CN108872210B - Electrochemical luminescence reagent prepared from macrocyclic compound and application thereof - Google Patents

Electrochemical luminescence reagent prepared from macrocyclic compound and application thereof Download PDF

Info

Publication number
CN108872210B
CN108872210B CN201811090232.5A CN201811090232A CN108872210B CN 108872210 B CN108872210 B CN 108872210B CN 201811090232 A CN201811090232 A CN 201811090232A CN 108872210 B CN108872210 B CN 108872210B
Authority
CN
China
Prior art keywords
macrocyclic compound
mol
solution
concentration
reagent prepared
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
Application number
CN201811090232.5A
Other languages
Chinese (zh)
Other versions
CN108872210A (en
Inventor
丛航
邱菲
赵永毅
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Guizhou University
Original Assignee
Guizhou University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Guizhou University filed Critical Guizhou University
Priority to CN201811090232.5A priority Critical patent/CN108872210B/en
Publication of CN108872210A publication Critical patent/CN108872210A/en
Application granted granted Critical
Publication of CN108872210B publication Critical patent/CN108872210B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Analytical Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Immunology (AREA)
  • Pathology (AREA)
  • Electrochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Plasma & Fusion (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)

Abstract

The invention discloses an electrochemiluminescence reagent prepared from macrocyclic compound and application thereof, wherein the molecular formula is C36H30N6O15The macrocyclic compound with the structural formula shown in figure 1 is dissolved in a neutral electrolyte aqueous solution to prepare the macrocyclic compound. The application is the detection of succinylcholine chloride. The luminescent reagent can detect succinylcholine chloride, and the sample is easy to prepare, simple in process, short in time consumption, low in cost and wide in detection range, and is a novel electrochemical luminescent substance.

Description

Electrochemical luminescence reagent prepared from macrocyclic compound and application thereof
Technical Field
The invention relates to an electrochemical luminescence reagent and application thereof, in particular to an electrochemical luminescence reagent prepared from a macrocyclic compound and application thereof.
Background
Electrochemiluminescence (EC L), also called Electrochemiluminescence, has become a new analytical means applied to biological and molecular trace analysis and detection, is a special chemiluminescence phenomenon generated by electrochemical redox reaction, and is a product combining chemiluminescence and electrochemistry.
Succinylcholine chloride (SUC) is a short-acting neuromuscular relaxant, which is commonly used in surgery, but excessive use can cause bradycardia, arrhythmia, sudden cardiac arrest, etc. more serious, SUC abuse can lead to death.
Disclosure of Invention
The invention aims to provide an electrochemiluminescence reagent prepared from a macrocyclic compound and application thereof. The luminescent reagent can detect succinylcholine chloride, and the sample is easy to prepare, simple in process, short in time consumption, low in cost and wide in detection range, and is a novel electrochemical luminescent substance.
The technical scheme of the invention is as follows: an electrochemiluminescence reagent prepared from macrocyclic compound is prepared by using the formula C36H30N6O15The macrocyclic compound with the structural formula shown in figure 1 is dissolved in a neutral electrolyte aqueous solution to prepare the macrocyclic compound.
In the electrochemiluminescence reagent prepared from the macrocyclic compound, the neutral electrolyte aqueous solution is prepared by mixing a 4-hydroxyethyl piperazine ethanesulfonic acid solution and hydrogen peroxide and adjusting the pH value to be neutral by using a NaOH solution.
In the electrochemiluminescence reagent prepared from the macrocyclic compound, the concentrations of the 4-hydroxyethyl piperazine ethanesulfonic acid solution and hydrogen peroxide in the neutral electrolyte aqueous solution are both 0.1 mol/L.
The electrochemiluminescence reagent prepared from the macrocyclic compound has the concentration of 0.1 mol/L in NaOH solution.
An electrochemiluminescent reagent prepared from the macrocyclic compound, wherein the concentration of the macrocyclic compound in the electrochemiluminescent reagent is 2 × 10-4mol/L。
The application of the electrochemiluminescence reagent prepared from the macrocyclic compound is detection of succinylcholine chloride.
The application of the electrochemiluminescence reagent prepared from the macrocyclic compound is as follows:
1) preparing a mixed solution containing 0.1 mol/L of 4-hydroxyethyl piperazine ethanesulfonic acid and 0.1 mol/L of hydrogen peroxide, and adding a NaOH solution with the concentration of 0.1 mol/L to adjust the pH value to be neutral to obtain a neutral electrolyte solution;
2) dissolving succinylcholine chloride in neutral electrolyte solution to obtain solution with concentration of 2.0 × 10-2A solution of succinylcholine chloride in mol/L;
3) taking the electrochemical luminescence reagent, and diluting until the concentration of the macrocyclic compound is 1.0 × 10-8mol/L, then adding the succinyl acetylcholine chloride solution prepared in the step 2) into the diluted electrochemical luminescence reagent to obtain a mixed solution;
4) with Al2O3Polishing the glassy carbon electrode by using the polishing powder, cleaning and drying to obtain a clean electrode, measuring 2ml of the mixed solution obtained in the step 3) in an electrolytic cell, and measuring in an electrochemical luminescence tester by using the clean electrode.
The application of the electrochemiluminescence reagent prepared from the macrocyclic compound is that in the step 3), the concentration of the succinylcholine chloride in the mixed solution is 1.0 × 10-12mol/L-1.0×10-4mol/L。
In the application of the electrochemiluminescence reagent prepared from the macrocyclic compound, in step 4), the detection parameters of the electrochemiluminescence tester are as follows: the potential range is-0.2- +0.9V, and the scanning speed is 100 mv/s.
The invention has the advantages of
The electrochemiluminescence reagent prepared by the macrocyclic compound can be used for detecting succinylcholine chloride, and compared with the conventional high performance liquid chromatography for detecting succinylcholine chloride, the electrochemiluminescence reagent has the advantages of simple operation, short consumed time and wide detection range, the traditional HP L C method has complicated detection process and long consumed time, and the linear range detected by the electrochemiluminescence reagent is only 1 × 10-7-1×10-5The detection range of the EC L sensor constructed by the macrocyclic compound of the invention is 1 × 10-12-1×10-4Obviously, the concentration response range of the succinylcholine chloride can be greatly enhanced by applying the electrochemiluminescence detection method, and the whole experiment operation is simple and rapid. The macrocyclic compound has a cavity structure, is different from common electrochemical luminescent substances (such as luminol, ruthenium terpyridyl and the like), develops a novel electrochemical luminescent substance, and is a macrocyclic host-guest substanceThe research and application of chemical compounds and electrochemiluminescence provide a new development direction.
Drawings
FIG. 1 is a structural formula of the macrocyclic compound of the present invention;
FIG. 2(a) is a cyclic voltammogram of a macrocyclic compound, and FIG. 2(b) is an electrochemiluminescence thereof;
FIG. 3(a) is an electrochemiluminescence plot of macrocyclic compound solutions with different concentrations of succinylcholine chloride added, and FIG. 3(b) is a negative log plot of EC L intensity versus succinylcholine chloride concentration.
Detailed Description
The present invention is further illustrated by the following examples, which are not to be construed as limiting the invention.
Examples of the invention
Example 1: an electrochemiluminescence reagent prepared from macrocyclic compound is prepared by using the formula C36H30N6O15The macrocyclic compound is prepared by dissolving a macrocyclic compound with a structural formula shown in figure 1 in a neutral electrolyte aqueous solution, wherein the neutral electrolyte aqueous solution is prepared by adding a mixed solution containing 4-hydroxyethyl piperazine ethanesulfonic acid and hydrogen peroxide with the concentration of 0.1 mol/L into a NaOH solution with the concentration of 0.1 mol/L to adjust the pH value to be neutral, and in an electrochemical luminescence reagent, the macrocyclic compound has the concentration of 2 × 10-4mol/L。
Observation group: with Al2O3Polishing the glassy carbon electrode with the polishing powder, cleaning and drying to obtain a clean electrode, measuring 2ml of the electrochemiluminescence reagent prepared in the example 1 in an electrolytic cell, and measuring in an electrochemiluminescence tester by using a conventional three-electrode system, a platinum wire as a counter electrode, a glassy carbon electrode (GCE, phi 3mm) as a working electrode and Ag/AgCl as a reference electrode.
As a result, referring to FIG. 2, it was observed that an electrochemiluminescence phenomenon occurred at +0.7 v.
Example 2: the application of the electrochemiluminescence reagent prepared by the macrocyclic compound is the detection of succinylcholine chloride. The specific method comprises the following steps:
1) preparing a mixed solution containing 0.1 mol/L of 4-hydroxyethyl piperazine ethanesulfonic acid and 0.1 mol/L of hydrogen peroxide, and adding a NaOH solution with the concentration of 0.1 mol/L to adjust the pH value to be neutral to obtain a neutral electrolyte solution;
2) dissolving succinylcholine chloride in neutral electrolyte solution to obtain solution with concentration of 2.0 × 10-2A solution of succinylcholine chloride in mol/L;
3) taking the electrochemical luminescence reagent, and diluting until the concentration of the macrocyclic compound is 1.0 × 10-8mol/L, adding the solution of the succinylcholine chloride prepared in the step 2) into the diluted electrochemical luminescence reagent to obtain a mixed solution, and adding water to adjust the concentration of the succinylcholine chloride in the mixed solution to be 1.0 × 10-8mol/L；
4) With Al2O3Polishing the glassy carbon electrode with the polishing powder, cleaning and drying to obtain a clean electrode, measuring 2ml of mixed solution obtained in the step 3) in an electrolytic cell, and measuring in an electrochemical luminescence tester with the clean electrode, wherein the detection parameters of the electrochemical luminescence tester are as follows: the potential range is-0.2- +0.9V, and the scanning speed is 100 mv/s.
The results of the detection are shown in FIG. 3.
Example 3: the application of the electrochemiluminescence reagent prepared by the macrocyclic compound is the detection of succinylcholine chloride. The specific method comprises the following steps:
1) preparing a mixed solution containing 0.1 mol/L of 4-hydroxyethyl piperazine ethanesulfonic acid and 0.1 mol/L of hydrogen peroxide, and adding a NaOH solution with the concentration of 0.1 mol/L to adjust the pH value to be neutral to obtain a neutral electrolyte solution;
2) dissolving succinylcholine chloride in neutral electrolyte solution to obtain solution with concentration of 2.0 × 10-2A solution of succinylcholine chloride in mol/L;
3) taking the electrochemical luminescence reagent, and diluting until the concentration of the macrocyclic compound is 1.0 × 10-8mol/L, adding the solution of the succinylcholine chloride prepared in the step 2) into the diluted electrochemical luminescence reagent to obtain a mixed solution, and adding water to adjust the concentration of the succinylcholine chloride in the mixed solution to be 1.0 × 10-12mol/L；
4) With Al2O3Polishing the glassy carbon electrode with the polishing powder, cleaning and drying to obtain a clean electrode, measuring 2ml of mixed solution obtained in the step 3) in an electrolytic cell, and measuring in an electrochemical luminescence tester with the clean electrode, wherein the detection parameters of the electrochemical luminescence tester are as follows: the potential range is-0.2- +0.9V, and the scanning speed is 100 mv/s.
Example 4: the application of the electrochemiluminescence reagent prepared by the macrocyclic compound is the detection of succinylcholine chloride. The specific method comprises the following steps:
1) preparing a mixed solution containing 0.1 mol/L of 4-hydroxyethyl piperazine ethanesulfonic acid and 0.1 mol/L of hydrogen peroxide, and adding a NaOH solution with the concentration of 0.1 mol/L to adjust the pH value to be neutral to obtain a neutral electrolyte solution;
2) dissolving succinylcholine chloride in neutral electrolyte solution to obtain solution with concentration of 2.0 × 10-2A solution of succinylcholine chloride in mol/L;
3) taking the electrochemical luminescence reagent, and diluting until the concentration of the macrocyclic compound is 1.0 × 10-8mol/L, adding the solution of the succinylcholine chloride prepared in the step 2) into the diluted electrochemical luminescence reagent to obtain a mixed solution, and adding water to adjust the concentration of the succinylcholine chloride in the mixed solution to be 1.0 × 10-4mol/L；
4) With Al2O3Polishing the glassy carbon electrode with the polishing powder, cleaning and drying to obtain a clean electrode, measuring 2ml of mixed solution obtained in the step 3) in an electrolytic cell, and measuring in an electrochemical luminescence tester with the clean electrode, wherein the detection parameters of the electrochemical luminescence tester are as follows: the potential range is-0.2- +0.9V, and the scanning speed is 100 mv/s.

Claims (8)

1. An electrochemiluminescent reagent prepared from macrocyclic compounds, which is characterized in that: is represented by the formula C36H30N6O15The structural formula is as follows:
Figure FDA0002534814220000011
the macrocyclic compound is dissolved in a neutral electrolyte aqueous solution to prepare the macrocyclic compound; the neutral electrolyte aqueous solution is prepared by mixing a 4-hydroxyethyl piperazine ethanesulfonic acid solution and hydrogen peroxide and adjusting the pH value to be neutral by using a NaOH solution.
2. The electrochemiluminescence reagent prepared from the macrocyclic compound as claimed in claim 1, wherein the concentrations of the 4-hydroxyethyl piperazine ethanesulfonic acid solution and hydrogen peroxide in the neutral electrolyte aqueous solution are both 0.1 mol/L.
3. The electrochemiluminescence reagent prepared from the macrocyclic compound of claim 1, wherein the concentration of the NaOH solution is 0.1 mol/L.
4. The electrochemiluminescence reagent prepared from macrocyclic compound according to claim 1, wherein the concentration of macrocyclic compound in the electrochemiluminescence reagent is 2 × 10-4mol/L。
5. Use of an electrochemiluminescent reagent prepared from a macrocyclic compound according to any of claims 1 to 4, wherein: is used for detecting succinylcholine chloride.
6. The use of an electrochemiluminescent reagent prepared from the macrocyclic compound according to claim 5, wherein the specific method for the use is as follows:
1) preparing a mixed solution containing 0.1 mol/L of 4-hydroxyethyl piperazine ethanesulfonic acid and 0.1 mol/L of hydrogen peroxide, and adding a NaOH solution with the concentration of 0.1 mol/L to adjust the pH value to be neutral to obtain a neutral electrolyte solution;
2) dissolving succinylcholine chloride in neutral electrolyte solution to obtain solution with concentration of 2.0 × 10-2A solution of succinylcholine chloride in mol/L;
3) taking the electrochemical luminescence reagent, and diluting until the concentration of the macrocyclic compound is 1.0 × 10-8mol/L, and then the chlorine obtained in step 2)Adding the amber acetylcholine solution into the diluted electrochemical luminescence reagent to obtain a mixed solution;
4) with Al2O3Polishing the glassy carbon electrode by using the polishing powder, cleaning and drying to obtain a clean electrode, measuring 2ml of the mixed solution obtained in the step 3) in an electrolytic cell, and measuring in an electrochemical luminescence tester by using the clean electrode.
7. The use of an electrochemiluminescent reagent prepared from the macrocyclic compound of claim 6, wherein the concentration of the succinylcholine chloride in the mixed solution in step 3) is 1.0 × 10-12mol/L-1.0×10-4mol/L。
8. Use of an electrochemiluminescent reagent prepared from a macrocyclic compound according to claim 6, wherein: in the step 4), the detection parameters of the electrochemical luminescence tester are as follows: the potential range is-0.2- +0.9V, and the scanning speed is 100 mv/s.
CN201811090232.5A 2018-09-18 2018-09-18 Electrochemical luminescence reagent prepared from macrocyclic compound and application thereof Active CN108872210B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201811090232.5A CN108872210B (en) 2018-09-18 2018-09-18 Electrochemical luminescence reagent prepared from macrocyclic compound and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201811090232.5A CN108872210B (en) 2018-09-18 2018-09-18 Electrochemical luminescence reagent prepared from macrocyclic compound and application thereof

Publications (2)

Publication Number Publication Date
CN108872210A CN108872210A (en) 2018-11-23
CN108872210B true CN108872210B (en) 2020-08-07

Family

ID=64324401

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201811090232.5A Active CN108872210B (en) 2018-09-18 2018-09-18 Electrochemical luminescence reagent prepared from macrocyclic compound and application thereof

Country Status (1)

Country Link
CN (1) CN108872210B (en)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040122145A1 (en) * 2002-05-09 2004-06-24 The C.P. Hall Company Adhesion promoters for sealants
CN101084437A (en) * 2004-01-22 2007-12-05 普罗美加公司 Luminogenic and nonluminogenic multiplex assay
CN102004100A (en) * 2010-11-24 2011-04-06 武汉大学 Method for detecting sulfur ions
CN105784689A (en) * 2016-04-20 2016-07-20 北京中航赛维生物科技有限公司 Magnetic particle chemiluminescence quantitative determination reagent kit of anti-centromere antibody IgG and preparation and detection method
CN106045915A (en) * 2016-05-30 2016-10-26 贵州大学 Novel macrocyclic compound and synthetic method and application thereof
CN106279187A (en) * 2016-07-24 2017-01-04 贵州大学 A kind of macrocyclic compound and synthetic method thereof and application
CN106323951A (en) * 2016-08-24 2017-01-11 济南大学 Preparing method for electrogenerated chemiluminescence cell sensor flexible detection of cancer cells

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040122145A1 (en) * 2002-05-09 2004-06-24 The C.P. Hall Company Adhesion promoters for sealants
CN101084437A (en) * 2004-01-22 2007-12-05 普罗美加公司 Luminogenic and nonluminogenic multiplex assay
CN102004100A (en) * 2010-11-24 2011-04-06 武汉大学 Method for detecting sulfur ions
CN105784689A (en) * 2016-04-20 2016-07-20 北京中航赛维生物科技有限公司 Magnetic particle chemiluminescence quantitative determination reagent kit of anti-centromere antibody IgG and preparation and detection method
CN106045915A (en) * 2016-05-30 2016-10-26 贵州大学 Novel macrocyclic compound and synthetic method and application thereof
CN106279187A (en) * 2016-07-24 2017-01-04 贵州大学 A kind of macrocyclic compound and synthetic method thereof and application
CN106323951A (en) * 2016-08-24 2017-01-11 济南大学 Preparing method for electrogenerated chemiluminescence cell sensor flexible detection of cancer cells

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Benzo[3]urils and their Recognition to Metal Cations and Anions;Fang Wang等;《Chemistry Select》;20161020;第5409-5413页 *
Carboxymethyl-substituted benzo[3]uril and its application in ion-pair recognition;Fang Wang 等;《Sensors and Actuators B: Chemical》;20170801;第254卷;第1182-1190页 *
Synthesis of benzo[6]urils and their selective interactions with bipyridines;Man Chen 等;《New Journal of Chemistry》;20171231;第41卷(第21期);第13051-13059页 *

Also Published As

Publication number Publication date
CN108872210A (en) 2018-11-23

Similar Documents

Publication Publication Date Title
Li et al. Cobalt hexacyanoferrate modified multi-walled carbon nanotubes/graphite composite electrode as electrochemical sensor on microfluidic chip
Mazloum-Ardakani et al. Simultaneous and selective voltammetric determination of epinephrine, acetaminophen and folic acid at a ZrO2 nanoparticles modified carbon paste electrode
Li et al. Nonenzymatic nitrite sensor based on a titanium dioxide nanoparticles/ionic liquid composite electrode
Mazloum-Ardakani et al. Electrochemical determination of vitamin C in the presence of uric acid by a novel TiO2 nanoparticles modified carbon paste electrode
Zheng et al. Flow-injection electrogenerated chemiluminescence determination of epinephrine using luminol
CN112697778A (en) Method and device for reading out potential change detection by using electrochemiluminescence method
Yang et al. CTAB functionalized graphene oxide/multiwalled carbon nanotube composite modified electrode for the simultaneous determination of sunset yellow and tartrazine
Zheng et al. Flow injection chemiluminescence determination of captopril with in situ electrogenerated Mn3+ as the oxidant
CN103575794A (en) Detecting method of iodide ions based on graphene/DNA (Deoxyribonucleic Acid)/sliver nano composite material
Duan et al. Determination of metoprolol tartrate and bisoprolol fumarate by capillary electrophoresis coupled with tris (2, 2′-bipyridyl)-ruthenium (ii) electrochemiluminescence detection and study on the interaction between the drugs and human serum albumin
Zeng et al. The electrochemical properties of Co (TPP), tetraphenylborate modified glassy carbon electrode: application to dopamine and uric acid analysis
CN108872210B (en) Electrochemical luminescence reagent prepared from macrocyclic compound and application thereof
Wang et al. Electrochemical detection of nitrite based on difference of surface charge of self-assembled monolayers
Zhou et al. Study on the electrochemical properties of maltol at a carbon paste electrode and its analytical application
Pan et al. On-line determination of lead in tap waters at two-step prepared bismuth electrode
Lin et al. An electrochemiluminescent biosensor for uric acid based on the electrochemiluminescence of bis-[3, 4, 6-trichloro-2-(pentyloxycarbonyl)-phenyl] oxalate on an ITO electrode modified by an electropolymerized nickel phthalocyanine film
Cruickshank et al. Rare elements electrochemistry: The development of a novel electrochemical sensor for the rapid detection of europium in environmental samples using gold electrode modified with 2-pyridinol-1-oxide
CN105758849B (en) A kind of preparation method and application of the difunctional stilbestrol without enzyme sensor based on Two-dimensional Composites structure
Ganjali et al. A Novel Sulfate Polymeric Membrane Sensor Based on a New Bis‐Pyrylium Derivative
bt Rahman et al. Adsorption enhancement of Pb (II) ion in the presence of Nicotinic acid during cyclic Voltammetry
Li et al. Sensitive determination of urapidil at an electrochemically pretreated glassy carbon electrode by linear sweep voltammetry
Jiang et al. Electrochemical investigation of Da and Ua on carboxylated graphene oxide/lanthanum electrodes with sundry content of Ctab
Liu et al. Manganese (III) meso-tetrakis (4-N-methylpyridyl)-porphyrin and mediator thionine co-decorated DNA nanowires for sensitive electrochemical monitoring of mercury (II)
RU94713U1 (en) FILM POTENTIOMETRIC SENSOR BASED ON A PRINTED GRAPHITE ELECTRODE
Sheet et al. Multifunctional dendritic molecular probe for selective detection of Cu 2+ ions using potentiometric and fluorometric techniques

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