CN115521224B - Organogel compound based on fluorine-containing sudan red I, preparation method, organogel and application - Google Patents
Organogel compound based on fluorine-containing sudan red I, preparation method, organogel and application Download PDFInfo
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Abstract
The application relates to an organogel compound based on fluorine-containing sudan red I, a preparation method, organogel and application thereof. The organogel compound structurally has azo groups, hydroxyl groups and fluoroalkoxy chains, which are capable of forming gels in a variety of organic solvents. The presence of copper ions can be selectively identified by detecting the presence of copper ions in a variety of organic solvents with a color change of 5% by mass of organogel formed (4:1 volume ratio of organic solvent to 0.05M ion containing solution) while measuring the uv-visible absorption at a 20:1 solution concentration ratio of organogel compound to metal ions. The minimum detection limit of the organogel compound based on the fluorine-containing sudan red I in the aqueous solution reaches 2.79 mu M, and Cu can be realized 2+ Has good application prospect for detecting copper ions in water quality monitoring and biological systems.
Description
Technical Field
The application belongs to the technical field of supermolecular chemistry, and particularly relates to an organogel compound based on fluorine-containing sudan red I, a preparation method, organogel and application.
Background
By means of weak intermolecular interaction, small molecules with specific structures can form aggregates with certain forms, and the small molecule gel has unique rheological behavior and stimulus response performance. Has wide application in many fields. The self-assembly of molecules has a great relation with the structure of the molecules, and the molecules can form aggregates with various forms, such as micelles, fibers, nanotubes, spiral bands and the like under the interaction of non-covalent bonds such as hydrogen bonding, van der Waals, coordination, pi-pi stacking, electrostatic interaction and the like. The structure which is gathered by virtue of weak intermolecular forces is responsive to external stimuli.
The excellent performance of the fluorine-containing compound is mainly derived from the special property of fluorine, and the electronegativity of the fluorine is the element with the largest electronegativity in the periodic table. Because of electronegativity, adjacent fluorine atoms repel each other, and the two fluorine atoms just can fill up gaps between two carbon atoms, so that other groups are prevented from being inserted, and an effective protection effect is achieved on a carbon-carbon main chain. Compounds incorporating fluoroalkyl groups into the molecule generally form molecular polymers in water that correspond to micelles, with organogel compounds containing fluoroalkyl chains having one more non-hydrogen bonding force than compounds without fluoroalkyl chains.
Heavy metal pollution can cause the change of the ecological structure, the function and the physicochemical property of soil, greatly reduce the yield of crops and endanger the ecological environment and the human health. Because heavy metals have the characteristics of potential danger, durability, non-biological degradability, biological enrichment and the like, when the concentration of the heavy metals is too high, the heavy metals can cause soil quality change, even enter a human body through a food chain, and various diseases such as osteoporosis, tumors, kidney injury and the like can be induced after the excessive heavy metals are enriched by the human body. Copper-containing wastewater irrigates farmlands, so that copper accumulates in soil and crops, which can cause poor growth of crops, especially rice and barley, and pollute grain particles. The organic gel can selectively identify copper ions, does not need a complex pretreatment process, and has the advantages of simple instrument operation, good repeatability, rapid detection, convenience and no pollution.
Disclosure of Invention
The application aims to provide organogel compounds based on fluorine-containing Sudan red I, which can be used for detecting Cu 2+ The detection method is simple and has good repeatability.
A second object of the present application is to provide a process for the preparation of organogel compounds based on fluorosudan red I. A third object of the present application is to provide an organogel.
A fourth object of the present application is to provide organogel compounds based on fluorosudan red I in the presence ofDetection of Cu 2+ Application to the above.
In order to achieve the above purpose, the technical scheme of the application is as follows:
organogel compounds based on fluorosudan red I having the structure shown in formula 1:
a process for the preparation of organogel compounds based on fluorosudan red I comprising the steps of:
step one, dissolving fluoroalkoxy aniline in a 2M hydrochloric acid solution, slowly dropwise adding a sodium nitrite solution, and then carrying out diazotization reaction;
slowly dripping the diazotization reaction liquid into a sodium hydroxide solution of 2-naphthol, and stirring at 0 ℃ for reaction for 4-6 hours;
step three, the pH of the reaction solution is adjusted to 8-9 by 10% sodium hydroxide solution;
step four, carrying out suction filtration;
and fifthly, washing the filter cake with sodium hydroxide solution and water sequentially to obtain red solid, namely the crude product of the organogel compound.
Preferably, the molar ratio of the fluorine-containing oxyaniline to the 2-naphthol is 1:1.
And (3) as optimization, recrystallizing the organogel compound crude product in the step (V) by using an aqueous solution of ethanol to obtain the organogel compound.
A method for preparing an organogel comprising the steps of:
step one, putting the organogel compound into an organic solvent, and heating until the organogel compound is dissolved;
and step two, cooling to room temperature, and judging by a bottle inversion method to obtain the organogel.
The bottle inversion method comprises the following steps: weighing a certain amount of organogel compound, putting into a small reagent bottle, adding an organic solvent, preparing a corresponding concentration, heating the mixture to dissolve, cooling to room temperature, standing for 30 minutes, putting a glass bottle, observing whether a solution flows or not, and if no liquid flows along the bottle wall, indicating that the whole is completely gelled.
As optimization, the organic solvent in the first step is any one of polyethylene glycol 400, dimethyl silicone oil, methyl silicone oil, mineral oil and liquid paraffin.
Preferably, the heating temperature in the first step is above 90 ℃.
Organogel compounds based on fluorine-containing sudan red I for Cu detection 2+ The application of (a) is as follows: heating and dissolving the organogel compound and the organic solvent, wherein the mass concentration of the organogel compound in the organic solvent is 5%, adding 0.05M metal ion solution, mixing, and judging whether the metal ion solution contains Cu or not through the color change of the formed gel 2+ . Wherein the volume ratio of the organic solvent solution of 5% of the organogel compound to the 0.05M metal ion solution is 4:1, and the organic solvent is any one of polyethylene glycol 400, dimethyl silicone oil, methyl silicone oil, mineral oil and liquid paraffin.
Meanwhile, the organogel compound based on fluorine-containing sudan red I is used for detecting Cu 2+ The application of the method can also adopt a gradient dilution mode to test ultraviolet visible absorption. 24. Mu.L of 0.05M aqueous metal ion solution is first placed in a cuvette, 1960. Mu.L of acetonitrile is then added, and 60. Mu.L of 1.0X10. Mu.L of acetonitrile is then added -3 M in acetonitrile, at which the concentration of organogel compound is 3X 10 -5 M, the concentration of metal ions was 6.0X10 -4 M, the molar concentration of the metal ions is 20 times of that of the organogel compound, the ultraviolet visible absorption is tested, and whether the metal ion solution contains Cu is judged by whether obvious absorption peaks appear at the wavelength of 310+/-5 nm 2+ 。
The beneficial effects are as follows: the application is based on the existence of azo groups, hydrogen bond interaction, intermolecular perfluoroalkyl interactions and pi-pi stacking interaction between aromatic rings in the organogel compound containing the fluorosudan red I, and can enable the organogel compound to form gel in various organic solvents. The organogel compound based on the fluorine-containing sudan red I can change the ultraviolet-visible absorption spectrum of the organogel compound by coordination between oxygen atoms on hydroxyl groups and nitrogen atoms on azo groups due to structural influence. Meanwhile, in the gel system, after copper ions are added, gel can still be formed, but the gel color is changed due to the fact that the organic gel compound is coordinated with the copper ions.
The organogel compound based on the fluorine-containing sudan red I can realize Cu 2+ The detection method is simple and quick, the organic gel compound and the organic solvent are heated and dissolved, then 0.05M metal ion solution is added for mixing, and whether the metal ion solution contains Cu or not is judged through the color change of the formed gel 2+ Meanwhile, the ultraviolet visible absorption is tested according to the molar concentration ratio of the organogel compound to the metal ion solution of 20:1, and whether the metal ion solution contains Cu is judged by judging whether an obvious absorption peak appears at the wavelength of 310+/-5 nm or not 2+ 。
Drawings
FIG. 1 is a diagram of Compound 1 1 H NMR spectrum;
FIG. 2 is a diagram of Compound 1 13 C NMR spectrum;
FIG. 3 is a schematic representation of the gel formed in a variety of organic solvents for Compound 1 of example 2;
FIG. 4 is a schematic representation of the morphology of compound 1 in polyethylene glycol 400 forming an organogel in example 2;
FIG. 5 is a graph showing organogel of example 3 after adding 0.05M metal ion in water (5% organic solvent solution of Compound 1 and 0.05M metal ion in a volume ratio of 4:1) to 5% organic solvent solution of Compound 1;
FIG. 6 is a graph showing the comparison of compound 1 of example 4 after organogel formation in polyethylene glycol 400 and further addition of 0.05M copper ion in water;
FIG. 7 is a graph showing the UV-visible absorption spectrum of an acetonitrile solution of Compound 1 (organogel compound to metal ion concentration ratio 20:1) added to a different metal ion solution in example 5;
FIG. 8 shows the solid powder of Compound 1, compound 1 and Cu in example 6 2+ Cation-complexed xerogel (xerogel-Cu) 2+ ) Compounds and methods of treatment1 FT-IR spectrum of xerogel formed in polyethylene glycol 400.
Detailed Description
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the application. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the present application. As used herein, the singular is also intended to include the plural unless the context clearly indicates otherwise, and furthermore, it is to be understood that the terms "comprises" and/or "comprising" when used in this specification are taken to specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof.
Example 1
This example is based on the preparation of organogel compounds containing C6 perfluoroalkoxy chain sudan red I (abbreviated as compound 1) as follows:
4.4018mmol of C6-containing perfluoroalkoxy chain aniline is dissolved in 30mL of 2mol/L hydrochloric acid solution, 4.4018mmol of aqueous solution of sodium nitrite is slowly dripped at 0 ℃, stirring is carried out for 1 hour, the reaction solution is slowly dripped into 4.4018mmol of 10% sodium hydroxide solution of 2-naphthol, after dripping is finished, stirring is carried out for 5 hours at 0 ℃, the reaction progress is monitored by thin layer chromatography, 10% NaOH solution is used for regulating the pH value to 8-9 at normal temperature, suction filtration is carried out, a filter cake is taken, the filter cake is washed by 10% wt of sodium hydroxide solution and water sequentially, and then the water solution of ethanol (the volume ratio of ethanol to water is 1:2) is used for recrystallization, thus 2.3722g of red solid is obtained, and the red solid is the organogel compound containing C6-containing perfluoroalkoxy chain based on fluorine sudan red I.
1H NMR (400 MHz, CDCl 3) delta 15.75 (s, 1H), 8.68 (d, J=8.4 Hz, 1H), 7.81 (d, J=8.8 Hz, 2H), 7.76 (d, J=9.2 Hz, 1H), 7.69 (d, J=8.0 Hz, 1H), 7.58 (t, J=7.4 Hz, 1H), 7.41 (t, J=7.4 Hz, 1H), 7.02 (dd, J=3.2, 2.4Hz, 4H), 4.31 (t, J=6.8 Hz, 2H), 2.74-2.60 (m, 2H) 13C NMR 162.6,159.0,142.2,137.4,133.5,129.7,128.5,128.4,128.3,125.1,122.6,122.0,121.7,115.5,60.6,60.5,60.4,31.6,31.4,31.2. Yield: 88.16%, melting point: 116-117 ℃.
Compound 1 1 HNMR spectrum is shown in FIG. 1, compound 1 13 The CNMR spectrum is shown in fig. 2.
Example 2
Compound 1 prepared in example 1 and various organic solvents were heated to about 90 ℃ in a vial to dissolve compound 1, then allowed to stand and cool to 25 ℃ and allowed to stand for 1 hour to observe the gel forming ability in various solvents.
Compound 1 can form organogel in polyethylene glycol 400, simethicone, methyl silicone oil, mineral oil and liquid paraffin, and the organogel has good stability and is red opaque. The gel of compound 1 in different organic solvents is schematically shown in fig. 3, and the morphology of the organogel of compound 1 in polyethylene glycol 400 is schematically shown in fig. 4.
Table 1 gel formation ability table of compound 1 in different solvents
| Organic solvents | Gel state | Organic solvents | Gel state |
| Polyethylene glycol 400 | G | Mineral oil | G |
| Dimethicone | G | Liquid paraffin | G |
| Methyl silicone oil | G | Acetic acid ethyl ester | S |
| Dimethyl sulfoxide | S | Acetone (acetone) | S |
| Tetrahydrofuran (THF) | S | Toluene (toluene) | S |
Annotation: wherein G represents a gel, PG represents a partial gel, and S represents a sol.
Example 3
The detection and research of organogel based on fluorine-containing Sudan red I shown in formula I on metal ions are respectively selected from Mg 2+ 、Na + 、K + 、Li + 、Al 3+ 、Cu 2+ 、Co 2+ 、Mn 2+ 、Ni 2+ 、Ca 2+ 、Zn 2+ 、Fe 3+ 、Ba 2+ 、Cs + Experiments were performed.
Respectively to Mg 2+ 、Na + 、K + 、Li + 、Al 3+ 、Cu 2+ 、Co 2+ 、Mn 2+ 、Ni 2+ 、Ca 2+ 、Zn 2+ 、Fe 3+ 、Ba 2+ 、Cs + Wherein the organic solvent is any one of polyethylene glycol 400, dimethyl silicone oil, methyl silicone oil, mineral oil and liquid paraffin, the molar concentration of the aqueous solution of the metal ions is 0.05M, and the volume ratio of the 5% organic solvent solution of the compound 1 to the 0.05M metal ion solution is 4:1. The results showed that only the Cu < 2+ > containing system formed a clear change in gel color to reddish brown. Organogel diagrams after addition of 0.05M aqueous metal ion solution (5% organic solvent solution of Compound 1 and 0.05M metal ion solution in a 4:1 ratio by volume) to 5% organic solvent solution of Compound 1 are shown in FIG. 5.
Example 4
To further demonstrate the use of the organogel formed by Compound 1, 10mg of Compound 1 and 190mg of polyethylene glycol 400 were added to a vial, heated to about 90℃to dissolve Compound 1, then allowed to stand and cool to 25℃for 1 hour to form a gel, the mass concentration of Compound 1 in polyethylene glycol 400 was 5%, then 20mg of 0.05M copper ion in water was added, and heated again to dissolve, then allowed to stand and cool, and the vial was inverted. The results showed that the organogel system changed significantly in color to reddish brown as shown in fig. 6.
Example 5
To further demonstrate that Compound 1 is against Cu 2+ 24. Mu.L of 0.05M Cu was first taken 2+ Ionic aqueous solution in cuvette, 1960. Mu.L acetonitrile and 60. Mu.L 10 were added -3 M in acetonitrile of Compound 1, at which point the concentration of Compound 1 was diluted to 3X 10 -5 M，Cu 2+ The concentration of the ionic solution was 6.0X10 -4 M，Cu 2+ The molar concentration of the ion solution was 20 times that of compound 1. Mg of 2+ 、Na + 、K + 、Li + 、Al 3+ 、Co 2+ 、Mn 2+ 、Ni 2+ 、Ca 2+ 、Zn 2+ 、Fe 3+ 、Ba 2+ All of the aqueous solutions of (a) are chloride salts, only Cu 2+ Is sulfate and Cs + Is carbonate. The results showed that onlyPresence of Cu 2+ When the absorption peak was observed at a wavelength of 310.+ -. 5nm, the result was shown in FIG. 7.
Example 6
Solid powder of compound 1, compound 1 and Cu 2+ Xerogel after cation complexation (xerogel-Cu) 2+ ) FT-IR spectrum of compound 1 in xerogel formed in polyethylene glycol 400. The position of the characteristic peak of hydroxyl group of the solid powder of Compound 1 was 3428cm -1 The organic gel formed by the compound 1 has the characteristic peak of hydroxyl shifted red to 3448cm -1 At the same time, after the compound 1 is complexed with copper ions, the characteristic peak of hydroxyl is also 3448cm -1 Indicating the presence of hydrogen bonding upon gel formation. C=o expansion key (1565 cm) -1 ) And an iminoc=n expansion bond (1640 cm) -1 ) Which means that the organogel compound remains predominantly in azo form in the xerogel. Due to van der Waals interactions, methylene (CH 2 ) Stretching key (2921 cm) -1 ) The peaks of (2) appear in the xerogel state, indicating intermolecular perfluoroalkyl interactions when the gel state is formed, and the results are shown in FIG. 8.
The copper ion coordinates with the nitrogen atom and the oxygen atom in the compound 1, and Cu is added 2+ The structure of the post organogel compound was changed as follows:
it will be apparent to those skilled in the art from this disclosure that various other changes and modifications can be made which are within the scope of the application as defined in the appended claims.
Claims (10)
1. A series of organogel compounds based on fluorosudan red I, characterized by the structure of formula I:
2. a process for preparing an organogel compound according to claim 1, comprising the steps of: step one, dissolving fluoroalkoxy aniline in a 2M hydrochloric acid solution, slowly dropwise adding a sodium nitrite solution, and then carrying out diazotization reaction; slowly dripping the diazotization reaction liquid into a sodium hydroxide solution of 2-naphthol, and stirring at 0 ℃ for reaction for 4-6 hours; step three, the pH of the reaction solution is adjusted to 8-9 by 10% sodium hydroxide solution; step four, carrying out suction filtration; and fifthly, washing the filter cake with sodium hydroxide solution and water sequentially to obtain red solid, namely the crude product of the organogel compound.
3. The method according to claim 2, wherein the molar ratio of fluoroalkoxy aniline to 2-naphthol is 1:1.
4. The process according to claim 2, wherein the organogel compound crude product in step five is recrystallized from an aqueous solution of ethanol to obtain a purified organogel compound.
5. A method for preparing organogel, comprising the steps of: step one, putting the organogel compound of claim 1 into an organic solvent, and heating to dissolve; and step two, cooling to room temperature, and judging by a bottle inversion method to obtain the organogel.
6. The method according to claim 5, wherein the organic solvent in the first step is any one of polyethylene glycol 400, simethicone, methyl silicone oil, mineral oil, and liquid paraffin.
7. The method according to claim 5, wherein the heating temperature in the first step is 90 ℃ or higher.
8. Organogel compounds based on fluorosudan red I according to claim 1 for Cu outside the field of diagnostic and therapeutic methods of disease 2+ Application in detection.
9. The fluorosudan red I-based organogel compound of claim 8 at Cu 2+ The application in detection is characterized in that the detection method comprises the following steps: the organic gel compound and the organic solvent are heated and dissolved, the mass concentration of the organic gel compound in the organic solvent is 5%, then 0.05M metal ion solution is added for mixing, and whether Cu < 2+ > is contained in the metal ion solution is judged through the color change of the formed gel, wherein the volume ratio of the organic solvent solution of the 5% organic gel compound to the 0.05M metal ion solution is 4:1, and the organic solvent is any one of polyethylene glycol 400, simethicone, methyl silicone oil, mineral oil and liquid paraffin.
10. The fluorosudan red I-based organogel compound of claim 8 at Cu 2+ The application in detection is characterized in that the detection method comprises the following steps: firstly, taking a metal ion aqueous solution in a cuvette, adding acetonitrile, then adding an acetonitrile solution of an organogel compound, wherein the molar concentration of metal ions is 20 times that of the organogel compound, testing ultraviolet visible absorption, and judging whether the metal ion solution contains Cu or not by judging whether an obvious absorption peak appears at the position of 310+/-5 nm of wavelength 2+ 。
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| CN102702020A (en) * | 2012-06-01 | 2012-10-03 | 吉林大学 | Azo radical-substituted organic small molecular gel, preparation method thereof and application of azo radical-substituted organic small molecular gel to preparation of organic gel |
| CN114736138A (en) * | 2022-04-28 | 2022-07-12 | 云南民族大学 | Visual probe 3aa for detecting copper ions and synthetic path thereof |
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| CN102702020A (en) * | 2012-06-01 | 2012-10-03 | 吉林大学 | Azo radical-substituted organic small molecular gel, preparation method thereof and application of azo radical-substituted organic small molecular gel to preparation of organic gel |
| CN114736138A (en) * | 2022-04-28 | 2022-07-12 | 云南民族大学 | Visual probe 3aa for detecting copper ions and synthetic path thereof |
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