CN113285243A - Covalent organic framework composite material and preparation method and application thereof - Google Patents
Covalent organic framework composite material and preparation method and application thereof Download PDFInfo
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- H01—ELECTRIC ELEMENTS
- H01Q—ANTENNAS, i.e. RADIO AERIALS
- H01Q17/00—Devices for absorbing waves radiated from an antenna; Combinations of such devices with active antenna elements or systems
- H01Q17/004—Devices for absorbing waves radiated from an antenna; Combinations of such devices with active antenna elements or systems using non-directional dissipative particles, e.g. ferrite powders
Abstract
The invention belongs to the field of functional materials, and particularly relates to a covalent organic framework composite material, and a preparation method and application thereof. A covalent organic frame composite material is a particle with a core-shell structure, wherein the core is Fe3O4Hollow nanospheres, the shell consisting of a covalent organic framework material; the covalent organic framework material is obtained by performing Schiff base condensation reaction on terephthalaldehyde and 1,3, 5-tri (4-aminophenyl) benzene; terephthalaldehyde, 1,3, 5-tris (4-aminophenyl) benzene and Fe3O4The mass ratio of the hollow nanospheres is 1: (0.5-3): (5-8). The preparation method has the characteristics of stability, controllability, simplicity and easiness in operation, and the prepared covalent organic framework composite material has the electromagnetic wave absorption characteristics of thin thickness, wide absorption frequency band, light load and strong absorption capacity.
Description
Technical Field
The invention belongs to the field of functional materials, and particularly relates to a covalent organic framework composite material, and a preparation method and application thereof.
Background
With the rapid development and widespread use of wireless communication devices, electromagnetic wave pollution has a negative impact on industrial production and people's daily life. To reduce this contamination, microwave absorbing materials have been rapidly developed. The ideal absorbing material should simultaneously satisfy six requirements of strong absorbing capacity, wide absorbing range, low density, thin thickness, low cost, easy processing and the like as far as possible. However, it is not easy for a single type of material to simultaneously satisfy these requirements, and therefore, researchers have made great efforts to design and synthesize materials having specific compositions and structures.
In recent years, porous materials have attracted more and more attention due to their low relative density, high specific strength, high surface area, sound and heat insulation, and the like. The porous nature of these materials can make electromagnetic waves more susceptible to reflection, refraction, and diffraction during propagation. In addition, the porous material has the characteristics of large surface area and rich heterogeneous interfaces, so that the porous material can generate rich dipole polarization and interface polarization in the process of electromagnetic wave propagation, thereby improving the loss of the electromagnetic wave. Common porous materials can be generally classified into zeolite porous materials, activated carbon, mesoporous silica, metal organic framework Materials (MOFs), covalent organic framework materials (COFs), and the like. Compared with other traditional porous materials, the MOFs and the COFs have the characteristics of large specific surface area, adjustable pore channels, designable components and the like, so that the MOFs and the COFs have wide application in the fields of molecular storage, separation and catalysis, sensing, light guide, electro-catalysis and the like.
The MOFs are considered to be a potential wave-absorbing material due to the characteristics that the derivative material has magnetic metal particles with good dispersibility and a porous carbon layer. However, the MOFs is composed of a metal (cluster) center and an organic bridging ligand, and its weak coordination bond makes the stability of the MOFs poor, and the pore structure is easy to collapse, which limits the application of the MOFs. In addition, most of the reported MOFs derivative composite materials used in the wave absorbing field have the defect of high paraffin matrix loading rate (more than or equal to 40 wt%). Therefore, the development of a novel stable, light and efficient porous composite material has important significance.
Different from MOFs, the monomers of COFs are connected through a firm covalent bond, so that the stability is better. Meanwhile, COFs are composed of only light elements (e.g., H, B, C, N and O), which gives them a light weight feature. In addition, COFs have highly ordered channels of 1-5nm, and the structure of the COFs can be regulated and controlled by adjusting monomers. Since the pioneering work of Yaghi in 2005, the functional applications of COFs have been greatly developed, and relate to the fields of gas storage, sensing, adsorption, luminescence, photoelectric carriers, catalysis and the like, but the applications of COFs in the field of electromagnetic wave absorption are rarely reported.
Disclosure of Invention
In view of the above-mentioned drawbacks of the prior art, it is an object of the present invention to provide a covalent organic framework composite, a method for its preparation and use, which solves the problems of the prior art.
To achieve the above objects and other related objects, the present invention is achieved by the following technical solutions.
One of the purposes of the invention is to provide a covalent organic framework composite material, wherein the material is a particle with a core-shell structure, and the core is Fe3O4Hollow nanospheres, the shell consisting of a covalent organic framework material; the covalent organic framework material is obtained by performing Schiff base condensation reaction on terephthalaldehyde and 1,3, 5-tri (4-aminophenyl) benzene; terephthalaldehyde, 1,3, 5-tris (4-aminophenyl) benzene and Fe3O4The mass ratio of the hollow nanospheres is 1: (0.5-3): (5-8).
Preferably, the outer diameter of the core is 80nm to 100nm, and the inner diameter of the core is 50nm to 75 nm; the outer diameter of the shell is 105-125 nm, and the inner diameter of the shell is 80-100 nm.
The second purpose of the present invention is to provide a method for preparing the covalent organic framework composite material, comprising the following steps:
1) obtaining Fe3O4Hollow nanospheres;
2) subjecting said Fe to3O4Dissolving the hollow nanospheres, terephthalaldehyde and 1,3, 5-tri (4-aminophenyl) benzene in a solvent, and carrying out catalytic reaction under a catalyst to obtain a reaction product;
3) and calcining the reaction product to obtain the covalent organic framework composite material.
Preferably, in step 1), the Fe3O4The preparation method of the hollow nanosphere comprises the following steps: ferric chloride hexahydrate, sodium acetate, trisodium citrate and ethylene glycol are mixed, and then hydrothermal reaction is carried out.
More preferably, the mass ratio of the trisodium citrate, ferric chloride hexahydrate, sodium acetate and ethylene glycol is 1: (3-6): (5-10): (100-200).
More preferably, the temperature of the hydrothermal reaction is 100 ℃ to 300 ℃.
Further preferably, the temperature of the hydrothermal reaction is 180 to 240 ℃.
Further preferably, the temperature rise rate is 1 ℃/min to 8 ℃/min.
More preferably, the ferric chloride hexahydrate, sodium acetate, trisodium citrate are dissolved in ethylene glycol by stirring for at least 5 min.
More preferably, the hydrothermal reaction further comprises magnetic separation, washing and drying.
Further preferably, the magnetic separation is performed by using a magnet.
Further preferably, the washing is performed 3 times by using deionized water and ethanol respectively.
Further preferably, the drying is carried out under vacuum for 5 to 20 hours.
Preferably, the solvent is selected from one of dimethyl sulfoxide and N, N-dimethylformamide.
Preferably, the catalyst is selected from one of glacial acetic acid and isoquinoline.
Preferably, in the step 2), the terephthalaldehyde, 1,3, 5-tri (4-aminophenyl) benzene and Fe3O4And the mass ratio of the catalyst to the solvent is 1: (0.5-3): (1-5): (20-50): (500-2000).
More preferably, terephthalaldehyde, 1,3, 5-tris (4-aminophenyl) benzene and Fe3O4The hollow nanospheres are dissolved in the solvent by ultrasonic treatment for 5-20 min.
More preferably, the catalyst is dropwise added to terephthalaldehyde, 1,3, 5-tri (4-aminophenyl) benzene and Fe3O4The hollow nanospheres and the solvent.
Preferably, in the step 2), the temperature of the catalytic reaction is 15-25 ℃.
Preferably, in the step 2), the catalytic reaction is carried out for 20-50 min in ultrasound.
Preferably, in step 2), the catalytic reaction further comprises magnetic separation, washing and drying.
More preferably, the magnetic separation is performed using a magnet.
More preferably, the washes are 3 washes each with methanol and tetrahydrofuran.
More preferably, the drying is carried out under vacuum for 5 to 20 hours.
Preferably, in the step 3), the temperature of the calcination is 500-800 ℃.
More preferably, the temperature of the calcination is 600 ℃ to 800 ℃.
Preferably, in the step 3), the calcination time is 80min to 150 min.
More preferably, the temperature rise rate of the calcination is 2 ℃/min to 8 ℃/min.
Preferably, in step 3), the calcination is carried out under a protective atmosphere.
More preferably, the protective atmosphere is selected from one of argon and nitrogen.
The invention also aims to provide the application of the covalent organic framework composite material as a wave-absorbing material in the field of electromagnetic waves.
The application prepares Fe by a hydrothermal method3O4Hollow nanospheres prepared by performing Schiff base condensation reaction on Fe through ultrasonic-assisted hydrothermal reaction3O4The surface of the hollow nanosphere is coated with a covalent organic framework COFs outer layer, and then the covalent organic framework composite material is obtained by calcining.
Compared with the prior art, the invention has the following beneficial effects:
1) the preparation method of the covalent organic framework composite material has the characteristics of stability, controllability, simplicity and easy operation
2) The covalent organic framework composite material prepared by the invention has the characteristics of thin thickness, wide absorption frequency band, light load and strong absorption capacity of electromagnetic wave absorption, and shows excellent wave absorption performance in a wider frequency range (11.76-16.96GHz) when the thickness of the covalent organic framework composite material is 1-5 mm.
3) The invention not only widens the application field of the covalent organic framework material, but also provides a novel idea for the design and synthesis of the electromagnetic wave absorption material for industrial production.
Drawings
Fig. 1 shows XRD patterns of example 1, example 2, example 3 and comparative example.
Fig. 2 shows TEM images of example 1, example 2, example 3 and a comparative example.
Wherein the reference numerals in fig. 2 are as follows: a-TEM image of comparative example, b-TEM image of example 1, c-TEM image of example 2, d-TEM image of example 3.
Fig. 3 shows the wave-absorbing performance graphs of example 1, example 2, example 3 and comparative example.
Wherein the reference numerals in fig. 3 are as follows: a-comparative example, b-example 1, c-example 2, d-example 3
Detailed Description
The following description of the embodiments of the present invention is provided for illustrative purposes, and other advantages and effects of the present invention will become apparent to those skilled in the art from the present disclosure.
Before the present embodiments are further described, it is to be understood that the scope of the invention is not limited to the particular embodiments described below; it is also to be understood that the terminology used in the examples is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention. Test methods in which specific conditions are not specified in the following examples are generally carried out under conventional conditions or under conditions recommended by the respective manufacturers.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. 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 invention belongs. In addition to the specific methods, devices, and materials used in the examples, any methods, devices, and materials similar or equivalent to those described in the examples may be used in the practice of the invention in addition to the specific methods, devices, and materials used in the examples, in keeping with the knowledge of one skilled in the art and with the description of the invention.
In the examples of the present application, the products obtained by the preparation of each example and comparative example were irradiated with an irradiation source of
To determine the crystal structure.
In the examples of the present application, the morphology of the products obtained by the preparation of each example and comparative example was observed by using a scanning electron microscope and a transmission electron microscope.
In the examples of the present application, the products obtained for each of the examples and comparative examples were uniformly dispersed in paraffin wax, which was 30% by weight based on the total weight, and then pressed by a die into coaxial sample rings having an outer diameter of 7.0mm and an inner diameter of 3.04 mm. The electrical complex permittivity and complex permeability of the material are measured by adopting a Ceyear 3672B-S vector network analyzer based on the measurement technical requirement of a coaxial line transmission/reflection method in the American society for testing and materials standard ASTM D7449/D7449M-08, and the RL value of the material is calculated according to the transmission line theory.
Example 1
In this example, the preparation of a covalent organic framework composite includes the following steps:
1)Fe3O4preparation of hollow nanospheres:
dissolving 8.1g ferric chloride hexahydrate, 12.0g sodium acetate and 1.5g trisodium citrate in 200ml ethylene glycol, and stirring vigorously at room temperature for 5 minutes; then pouring the mixture into a reaction kettle with a 100ml polytetrafluoroethylene lining, preserving the heat for 12 hours at 200 ℃ to carry out hydrothermal synthesis reaction, and naturally cooling to room temperature; magnetic separation with magnet, washing with deionized water and ethanol for 3 times, and vacuum drying for 12 hr to obtain Fe3O4Hollow nanospheres.
2)Fe3O4Reacting hollow nanospheres with a covalent organic framework material
Step 1) to obtain 0.15g of Fe3O4Dissolving 0.106g of 1,3, 5-tri (4-aminophenyl) benzene and 0.06g of terephthalaldehyde in 60ml of DMSO, and performing ultrasonic treatment for 10min to completely dissolve the spheres to obtain a mixed solution; 2ml of glacial acetic acid is dropwise added into the mixed solutionAnd (3) performing ultrasonic treatment for 45min, and performing Schiff base condensation reaction at the temperature of 25 ℃ to obtain a reaction product.
3) Calcination treatment
Calcining the reaction product obtained in the step 2) at 700 ℃ for 120min in an argon atmosphere, wherein the heating rate during calcining is 5 ℃/min, and obtaining the covalent organic framework composite material.
The appearance of the covalent organic framework composite material obtained in this example was observed by transmission electron microscopy, as shown in fig. 2. As can be seen from the figure, Fe3O4The hollow nanospheres are all wrapped with a layer of shell to form a hollow core-shell structure. In the hollow core-shell structure, the outer diameter of the core is 100nm, and the inner diameter of the core is 70 nm; the outer diameter of the shell was 110nm and the inner diameter of the shell was 100 nm.
From the XRD pattern of FIG. 1, the covalent organic framework composite material obtained in this example mainly contains Fe and Fe3O4。
As can be seen from the wave-absorbing performance chart in FIG. 3, the thickness range of the sample of the covalent organic framework composite material obtained in the embodiment is 1-5mm, and when the frequency is 14.08GHz and the thickness of the sample is 1.8mm, RL is adoptedminIs-50.05 dB, absorption bandwidth (RL)<-10dB) is 5.20 GHz.
Example 2
In this example, the preparation of a covalent organic framework composite includes the following steps:
1)Fe3O4preparation of hollow nanospheres:
dissolving 8.1g ferric chloride hexahydrate, 12.0g sodium acetate and 1.5g trisodium citrate in 200ml ethylene glycol, and stirring vigorously at room temperature for 5 minutes; then pouring the mixture into a reaction kettle with a 100ml polytetrafluoroethylene lining, preserving the heat for 12 hours at 200 ℃ to carry out hydrothermal synthesis reaction, and naturally cooling to room temperature; magnetic separation with magnet, washing with deionized water and ethanol for 3 times, and vacuum drying for 12 hr to obtain Fe3O4Hollow nanospheres.
2)Fe3O4Reacting hollow nanospheres with a covalent organic framework material
Step 1) to obtain 0.15g of Fe3O4Hollow nanosphere0.106g of 1,3, 5-tri (4-aminophenyl) benzene and 0.06g of terephthalaldehyde are dissolved in 60ml of DMSO, and ultrasonic treatment is carried out for 10min to ensure that the solutions are completely dissolved, so as to obtain a mixed solution; dropwise adding 2ml of glacial acetic acid into the mixed solution, performing ultrasonic treatment for 45min, and performing Schiff base condensation reaction at the temperature of 25 ℃ to obtain a reaction product.
3) Calcination treatment
Calcining the reaction product obtained in the step 2) at 800 ℃ for 120min in an argon atmosphere, wherein the heating rate during calcining is 5 ℃/min, and obtaining the covalent organic framework composite material.
The appearance of the covalent organic framework composite material obtained in this example was observed by transmission electron microscopy, as shown in fig. 2. As can be seen from the figure, the obtained covalent organic framework composite material has a hollow core-shell structure. In the hollow core-shell structure, the outer diameter of the core is 80nm, and the inner diameter of the core is 50 nm; the outer diameter of the shell was 105nm and the inner diameter of the shell was 80 nm. But part of Fe3O4The core structure is broken and the inner grains are enlarged, mainly due to rapid growth of reduced Fe due to an increase in heat treatment temperature.
From the XRD pattern of FIG. 1, the covalent organic framework composite material obtained in this example mainly contains Fe and Fe3O4。
As can be seen from the wave-absorbing performance chart of FIG. 3, the thickness range of the sample of the covalent organic framework composite material obtained in the embodiment is 1-5mm, the wave-absorbing performance in the measured range is poor, and the RL values are all larger than-10 dB.
Example 3
In this example, the preparation of a covalent organic framework composite includes the following steps:
1)Fe3O4preparation of hollow nanospheres:
dissolving 8.1g ferric chloride hexahydrate, 12.0g sodium acetate and 1.5g trisodium citrate in 200ml ethylene glycol, and stirring vigorously at room temperature for 5 minutes; then pouring the mixture into a reaction kettle with a 100ml polytetrafluoroethylene lining, preserving the heat for 12 hours at 200 ℃ to carry out hydrothermal synthesis reaction, and naturally cooling to room temperature; magnetic separation with magnet, washing with deionized water and ethanol for 3 times, and vacuum drying for 12 hr to obtain Fe3O4The hollow ball.
2)Fe3O4Reacting hollow nanospheres with a covalent organic framework material
Step 1) to obtain 0.15g of Fe3O4Dissolving 0.106g of 1,3, 5-tri (4-aminophenyl) benzene and 0.06g of terephthalaldehyde in 60ml of DMSO, and performing ultrasonic treatment for 10min to completely dissolve the spheres to obtain a mixed solution; dropwise adding 2ml of glacial acetic acid into the mixed solution, performing ultrasonic treatment for 45min, and performing Schiff base condensation reaction at the temperature of 25 ℃ to obtain a reaction product.
3) Calcination treatment
Calcining the reaction product obtained in the step 2) at 600 ℃ for 120min in an argon atmosphere, wherein the heating rate during calcining is 5 ℃/min, and obtaining the covalent organic framework composite material.
The appearance of the covalent organic framework composite material obtained in this example was observed by transmission electron microscopy, as shown in fig. 2. As can be seen from the figure, the covalent organic framework composite material of the embodiment forms hollow core-shell structure particles with thick shell layers, and the interior of the hollow core-shell structure particles is Fe3O4The core structure is comparable to the comparative example. In the hollow core-shell structure of the composite material of the embodiment, the outer diameter of the core is 100nm, and the inner diameter of the core is 50 nm; the outer diameter of the shell was 125nm and the inner diameter of the shell was 100 nm.
From the XRD pattern of FIG. 1, the resulting covalent organic framework composite material of this example is typical of Fe3O4Diffraction peaks.
As can be seen from the wave-absorbing performance chart of FIG. 3, the thickness range of the sample of the covalent organic framework composite material obtained in the embodiment is 1-5mm, the wave-absorbing performance in the measured range is poor, and the RL values are all larger than-10 dB.
Comparative example
In this example, Fe was prepared3O4A hollow nanosphere comprising the steps of:
dissolving 8.1g ferric chloride hexahydrate, 12.0g sodium acetate and 1.5g trisodium citrate in 200ml ethylene glycol, and stirring vigorously at room temperature for 5 minutes; then pouring the mixture into a reaction kettle with a 100ml polytetrafluoroethylene lining, preserving the heat for 12 hours at 200 ℃ to carry out hydrothermal synthesis reaction, and naturally cooling the reaction product toRoom temperature; magnetic separation with magnet, washing with deionized water and ethanol for 3 times, and vacuum drying for 12 hr to obtain Fe3O4Hollow nanospheres.
For Fe obtained in this example3O4The hollow nanospheres were observed by projection electron microscopy, respectively, as shown in fig. 2.
From the XRD pattern of FIG. 1, Fe obtained in this example3O4Hollow nanospheres are typically Fe3O4Diffraction peaks.
From the wave-absorbing property diagram of FIG. 3, it can be seen that Fe obtained in this example3O4The thickness of the sample of the hollow nanosphere ranges from 1 mm to 5mm, and the absorption bandwidth (RL) is obtained when the thickness of the sample is 5mm<-10dB) is 0.96 GHz.
The foregoing embodiments are merely illustrative of the principles and utilities of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or change the above-mentioned embodiments without departing from the spirit and scope of the present invention. Accordingly, it is intended that all equivalent modifications or changes which can be made by those skilled in the art without departing from the spirit and technical spirit of the present invention be covered by the claims of the present invention.
Claims (10)
1. A covalent organic framework composite material is characterized in that the material is a particle with a core-shell structure, and the core is Fe3O4Hollow nanospheres, the shell consisting of a covalent organic framework material; the covalent organic framework material is obtained by performing Schiff base condensation reaction on terephthalaldehyde and 1,3, 5-tri (4-aminophenyl) benzene; terephthalaldehyde, 1,3, 5-tris (4-aminophenyl) benzene and Fe3O4The mass ratio of the hollow nanospheres is 1: (0.5-3): (5-8).
2. The covalent organic framework composite of claim 1, wherein the core has an outer diameter of 80nm to 100nm and an inner diameter of 50nm to 75 nm; the outer diameter of the shell is 105-125 nm, and the inner diameter of the shell is 80-100 nm.
3. The method of preparing a covalent organic framework composite material according to any one of claims 1 to 2, comprising the steps of:
1) providing Fe3O4Hollow nanospheres;
2) subjecting said Fe to3O4Dissolving the hollow nanospheres, terephthalaldehyde and 1,3, 5-tri (4-aminophenyl) benzene in a solvent, and carrying out catalytic reaction under a catalyst to obtain a reaction product;
3) and calcining the reaction product to obtain the covalent organic framework composite material.
4. The production method according to claim 3, wherein the solvent is one selected from the group consisting of dimethyl sulfoxide and N, N-dimethylformamide;
and/or the catalyst is selected from one of glacial acetic acid and isoquinoline.
5. The method according to claim 3, wherein the Fe3O4The preparation method of the hollow nanosphere comprises the following steps: ferric chloride hexahydrate, sodium acetate, trisodium citrate and ethylene glycol are mixed, and then hydrothermal reaction is carried out.
6. The preparation method according to claim 5, wherein the weight ratio of the trisodium citrate, ferric chloride hexahydrate, sodium acetate and glycol is 1: (3-6): (5-10): (100-200);
and/or the temperature of the hydrothermal reaction is 100-300 ℃.
7. The method according to claim 3, wherein terephthalaldehyde, 1,3, 5-tris (4-aminophenyl) benzene, and Fe are used as the main raw material3O4The mass ratio of the hollow nanospheres, the catalyst and the solvent is 1: (0.5-3): (1-5): (20-50): (800-1500); and/or the temperature of the catalytic reaction is 15-25 ℃.
8. The preparation method according to claim 3, wherein the catalytic reaction is carried out in ultrasound for 20-50 min.
9. The preparation method according to claim 3, wherein the calcination temperature is 500 ℃ to 800 ℃;
and/or the heating rate of the calcination is 2-8 ℃/min;
and/or, the calcining is carried out under a protective atmosphere.
10. The covalent organic framework composite material according to any one of claims 1 to 2, as a wave-absorbing material, for use in the field of electromagnetic waves.
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Application publication date: 20210820 |