h, by product dichloromethane
Alkane and saturated salt solution extraction, are then spin-dried for, with ethyl alcohol recrystallization, rear filtration drying obtains product A；
(2) product A is dissolved in n,N-Dimethylformamide, 1- bromine normal octane is then added, is heated to 80-90 DEG C,
React 20-24h, add ether to its completely precipitate, filter, with ether by washing of precipitate twice, drying, obtain probe.
The preparation method of the fluorescence probe of identification molybdenum acid ion above-mentioned, the concentration of the ethyl alcohol are 95% or more.
The preparation method of the fluorescence probe of identification molybdenum acid ion above-mentioned, in the step (1), every 3-5ml triethylamine
Middle addition 286mg1,4- dibromine naphthalene, 263mg4- vinylpyridine, 30mg palladium chloride, 100mg triphenylphosphine and 400mg carbonic acid
Potassium.
The preparation method of the fluorescence probe of identification molybdenum acid ion above-mentioned, in the step (1), product first uses dichloromethane
Alkane extracts 3 times, then is extracted 3 times with saturated salt solution.
The preparation method of the fluorescence probe of identification molybdenum acid ion above-mentioned, in the step (1), first with anhydrous after extraction
It is spin-dried for again after the dry 1-2h of magnesium sulfate.
The preparation method of the fluorescence probe of identification molybdenum acid ion above-mentioned, in the step (2), product A object and 1- bromine
The ratio between amount of substance of normal octane is 1:20.
It is a kind of it is above-mentioned identification molybdenum acid ion fluorescence probe application, be for detect the molybdate in aqueous systems from
Son.
The application of the fluorescence probe of identification molybdenum acid ion above-mentioned, is that the probe is dissolved in DMSO, uses secondary water
Dilution, obtains fluorescent reagent, sample to be identified is then instilled into reagent, obtains sample solution, carries out fluorescence excitation to sample solution
And the glimmering light activated wavelength of fluorescence of test analysis, fluorescence exciting wavelength used are 438.03nm, when addition sample to be identified
And when recognizing molybdenum acid ion, the fluorescence maximum emission wavelength of reagent is by 542.98nm red shift to 626.02nm.
The application of the fluorescence probe of identification molybdenum acid ion above-mentioned, the concentration of the fluorescent reagent middle probe are 10- 5mol.L-1。
Beneficial effects of the present invention
(1) the advantages of fluorescence probe of the invention can identify molybdenum acid ion in aqueous solution；
(2) common yin coexists from having compared with strong anti-interference ability for other in fluorescence probe of the invention, has selection
The high advantage of property, and the identification concentration of fluorescence probe of the invention is lower, has the advantages that high sensitivity；
(3) fluorescence probe of the invention is only a kind of chemical reagent, has identification at low cost, easy to operate, and identifies knot
The visual advantage of fruit.
To further illustrate beneficial effects of the present invention, inventor has done following experiment:
One, qualitative analysis is tested
It is 10 in concentration range-6~10-4In the fluorescence probe aqueous solution of mol/L, when excitation wavelength is 438.03nm,
The maximum emission wavelength of fluorescence probe is 542.98nm, as addition molybdenum acid ion (Mo in fluorescence probe aqueous solution7O24 6-) after,
The maximum emission wavelength of fluorescence probe shows as fluorescent quenching from 542.98nm red shift to 626.02nm.
Two, detection limit analysis test
1, the preparation method of fluorescence probe solution: weighing the probe of 5.6mg, and being configured to volume with DMSO is 10mL, concentration
It is 1.0 × 10-3mol·L-1Solution, take 1 100.0mL volumetric flask, take 1mL in capacity configured probe solution,
It is diluted to graduation mark with secondary water, obtaining concentration is 1.0 × 10-5mol·L-1Probe solution.
2, the ammonium molybdate for weighing excellent pure grade is configured to 10mL aqueous solution, and concentration is all 1.0 × 10-2mol·L-1, according to need
It is diluted step by step with secondary water.
3, fluorescent reagent 1.0 × 10 is taken-5MolL-1 titer, toward cuvette in be added 3mL fluorescent reagent, be added dropwise respectively
Enter 1.0 × 10-3mol·L-1Mo7O24 6-Solion introduces fluorescence spectrum and is measured, excitation wavelength 438.98nm.
4, respectively with Mo7O24 6-Ion concentration is abscissa, and fluorescence intensity is ordinate, obtains working curve.
5, sample measures: taking two 10.0mL volumetric flasks, is separately added into fluorescent reagent 1.0 × 10-3mol·L-10.1mL mark
Quasi- liquid is separately added into molybdenum acid ion solution in two capacity, is diluted to scale, is placed at room temperature for 5 minutes, introduces 3.0cm's
Quartz colorimetric utensil carries out fluoremetry, and sample concentration is found on working curve according to fluorescence intensity.Detection identifies minimum dense
Angle value is 1.29 × 10-7mol·L-1。
Detailed description of the invention
Fig. 1 is the chemical structural formula of fluorescent probe molecule of the present invention；
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of fluorescent probe molecule of the present invention；
Fig. 3 is the fluorescence spectra of fluorescent probe molecule of the present invention and different anions effect；
Fig. 4 is that take pictures figure of each anion under the ultraviolet light irradiation of 254nm is added in probe solution of the present invention；
Fig. 5 is fluorescent probe molecule of the present invention in water with the change in fluorescence figure after addition molybdenum acid ion；
Fig. 6 is the calibration curve of molybdenum acid ion and probe of the present invention effect；
Fig. 7 is the ultraviolet spectrogram of fluorescent probe molecule of the present invention and different anions effect.
From the figure 3, it may be seen that there is fluorescent quenching only when recognizing molybdenum acid ion, illustrate probe tool of the invention
There is preferable anti-interference ability.
Specific embodiment
Below with reference to embodiment, the present invention is further illustrated, but is not intended as the foundation limited the present invention.
The embodiment of the present invention
Embodiment 1: a kind of preparation method for the fluorescence probe identifying molybdenum acid ion, steps are as follows:
(1) by 286mg1,4- dibromine naphthalene, 263mg4- vinylpyridine, 30mg palladium chloride, 100mg triphenylphosphine and
400mg potassium carbonate is added in 4ml triethylamine and mixes, and mixture is sealed in N2It is anti-at 115 DEG C in reaction under high pressure bottle under atmosphere
30h is answered, product is first extracted with dichloromethane 3 times, then is extracted 3 times with saturated salt solution, it is then dry with anhydrous magnesium sulfate
It is spin-dried for after 1.5h, the ethyl alcohol recrystallization for being 95% with concentration, rear filtration drying obtains product A；
(2) product A is dissolved in n,N-Dimethylformamide, then by the substance of product A object and 1- bromine normal octane
1- bromine normal octane is added for 1:20 in the ratio between amount, is heated to 85 DEG C, reacts 22h, adds ether and precipitates completely to it, filters, use
Twice by washing of precipitate, drying obtains probe to ether.
Embodiment 2: a kind of preparation method for the fluorescence probe identifying molybdenum acid ion, steps are as follows:
(1) by 286mg1,4- dibromine naphthalene, 263mg4- vinylpyridine, 30mg palladium chloride, 100mg triphenylphosphine and
400mg potassium carbonate is added in 3ml triethylamine and mixes, and mixture is sealed in N2It is anti-at 110 DEG C in reaction under high pressure bottle under atmosphere
Product should be first extracted with dichloromethane 3 times, then be extracted 3 times with saturated salt solution for 24 hours, then with the dry 1h of anhydrous magnesium sulfate
It is spin-dried for later, the ethyl alcohol recrystallization for being 96% with concentration, rear filtration drying obtains product A；
(2) product A is dissolved in n,N-Dimethylformamide, then by the substance of product A object and 1- bromine normal octane
1- bromine normal octane is added for 1:20 in the ratio between amount, is heated to 80 DEG C, reacts 20h, adds ether and precipitates completely to it, filters, use
Twice by washing of precipitate, drying obtains probe to ether.
Embodiment 3: a kind of preparation method for the fluorescence probe identifying molybdenum acid ion, steps are as follows:
(1) by 286mg1,4- dibromine naphthalene, 263mg4- vinylpyridine, 30mg palladium chloride, 100mg triphenylphosphine and
400mg potassium carbonate is added in 5ml triethylamine and mixes, and mixture is sealed in N2It is anti-at 120 DEG C in reaction under high pressure bottle under atmosphere
36h is answered, product is first extracted with dichloromethane 3 times, then is extracted 3 times with saturated salt solution, then with the dry 2h of anhydrous magnesium sulfate
It is spin-dried for later, the ethyl alcohol recrystallization for being 96% with concentration, rear filtration drying obtains product A；
(2) product A is dissolved in n,N-Dimethylformamide, then by the substance of product A object and 1- bromine normal octane
1- bromine normal octane is added for 1:20 in the ratio between amount, is heated to 90 DEG C, reaction for 24 hours, adds ether and precipitates completely to it, filter, use
Twice by washing of precipitate, drying obtains probe to ether.
Embodiment 4: a method of molybdenum acid ion in identification aqueous systems, is by fluorescence probe made from embodiment 1-3
It is dissolved in DMSO, is diluted with secondary water, it is 10 that concentration, which is made,-5mol.L-1Then fluorescent reagent instills sample to be identified into reagent
Product obtain sample solution, carry out fluorescence excitation and the glimmering light activated wavelength of fluorescence of test analysis, fluorescence used to sample solution
Excitation wavelength is 438.03nm, when sample to be identified is added and recognizes molybdenum acid ion, the fluorescence emission maximum wave of reagent
Length is by 542.98nm red shift to 626.02nm, conversely, not recognizing molybdenum acid ion then.
Claims (10)
1. a kind of fluorescence probe for identifying molybdenum acid ion, it is characterised in that: the molecular formula of the fluorescence probe are as follows:
C40H52Br2N2, structural formula are as follows:
2. a kind of preparation method of the fluorescence probe of identification molybdenum acid ion according to claim 1, it is characterised in that: packet
Include following steps:
(1) Isosorbide-5-Nitrae-dibromine naphthalene, 4-vinylpyridine, palladium chloride, triphenylphosphine and potassium carbonate are added in triethylamine and are mixed, it will
Mixture is sealed in N2In reaction under high pressure bottle under atmosphere, in 110-120 DEG C of reaction 24-36h, by product methylene chloride and satisfy
It extracts, is then spin-dried for, with ethyl alcohol recrystallization, rear filtration drying obtains product A with saline solution；
(2) product A is dissolved in n,N-Dimethylformamide, 1- bromine normal octane is then added, be heated to 80-90 DEG C, reaction
20-24h, add ether to its completely precipitate, filter, with ether by washing of precipitate twice, drying, obtain probe.
3. the preparation method of the fluorescence probe of identification molybdenum acid ion according to claim 2, it is characterised in that: the second
The concentration of alcohol is 95% or more.
4. the preparation method of the fluorescence probe of identification molybdenum acid ion according to claim 2, it is characterised in that: the step
Suddenly in (1), 286mg1,4- dibromine naphthalene, 263mg4- vinylpyridine, 30mg palladium chloride, 100mg are added in every 3-5ml triethylamine
Triphenylphosphine and 400mg potassium carbonate.
5. the preparation method of the fluorescence probe of identification molybdenum acid ion according to claim 2, it is characterised in that: the step
Suddenly in (1), product is first extracted with dichloromethane 3 times, then is extracted 3 times with saturated salt solution.
6. the preparation method of the fluorescence probe of identification molybdenum acid ion according to claim 2, it is characterised in that: the step
Suddenly it in (1), is first spin-dried for again later with the dry 1-2h of anhydrous magnesium sulfate after extraction.
7. the preparation method of the fluorescence probe of identification molybdenum acid ion according to claim 2, it is characterised in that: the step
Suddenly in (2), the ratio between amount of substance of product A object and 1- bromine normal octane is 1:20.
8. a kind of application of the fluorescence probe of identification molybdenum acid ion described in claim 1, it is characterised in that: be for detecting
Molybdenum acid ion in aqueous systems.
9. the application of the fluorescence probe of identification molybdenum acid ion according to claim 8, it is characterised in that: be by the spy
Needle is dissolved in DMSO, is diluted with secondary water, and fluorescent reagent is obtained, and sample to be identified is then instilled into reagent, obtains sample solution, right
Sample solution carries out fluorescence excitation and the glimmering light activated wavelength of fluorescence of test analysis, fluorescence exciting wavelength used are
438.03nm, when sample to be identified is added and recognizes molybdenum acid ion, the fluorescence maximum emission wavelength of reagent by
542.98nm red shift is to 626.02nm.
10. the application of the fluorescence probe of identification molybdenum acid ion according to claim 9, it is characterised in that: the fluorescence
The concentration of reagent middle probe is 10-5mol.L-1。
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110698390A (en) * | 2019-10-25 | 2020-01-17 | 贵州医科大学 | Fluorescent probe for identifying bisulfite and preparation method and detection method thereof |
| CN110818616A (en) * | 2019-10-25 | 2020-02-21 | 贵州医科大学 | Fluorescent probe for identifying thiocyanate radical and preparation method and detection method thereof |
Citations (1)
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|---|---|---|---|---|
| CN104962279A (en) * | 2015-05-26 | 2015-10-07 | 贵州大学 | NO<3><-> ion detection reagent and application thereof |
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| CN104962279A (en) * | 2015-05-26 | 2015-10-07 | 贵州大学 | NO<3><-> ion detection reagent and application thereof |
Non-Patent Citations (2)
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| BERNARD JUSKOWIA，ET AL.: "Detection of noncovalent interactions of hairpin oligonucleotide with stilbazolium ligands by MALDI TOF mass spectrometry", 《INTERNATIONAL JOURNAL OF MASS SPECTROMETRY》 * |
| DONG-SHENG GUO: "Hierarchically self-assembled fluorescent nanoparticles for near-infrared lysosome-targeted imaging", 《CHINESE CHEMICAL LETTERS》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110698390A (en) * | 2019-10-25 | 2020-01-17 | 贵州医科大学 | Fluorescent probe for identifying bisulfite and preparation method and detection method thereof |
| CN110818616A (en) * | 2019-10-25 | 2020-02-21 | 贵州医科大学 | Fluorescent probe for identifying thiocyanate radical and preparation method and detection method thereof |
| CN110818616B (en) * | 2019-10-25 | 2022-11-22 | 贵州医科大学 | Fluorescent probe for identifying thiocyanate radical and preparation method and detection method thereof |
| CN110698390B (en) * | 2019-10-25 | 2022-11-22 | 贵州医科大学 | Fluorescent probe for identifying bisulfite and preparation method and detection method thereof |
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