CN113603712B - Preparation method of reactive fluorescent probe for rapid detection of hydrazine - Google Patents
Preparation method of reactive fluorescent probe for rapid detection of hydrazine Download PDFInfo
- Publication number
- CN113603712B CN113603712B CN202110927485.9A CN202110927485A CN113603712B CN 113603712 B CN113603712 B CN 113603712B CN 202110927485 A CN202110927485 A CN 202110927485A CN 113603712 B CN113603712 B CN 113603712B
- Authority
- CN
- China
- Prior art keywords
- reaction
- hydrazine
- room temperature
- solution
- fluorescent probe
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic System without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
Abstract
The invention discloses a preparation method of a reactive fluorescent probe for rapid detection of hydrazine, and relates to the field of fluorescent probes. To FeCl 3 ·6H 2 Adding powdery 2-naphthol into O aqueous solution to obtain suspension, dissolving the separated solid in CH 2 Cl 2 And (3) recrystallizing to obtain the 1,1' -bi-2-naphthol. 1,1' -binaphthol, K 2 CO 3 Mixing CuCl and m-xylene, heating, and adding methylimidazole to obtain yellow solid; recrystallizing to obtain yellow powdery solid PXX; after the synthesized PXX was completely dissolved in DMF in an ice water bath at 0deg.C, POCl was slowly added dropwise to the solution 3 After the dripping is finished, the temperature is raised to room temperature for reaction, the temperature is raised again for continuous reaction, the reaction is finished, the heating is stopped, after the reaction is cooled to room temperature, the target probe is obtained after precipitation, filtration, drying and recrystallization. The method has the advantages of naked eye identification, rapidness, high efficiency, high selectivity, strong anti-interference performance, short detection time and low production cost.
Description
Technical Field
The invention belongs to the field of fluorescent probes, and particularly relates to a preparation method of a reactive fluorescent probe for rapid detection of hydrazine.
Background
Hydrazine (N) 2 H 4 ) Because of high activity, the modified cellulose has wide application in pharmaceutical and agricultural industries. And because of its high enthalpy, combustion can produce a large amount of heat and gas, and is commonly used as a rocket propellant in the aerospace industry. Meanwhile, because of the strong nucleophilicity, various derivatives can be formed. However, because of its great toxicity and good water solubility, it can be mixed with water in any volume ratio, and is easy to be taken orally, transdermally or inhaled by human body, and it causes serious damage to liver, lung, kidney and nerve. Purified hydrazine is classified as a potential carcinogen according to the U.S. Environmental Protection Agency (EPA) and has a threshold limit (10 ppb). Meanwhile, some medicines can be metabolized in vivo to generate hydrazine so as to cause toxicity, so that the realization of a high-sensitivity and high-selectivity detection technology for the hydrazine has profound significance.
Heretofore, there have been various techniques for detecting hydrazine, such as chromatography techniques, electrochemical techniques, surface-enhanced raman spectroscopy, colorimetric techniques, and the like. However, these techniques are often time consuming or require a rigorous sample handling process. The fluorescence detection technology is widely focused because of simple operation, real-time detection and adaptability to environmental samples and biology. Probes capable of detecting hydrazine with high efficiency have yet to be developed. The probe can detect hydrazine in a complex environment, the response time is as fast as possible, obvious color change exists before and after hydrazine identification, and naked eye detection can be achieved, namely, the probe has high sensitivity and high selectivity for hydrazine detection.
Disclosure of Invention
The invention aims to provide a reaction type fluorescent probe for detecting hydrazine, which is identified by naked eyes, is quick and efficient, has high selectivity, strong anti-interference performance, short detection time and low production cost.
The invention provides the following technical scheme:
a preparation method of a reactive fluorescent probe for rapidly detecting hydrazine comprises the following steps,
s1, to FeCl 3 ·6H 2 Adding powdery 2-naphthol into O aqueous solutionObtaining a suspension, heating the suspension, fully stirring, cooling, filtering, and dissolving the separated solid in CH 2 Cl 2 In the obtained CH 2 Cl 2 Washing, decolorizing, drying, filtering, vacuum removing solvent to obtain solid crude product, vacuum drying the crude product at room temperature, and recrystallizing with toluene to obtain white needle-like pure 1,1' -bi-2-naphthol.
S2, 1' -binaphthol, K 2 CO 3 Adding CuCl into a round-bottom flask, adding meta-xylene at room temperature, heating, stirring to dissolve, slowly adding methylimidazole after the solution is transparent, heating continuously to allow the reaction to be heated, and monitoring the reaction by TLC during the reaction; after the reaction is finished, spin-drying the solvent to obtain yellow solid; separating by column chromatography with eluent, recrystallizing to obtain yellow powdery solid PXX
S3, under the ice water bath at 0 ℃, after the PXX synthesized in the step S2 is completely dissolved in DMF, POCl is slowly added dropwise into the solution 3 After the dripping is finished, the temperature is raised to room temperature for reaction, the temperature is raised again for continuous reaction, the reaction is finished, the heating is stopped, after the reaction is cooled to room temperature, the target probe is obtained after precipitation, filtration, drying and recrystallization.
Preferably, in step S1, at room temperature, at 162.17g,0.6mol,0.0024mol/L FeCl 3 ·6H 2 43.25g of 0.3mol of 2-naphthol in powder form are added to the O aqueous solution, and the suspension is heated to 50℃and stirred for 3 hours. Cooling, filtering, dissolving the separated solid in CH 2 Cl 2 Is a kind of medium.
Preferably, in step S1, the CH is obtained 2 Cl 2 Washing the solution with distilled water, decolorizing with active carbon, drying with magnesium sulfate, filtering to remove magnesium sulfate, and vacuum removing solvent to obtain solid crude product.
Preferably, in step S2, 1.0047g,3.5mmol of 1,1' -binaphthol, 0.9696g,7mmol of K are added 2 CO 3 0.1054g of CuCl (1.05 mmol) is added into a round bottom flask, 20mL of m-xylene is added at room temperature, the mixture is heated and fully stirred to dissolve, and after the solution is transparent, the mixture is slowly added157. Mu.L of methylimidazole (2.0 mmol) was added thereto, and the reaction was continued with heating to 120℃for 20 hours.
Preferably, in step S2, the reaction is monitored by TLC during the reaction, as CHCl 3 The solid obtained was separated by column chromatography as eluent and recrystallized from toluene to give yellow powdery solid PXX.
Preferably, in the step S3, PXX synthesized in the previous step is completely dissolved in DMF under an ice water bath at 0 ℃, and POCl is slowly added dropwise to the solution 3 After the completion of the dropwise addition, the reaction was continued for 3 hours after the temperature was raised to room temperature for 30 minutes and then to 80 ℃.
Preferably, in the step S3, after the reaction is finished and the heating is stopped, 15g of crushed ice is added into the mixture after the mixture is cooled to room temperature, the mixture is fully stirred, yellow precipitation occurs in the solution, and the target probe is obtained after filtration, drying and recrystallization.
The beneficial effects of the invention are that:
1. the method has the advantages of low cost and easy acquisition of raw materials required by PXX synthesis, simple synthesis steps and higher reaction selectivity and yield.
2. The method selects PXX as a parent body of a synthetic target fluorescent probe, and then modifies the parent body, and introduces a functional group capable of reacting with hydrazine to cause the hydrazine to undergo nucleophilic attack; the hydrazine carries out nucleophilic attack on aldehyde groups, a specific reaction-Schiff base reaction occurs, hydrazone compounds are generated, the PET effect can lead to fluorescence recovery or enhancement, and the hydrazone compounds can be identified through a simple fluorescence experiment.
3. The fluorescent probe can realize the specificity of hydrazine detection.
Drawings
The accompanying drawings are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate the invention and together with the embodiments of the invention, serve to explain the invention. In the drawings:
FIG. 1a shows the color change of the probe before and after hydrazine identification, from yellow to colorless;
FIG. 1b shows the color change of the probe before and after hydrazine identification, and the fluorescence changes from yellow-green to blue;
FIG. 2 shows fluorescence titration spectra (. Lambda.) of probes (10. Mu. Mol) for hydrazine (0, 10,15,20,25,30,35,40,45,50 eq) at various concentrations ex =415 nm, response time of 30 s);
FIG. 3a is a fluorescence emission spectrum (. Lambda.) of 10. Mu. Mol probe after addition of 200. Mu. Mol hydrazine ex =415 nm) over time within 0-240 s;
FIG. 3b shows probe response time at lambda ex Fluorescence intensity change at 516nm at 415nm, showing the response rate of probe to hydrazine, which is complete at around 90 s;
FIG. 4a is a change in fluorescence emission spectrum of a probe (10. Mu. Mol) in a common interfering ion (20 eq);
FIG. 4b is a graph of fluorescence intensity vs. bar graph of probe (10. Mu. Mol) at 480nm in common interfering ions (20 eq);
FIG. 5a is a plot of probe 10. Mu.M with cationic interference (20 eq) added;
FIG. 5b is a plot of probe 10. Mu.M interfering (20 eq) with the addition of anions;
FIG. 5c shows the fluorescence intensity contrast (. Lambda.) at 480nm before and after detection of hydrazine under the interference of small molecules containing nitrogen ex =415 nm, response time 30 s).
Detailed Description
First, at room temperature, feCl is added to 3 ·6H 2 To an aqueous solution of O (162.17 g,0.6mol,0.0024 mol/L) was added 2-naphthol (43.25 g,0.3 mol) in powder form, and the suspension was stirred at 50℃for 3 hours. Cooling, filtering, dissolving the separated solid in CH 2 Cl 2 In the obtained CH 2 Cl 2 Washing the solution with distilled water for three times, decolorizing with active carbon, drying with magnesium sulfate, filtering to remove magnesium sulfate, removing solvent in vacuum to obtain solid crude product, vacuum drying the crude product at room temperature, and recrystallizing with toluene to obtain white needle-like pure 1,1' -bi-2-naphthol.
Then, 1' -binaphthol (1.0047 g,3.5 mmol), K 2 CO 3 (0.9696 g,7 mmol) and CuCl (0.1054 g,1.05 mmol) were added to a round bottom flask, 20mL of meta-xylene was added at room temperature, heated and stirred well to dissolve, and after the solution was clear, methylimidazole (157. Mu.L was slowly added2.0 mmol) was heated to 120℃and reacted for 20h, during which time the reaction was monitored by TLC. After the reaction, the solvent was dried by spin-drying to obtain a yellow solid. By CHCl 3 The solid obtained was separated by column chromatography as eluent and recrystallized from toluene to give yellow powdery solid PXX.
Finally, after PXX synthesized in the previous step is completely dissolved in DMF under the ice water bath at 0 ℃, POCl is slowly added dropwise to the solution 3 After the dripping is completed, the temperature is raised to room temperature for reaction for 30min, the temperature is raised to 80 ℃ again for reaction for 3h, heating is stopped, after the mixture is cooled to room temperature, about 15g of crushed ice is added into the mixture, the mixture is fully stirred, yellow precipitation of the solution occurs, and the probe is obtained after filtering, drying and recrystallization.
Experimental analysis:
after adding 200. Mu.L of a 10. Mu.M probe DMF solution to 1mL of a 200. Mu. Mol hydrazine DMF solution and allowing the reaction to proceed well for 30s at room temperature, the reaction solution was clearly seen to change from yellow to almost colorless after the reaction of the probe with hydrazine, as compared with the blank (10. Mu. Mol probe DMF solution without hydrazine). Under UV light (325 nm), it was clearly observed that the solution changed from yellow-green fluorescence to blue fluorescence after the probe reacted with hydrazine, as shown in FIGS. 1a and 1 b. Therefore, the probe is used as a fluorescence detector of hydrazine, has high sensitivity, obvious color change, short response time and good effect.
Probe mother liquor was added to DMF solution to prepare a solution with a concentration of 10 μmol, and hydrazine test solutions (0, 10,15,20,25,30,35,40,45,50 eq) with different equivalent concentrations were added thereto, and fluorescence titration spectra thereof were measured, respectively, and the results are shown in fig. 2.
As can be seen from fig. 2, in the experimental test, the maximum emission peak of the probe before response is 530nm, the emission peak at 530nm disappears after hydrazine is added, the fluorescence spectrum is blue-shifted, two new emission peaks appear at 450nm and 480nm, and the fluorescence intensity of the emission peaks is continuously enhanced with the continuous addition of hydrazine. Again, the probe proved to have a higher sensitivity to hydrazine.
In addition, the detection limit of the probe was low, 11.76. Mu.M.
And adding hydrazine (200 mu mol) into a 10 mu mol probe DMF solution at 25 ℃, enabling the probe to respond to the hydrazine within 30 seconds, enabling the response duration to be long, enabling the color of the solution to be changed from yellow to almost colorless under the irradiation of an indoor lamp, enabling the fluorescence of the solution to be changed from yellow to blue under the irradiation of an ultraviolet lamp, and enabling the solution to be recognized by naked eyes.
The probe had good selectivity for hydrazine, and after addition of common anions and cations and a nitrogen-containing nucleophilic small molecule, it was observed from fig. 4a and 4b that the fluorescence intensity of the solution did not change significantly (about 300 a.u.), whereas after addition of hydrazine, the fluorescence intensity of the solution changed significantly about 1400a.u., indicating a better selectivity for hydrazine.
From the competitive experimental result, even though the interference object exists after the hydrazine is added, the fluorescence intensity of the liquid to be detected at 480nm is still high, and the fluorescence intensity is increased by more than 3 times, which indicates that the probe has better competition to the hydrazine in the interference environment of experimental test, and the probe is shown in fig. 5a, 5b and 5c.
The selection of the fluorescent group is required to meet the requirement of large conjugated pi bond and have an active site. After a lot of documents are reviewed, the xanthene (PXX) meets the conditions, the raw materials required for synthesizing the PXX are cheap and easy to obtain, the synthesis steps are simple, and the reaction selectivity and the yield are high. Therefore, we select PXX as the parent of the synthetic target fluorescent probe, and then modify it to introduce a functional group capable of reacting with hydrazine in the parent to make the hydrazine undergo nucleophilic attack; the identification group is the most critical part of the fluorescent probe, and the process of detecting the object to be detected by the probe is the process of reacting the identification group with the object to be detected. Hydrazine has two electron donating nitrogen atoms and can react with a plurality of functional groups with electron withdrawing capability, such as aldehyde groups with strong electron withdrawing capability, and the like. The hydrazine carries out nucleophilic attack on aldehyde groups, and generates a specific reaction, namely Schiff base reaction, to generate hydrazone compounds. Since the PET effect can lead to fluorescence recovery or enhancement, it can be identified by simple fluorescence experiments. This shows that the fluorescent probe designed by using aldehyde group as recognition group can implement specificity for hydrazine detection.
The foregoing description is only a preferred embodiment of the present invention, and the present invention is not limited thereto, but it is to be understood that modifications and equivalents of some of the technical features described in the foregoing embodiments may be made by those skilled in the art, although the present invention has been described in detail with reference to the foregoing embodiments. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. A preparation method of a reactive fluorescent probe for rapidly detecting hydrazine is characterized by comprising the following steps:
s1, to FeCl 3 ·6H 2 Adding powdered 2-naphthol into O aqueous solution to obtain suspension, heating the suspension, stirring thoroughly, cooling, filtering, dissolving the separated solid in CH 2 Cl 2 In the obtained CH 2 Cl 2 Washing, decolorizing, drying, filtering and removing solvent in vacuum to obtain solid crude product, vacuum drying the crude product at room temperature, and recrystallizing with toluene to obtain white needle-like pure 1,1' -bi-2-naphthol;
s2, 1' -binaphthol, K 2 CO 3 Adding CuCl into a round-bottom flask, adding meta-xylene at room temperature, heating, stirring to dissolve, slowly adding methylimidazole after the solution is transparent, heating continuously to allow the reaction to be heated, and monitoring the reaction by TLC during the reaction; after the reaction is finished, spin-drying the solvent to obtain yellow solid; separating by column chromatography with eluent, and recrystallizing to obtain yellow powdery solid PXX;
s3, under the ice water bath at 0 ℃, after the PXX synthesized in the step S2 is completely dissolved in DMF, POCl is slowly added dropwise into the solution 3 After the dripping is completed, the temperature is raised to room temperature for reaction, the temperature is raised again for continuous reaction, the reaction is finished, the heating is stopped, after the reaction is cooled to room temperature, the target probe is obtained after precipitation, filtration, drying and recrystallization;
in the step S3, after the reaction is finished and the reaction is cooled to room temperature, 15g of crushed ice is added into the mixture, the mixture is fully stirred, yellow precipitation appears in the solution, and the target probe is obtained after filtration, drying and recrystallization.
2. The method for preparing the reactive fluorescent probe for rapid detection of hydrazine according to claim 1, wherein the method comprises the following steps: in the S1 step, at room temperature, 162.17g,0.6mol and 0.0024mol/L FeCl 3 ·6H 2 Adding 43.25g of powdery 2-naphthol (0.3 mol) into O aqueous solution, heating the suspension to 50 ℃ and stirring for 3h, cooling, filtering, dissolving the separated solid in CH 2 Cl 2 Is a kind of medium.
3. The method for preparing the reactive fluorescent probe for rapid detection of hydrazine according to claim 1, wherein the method comprises the following steps: in the S1 step, the CH is obtained 2 Cl 2 Washing the solution with distilled water, decolorizing with active carbon, drying with magnesium sulfate, filtering to remove magnesium sulfate, and vacuum removing solvent to obtain solid crude product.
4. The method for preparing the reactive fluorescent probe for rapid detection of hydrazine according to claim 1, wherein the method comprises the following steps: in step S2, 1.0047g,3.5mmol of 1,1' -binaphthol, 0.96 g,7mmol of K are added 2 CO 3 0.1054g of CuCl with 1.05mmol is added into a round bottom flask, 20mL of m-xylene is added at room temperature, the mixture is heated and fully stirred to be dissolved, after the solution is transparent, 157 mu L of methylimidazole with 2.0mmol is slowly added, and the mixture is continuously heated to be heated to 120 ℃ for reaction for 20 hours.
5. The method for preparing the reactive fluorescent probe for rapid detection of hydrazine according to claim 1, wherein the method comprises the following steps: in step S2, the reaction was monitored by TLC during the reaction as CHCl 3 The solid obtained was separated by column chromatography as eluent and recrystallized from toluene to give yellow powdery solid PXX.
6. The method for preparing the reactive fluorescent probe for rapid detection of hydrazine according to claim 1, wherein the method comprises the following steps: in the S3 step, the PXX synthesized in the previous step is completely dissolved in an ice water bath at 0 DEG CAfter DMF, POCl was slowly added dropwise to the solution 3 After the completion of the dropwise addition, the reaction was continued for 3 hours after the temperature was raised to room temperature for 30 minutes and then to 80 ℃.
7. The method for preparing the reactive fluorescent probe for rapid detection of hydrazine according to claim 1, wherein the method comprises the following steps: the obtained fluorescent probe is applied to the specific detection of hydrazine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110927485.9A CN113603712B (en) | 2021-08-12 | 2021-08-12 | Preparation method of reactive fluorescent probe for rapid detection of hydrazine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110927485.9A CN113603712B (en) | 2021-08-12 | 2021-08-12 | Preparation method of reactive fluorescent probe for rapid detection of hydrazine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113603712A CN113603712A (en) | 2021-11-05 |
| CN113603712B true CN113603712B (en) | 2023-07-14 |
Family
ID=78340607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110927485.9A Active CN113603712B (en) | 2021-08-12 | 2021-08-12 | Preparation method of reactive fluorescent probe for rapid detection of hydrazine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113603712B (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106432041A (en) * | 2016-09-26 | 2017-02-22 | 济南大学 | Preparation and application of ratio type near infrared hydrazine fluorescent probe compound |
| CN107880052A (en) * | 2017-11-02 | 2018-04-06 | 济南大学 | A kind of fluorescence probe for detecting hydrazine and its application |
| CN108982447A (en) * | 2018-07-19 | 2018-12-11 | 曲阜师范大学 | It is a kind of for detecting the preparation method and application of the ratio formula fluorescence probe of hydrazine |
| CN110452250A (en) * | 2019-07-16 | 2019-11-15 | 兰州大学 | A kind of detection hydrazine fluorescence probe of fluorescein precursor structure |
| CN110452171A (en) * | 2019-07-16 | 2019-11-15 | 兰州大学 | Fluorescence probe is used in a kind of hydrazine detection of naphthalimide precursor structure |
| CN110590756A (en) * | 2019-09-01 | 2019-12-20 | 南通大学 | Phenolphthalein Schiff base fluorescent probe and preparation method and application thereof |
-
2021
- 2021-08-12 CN CN202110927485.9A patent/CN113603712B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106432041A (en) * | 2016-09-26 | 2017-02-22 | 济南大学 | Preparation and application of ratio type near infrared hydrazine fluorescent probe compound |
| CN107880052A (en) * | 2017-11-02 | 2018-04-06 | 济南大学 | A kind of fluorescence probe for detecting hydrazine and its application |
| CN108982447A (en) * | 2018-07-19 | 2018-12-11 | 曲阜师范大学 | It is a kind of for detecting the preparation method and application of the ratio formula fluorescence probe of hydrazine |
| CN110452250A (en) * | 2019-07-16 | 2019-11-15 | 兰州大学 | A kind of detection hydrazine fluorescence probe of fluorescein precursor structure |
| CN110452171A (en) * | 2019-07-16 | 2019-11-15 | 兰州大学 | Fluorescence probe is used in a kind of hydrazine detection of naphthalimide precursor structure |
| CN110590756A (en) * | 2019-09-01 | 2019-12-20 | 南通大学 | Phenolphthalein Schiff base fluorescent probe and preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| Jing-can Qin et al..Recognition of Mg2+ and Zn2+ based on a naphthalene-based fluorescent probe by regulating solvents.Inorganica Chimica Acta.2015,(第435期),194-199. * |
| Toshiyuki Kamei et al..Cu-Catalyzed Aerobic Oxidative C−H/C−O Cyclization of 2,2′- Binaphthols: Practical Synthesis of PXX Derivatives.Org. Lett..2017,第19卷第2714−2717页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113603712A (en) | 2021-11-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108070092B (en) | Supermolecular gel based on functionalized column [5] arene and application thereof in identifying iron ions and L-Cys | |
| CN106632064B (en) | Reversible dihydroxy phenanthroimidazole Hg2+Fluorescent probe synthesis and methods of use | |
| CN106496197A (en) | A kind of Fluorescence Increasing type quick detection sulfurous acid hydrogen radical ion or the synthesis and application of sulfite ion fluorescent molecular probe | |
| CN108658838B (en) | Heptamethine indocyanine-based formaldehyde fluorescent probe and preparation method and use method thereof | |
| CN113136205A (en) | Fluorescent carbon quantum dot, preparation method and application thereof in detecting superoxide anion | |
| Kong et al. | Dicyanoisophorone-based fluorescent probe with large Stokes shift for ratiometric detection and imaging of exogenous/endogenous hypochlorite in cell and zebrafish | |
| CN108640867B (en) | Fluorescent probe compound containing cyano-carbazolyl Schiff base as well as preparation method and application thereof | |
| CN108164448B (en) | A kind of anthraquinone derivative and synthetic method and application | |
| CN109021000B (en) | Fluorescent probe for detecting hydrogen peroxide, synthetic method and application | |
| CN110950854A (en) | Off-on molecular fluorescent probe CMTAH and preparation method and application thereof | |
| CN113603712B (en) | Preparation method of reactive fluorescent probe for rapid detection of hydrazine | |
| CN111138431B (en) | Reactive fluorescent probe for detecting thiophenol and synthetic method and application thereof | |
| CN111393461B (en) | Palladium ion fluorescent probe compound based on BODIPY and synthetic method thereof | |
| CN108623611B (en) | Synthesis and application of fluorescent probe for detecting hydrogen peroxide | |
| CN113214108B (en) | Fluorescent probe for detecting cyanide ions and preparation method and application thereof | |
| CN114573519B (en) | Fluorescent probe for copper ion detection and preparation method and application thereof | |
| CN107739604B (en) | Fluorescent sensing material based on rhodamine B and cyano diphenol and preparation and application thereof | |
| CN107628997B (en) | Quinoline derivative-based fluorescent probe and preparation method and application thereof | |
| CN113912612B (en) | Alkaline pH fluorescent probe pyridazino [4,5-b ] quinoxaline-1, 4-diamine Schiff base and preparation method and application thereof | |
| CN115286646A (en) | Probe for detecting amine compound residue in polyurethane, preparation method and application thereof | |
| CN110551499B (en) | Fluorescent probe for detecting copper ions and synthetic method thereof | |
| CN110818702B (en) | Pyridine-coumarin derivative fluorescent probe and preparation method and application thereof | |
| CN114456114A (en) | Naphthalene diimide fluorescent chemical sensor based on ICT and PET dual mechanisms and synthetic method and application thereof | |
| CN113025313A (en) | Application of morpholine-pyridine-part cyanine derivative as hydrogen sulfide fluorescent probe | |
| CN108191760B (en) | Fluorescent probe for detecting Cu (II) and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |