CN107382935B - A kind of coumarin fluorescent probe C1 and its preparation method and application - Google Patents
A kind of coumarin fluorescent probe C1 and its preparation method and application Download PDFInfo
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Abstract
The invention discloses coumarin fluorescent probe molecule C1.The invention also discloses the preparation methods of coumarin fluorescent probe molecule C1.The invention also discloses application of the coumarin fluorescent probe molecule C1 in terms of hydrazine Molecular Detection.Extraordinary linear relationship is presented in the detection signal and hydrazine molecular concentration of fluorescent probe molecule C1 of the present invention；The detection can carry out under a variety of pH environment, the influence of complicated ingredient in not examined environment and detection architecture；Detection of the invention speed easy to operate is fast, and this method only need to mix sample with fluorescence probe, tests its fluorescence intensity immediately after it can be learnt that corresponding hydrazine molecular concentration；Detection process product water of the invention and nitrogen, without any by-product.
Description
Technical field
The invention belongs to environmental analyses, environmental monitoring field, and in particular to a kind of coumarin fluorescent probe C1 and its preparation
Methods and applications.
Background technique
Hydrazine (N2H4) very extensive in industrial, in agriculture and medicine production purposes, it can be used for preparing plastics and rubber
The foaming agent of glue product；Propellant as rocket, guided missile and satellite；It is used to prepare the gas-forming agent of air bag；For
Produce herbicide, fungicide, insecticide and plant growth regulator etc..However, hydrazine itself is a kind of toxicant, human body is missed
Taking in a certain amount of hydrazine will lead to the damage of liver, lungs, kidney and central nervous system.Hydrazine is also classified as people by U.S.EPA
One of body carcinogen, and its minimum intoxicating intake is set as 10ppb.It can be seen that development is efficient, convenient, inexpensive
Analysis method has great research valence for detecting Determination of Trace Hydrazine molecular contaminants that may be present in environmental water sample and organism
Value.
However hydrazine analysis of molecules detection method reported in the world and few, and wherein gas chromatography-mass spectrometry at present
With, instrument and equipment is expensive, sample preparation is cumbersome for the methods of titration, Surface enhanced Raman spectroscopy method, operation specialization is wanted
Ask high.In contrast, the analysis and detection technology based on small organic molecule fluorescence probe shows following advantages: 1) easy to operate,
Signal is intuitive；2) high sensitivity of fluorescence detection；3) at low cost, many fluorescent probe molecules can be with Reusability；It 4) can be with
Regulate and control detection behavior by the method for structural modification to meet the needs under different condition.Therefore, have if development is efficient, novel
Machine fluorescence probe is used for the detection of hydrazine molecule, then is expected to substantially reduce cost, while improving detection efficiency.
Regrettably, about fluorescent molecular probe, for the research of hydrazine analysis detection, there is also water solubilitys both at home and abroad at present
Difference, the problems such as response time is long, signal resolution is low, detection sensitivity is to be improved.For example, Swager in 2006 et al. is reported
Hydrazine steam detection method based on fluorescent polymer reduction reaction mechanism, but this method cannot be used for the inspection of hydrazine in aqueous solution
It surveys.And the hydrazine response test of Sessler and Kim et al. the 2013 naphthalimide fluorescence probes reported is then in pure acetonitrile
It carries out.Based on Gabriel reaction mechanism, phthalimide is modified as hydrazine response unit in naphthalimide, cumarin
Also all there is the problems such as water-soluble not high, the reaction time is long with the hydrazine detection probe of the building units such as dansyl.In addition, at present
The hydrazine fluorescence probe developed is carried out using the necleophilic reaction activity of hydrazine, and such mechanism of action causes to generate complicated
Byproduct of reaction, bring negative effect while detecting hydrazine molecule.
Therefore, develop the novel hydrazine Molecular Detection fluorescence spy that good water solubility, high sensitivity, detection process do not generate by-product
Needle set has great practical value.
Summary of the invention
Technical problem: in order to overcome, time-consuming, poorly water-soluble, is also easy to produce by-product existing for current hydrazine molecular detecting method
Etc. statuses, highly selective, high sensitivity detection is carried out to hydrazine molecule by Development of Novel fluorescent probe technique, the present invention is wanted
The technical issues of solution, there is provided a kind of coumarin fluorescent probe C1.
Also there is provided the preparation methods of coumarin fluorescent probe C1 a kind of for technical problems to be solved by the present invention.
There is provided coumarin fluorescent probe C1 in terms of hydrazine Molecular Detection for the last technical problems to be solved of the present invention
Using.
Technical solution: in order to solve the above-mentioned technical problem, the invention discloses a kind of coumarin fluorescent probe molecule C1, institutes
The structural formula for stating coumarin fluorescent probe molecule C1 is as follows:
The content of present invention further includes the preparation method of above-mentioned coumarin fluorescent probe molecule C1, comprising the following steps:
1) 4- trifluoromethyl-umbelliferone C-OH synthesis；
2) preparation of coumarin fluorescent probe molecule C1:
C-OH, triethylamine and methylene chloride 2a) are stirred to get into mixed liquor in ice bath；
2b) under nitrogen protection, allyl chloroformate is dissolved in methylene chloride, and is slowly added into above-mentioned mixed liquor；
Ice bath 2c) is removed, reaction is placed in and is stirred under room temperature, is spin-dried for reaction dissolvent, product is subjected to column chromatography and is mentioned
Pure, using methylene chloride/petroleum ether as eluent, products therefrom is further recrystallized to give target product perfume in n-hexane
Legumin fluorescent probe molecule C1.
Wherein, above-mentioned steps 2a) in mixed liquor in C-OH molar concentration be 0.05~0.2mol/L, triethylamine
Molar concentration is 0.5~2.0mol/L.
Wherein, above-mentioned steps 2b) in the volume ratio of allyl chloroformate and methylene chloride be (0.6~1.2): (10~
20)。
Wherein, above-mentioned steps 2c) in the condition being spin-dried for be 30~60 DEG C of bath temperature, water pump vacuum distillation.
Wherein, above-mentioned steps 2c) in methylene chloride/petroleum ether with volume ratio 1:1~3:1.
Wherein, above-mentioned steps 2c) in n-hexane in recrystallization condition be 20~40 DEG C of dissolution crude products, -20~0 DEG C tie
Crystalline substance obtains sterling.
The content of present invention further includes application of the above-mentioned coumarin fluorescent probe molecule C1 in terms of hydrazine Molecular Detection.
The content of present invention further includes above-mentioned coumarin fluorescent probe molecule C1 and Pd2+The prepared probe solution of mixing is in hydrazine
Application in terms of Molecular Detection.
Testing principle of the invention: fluorescent probe molecule C1 itself does not fluoresce, with Pd2+Do not react, therefore, by C1 with
Pd2+Mix acquired solution C1-Pd2+It is still not no fluorescence.And work as to C1-Pd2+Being added in probe solution has strong reducing property
Hydrazine when, hydrazine can be by Pd2+It is reduced to Pd0.Hereafter, the Pd of generation0Continue that specific reaction occurs with fluorescent probe molecule C1, takes off
The allyl carbamate base for going 7- in C1 molecule, obtains the C-OH molecule that can issue intense fluorescence, issues at this time strongly
Fluorescence, and fluorescence intensity is directly proportional to the hydrazine molecular weight of addition, so as to pass through the variation quantitative detection of solution fluorescence intensity
The concentration of hydrazine solution.Referring to Fig. 1, to the quantitative detection principle of hydrazine molecule: to C1-Pd2+Hydrazine molecule is added in probe solution to be made
It issues strong fluorescence, and linear relationship is presented in fluorescence intensity and the concentration of hydrazine molecule.
The utility model has the advantages that the present invention compared with the existing technology, has following advantages:
1) extraordinary linear relationship is presented in the detection signal of fluorescence probe of the invention and hydrazine molecular concentration；
2) detection can carry out under a variety of pH environment, the shadow of complicated ingredient in not examined environment and detection architecture
It rings；
3) detection of the invention speed easy to operate is fast, and this method only need to mix sample with fluorescence probe, immediately after
Its fluorescence intensity is tested it can be learnt that corresponding hydrazine molecular concentration；
4) detection process product water and nitrogen of the invention, without any by-product.
Detailed description of the invention
Quantitative detection schematic diagram of Fig. 1 fluorescent probe molecule C1 to hydrazine molecule；
Fig. 2 a) C1-Pd2+The hydrazine titration fluorescence spectrum change of probe solution；b)C1-Pd2+Probe solution fluorescence intensity with plus
Enter the linear relationship working curve of hydrazine concentration；
Fig. 3 is to C1-Pd2+The fluorescence spectrum of 100 times of sample hydrazine solutions of dilution is added in probe solution；
Fig. 4 uses C1-Pd2+The concentration of hydrazine in probe solution quantitative detection water sample；
Fig. 5 a) C1-Pd2+Fluorescence spectra of the probe solution to hydrazine selective response；b)C1-Pd2+Probe solution selects hydrazine
The histogram of selecting property response；
Fig. 6 C1-Pd2+Anti- pH interference performance of the probe solution when detecting hydrazine；
Fig. 7 C1-Pd2+The trend that fluorescence intensity of the probe solution at 500nm wavelength changes over time after hydrazine is added
Figure；
Fig. 8 C1-Pd2+The high resolution mass spectrum of probe solution and hydrazine reaction product characterizes；
Fig. 9 is to C1-Pd2+The fluorescence spectrum of 100 times of mixing sample hydrazine solutions of dilution is added in probe solution；
Figure 10 uses C1-Pd2+The concentration of hydrazine in probe solution quantitative detection aggregate sample.
Specific embodiment
To further illustrate details of the invention, several embodiments are set forth below, but the present invention should not be limited thereto.
The preparation of 1 4- trifluoromethyl -7- allyl carbamate butylcoumariii C1 of embodiment
1,4- trifluoromethyl-umbelliferone C-OH synthesis
4- trifluoromethyl-umbelliferone (is named as 7-hydroxy-4-trifluoromethyl in the document
Coumarin (M2)) synthetic method see reference document (Qi Sun, Jun Li, Wan-Nian Liu, Qing-Jian Dong,
Wen-Chao Yang and Guang-Fu Yang.Non-Peptide-Based Fluorogenic Small-Molecule
Probe for Elastase.Anal.Chem.,2013,85,11304-11311.).4- trifluoromethyl-umbelliferone
Structural formula is as follows:
2, the preparation of 4- trifluoromethyl -7- allyl carbamate butylcoumariii C1
Using 4- trifluoromethyl-umbelliferone C-OH as raw material, in its 7- modification allyl chloroformate, 4- tri- is obtained
Methyl fluoride -7- allyl carbamate butylcoumariii C1.Synthetic method is as follows: by C-OH (228mg, 1mmol), triethylamine
(1.4mL) and methylene chloride (10mL) stir in ice bath, nitrogen protection.Allyl chloroformate (0.6mL, 10mmol) is dissolved in
10mL methylene chloride, and be slowly added into above-mentioned mixed liquor.Ice-water bath is removed, reaction is stirred at room temperature 2 hours.It is spin-dried for reacting molten
Agent, 40 DEG C of the bath temperature being spin-dried for, water pump vacuum distillation, by product carry out column Chromatographic purification, with methylene chloride/petroleum ether (2:
It 1, v:v) is eluant, eluent, products therefrom further recrystallizes in n-hexane, and recrystallization condition is 30 DEG C of dissolution crude products, and -10
DEG C crystallization obtains sterling target product C1 (213mg, 67.8%)
1H NMR(CDCl3, Bruker 400MHz, ppm): δ=7.77 (q, 1H), 7.35 (d, J=2.4Hz, 1H), 7.26
(q, 1H), 6.81 (s, 1H), 6.06-5.99 (m, 1H), 5.47 (t, 1H), 5.39 (d, J=10.4Hz, 1H), 4.80 (d, J=
6Hz,2H).13C NMR(CDCl3, Bruker 100MHz, ppm): δ=158.44,155.04,154.14,152.28,
130.57,126.44,126.41,120.24,118.33,115.53,115.48,111.44,110.51,69.82.MS:
observed:315.0472,calculated for C14H10F3O5([M+H]+):315.0480.
The synthetic route of fluorescent probe molecule C1 is as follows:
The preparation of 2 4- trifluoromethyl -7- allyl carbamate butylcoumariii C1 of embodiment
1,4- trifluoromethyl-umbelliferone C-OH synthesis
Referring to 4- trifluoromethyl-umbelliferone C-OH synthesis of embodiment 1
2, the preparation of 4- trifluoromethyl -7- allyl carbamate butylcoumariii C1
Using 4- trifluoromethyl-umbelliferone C-OH as raw material, in its 7- modification allyl chloroformate, 4- tri- is obtained
Methyl fluoride -7- allyl carbamate butylcoumariii C1.Synthetic method is as follows: by C-OH (456mg, 2mmol), triethylamine
(1.4mL) and methylene chloride (15mL) stir in ice bath, nitrogen protection.Allyl chloroformate (1.2mL) is dissolved in 15mL bis-
Chloromethanes, and be slowly added into above-mentioned mixed liquor.Ice-water bath is removed, reaction is stirred at room temperature 3 hours.It is spin-dried for reaction dissolvent, is revolved
Product is carried out column Chromatographic purification, with methylene chloride/petroleum ether (1:1, v:v) by 50 DEG C of dry bath temperature, water pump vacuum distillation
For eluant, eluent, products therefrom is further recrystallized in n-hexane, and recrystallization condition is 40 DEG C of dissolution crude products, -20 DEG C of crystallizations
Obtain sterling target product C1.
The mass spectrometric data result of target product C1 is the same as embodiment 1.
The preparation of 3 4- trifluoromethyl -7- allyl carbamate butylcoumariii C1 of embodiment
1,4- trifluoromethyl-umbelliferone C-OH synthesis
Referring to 4- trifluoromethyl-umbelliferone C-OH synthesis of embodiment 1
2, the preparation of 4- trifluoromethyl -7- allyl carbamate butylcoumariii C1
Using 4- trifluoromethyl-umbelliferone C-OH as raw material, in its 7- modification allyl chloroformate, 4- tri- is obtained
Methyl fluoride -7- allyl carbamate butylcoumariii C1.Synthetic method is as follows: by C-OH (228mg, 1mmol), triethylamine
(2.8mL) and methylene chloride (20mL) stir in ice bath, nitrogen protection.Allyl chloroformate (1.2mL) is dissolved in 20mL bis-
Chloromethanes, and be slowly added into above-mentioned mixed liquor.Ice-water bath is removed, reaction is stirred at room temperature 4 hours.It is spin-dried for reaction dissolvent, is revolved
Product is carried out column Chromatographic purification, with methylene chloride/petroleum ether (3:1, v:v) by 30 DEG C of dry bath temperature, water pump vacuum distillation
For eluant, eluent, products therefrom is further recrystallized in n-hexane, and recrystallization condition is 40 DEG C of dissolution crude products, and 0 DEG C crystallizes
To sterling target product C1.
The mass spectrometric data result of target product C1 is the same as embodiment 1.
Experimental example 1: probe solution C1-Pd2+Preparation, hydrazine Molecular Detection working curve foundation and hydrazine molecular concentration
Detection
It is stand-by to prepare the 10mM PBS buffer solution 100mL that pH is 7.4.Probe molecule C1 prepared by embodiment 1 is prepared
Stock solution 1.C1 (3.1mg, 0.01mmol) is taken, is dissolved in 10mL acetonitrile, the stock solution 1 of C1, concentration 1mM are obtained.Configure diethyl
The aqueous solution of nitrile palladium chloride is as stock solution 2, palladium ion concentration 10mM.3mL PBS buffer solution is added in cuvette,
30 μ L C1 stock solutions 1 are added, add 30 μ L stock solutions 2, are uniformly mixed to obtain probe solution C1-Pd2+。
Hydrazine solution to be tested is taken into a certain amount of above-mentioned probe solution C1-Pd of addition2+In, its fluorescence intensity is tested, is compareed
The concentration of hydrazine molecule in working curve you can get it sample.
The working curve of hydrazine Molecular Detection is initially set up according to the method described above.By Fig. 2 a as it can be seen that with hydrazine in probe solution
The increase of content, the fluorescence of solution obviously gradually enhance.By Fig. 2 b as it can be seen that C1-Pd2+The fluorescence intensity and addition hydrazine of probe solution
The concentration of molecule shows extraordinary linear relationship, and linearly dependent coefficient has reached 0.992, and the range of linearity is 0~12 μM.This
When hydrazine molecule detection be limited to 37nM.
In the present embodiment, wherein the concentration of C1 molecule is 10 μM, Pd2+Concentration be 100 μM.Taking hydrazine concentration is 0.81mM's
30 μ L of hydrazine hydrate aqueous solution, is added above-mentioned 3mL C1-Pd2+In probe solution, its fluorescence intensity is tested, curve graph is obtained, sees Fig. 3,
Fluorescence intensity is 4524345.9 at the curve maximum emission wavelength, using the value as Y value, substitutes into probe established by the present invention
Solution C 1-Pd2+Working curve equation: Y=5.35 × 1011X+238791.9 can calculate X=8.01 × 10-6M (Fig. 4),
Since the test concentrations of hydrazine solution are the 1/100 of actual sample solution, it can calculate that the concentration of hydrazine in sample liquid is
The 0.801mM. result differs only 1.1% with hydrazine sample solution actual concentrations, and it is very good to coincide, and illustrates practicability of the invention
Energy.2 fluorescence probe solution C 1-Pd of experimental example2+To the specific detection capacity experimental of hydrazine
By fluorescence probe C1 and Pd2+Prepared probe solution (the C1-Pd of mixing2+) choosing well is gone out to hydrazine molecule displays
Selecting property can be avoided the interference of the common biomolecule of other in detection architecture or amine substance.Containing 30% acetonitrile (v%)
In PBS aqueous solution, C1-Pd2+Probe solution is almost without fluorescence.It is molten when the test sample being gradually added is hydrazine molecule
Liquid issues strong blue-green fluorescent immediately, and when 15 μM of hydrazines are added, the fluorescence intensity of probe solution enhances about 88 times of (figures
5a).If test sample be common amino acid such as cysteine and lysine or other amine substances such as methyl amine in organism,
When ethylenediamine, triethylamine, ammonium hydroxide, almost without any fluorescence response (Fig. 5 b).
3 fluorescence probe solution C 1-Pd of experimental example2+Anti-interference detectability experiment
Probe C1-Pd2+Performance is sufficiently stable, can work normally under very extensive pH environment.By test system
PH control range utilizes C1-Pd between 3-122+Probe solution carries out the discovery of hydrazine Molecular Detection, in the pH range of 5.9-8.0
Interior, the hydrazine molecule that comparable sodium is added obtains the fluorescence signal (Fig. 6) of same intensity.Illustrate C1-Pd2+Probe solution is to hydrazine molecule
Detection can be carried out in the range of pH 5.9-8.0 completely.Such pH tolerance range makes C1-Pd2+Probe solution can
Meet the detection needs of hydrazine molecule in most cases.
4 fluorescence probe solution C 1-Pd of experimental example2+Quick detectability experiment
C1-Pd2+Probe solution is strong in addition to chemical stability, has except good environment resistant interference performance, is used for hydrazine
The detection of molecule also shows cracking response speed.C1-Pd is tracked by fluorescence spectrum2+With when hydrazine reaction in 500nm wavelength
Place's fluorescence intensity change is it can be found that reaction basically reaches balance (Fig. 7) in about 4min.That is, what the present invention was developed
C1-Pd2+Probe system has the advantages that the speed of response is high for hydrazine Molecular Detection, is conducive to the use under physical condition.
5 fluorescence probe solution C 1-Pd of experimental example2+Detection process no coupling product confirmatory experiment
Currently, the existing fluorescence probe that can be used for hydrazine detection is all the necleophilic reaction mechanism using hydrazine molecule, this meeting
The by-products such as the nucleophilic addition product of hydrazine are generated, produce secondary pollution in the detection process.And C1-Pd in the present invention2+Probe
It is zeroth order palladium that solution, which is hydrazine reduction divalent palladium ion for reaction mechanism involved in hydrazine Molecular Detection, so that zeroth order palladium sloughs C1
Allyl carbamate base on molecule, obtains hyperfluorescence molecule C-OH, while hydrazine is oxidized to obtain water and nitrogen, does not make to environment
At secondary pollution.The novelty mechanism has obtained good proof (Fig. 8) via mass spectrometric data.
Hydrazine Molecular Detection is tested in 6 complex sample of experimental example
It is stand-by to prepare the 10mM PBS buffer solution 100mL that pH is 7.4.C1 (3.1mg, 0.01mmol) is taken, 10mL is dissolved in
In acetonitrile, the stock solution 1 of C1, concentration 1mM are obtained.The aqueous solution of diacetonitrile palladium chloride is configured as stock solution 2, palladium ion is dense
Degree is 10mM.3mL PBS buffer solution is added in cuvette, 30 μ L C1 stock solutions 1 are added, add 30 μ L stock solutions 2,
It is uniformly mixed to obtain probe solution C1-Pd2+, wherein the concentration of C1 molecule is 10 μM, Pd2+Concentration be 100 μM.
Methylamine, ethylenediamine, triethylamine, ammonia, azanol that concentration is 10mM, the acetonitrile of cysteine and lysine is respectively configured
Solution is as stock solution 3~9.Each 30 μ L of stock solution 3~9 is taken to mix in 500 μ L centrifuge tubes respectively, and it is 1mM that concentration, which is added,
30 μ L of hydrazine hydrate solution mix.Above-mentioned 3mL C1-Pd is added in amine substance mixture by gained containing hydrazine2+Probe solution
In, its fluorescence intensity is tested, curve (Fig. 9) is obtained:
Fluorescence intensity is 5485020.2 at the curve maximum emission wavelength, using the value as Y value, substitutes into the present invention and is built
Vertical probe solution C1-Pd2+Working curve equation: Y=5.35 × 1011X+238791.9 can calculate X=9.81 × 10-6M
(Figure 10) can calculate that the concentration of hydrazine in sample liquid is since the test concentrations of hydrazine solution are the 1/100 of actual sample solution
The 0.981mM. result differs only 1.9% with hydrazine sample solution actual concentrations, and it is very good to coincide, and illustrates practicability of the invention
Energy.
In conclusion by fluorescence probe C1 and Pd2+The C1-Pd being mixed with2+Probe solution can be to hydrazine in solution to be measured
The content of molecule carries out quantitative detection.Detection behavior has good linear relationship, not by hydrazine molecular mimics or
The high sensitivity of interference, the detection of common biomolecule, fast response time, detection probe performance stabilization with long-term preservation and can make
With, can be detected under extensive pH range.In addition, C1-Pd2+Probe solution is used to not generate when hydrazine Molecular Detection any
Harmful side product, without secondary pollution.Taking into account the above, C1-Pd2+The performance of probe solution is substantially better than existing hydrazine detection fluorescence
Probe.
Claims (9)
1. a kind of coumarin fluorescent probe molecule C1, which is characterized in that the structural formula of the coumarin fluorescent probe molecule C1 is such as
Under:
2. the preparation method of coumarin fluorescent probe molecule C1 described in claim 1, which comprises the following steps:
1) 4- trifluoromethyl-umbelliferone C-OH synthesis；
2) preparation of coumarin fluorescent probe molecule C1:
C-OH, triethylamine and methylene chloride 2a) are stirred to get into mixed liquor in ice bath；
2b) under nitrogen protection, allyl chloroformate is dissolved in methylene chloride, and is slowly added into above-mentioned mixed liquor；
Ice bath 2c) is removed, reaction is placed in and is stirred under room temperature, is spin-dried for reaction dissolvent, product is subjected to column Chromatographic purification, with
Methylene chloride/petroleum ether is eluent, and products therefrom is further recrystallized to give target product cumarin in n-hexane
Fluorescent probe molecule C1.
3. the preparation method of coumarin fluorescent probe molecule C1 according to claim 2, which is characterized in that the step
2a) molar concentration of the C-OH in mixed liquor is 0.05~0.2mol/L, and the molar concentration of triethylamine is 0.5~2.0mol/L.
4. the preparation method of coumarin fluorescent probe molecule C1 according to claim 2, which is characterized in that the step
The volume ratio of allyl chloroformate and methylene chloride is (0.6~1.2): (10~20) in 2b).
5. the preparation method of coumarin fluorescent probe molecule C1 according to claim 2, which is characterized in that the step
The condition being spin-dried in 2c) is 30~60 DEG C of bath temperature, water pump vacuum distillation.
6. the preparation method of coumarin fluorescent probe molecule C1 according to claim 2, which is characterized in that the step
Methylene chloride/petroleum ether in 2c) is with volume ratio 1: 1~3: 1.
7. the preparation method of coumarin fluorescent probe molecule C1 according to claim 2, which is characterized in that the step
It is 20~40 DEG C of dissolution crude products that condition is recrystallized in n-hexane in 2c), and -20~0 DEG C of crystallization obtains sterling.
8. application of the coumarin fluorescent probe molecule C1 described in claim 1 in the fluorescence probe of preparation detection hydrazine molecule.
9. application according to claim 8, which is characterized in that the application be by coumarin fluorescent probe molecule C1 with
Pd2+ is mixed with the fluorescence probe of detection hydrazine molecule.
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| CN112920175B (en) * | 2020-12-17 | 2022-05-31 | 吉林大学 | Coumarin-based palladium ion fluorescent probe compound and preparation method thereof |
| CN112945925B (en) * | 2021-02-07 | 2022-07-05 | 中国科学院新疆理化技术研究所 | Method for detecting permanganate acid radicals by coumarin-based probe |
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| CN103755672A (en) * | 2014-01-26 | 2014-04-30 | 大连理工常熟研究院有限公司 | Specific fluorescence probe for identifying cysteine and application thereof |
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