CN116183571A - Picric acid rapid visual detection method based on water-soluble perylene imide derivative - Google Patents
Picric acid rapid visual detection method based on water-soluble perylene imide derivative Download PDFInfo
- Publication number
- CN116183571A CN116183571A CN202310147881.9A CN202310147881A CN116183571A CN 116183571 A CN116183571 A CN 116183571A CN 202310147881 A CN202310147881 A CN 202310147881A CN 116183571 A CN116183571 A CN 116183571A
- Authority
- CN
- China
- Prior art keywords
- picric acid
- detection
- perylene imide
- perylene
- fluorescence
- 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.)
- Pending
Links
Images
Classifications
-
- 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"
-
- 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"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
-
- 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
-
- 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"
- G01N2021/6432—Quenching
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Optics & Photonics (AREA)
- Biochemistry (AREA)
- Pathology (AREA)
- General Physics & Mathematics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Indole Compounds (AREA)
Abstract
The invention relates to the field of picric acid detection, and discloses a rapid visual detection method based on a perylene bisimide derivative. Specifically, a method for detecting picric acid is disclosed, wherein perylene imide derivatives with the structure shown in the formula (I) are used as probes. The probe has good water solubility and can realize high-sensitivity, specific and visual detection of picric acid. The detection method provided by the invention has higher detection efficiency and sensitivity.
Description
Technical Field
The invention relates to the technical field of picric acid detection, in particular to a rapid visual picric acid detection method based on a water-soluble perylene bisimide derivative.
Background
2,4, 6-Trinitrophenol (TNP), also known as picric acid, exhibits a yellow crystalline state at room temperature. TNP is a very dangerous nitroaromatic organic compound, has great explosion power and is a common component in military explosives. Meanwhile, TNP is widely applied in the current society: in the agricultural field, it is commonly used as a bactericide; in the medical field, it can be used for animal marking and the like.
However, TNP contains phenolic hydroxyl groups, has good water solubility, is extremely easy to be remained in a large amount in the environment, pollutes soil and underground water, and further damages human bodies directly or through biological enrichment. TNP causes symptoms such as inflammation, poisoning, dizziness, fever, and the like, and has strong hepatotoxicity and hematotoxicity. It can be seen that TNP is extremely harmful to public safety, natural environment and human health. Therefore, it is necessary to establish a high-sensitivity and high-specificity TNP detection method, and especially to perform direct and rapid visual detection on TNP in an aqueous phase.
Disclosure of Invention
In view of the above, the technical problem to be solved by the invention is to provide a rapid visual detection method of picric acid based on a water-soluble perylene imide derivative, in particular to a method for detecting picric acid, which overcomes the defects of low detection efficiency and low sensitivity in the existing method for detecting picric acid.
In order to achieve the above object, the present invention provides the following technical solutions:
first, the invention provides application of a perylene bisimide derivative shown in a formula (I) in detecting picric acid:
the perylene imide derivative with the structure shown in the formula (I) has good water solubility, can realize high-sensitivity and specific detection of picric acid, and has obvious specificity and anti-interference capability in detection.
The perylene imide derivative with the structure shown in the formula (I) shows different states in the solution conformation and aggregation state to external stimulus, and further causes the change of optical characteristics, such as the change of solution color and the opening or quenching phenomenon of fluorescence. Therefore, when the perylene imide derivative is used for detecting picric acid, the effect of fluorescence response, namely quenching of fluorescence of the perylene imide derivative can be achieved, and the quenching effect is visible to the naked eye under the irradiation of an ultraviolet lamp. Meanwhile, the color of the perylene bisimide derivative solution is changed, and the effect can be more obviously reflected by extracting RGB values.
In addition, the detection limit of the perylene bisimide derivative is as low as 9nmol/L, the visualization effect in the solution is obvious, and the visual detection limit is as low as 10 mu mol/L.
The perylene bisimide derivative provided by the invention has excellent picric acid detection performance, and is probably based on the following principle: the perylene imide derivative and the picric acid can be identified through multiple non-covalent actions, and the picric acid can induce the perylene imide derivative to generate fluorescence quenching, and the process is mainly based on electrostatic interaction and is accompanied by the synergistic effects of pi-pi accumulation, charge transfer, hydrophobic action and the like.
The source of the perylene imide derivative having the structure represented by the above formula (I) is not particularly limited, and it may be generally commercially available or may be prepared according to a method well known to those skilled in the art.
The second, the invention provides a reagent, test paper or kit for detecting picric acid, which comprises the perylene imide derivative or the perylene imide derivative prepared by the preparation method.
Thirdly, the invention provides a quantitative detection method based on a water-soluble perylene imide derivative, in particular to a method for detecting picric acid, and the perylene imide derivative or the perylene imide derivative prepared by the preparation method is used as a probe.
In the present invention, the concentration of the probe is preferably 2. Mu. Mol/L.
Specifically, the specific detection method of the invention comprises the following steps: in 10mmol/L of 4-hydroxyethyl piperazine ethane sulfonic acid (HEPES) buffer with pH=7.0, the probe concentration was 2. Mu. Mol/L, and the picric acid was subjected to spectroscopic test, and the excitation wavelength at the time of detection was 440nm. And (3) selecting the fluorescence intensity with the emission wavelength of 490nm to calculate the fluorescence quenching efficiency of the probe, taking picric acid concentration as an abscissa and taking the fluorescence quenching efficiency of the probe as an ordinate, and establishing a detection standard curve.
Fourth, the invention provides a rapid visual detection method based on a water-soluble perylene imide derivative, and in particular provides a method for detecting picric acid, wherein the perylene imide derivative or the perylene imide derivative prepared by the preparation method is used as a probe.
In the present invention, the concentration of the probe is preferably 2. Mu. Mol/L.
Specifically, the specific detection method of the invention comprises the following steps: in 10mmol/L HEPES buffer solution with pH=7.0, the probe concentration is 2 mu mol/L for visual detection of picric acid, and the probe is subjected to visual fluorescence quenching under the irradiation of an ultraviolet lamp. Photographs were taken and RGB values of the reagents, test strips or kits were extracted by methods well known to those skilled in the art, with picric acid concentration on the abscissa and G/B on the ordinate, to establish a detection standard curve.
Compared with the prior art, the invention provides a rapid visual detection method based on a water-soluble perylene imide derivative, which takes the perylene imide derivative with a structure shown in a formula (I) as a probe. The perylene bisimide derivative has good water solubility, can realize high-sensitivity and specific detection of picric acid, and can perform rapid visual quantitative detection. The detection method provided by the invention has higher detection efficiency and sensitivity.
Drawings
FIG. 1 shows the fluorescence emission spectra (. Lamda.) of perylene imide derivative probes (2. Mu. Mol/L) after addition of picric acid at various concentrations to HEPES buffer (10 mmol/L pH=7.0) ex ＝440nm，λ em ＝450-600nm)；
FIG. 2 is a graph showing fluorescence quenching efficiency (lambda) of perylene imide derivative probe (2. Mu. Mol/L) after addition of picric acid at various concentrations in HEPES buffer (10 mmol/L pH=7.0) ex ＝440nm，λ em ＝490nm)；
FIG. 3 shows the relative fluorescence intensities (. Lamda.) of perylene imide derivative probe (2. Mu. Mol/L) and different substance (50. Mu. Mol/L) in HEPES buffer (10 mmol/L pH=7.0) ex ＝440nm，λ em =490 nm), the inset is the change in fluorescence under 365nm uv lamp irradiation,
1-picric acid, 2-Cl - ,3-H 2 PO 4 - ,4-SO 4 2- ,5-NO 3- ,6-CO 3 2- ,7-HCO 3 - ,8-Ca 2+ ,9-K + ,10-Na + ,11-Mg 2+ ,12-Pb 2+ ,13-Cu 2+ ,14-Al 3+ ,15-Zn 2+ ,16-Cd 2+ ,17-Mn 2+ ,18-Ag + 19-nitropropionic acid (NPA), 20-p-Nitrophenol (NP), 21-phenol (Phe), 22-2, 4-Dinitrotoluene (DNT), 23-2, 4-Dinitrophenol (DNP), 24-toluene (MB), 25-Nitrobenzene (NB), 26-2,4, 6-trinitrotoluene (TNT);
FIG. 4 is a photograph of perylene imide derivative solutions after addition of picric acid (μmol/L) at various concentrations under irradiation of 365nm ultraviolet light;
FIG. 5 shows the G/B dependence on picric acid concentration of perylene imide derivative probe (2. Mu. Mol/L) after addition of picric acid at different concentrations to HEPES buffer (10 mmol/L pH=7.0) under irradiation of 365nm UV lamp;
FIG. 6 is a photograph of perylene imide derivative probe paper irradiated with 365nm ultraviolet light after addition of picric acid (μmol/L) at different concentrations;
FIG. 7 is a photograph of perylene bisimide derivative probe test paper with picric acid and other interferents (10. Mu.L 100. Mu. Mol/L) under 365nm ultraviolet light.
Detailed Description
In order to further illustrate the present invention, the following describes in detail the method for rapid visualization detection based on water-soluble perylene imide derivatives provided by the present invention in connection with examples.
Preparation of standby substances:
preparation of the buffer: the solid 4-hydroxyethyl piperazine ethane sulfonic acid is weighed, 500mL of HEPES buffer solution with the concentration of 10mmol/L is prepared by distilled water, and the pH value of the HEPES buffer solution is adjusted to 7.0 by 1mol/L of sodium hydroxide standard solution. And placing the mixture in a refrigerator at the temperature of 4 ℃ for standby.
Preparation of probe mother liquor: weighing the solid shown in the formula (I), preparing a mother solution with the concentration of 1mmol/L by using distilled water, and sub-packaging the mother solution into a solution with the same volume for later use in a small bottle. The spectra were tested by dilution with HEPES buffer (10 mmol/L, pH=7.0) to a certain concentration.
Preparation of the object to be detected and the interfering object: picric acid was prepared as a stock solution at a concentration of 1mmol/L with distilled water for use. The other interferents were prepared as 1mmol/L stock solution with distilled water. The solutions were kept in a refrigerator at 4℃until use.
Preparation of test paper: the 2. Mu. Mol/L perylene imide derivative solution was placed in a disposable plastic cuvette and the filter paper was processed into circles of the same diameter using a 2.5cm punch. And ensuring that different round filter papers are not contacted and overlapped, immersing the round filter papers into the perylene diimide derivative solution for 10 seconds, taking out, and naturally drying at room temperature to prepare test paper for subsequent visual detection.
Preparation of actual samples: tap water and lake water obtained by sampling are boiled for half an hour, cooled to room temperature and filtered by a 0.22 mu m PES filter membrane, and the filtrate is used for actual sample detection. 0.1g of the soil sample was dissolved in 100mL of HEPES buffer solution (10 mmol/L, pH=7.0), filtered through 0.22 μm PES filter, and the filtrate was used for actual sample detection.
Example 1
Testing of fluorescence spectra：
2 mu L of probe mother solution and 950 mu L of 10mmol/L HEPES buffer solution are mixed and added into a 1mL sample cell, after the mixture is uniform, the fluorescence spectrum of the probe buffer solution is measured, the probe buffer solution is excited by 440nm fluorescence, and 450-600nm fluorescence is detected, and the result is shown in figure 1. The perylene imide derivative has two emission peaks of 490nm and 520nm under 440nm excitation, and the emission peak of the perylene imide derivative gradually decreases with the addition of picric acid.
The fluorescence intensity of the probe at 490nm is recorded as I 0 Adding picric acid solution with a certain concentration, recording fluorescence intensity at 490nm as I, picric acid concentration as abscissa, and probe fluorescence quenching efficiency as ordinate, and establishing detection standard curve, wherein the result is shown in figure 2 (namely, figure 2 shows that HEPES (10 mmol/L, pH=7.0) buffer solution, fluorescence of the perylene imide derivative at 490nm is quenched with picric acid concentration. QI= [ (I) 0 -I)/I 0 ]×100％，λ ex =440 nm). According to the estimation method of the detection limit, the detection limit of the perylene bisimide derivative on picric acid is 9nmol/L.
Example 2
Selectivity study:
interference and structural analogues often occur in the selection and detection of picric acid, including Cl - 、H 2 PO 4 - 、SO 4 2- 、NO 3- 、CO 3 2- 、HCO 3 - 、Ca 2+ 、K + 、Na + 、Mg 2+ 、Pb 2+ 、Cu 2+ 、Al 3+ 、Zn 2+ 、Cd 2+ 、Mn 2+ 、Ag + Nitropropionic acid (NPA), p-Nitrophenol (NP), phenol (Phe), 2, 4-Dinitrotoluene (DNT), 2, 4-Dinitrophenol (DNP), toluene (MB), nitrobenzene (NB), 2,4, 6-trinitrotoluene (TNT). In the test, the concentration of the perylene imide derivative is 2 mu mol/L, the concentration of picric acid and other all interferents are 50 mu mol/L, and the fluorescence spectrum test is carried out under the same test conditions. The absorption value of perylene imide derivative at 490nm before and after adding the interfering substance is used as the ratio, I 0 I is a parameter for measuring the degree of influence of the perylene bisimide derivative on the test object.
The results are shown in FIG. 3 (i.e., FIG. 3 shows a graph of the relative absorption values of the effect of the perylene bisimide derivative and picric acid and other interferents in HEPES (10 mmol/L, pH=7.0) buffer.
As can be seen from the figure, in addition to picric acid I 0 I is about 5.6, 3.3 times that of DNP which responds most strongly in the interferents, while all other substances are I 0 The result that I is kept at a lower level (. Ltoreq.1.6) than other compounds indicates that the aforesaid perylene bisimide derivatives have excellent selectivity for picric acid. The inset in FIG. 3 shows the change in fluorescence of perylene bisimide derivatives under 365nm UV light before and after addition of picric acid and other interferents. Perylene imide derivatives initially exhibit bright fluorescence, with the addition of picric acid producing a significant fluorescence quenching, which can be observed visually. And after other interferents are added, the fluorescence of the perylene bisimide derivative is not obviously quenched.
The above results indicate that perylene imide derivatives have excellent selectivity for picric acid.
Example 3
Solution visualization detection：
The concentration of the perylene bisimide derivative is 2 mu mol/L, and picric acid with different concentrations is added.
FIG. 4 is a photograph of an ultraviolet lamp at 365nm with the addition of different concentrations of picric acid, and it can be seen that as the concentration of picric acid increases, the fluorescence of the corresponding solution gradually darkens from green until complete quenching, and the visual detection limit of the solution is 10. Mu. Mol/L.
Example 4
The concentration of the perylene bisimide derivative is 2 mu mol/L, picric acid with different concentrations is added, and RGB values are extracted. The detection standard curve was established on the abscissa and on the ordinate of G/B, and as a result, as shown in FIG. 5 (that is, as shown in FIG. 5, in HEPES (10 mmol/L, pH=7.0) buffer, the change curve of G/B value of the perylene bisimide derivative with picric acid concentration) was obtained, and the minimum detection concentration was 1.05. Mu. Mol/L.
Example 5
Visual test paper：
The same volume and different concentrations of picric acid solutions are added to the perylene bisimide derivative test paper. FIG. 6 is a photograph of the test paper irradiated with 365nm ultraviolet light after adding picric acid at different concentrations, and it can be seen that when picric acid concentration is 0.1. Mu. Mol/L, the test paper shows significant fluorescence quenching, and thus, 0.1. Mu. Mol/L is the visual detection limit of the test paper.
Example 6
In order to more intuitively observe the effect graph of the interaction of the perylene bisimide derivative, picric acid and the interference thereof, the perylene bisimide derivative is detected under the irradiation of an ultraviolet lamp at 365 nm; hiccup the solution fluorescence change in the process of selectively investigating picric acid by the perylene imide derivative test paper.
When picric acid and the aforementioned interfering substances were selected, as shown in FIG. 7, the fluorescence of the test paper was not changed after the interfering substances were added to the test paper at a concentration of 10. Mu.L and 100. Mu. Mol/L, and the fluorescence of the solution was strongly quenched after the picric acid was added.
Example 7
Application of actual sample：
To verify the feasibility of the detection method in practical samples, tap water, lake water and soil samples were selected for recovery rate determination.
Tap water samples after 0.6 mu mol/L and 1.0 mu mol/L picric acid were added, the standard recovery rates were 108.2% and 104.6% (RSD < 3%), respectively, lake water samples after 0.4 mu mol/L, 1.4 mu mol/L and 2.20 mu mol/L picric acid were added, the standard recovery rates were 102.5%, 100.7% and 95.5% (RSD < 3%), respectively, and soil samples after 0.4 mu mol/L, 1.4 mu mol/L and 2.20 mu mol/L picric acid were added, the standard recovery rates were 107.5%, 94.0% and 98.0% (RSD < 6%), respectively, and the results showed that the method had good accuracy.
Claims (7)
1. The application of perylene imide derivatives shown in the formula (I) in detecting picric acid;
2. a method for detecting picric acid, characterized in that a perylene imide derivative shown in a formula (I) is used as a probe;
3. a reagent, test paper or kit for detecting picric acid is characterized by comprising perylene imide derivatives shown in a formula (I) as probes;
4. the use according to claim 1, wherein the fluorescent detection conditions are excitation with 440nm fluorescence and 450-600nm fluorescence detection.
5. The method according to claim 2, wherein the detection reaction system is: 600-3000 mu L of total system, 10mmol/L HEPES buffer with pH value of 7.0, 1-4 mu mol/L probe and the balance of distilled water.
6. The method according to claim 2 and the reagent, test strip or kit according to claim 3, wherein the RGB values of the reagent, test strip or kit photograph are extracted and the quantitative determination of picric acid is performed based on G/B.
7. A reagent, test strip or kit according to claim 3, wherein the visual qualitative or semi-quantitative detection is performed under an ultraviolet lamp.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310147881.9A CN116183571A (en) | 2023-02-21 | 2023-02-21 | Picric acid rapid visual detection method based on water-soluble perylene imide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310147881.9A CN116183571A (en) | 2023-02-21 | 2023-02-21 | Picric acid rapid visual detection method based on water-soluble perylene imide derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116183571A true CN116183571A (en) | 2023-05-30 |
Family
ID=86440042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310147881.9A Pending CN116183571A (en) | 2023-02-21 | 2023-02-21 | Picric acid rapid visual detection method based on water-soluble perylene imide derivative |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116183571A (en) |
-
2023
- 2023-02-21 CN CN202310147881.9A patent/CN116183571A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Hu et al. | Highly selective and effective mercury (II) fluorescent sensors | |
| Zeng et al. | Naphthalene-based fluorescent probe for on-site detection of hydrazine in the environment | |
| Rao et al. | Highly selective reaction based colorimetric and fluorometric chemosensors for cyanide detection via ICT off in aqueous solution | |
| CN108329904B (en) | Cysteamine modified copper nanocluster solution fluorescent probe and preparation and application thereof | |
| WO2013001534A1 (en) | A reagent method and kit for the detection of nitro aliphatic compounds | |
| EP2531299A2 (en) | Method and kit for identification of an explosive substance which contains an oxidant | |
| Rani et al. | Pyrene–antipyrine based highly selective and sensitive turn-on fluorescent sensor for Th (IV) | |
| US10989659B2 (en) | Chemical probes for hydrogen sulfide | |
| Jothi et al. | Benzothiazole appended 2, 2′-(1, 4-phenylene) diacetonitrile for the colorimetric and fluorescence detection of cyanide ions | |
| CN101281139B (en) | Copper ion test paper and preparation thereof | |
| Kuang et al. | A carbon-dot-based dual-emission probe for ultrasensitive visual detection of copper ions | |
| CN116183571A (en) | Picric acid rapid visual detection method based on water-soluble perylene imide derivative | |
| Wang et al. | 1, 4-Dihydroxyanthraquinone–Cu 2+ ensemble probe for selective detection of sulfide anion in aqueous solution | |
| CN106518792A (en) | Cyanide ion fluorescent sensor molecule and synthesis and application thereof | |
| Ge et al. | Colorimetric and ratiometric supramolecular AIE fluorescent probe for the on-site monitoring of fipronil | |
| Kara et al. | The sensitive and selective determination of aluminium by spectrofluorimetric detection after complexation with N-o-vanillidine-2-amino-p-cresol | |
| Kumar et al. | Recent Advances in Designing Colorimetric Probes for Nitrite Ions | |
| CN110317175B (en) | Naphthalene derivative and synthesis method and application thereof | |
| Deng et al. | A novel coumarin based fluorescent sensor for high-sensitive detection of Cu2+ and water as well as applications in food and environmental analysis | |
| CN109239026B (en) | Amide group-containing fluorescent probe for Hg2+And methods of use | |
| CN106841132B (en) | Method for detecting concentration of mercury ions in sample | |
| Alesso et al. | Monitoring of chlorsulfuron in biological fluids and water samples by molecular fluorescence using rhodamine B as fluorophore | |
| CN110951052B (en) | Polythiophene derivative, preparation method thereof and application thereof in rapid detection of picric acid | |
| CN108774241B (en) | Probe and preparation and application thereof | |
| CN112759532B (en) | Reagent for visual rapid and sensitive detection of bacillus anthracis and detection method 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 |