CN114736138A - Visual probe 3aa for detecting copper ions and synthetic path thereof - Google Patents

Visual probe 3aa for detecting copper ions and synthetic path thereof Download PDF

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CN114736138A
CN114736138A CN202210470544.9A CN202210470544A CN114736138A CN 114736138 A CN114736138 A CN 114736138A CN 202210470544 A CN202210470544 A CN 202210470544A CN 114736138 A CN114736138 A CN 114736138A
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copper ions
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detecting copper
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何永辉
谢富兰
李干鹏
张丽珠
李文义
赵琦海
梁瑞
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Yunnan Minzu University
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Abstract

The invention discloses a visual probe 3aa for detecting copper ions, which is characterized in that the chemical name of the visual probe is 2-amino-5-anilino- [1,4]]Benzoquinone-4-phenylimine, having the molecular formula: c18H15N3O, reaction with the compound 2-aminophenol and aniline as template substrates, NH4I as a medium, LiClO4The electrolyte is acetonitrile as solvent, carbon rods are used as cathode and anode of the electrode under room temperature, the reaction mixture is firstly stirred and then reacts in an undivided electrolytic cell under constant current of 5-15 mA. The invention prepares the needed 2-amino-5-anilino- [1,4]]The synthesis method of the benzoquinone-4-phenylimine is simple and easy to operateThe reaction condition is mild, and the yield is high. The absorption spectrum is obviously changed in the presence of divalent copper ions, the selectivity is strong, the specificity is realized, the interference of other metal cations is not easy, the biocompatibility is good, the real-time performance is realized, the visual reaction of filter paper can be instantly realized, and the detection limit is 2.8‑7mol/L, and has higher sensitivity.

Description

Visual probe 3aa for detecting copper ions and synthetic path thereof
Technical Field
The invention belongs to the technical field of organic chemistry and analytical chemistry detection, and particularly relates to a visual probe 3aa for detecting copper ions and a synthetic path thereof.
Background
Copper is the No. 29 element in the periodic table of elements, is a third abundant soft transition metal element contained in a human body after iron ions and zinc ions, participates in various physiological processes, and plays an important role in gene expression, protein structure and function. Studies have shown that imbalance of copper ions in the body can lead to serious damage to the liver and kidneys, as well as induce a series of neurodegenerative diseases such as vitiligo, anemia, and men's syndrome, wilson's disease, senile dementia, parkinson's disease, prion diseases, and alzheimer's disease. In recent years, with the acceleration of industrialization, a large amount of industrial wastewater is discharged into the environment, which not only affects the ecological environment, but also poses a great threat to human health. Copper is widely applied to industrial production as a heavy metal and is a ubiquitous heavy metal pollution source in industrial wastewater. High copper content, such as Cu, can produce significant poisoning effects2+Is generally considered as the main toxic ion of aquatic organisms, and the concentration of the main toxic ion reaches 0.1-0.2mg/L, so that the fishes can die. Copper can also be enriched in the soil and absorbed by crops, however, when the copper content in the soil reaches 0.2-0.25mg/g, wheat and rice die. Therefore, based on the important position of the copper ions in the ecological environment and the bodies of animals and plants, it is very important to develop a detection method for rapidly and accurately monitoring the copper ions with high specificity and high sensitivity.
In recent years, various methods for detecting copper ions have been reported, mainly including atomic absorption spectroscopy, inductively coupled plasma mass spectrometry, inductively coupled plasma emission spectroscopy, high performance liquid chromatography, and electrochemical methods. Although these detection methods have higher accuracy, the instruments are expensive and often require maintenance, cumbersome operation, time-consuming calculations, and long detection times, and cannot be an analytical tool for real-time and on-site detection of target compounds. Compared with the prior art, the visual probe analysis technology has the advantages of high sensitivity, low detection limit, simple and convenient operation, rapid reaction, visual result, low cost, good selectivity, convenient carrying and the like, and is widely applied to the detection of various ions, active oxygen (ROS, RON) and biological mercaptan.
With the field of visual probes becoming more mature, more researchers have developed simpler and more convenient detection methods, for example, test paper for ion detection can quickly detect target ions according to the visible characteristics of visual naked eyes, which provides a new opportunity for quick and convenient analysis of field detection, and the visual analysis technology has shown better advantages in field analysis and detection.
Therefore, based on the above research results, a visualization probe 3aa for detecting copper ions and a synthetic path thereof are proposed herein.
Disclosure of Invention
In order to solve the technical problems, the invention designs the visual probe 3aa for detecting the copper ions and the synthesis path thereof, the preparation method is simple, green and environment-friendly, good in biocompatibility, high in selectivity, strong in specificity, low in detection limit, good in anti-interference performance, low in economic cost, capable of realizing real-time filter paper visual reaction, extremely high in sensitivity, and high in practical value, and provides a quick, convenient and effective method for detecting the copper ions in organisms or environments.
In order to achieve the technical effects, the invention is realized by the following technical scheme: a visual probe 3aa for rapidly detecting copper ions is characterized in that the chemical name of the visual probe is 2-amino-5-anilino- [1,4]]Benzoquinone-4-phenylimine having the molecular formula: c18H15N3O, structural formula as follows:
Figure BDA0003622275580000031
another objective of the present invention is to provide a synthetic path of a visual probe 3aa for rapidly detecting copper ions, which is characterized by the following chemical relationship:
Figure BDA0003622275580000032
further, the reaction uses the compound 2-aminophenol and aniline as template substrate, NH4I as a medium, LiClO4Acetonitrile is used as a solvent for electrolyte, carbon rods are used as an electrode cathode and an electrode anode under the condition of room temperature, the reaction mixture is firstly stirred for 5-20 minutes, and then a constant current of 5-15mA is reacted in an undivided electrolytic cell for 3-12 hours.
Further, after the reaction was completed, the resulting mixture was diluted with water and extracted with ethyl acetate, and the combined organic layers were washed with saturated sodium chloride, and finally dried over anhydrous magnesium sulfate and concentrated under vacuum to obtain a crude product, which was purified by silica gel column using petroleum ether/ethyl acetate as an eluent to obtain a pure product with a yield of 85%.
The invention has the beneficial effects that:
1. the synthesis method of the prepared 2-amino-5-anilino- [1,4] benzoquinone-4-phenylimine is simple, easy to operate, mild in reaction condition, high in yield, strong in selectivity, specific, not easy to be interfered by other metal cations, good in biocompatibility, real-time, capable of instantly realizing the visual reaction of filter paper, high in selectivity and capable of being used for detecting copper ions in organisms or environments at high selectivity under the conventional condition, and the absorption spectrum of the copper ions is obviously changed in the presence of divalent copper ions;
2. the invention provides a visual probe 3aa for detecting copper ions and a synthesis path thereof, the preparation method is simple, green and environment-friendly, good in biocompatibility, high in selectivity, strong in specificity, low in detection limit, good in anti-interference performance, low in economic cost, capable of realizing real-time filter paper visual reaction, extremely high in sensitivity, and high in practical value, and the method is quick, convenient and effective for detecting copper ions in organisms or environments.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings used in the description of the embodiments will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art that other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 shows 2-amino-5-anilino- [1,4]]Nuclear magnetic resonance hydrogen spectrum of benzoquinone-4-phenylimine (A)1H NMR)；
FIG. 2 shows 2-amino-5-anilino- [1,4]]Nuclear magnetic resonance carbon spectrum of benzoquinone-4-phenylimine (C: (A))13C NMR)；
FIG. 3 is a UV absorption spectrum of a probe of the present invention;
FIG. 4 is a graph of the UV absorption of the probe of the present invention at various pH conditions;
FIG. 5 is a color change chart of the Tris-HCl solution to which different metal ions are added;
FIG. 6 is a graph showing the UV absorption spectrum of the probe of the present invention after adding different metal ions to a Tris-HCl solution;
FIG. 7 shows the addition of Cu to Tris-HCl solution for the probe of the present invention2+And adding ultraviolet absorption histogram of other interfering ions;
FIG. 8 is a graph of color change in a visual reaction of the probe filter paper of the present invention;
FIG. 9 shows that the probe of the present invention is added with Cu of different concentrations in Tris-HCl solution2+Then ultraviolet titration color chart;
FIG. 10 shows the addition of Cu of different concentrations to Tris-HCl solution by the probe of the present invention2+Then ultraviolet titration spectrogram;
FIG. 11 shows that the probe of the present invention is added with Cu of different concentrations in Tris-HCl solution2+Then ultraviolet titration trend chart;
FIG. 12 shows the probe of the present invention and Cu2+The lowest detection limit map of (2);
FIG. 13 shows the probe of the present invention and Cu2+Complex ultraviolet absorption Job-Plot
FIG. 14 shows the probe of the present invention and Cu2+Color change profile of binding to S2-after complexation;
FIG. 15 shows a probe pair Cu of the present invention2+The recognition mechanism diagram of (1).
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Referring to fig. 1 to 15, a visual probe 3aa for rapidly detecting copper ions, which has a chemical name of 2-amino-5-anilino- [1,4] benzoquinone-4-phenylimine, has a molecular formula of: C18H15N3O, structural formula as follows:
Figure BDA0003622275580000061
a synthetic path of a visual probe 3aa for rapidly detecting copper ions, which comprises the following steps:
Figure BDA0003622275580000062
the reaction uses compound 2-aminophenol and aniline as template substrate, NH4I as a medium, LiClO4Acetonitrile as solvent as electrolyte, and carbon rod as cathode at room temperatureAnd an anode, wherein the reaction mixture is firstly stirred for 5-20 minutes and then reacts for 3-12 hours in an undivided electrolytic cell under a constant current of 5-15 mA. After completion of the reaction, the resulting mixture was diluted with water and extracted with ethyl acetate, and the combined organic layers were washed with saturated sodium chloride, finally dried over anhydrous magnesium sulfate and concentrated under vacuum to give the crude product which was purified by silica gel column using petroleum ether/ethyl acetate as eluent to give the pure product in 85% yield.
The prepared visual probe 3aa for rapidly detecting copper ions is subjected to structural identification and is characterized by a nuclear magnetic resonance spectrometer, a nuclear magnetic resonance hydrogen spectrogram is shown in figure 1, a carbon spectrogram is shown in figure 2, and the chemical name of the visual probe 3aa for copper ions is 2-amino-5-anilino- [1,4] -anilino ] can be found through nuclear magnetic resonance spectrogram analysis]Benzoquinone-4-phenylimine, having the molecular formula: c18H15N3O, structure is as described above.
Hydrogen spectrum:
1HNMR(400MHz,CDCl3) NMR (400MHz, CDCl, organic layer with NMR chart as shown in chart as hydrogen, washed with saturated sodium chloride, dried with anhydrous magnesium sulfate, and concentrated under vacuum to obtain crude product, which is purified by silica gel column, petroleum ether, all other examples obtained by one of ordinary skill in the art without creative work are included in the protection scope of the present invention. Generate great toxicity
Carbon spectrum:
13C NMR(100MHz,CDCl3) NMR (100MHz, CDCl, organic layer with NMR chart as shown in chart was washed with saturated sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under vacuum to obtain crude product, which was purified by silica gel column with petroleum ether, and one of ordinary skill in the art made no creation
Example 2
A visualization probe 3aa ultraviolet absorption and visualization assay for rapid detection of copper ions is described as follows:
preparation of a visual probe 3aa test solution for rapidly detecting copper ions: mixing copperDissolving the ion visualization probe 3aa in absolute ethyl alcohol to obtain the concentration of 1 × 10-3And (3) a copper ion visualization probe 3aa stock solution in mol/L. Precisely transferring 1.0ml of copper ion visualization probe 3aa stock solution into a 100ml volumetric flask, diluting with ethanol-Tris-HCl solution (ethanol: Tris-HCl ═ 2: 8) to scale, shaking up to obtain the product with the concentration of 1 × 10-5And (3) a copper ion visualization probe 3aa solution in mol/L.
The preparation method of the Tris-HCl buffer solution comprises the following steps: 1.21g of Tris (hydroxymethyl) aminomethane and 2.92g of sodium chloride were weighed and dissolved in water, and the pH was adjusted to 7.05 with hydrochloric acid, to obtain a 20mmol Tris-HCl buffer solution having a pH of 7.05.
The ethanol-Tris-HCl solution is prepared by mixing absolute ethanol and Tris-HCl buffer solution according to the volume ratio of 2: 8, preparing the medicament.
Ultraviolet absorption measurement: the concentration is 1 x 10-5measuring the absorption spectrum of the copper ion visualization probe 3aa solution of mol/L in the wavelength range of 190nm-1100nm under an ultraviolet-visible spectrophotometer. The ultraviolet-visible absorption spectrum test result is shown in fig. 3, and the maximum absorption peak of the copper ion visualization probe 3aa is located at 352 nm.
Example 3
The stability of a visual probe 3aa for rapidly detecting copper ions under different pH conditions is examined by the following method:
the pH value of the solution of the copper ion visualization probe 3aa is adjusted by hydrochloric acid and sodium hydroxide solution, so as to obtain solutions with pH values of 2.47, 3.59, 4.17, 5.03, 6.59, 7.76, 8.59, 9.40, 10.32 and 11.14 respectively. And (3) measuring the ultraviolet spectrum change condition of the copper ion visualization probe 3aa solution in the pH range under an ultraviolet-visible spectrophotometer. Through ultraviolet spectrum tests of copper ion visualization probe 3aa solutions under different pH conditions, as shown in FIG. 4, in the pH range of 3-12, copper ion visualization probes 3aa all absorb at 352nm and are all light pink in color, and as the pH is reduced from 3.59 to 2.47, compound 3aa has a wider absorption peak at 352nm, the solution color changes from light pink to light green, which is presumed to be possibly caused by H in an acidic medium+Preferentially attack the N atom, causing a color change.
Example 4
A visual probe 3aa metal ion selectivity test for rapidly detecting copper ions is disclosed, and the test method is as follows:
18 vials were prepared and 50ul of a 3aa stock solution of copper ion visualization probe, 950ul of absolute ethanol, 3900ul of Tris-HCl solution (except for Ag) at a concentration of 1 degree per vial was added to each vial+) Separately, 100ul (20 times equivalent) of 1 equivalent in concentration) of metal ion Hg in one vial was added to each vial2+、Ca2+、Cd2+、Pb2+、Fe2+、Fe3+、Mn2+、Zn2+、Cr3+、Ag+、Mg2+、Sn4+、K+、Ni2+、Al3+、Ba2+、Na+、Cu2+The water solution of (3) is prepared simultaneously, the water solution with the concentration of 1 is prepared, and the copper ion visualization probe solution with the concentration of 3aa is prepared simultaneously as a blank sample. And (3) measuring the change condition of the ultraviolet spectrum of the prepared solution under an ultraviolet-visible spectrophotometer. As shown in FIG. 5, in a plurality of metal ion-added vials, Fe was removed3+The solution is yellow, and only Cu is added2+The probe solution showed a pale yellow-green color, and only Cu was added as found by UV testing2+The absorption wavelength of the probe solution is red-shifted from the original 352nm to 480nm, and other ions have absorption at the wavelength of 352nm, which is probably due to Cu2+And selective complexation with copper ion visualization probe 3aa, and the ultraviolet spectrum is shown in figure 6.
Example 5
A metal ion interference test of a visual probe 3aa for detecting copper ions is carried out by the following steps:
18 vials were prepared and 50ul of a 3aa stock solution of a copper ion visualisation probe at 1 degree per vial, 950ul of absolute ethanol, 3800ul of Tris-HCl solution, 100ul (20 fold equiv) 1 equiv) of ris-Cu were added to each vial2+Respectively, to each vial, and 100ul (20 times equivalent) of 1 equivalent) of a concentrationTo each of the other metal ions Hg2+、Ca2+、Cd2+、Pb2+、Fe2+、Fe3+、Mn2+、Zn2+、Cr3+、Ag+、Mg2+、Sn4+、K+、Ni2+、Al3+、Ba2+、Na+Preparing a copper ion visualization probe 3aa-Cu simultaneously2+The solution served as a blank. And (3) measuring the change condition of the ultraviolet spectrum of the prepared solution under an ultraviolet-visible spectrophotometer. As shown in FIG. 7, the probe 3aa and Cu for copper ion visualization2+Adding a plurality of other metal ions into the mixed solution, the absorption wavelength is red shifted to 480nm, and the metal ions are not paired with the visual probe 3aa-Cu2+Causing interference and having strong specificity.
Example 6
A visual probe 3aa filter paper visual test for rapidly detecting copper ions is disclosed, and the test method is as follows:
preparing a 2cm piece of rectangular white filter paper for testing, soaking the filter paper with a compound 3aa solution, and dripping Cu after the filter paper is completely dried2+The filter paper is soaked by the aqueous solution, and the color change condition is recorded by photographing each time the filter paper is soaked. Simultaneously adding Cu into the prepared visual probe solution2+And simultaneously comparing the color change condition of the solution with that of the filter paper strip, and the test result shows that the filter paper strip or the sample solution is added with Cu2+The color change can be instantly generated after the reaction, and a comparison graph is shown in figure 8.
Example 7
A visual probe 3aa for rapidly detecting copper ions is used for ultraviolet titration research, and the titration method is as follows:
preparing 18 vials, adding 50ul of a copper ion visualization probe 3aa stock solution with a concentration of 1 degree/to each vial, 950ul of absolute ethanol, adding a Tris-HCl solution, and adding Cu with different concentrations to the compound 3aa solution, respectively2+The aqueous solution (0-6 solution (different concentrations added) of (1) is prepared at the same time, and the copper ion visualization probe 3aa solution with the concentration added is prepared at the same time as a blank sample. And (3) measuring the change condition of the ultraviolet spectrum of the prepared solution under an ultraviolet-visible spectrophotometer. As shown in FIG. 9, Cu was added2+The probe solution shows light yellow green, the absorption wavelength is red-shifted from original 352nm to 480nm, and Cu2+The absorbance value gradually approaches to balance after the addition amount reaches 2 times, and after 2 times, the absorbance value gradually approaches to balance along with Cu at 237nm2+The increase of the added amount resulted in a new absorption peak, which is presumed to be due to Cu2+Cu remaining after completion of the complexation with the amino group of compound 3aa and the carbonyl group2+Reacted with the middle N atom of compound 3aa, the UV spectrum is shown in FIG. 10, and the result is shown in FIG. 11.
Example 8
The detection limit of a visual probe 3aa for detecting copper ions is determined by the following method:
copper ion visualization probe 3aa-Cu2+The detection limit of (2) was calculated based on the UV titration under the item of example 7, in Cu2+The amount of addition is plotted on the abscissa and the absorbance is plotted on the ordinate, a line y of 0.0337x +0.0686, a standard deviation SD of 0.00317, a slope K of 0.0337 are obtained by linear fitting, and the compound 3aa-Cu is calculated according to a limit detection formula limit detection of 3SD/K2+The detection limit is 0.28Cudet, and the fitted graph is shown in FIG. 12.
Example 9
A visual probe 3aa for detecting copper ions is used for researching the complexing ratio of the copper ions, and the determination method is as follows:
according to the formula C [ Cu ]2+]/C[Cu2+]+C[probe-3aa]Preparing copper ion visualization probe 3aa-Cu with corresponding complexing proportion2+Measuring the ultraviolet spectrum change condition under an ultraviolet-visible spectrophotometer, drawing, and obtaining a copper ion visualization probe 3aa and a Cu when the ultraviolet absorbance reaches the maximum at the intersection point of a fitting line at 0.3 according to a fitting Job-Plot curve2+The binding ratio of (a) to (b) is 2: FIG. 13 shows the Job-Plot.
Example 10
Visual probe 3aa and Cu for detecting copper ions2+In combination with the study of the recognition mechanism,the identification method is as follows:
taking a picture of the prepared copper ion visualization probe 3aa solution, recording, and adding a certain amount of Cu into the probe solution2+Aqueous solution, photographing to record color change, and then visualizing the probe 3aa-Cu to copper ions2+Adding mercaptoethanol into the mixed solution, photographing to record color change, and finally adding Cu again2+Aqueous solution, and color change was recorded by photographing. Test results show that pink solution of the visual probe 3aa for copper ions visible to the naked eye contacts Cu2+Meanwhile, the color of the solution can be instantly changed into yellow green, the yellow green of the solution is changed into light pink after mercaptoethanol is added, and Cu is added again2+Then the copper ion visualized probe 3aa-Cu is shown to be light yellow green2+Shows good reversibility and color change as shown in figure 14, and infers that the copper ion visualization probe 3aa is opposite to Cu2+The mechanism of identification of (2) is shown in FIG. 15.
Example 11
A visual probe 3aa for rapidly detecting copper ions is used for preparing the required 2-amino-5-anilino- [1,4] benzoquinone-4-phenylimine, and has the advantages of simple synthetic method, easy operation, mild reaction conditions, high yield, obvious change of ultraviolet absorption in the presence of divalent copper ions, strong selectivity, specificity, no easy interference of other metal cations, good biocompatibility, real-time property, instant realization of filter paper visual reaction, simple synthetic method with detection limit of 2.8 amine, easiness, high sensitivity and capability of being used for highly selectively detecting copper ions in organisms or environments under conventional conditions; the invention provides a visual probe 3aa for detecting copper ions and a synthesis path thereof, the preparation method is simple, green and environment-friendly, good in biocompatibility, high in selectivity, strong in specificity, low in detection limit, good in anti-interference performance, low in economic cost, capable of realizing real-time filter paper visual reaction, extremely high in sensitivity, and high in practical value, and the method is quick, convenient and effective for detecting copper ions in organisms or environments.
In the description herein, references to the description of "one embodiment," "an example," "a specific example" or the like are intended to mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The preferred embodiments of the invention disclosed above are intended to be illustrative only. The preferred embodiments are not intended to be exhaustive or to limit the invention to the precise embodiments disclosed. Obviously, many modifications and variations are possible in light of the above teaching. The embodiments were chosen and described in order to best explain the principles of the invention and the practical application, to thereby enable others skilled in the art to best utilize the invention. The invention is limited only by the claims and their full scope and equivalents.

Claims (5)

1. A visual probe 3aa for detecting copper ions is characterized in that the chemical name of the visual probe is 2-amino-5-anilino- [1,4]]Benzoquinone-4-phenylimine, having the molecular formula: c18H15N3O, structural formula as follows:
Figure FDA0003622275570000011
2. a synthetic path of a visual probe 3aa for detecting copper ions is characterized in that the chemical relation is as follows:
Figure FDA0003622275570000012
3. the synthetic path of the visualization probe 3aa for detecting copper ions of claim 2, which isIs characterized in that: the reaction uses compound 2-aminophenol and aniline as template substrate, NH4I as a medium, LiClO4Acetonitrile is used as a solvent for electrolyte, carbon rods are used as an electrode cathode and an electrode anode under the condition of room temperature, the reaction mixture is firstly stirred for 5-20 minutes, and then a constant current of 5-15mA is reacted in an undivided electrolytic cell for 3-12 hours.
4. A synthetic path for a visualization probe 3aa for detecting copper ions according to claim 3, characterized in that: after the reaction was complete, the resulting mixture was diluted with water and extracted with ethyl acetate, the combined organic layers were washed with saturated sodium chloride, finally dried over anhydrous magnesium sulfate and concentrated under vacuum to give the crude product which was purified by silica gel column using petroleum ether/ethyl acetate as eluent to give the pure product in 85% yield.
5. The visual probe 3aa for detecting copper ions and the synthetic route thereof according to any one of claims 1 to 4, which discloses the application of the visual probe 3aa for detecting copper ions in the technical field of organic chemistry and analytical chemistry detection.
CN202210470544.9A 2022-04-28 2022-04-28 Visual probe 3aa for detecting copper ions and synthetic path thereof Withdrawn CN114736138A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115521224A (en) * 2022-11-04 2022-12-27 江西科技师范大学 Organogel compound based on fluorine-containing Sudan red I, preparation method, organogel and application

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115521224A (en) * 2022-11-04 2022-12-27 江西科技师范大学 Organogel compound based on fluorine-containing Sudan red I, preparation method, organogel and application
CN115521224B (en) * 2022-11-04 2023-09-15 江西科技师范大学 Organogel compound based on fluorine-containing sudan red I, preparation method, organogel and application

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