CN113189160B - Application of tetraphenyl ethylene derivative in electrochemiluminescence detection of hypochlorite ion - Google Patents
Application of tetraphenyl ethylene derivative in electrochemiluminescence detection of hypochlorite ion Download PDFInfo
- Publication number
- CN113189160B CN113189160B CN202110526821.9A CN202110526821A CN113189160B CN 113189160 B CN113189160 B CN 113189160B CN 202110526821 A CN202110526821 A CN 202110526821A CN 113189160 B CN113189160 B CN 113189160B
- Authority
- CN
- China
- Prior art keywords
- tetraphenyl ethylene
- ethylene derivative
- electrochemiluminescence
- electrode
- clo
- 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
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
-
- 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
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/76—Chemiluminescence; Bioluminescence
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/28—Electrolytic cell components
- G01N27/30—Electrodes, e.g. test electrodes; Half-cells
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/28—Electrolytic cell components
- G01N27/30—Electrodes, e.g. test electrodes; Half-cells
- G01N27/333—Ion-selective electrodes or membranes
- G01N27/3335—Ion-selective electrodes or membranes the membrane containing at least one organic component
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Electrochemistry (AREA)
- Plasma & Fusion (AREA)
- Engineering & Computer Science (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses an application of a tetraphenyl ethylene derivative in electrochemiluminescence detection of hypochlorite ions, which comprises DMF solution of the tetraphenyl ethylene derivative and K-containing compounds 2 S 2 O 8 Is mixed with phosphate buffer solution of (C), and added with HSO respectively 3 ‑ 、SO 3 2‑ 、OH ‑ 、HPO 4 2‑ 、Cl ‑ 、CO 3 2‑ 、H 2 O 2 、F ‑ 、NO 3 ‑ 、ONOO ‑ And ClO ‑ The electrochemiluminescence signal was detected in a three-electrode system with Ag/AgCI as reference electrode, platinum electrode as counter electrode, and glassy carbon electrode as working electrode, with ClO alone ‑ The addition of (3) can reduce the electrochemiluminescence signal intensity of the tetraphenyl ethylene derivative. Therefore, the tetraphenyl ethylene derivative can detect hypochlorite ions in a single selective way, and the lowest detection limit is 4.79 mu M.
Description
Technical Field
The invention relates to an application of a tetraphenyl ethylene derivative in electrochemiluminescence detection of hypochlorite ions, belonging to the field of electrochemiluminescence and anion detection.
Background
Molecular luminescence includes phosphorescence, fluorescence and chemiluminescence. Electrochemiluminescence (ECL) is a phenomenon in which substances formed on the surface of an electrode undergo an electron transfer reaction to generate an excited state under an applied voltage, and the excited state is unstable and returns to a ground state to emit light. ECL does not require the use of external light sources, which gives it the advantage of high emission purity and low optical background noise, and moreover ECL is also superior to Chemiluminescence (CL) in that it can precisely control the emission by applying a voltage. Because ECL combines the advantages of electrochemistry and luminescence technology, people pay more attention to ECL and have wide and important significance in fields of regenerative chemistry analysis, chemical substance detection, photochemistry, chemical analysis and the like.
Hypochlorous acid (HClO) is an unstable and weak acid with a strong pungent odor. HClO is well known for use as a disinfectant, which has been widely used in household bleach, disinfection drinking or cooling water treatment, and cyanide treatment in our daily lives. It is generally at 10 -5 -10 -2 In molar concentration ranges, otherwise superfluous ClO - Many unwanted byproducts, particularly Trihalomethanes (THMs), are produced, which are detrimental to humans and animals, and in addition, data suggest that abnormal levels of HClO can trigger tissue damage and lead to various diseases such as cystic fibrosis, atherosclerosis, lung injury, kidney disease, neuronal degeneration and certain cancers. About 400 tens of thousands of people die from annual cancer and cardiovascular diseases worldwide, which have recently been demonstrated with ClO - Is related to the abnormal concentration of (c).
Therefore, it is urgent to study a high-sensitivity chemical sensor for detecting hypochlorite, and electrochemiluminescence has the advantages of simple operation and high sensitivity compared with detection means such as weather chromatography, capillary electrophoresis, high performance liquid chromatography and the like.
Disclosure of Invention
The invention aims to provide an application of a tetraphenyl ethylene derivative in electrochemiluminescence detection of hypochlorite ions.
1. Tetraphenyl ethylene derivative and its synthesis
The invention relates to a tetraphenyl ethylene derivative, which is named as 2-amino-3- ((Z) - (4' - (1.2.2-triphenylvinyl) - [1.1 biphenyl ] -4-yl) methylene) amino) maleic nitrile, and has the following structural formula:
。
the synthesis method of the tetraphenyl ethylene derivative comprises the following steps: dissolving 4' - (1, 2-triphenylvinyl) biphenyl 4-benzaldehyde and diaminomaleonitrile in ethanol, adding 1.76mmol of 100 mu L acetic acid as a water scavenger, heating and refluxing for 12-16 hours at 70-90 ℃, performing rotary evaporation and concentration, and purifying by a silica gel chromatography to obtain a tetraphenyl ethylene derivative, wherein the tetraphenyl ethylene derivative is marked as TPE-MN. Wherein, the mol ratio of 4' - (1, 2-triphenylvinyl) biphenyl 4-benzaldehyde to diaminomaleonitrile is 1:1; the molar ratio of 4' - (1, 2-triphenylvinyl) biphenyl 4-benzaldehyde to acetic acid is 1:0.5-1:1.
FIG. 1 is a nuclear magnetic hydrogen spectrum of TPE-MN. As can be seen from the nuclear magnetic hydrogen spectrogram, the prepared polymer contains a tetraphenyl ethylene derivative (TPE-MN) 1 H NMR (400 MHz, acetate-d 6) delta 8.40 (s, 1H), 8.07 (d, j=8.1 Hz, 2H), 7.75 (d, j=8.1 Hz, 2H), 7.54 (d, j=8.1 Hz, 2H), 7.44-6.90 (m, 19H).
2. Detection of hypochlorite ion by tetraphenyl ethylene derivative
1. Electrochemiluminescence properties of tetraphenyl ethylene derivatives (TPE-MN)
Containing K 2 S 2 O 8 Phosphate buffer of (c): in the presence of water as a solvent, 1.7418g of monopotassium phosphate, 1.3609g of dipotassium phosphate, 2.7032g of potassium persulfate (2 parts) and 0.7455g of potassium chloride (2 parts) were respectively weighed, sonicated into a volumetric flask of 100ml and adjusted to pH with a pH meter.
The glassy carbon electrode was prepared with 0.3 μm and 0.05 μm Al, respectively 2 O 3 Polishing powder, washing with ultrapure water, ultrasonic cleaning for 2-3 times, and drying with nitrogen for later use.
A series of DMF solutions of tetraphenyl ethylene derivatives of different concentrations (0.01 mmol/L, 0.02 mmol/L, 0.03mmol/L, 0.04 mmol/L) were prepared. The electrochemiluminescence signals are detected in a three-electrode system which comprises a potassium persulfate phosphate buffer solution and 100uL of TPE-MN solution with different concentrations in a reaction container, ag/AgCl as a reference electrode, a platinum electrode as a counter electrode and a glassy carbon electrode as a working electrode, and the electrochemiluminescence diagrams of the tetraphenyl ethylene derivative solutions with different concentrations are shown in figure 2. As can be seen from the figure, ECL signal was strongest at a concentration of 0.02mM for the tetraphenyl ethylene derivative solution.
Respectively preparing pH=4.5, 5.0, 6.0, 6.5, 7.0, 7.5, 8.0 and 9.0 of buffer solution containing potassium peroxodisulfate phosphate, taking 5mL of buffer solution containing potassium peroxodisulfate phosphate at different pH values and 100 mu L of 0.02mM TPE-MN solution in a reaction container, taking Ag/AgCl as a reference electrode, taking a platinum electrode as a counter electrode, and detecting electrochemiluminescence signals in a three-electrode system taking a glassy carbon electrode as a working electrode, wherein the potential window of electrochemiluminescence and cyclic voltammetry is-0.1 to-1.7V, and the sweeping speed is set at 0.1Vs -1 . The electrochemiluminescence pattern of TPE-MN at different pH values is shown in FIG. 3. As can be seen from the figure, ECL signal is strongest at ph=7.
Taking 5mL of TPE-MN solution containing potassium persulfate phosphate buffer solution with pH value of 7 and 0.02mM of 100 mu L in a reaction container, testing stability in a three-electrode system with Ag/AgCl as a reference electrode, a platinum electrode as a counter electrode and a glassy carbon electrode as a working electrode, wherein the potential window of electrochemiluminescence and cyclic voltammetry is-0.1 to-1.7V, and the sweeping speed is set to 0.1Vs -1 . It was found that after 23 cycles of the cyclic scan, the ECL intensity did not change significantly, indicating good stability, as shown in fig. 4.
2. Detection of hypochlorite ion by tetraphenyl ethylene derivative
5mL of TPE-MN solution containing potassium persulfate phosphate buffer solution with pH=7 and 100 mu L of 0.02mM are taken in a reaction container, and HSO is added respectively 3 - 、SO 3 2- 、OH - 、HPO 4 2- 、Cl - 、CO 3 2- 、H 2 O 2 、F - 、NO 3 - 、ONOO - And ClO - (10 mu M) in Ag/AgClThe method is characterized in that the method comprises the steps of detecting electrochemiluminescence signals in a three-electrode system with a platinum electrode as a counter electrode and a glassy carbon electrode as a working electrode, wherein the reference electrode is used as a reference electrode. The electrochemiluminescence pattern of the addition of different anions to the tetraphenyl ethylene derivative solution is shown in FIG. 5, which shows that only ClO - The addition of (2) can reduce the electrochemiluminescence signal intensity of the TPE-MN, and the addition of other anions can not obviously change the electrochemiluminescence signal intensity of the TPE-MN. Thus, TPE-MN can realize the ClO - Is used for specific recognition detection of the strain.
To test for the para-ClO of tetraphenyl ethylene derivatives in complex environments - Specific recognition of (C) for detection of ClO for TPE-MN - An anti-interference experiment is carried out, 5mL of a solution containing potassium peroxodisulfate phosphate buffer with pH=7 and 100 mu L of 0.02mM of tetraphenyl ethylene derivative is taken in a reaction vessel, 10 mu M of hypochlorite ion solution is added in the reaction vessel, and the reaction vessel contains ClO - Adding the ClO-removing agent into the tetraphenyl ethylene derivative solution respectively - 10 anions (1 mM) were used to detect other anions for ClO - As shown in fig. 6. As can be seen, TPE-MN pair ClO in the presence of interfering ions - Still has higher recognition.
Preparing ClO with different concentrations - Solution (5 mu M,10 mu M,30 mu M,50 mu M,70 mu M,90 mu M,110 mu M,130 mu M) is used as detection solution, 5mL of TPE-MN solution containing potassium peroxodisulfate phosphate buffer solution with pH of 7 and 100 mu L of 0.02mM is taken in a reaction container, and ClO with different concentrations is added - The solution was tested for electrochemiluminescence signals in a three electrode system with Ag/AgCl as reference electrode, platinum electrode as counter electrode, and glassy carbon electrode as working electrode. FIG. 7 shows the addition of ClO at various concentrations to TPE-MN - Post electrochemiluminescence signal plot with ClO - The increase in concentration gradually decreases the electrochemiluminescence signal intensity. FIG. 8 shows the addition of ClO at various concentrations to TPE-MN - Post electrochemiluminescence signal intensity and ClO - A linear fitting curve of the concentration is calculated to obtain the ClO - The lowest detection limit of (2) is 4.79 mu M, which indicates that TPE-MN can detect low-concentration ClO - 。
3. Detection mechanism
Addition of ClO to tetraphenyl ethylene derivatives - ，ClO - Can break carbon-nitrogen bond in the tetraphenyl ethylene derivative to reduce electrochemiluminescence signal of the tetraphenyl ethylene derivative to realize ClO - Is detected. The detection mechanism is as follows:
。
drawings
FIG. 1 is a nuclear magnetic resonance spectrum of a tetraphenyl ethylene derivative (TPE-MN);
FIG. 2 is a graph of a concentration-optimized electrochemiluminescence of tetraphenyl ethylene derivative (TPE-MN);
FIG. 3 is an electrochemiluminescence diagram of a tetraphenyl ethylene derivative (TPE-MN) at different pH values;
FIG. 4 is a graph of the stability of tetraphenyl ethylene derivative (TPE-MN) in electrochemiluminescence;
FIG. 5 is an electrochemiluminescence diagram of the addition of different anions to a tetraphenyl ethylene derivative (TPE-MN);
FIG. 6 shows the effect of tetraphenyl ethylene derivative (TPE-MN) on ClO in the presence of various anions - A detected anti-interference graph; FIG. 7 shows the addition of ClO at various concentrations to TPE-MN - A post electrochemiluminescence signal pattern;
FIG. 8 shows the addition of ClO at various concentrations to TPE-MN - Post electrochemiluminescence signal intensity and ClO - Linear fitting curve of concentration.
Detailed Description
The present invention will be described in further detail with reference to the following specific embodiments.
Example 1 contains the synthesis of tetraphenyl ethylene derivatives.
Accurately weighing 4' - (1, 2-triphenylvinyl) biphenyl 4-benzaldehyde (TPE-CHO) (0.321 g,2 mmol) and diaminomaleonitrile (MN) (0.216 g,2 mmol) dissolved in 20ml ethanol and adding 1.76mmol 100 μl acetic acid. The mixed solution was heated to reflux at 80 ℃ for 15 hours, and then the solvent was spin-dried with a spin-evaporator. The crude product was purified by silica gel chromatography using petroleum ether: ethyl acetate = 10:1 as eluent, 0.483g (yield 51.5%) of a pale yellow solid of a tetraphenyl ethylene derivative was obtained.
Example 2 use of tetraphenyl ethylene derivatives in electrochemiluminescence detection of hypochlorite ions
5mL of a pH=7 solution containing potassium peroxodisulfate phosphate buffer and 100uL of 0.02mM TPE-MN was taken in a reaction vessel, and HSO was added separately 3 - 、SO 3 2- 、OH - 、HPO 4 2- 、Cl - 、CO 3 2- 、H 2 O 2 、F - 、NO 3 - 、ONOO - And ClO - (10 mu M) detecting electrochemiluminescence signals in a three-electrode system with Ag/AgCl as a reference electrode, a platinum electrode as a counter electrode and a glassy carbon electrode as a working electrode, wherein if the intensity of the electrochemiluminescence signals of TPE-MN is reduced, clO is added - If the electrochemiluminescence signal intensity of TPE-MN is reduced substantially unchanged, it is indicated that other anions are added.
Claims (6)
1. The application of the tetraphenyl ethylene derivative in electrochemiluminescence detection of hypochlorite ions is characterized in that: hypochlorite ions were detected in a solution containing potassium peroxodisulfate phosphate buffer at ph=7 and a tetraphenyl ethylene derivative having the following structural formula:
。
2. use of a tetraphenyl ethylene derivative according to claim 1 for electrochemiluminescence detection of hypochlorite ions, characterized in that: DMF solution of tetraphenyl ethylene derivative and containing K 2 S 2 O 8 Is mixed with phosphate buffer solution of (C), and added with HSO respectively 3 - 、SO 3 2- 、OH - 、HPO 4 2- 、Cl - 、CO 3 2- 、H 2 O 2 、F - 、NO 3 - 、ONOO - And ClO - Detecting electrochemiluminescence signals in a three-electrode system with Ag/AgCl as a reference electrode, a platinum electrode as a counter electrode and a glassy carbon electrode as a working electrode, with ClO only - The addition of (3) can reduce the electrochemiluminescence signal intensity of the tetraphenyl ethylene derivative.
3. Use of a tetraphenyl ethylene derivative according to claim 2 for electrochemiluminescence detection of hypochlorite ions, characterized in that: containing K 2 S 2 O 8 Is 7,K 2 S 2 O 8 Is 0.1M.
4. Use of a tetraphenyl ethylene derivative according to claim 1 for electrochemiluminescence detection of hypochlorite ions, characterized in that: the synthesis method of the tetraphenyl ethylene derivative comprises the following steps: dissolving 4' - (1, 2-triphenylvinyl) biphenyl 4-benzaldehyde and diaminomaleonitrile in ethanol, adding acetic acid as a water scavenger, heating and refluxing at 70-90 ℃ for 12-16 hours, and purifying by silica gel chromatography after rotary evaporation and concentration to obtain the tetraphenyl ethylene derivative.
5. The use of a tetraphenyl ethylene derivative according to claim 4 for electrochemiluminescence detection of hypochlorite ions, wherein: the molar ratio of 4' - (1, 2-triphenylvinyl) biphenyl 4-benzaldehyde to diaminomaleonitrile was 1:1.
6. The use of a tetraphenyl ethylene derivative according to claim 4 for electrochemiluminescence detection of hypochlorite ions, wherein: the molar ratio of 4' - (1, 2-triphenylvinyl) biphenyl 4-benzaldehyde to acetic acid is 1:0.5-1:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110526821.9A CN113189160B (en) | 2021-05-14 | 2021-05-14 | Application of tetraphenyl ethylene derivative in electrochemiluminescence detection of hypochlorite ion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110526821.9A CN113189160B (en) | 2021-05-14 | 2021-05-14 | Application of tetraphenyl ethylene derivative in electrochemiluminescence detection of hypochlorite ion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113189160A CN113189160A (en) | 2021-07-30 |
| CN113189160B true CN113189160B (en) | 2023-09-01 |
Family
ID=76982034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110526821.9A Active CN113189160B (en) | 2021-05-14 | 2021-05-14 | Application of tetraphenyl ethylene derivative in electrochemiluminescence detection of hypochlorite ion |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113189160B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103604783A (en) * | 2013-11-01 | 2014-02-26 | 大连理工大学 | Method for reversible detection on hypochlorite and hydrogen sulfide |
| CN111239110A (en) * | 2020-02-10 | 2020-06-05 | 西北师范大学 | Construction method of porphyrin derivative with aggregation-induced emission performance applied to electrochemiluminescence system |
-
2021
- 2021-05-14 CN CN202110526821.9A patent/CN113189160B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103604783A (en) * | 2013-11-01 | 2014-02-26 | 大连理工大学 | Method for reversible detection on hypochlorite and hydrogen sulfide |
| CN111239110A (en) * | 2020-02-10 | 2020-06-05 | 西北师范大学 | Construction method of porphyrin derivative with aggregation-induced emission performance applied to electrochemiluminescence system |
Non-Patent Citations (1)
| Title |
|---|
| 秦勤 等.饮用水中次氯酸根离子快速检测方法的探讨.《黑龙江环境通报》.2019,第43卷(第3期),31-35. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113189160A (en) | 2021-07-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| He et al. | A turn-on fluorescent BOPHY probe for Cu 2+ ion detection | |
| Bag et al. | Rhodamine-based probes for metal ion-induced chromo-/fluorogenic dual signaling and their selectivity towards Hg (II) ion | |
| CN106518900A (en) | Synthesis and application of BODIPY dye-based hypochlorite fluorescent probe | |
| CN104498024B (en) | A kind of copper ion Ratiometric fluorescent probe based on pyrene and its preparation method and application | |
| CN106632363A (en) | Mitochondrial targeted ratio type hypochlorous acid fluorescence probe and application thereof | |
| CN108003869A (en) | A kind of fluorescence probe of highly sensitive detection hypochlorite and its synthetic method and application | |
| CN111239110A (en) | Construction method of porphyrin derivative with aggregation-induced emission performance applied to electrochemiluminescence system | |
| Du et al. | A new coumarin-based “turn-on” fluorescence probe with high sensitivity and specificity for detecting hypochlorite ion | |
| CN107589162A (en) | A kind of preparation method and application based on complex of iridium Photoelectrochemistrbiosensor biosensor | |
| CN110372632A (en) | A kind of fluorescent probe molecule and its preparation method and application of quick identification hypochlorite ion | |
| CN114636746A (en) | Detect Pb2+Carboxyl ligand induced annihilation type ratio electrochemiluminescence aptamer sensing method | |
| CN108641713A (en) | A kind of fluorescence probe and its preparation method and application of detection hypochlorite ion | |
| CN110885327A (en) | Hypochlorous acid rapid response fluorescent probe and preparation method and application thereof | |
| CN113189160B (en) | Application of tetraphenyl ethylene derivative in electrochemiluminescence detection of hypochlorite ion | |
| Soni et al. | Disposable paper-based PET fluorescence probe linked with calix [4] arene for lithium and phosphate ion detection | |
| CN109021000A (en) | A kind of fluorescence probe, synthetic method and application detecting hydrogen peroxide | |
| CN117342803A (en) | Preparation method of hypochlorous acid photoelectrochemical sensor and application of sensor in detecting hypochlorous acid | |
| CN109053750B (en) | Rhodamine hydrazine Schiff base derivative and preparation method and application thereof | |
| CN114249740B (en) | Tanshinone benzimidazole type fluorescent probe and preparation method and application thereof | |
| CN112521376B (en) | Chromene-pyridine derivative fluorescent probe, preparation method and application | |
| CN110078772B (en) | Iridium complex-based fluorescent probe, preparation method thereof and application thereof in hypochlorous acid detection | |
| Li et al. | A fluorescent chemosensor for Hg2+ based on a rhodamine derivative in an aqueous solution | |
| CN109020917B (en) | Fluorescent molecular probe for identifying phosphate ions in water environment and preparation method thereof | |
| CN108276360B (en) | Synthesis method of novel fluorescent molecular probe PP for detecting lead ions | |
| Wu et al. | A Novel Ratiometric Cationic Iridium (III) Complex Phosphorescent Probe for Hydrogen Peroxide |
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 |