CN113336961B - Thiazolyl sulfur-rich covalent organic framework and preparation method and application thereof - Google Patents
Thiazolyl sulfur-rich covalent organic framework and preparation method and application thereof Download PDFInfo
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Abstract
The invention provides a preparation method of a sulfur-rich covalent organic framework of thiazolyl, which comprises the steps of dissolving an amino phenyl substituted aromatic compound, vinyl-containing aromatic aldehyde and sulfur powder serving as raw materials in a mixed organic solvent, carrying out one-pot reaction under the action of an oxidant and a catalyst, and purifying after the reaction is finished to obtain the sulfur-rich covalent organic framework of the thiazolyl. The invention also discloses a thiazolyl sulfur-rich covalent organic framework and application thereof. According to the invention, cheap and easily-obtained sulfur powder, amine and aldehyde compounds are used as raw materials, and the thiazolyl-rich covalent organic framework of the difunctional COFs catalytic material with thiazolyl and sulfur fixation is prepared by a one-pot method, so that the problems of high synthesis cost, poor stability and limitation of multifunctionality of the COFs are solved.
Description
Technical Field
The invention belongs to the technical field of conductive materials, and particularly relates to a sulfur-rich covalent organic framework of thiazolyl, which can be used for a conductive material, and a preparation method and application thereof.
Background
Covalent Organic Frameworks (COFs) are used as a class of pure organic frameworks with unique 'micro-nano structures'. Flexible monomer design, adjustable polymer skeleton (including pore diameter, functional modification and the like), periodic permanent pore channels and highly ordered pore channels can limit the domain to form a nano micro-reactor. Compared with three-dimensional COFs, the two-dimensional COFs have an ordered layered accumulation structure, and pi-pi interaction ensures strong interaction among layers and is beneficial to transmission of charges in a frame. Although the COFs structure has unique properties, it is more challenging to introduce a suitable photogen group into the backbone to impart unique photovoltaic properties. At the same time, the efficient introduction of multifunctional photoelectrically active groups in one step is also very challenging. Until now, scientists have successfully introduced pyrenyl, porphinyl, phthalocyaninyl, thiazolyl, and the like into COFs frameworks. In view of the fact that the materials have wide application and good application prospects in the fields of supercapacitors, lithium ion batteries, lithium sulfur batteries, photoelectric display materials and the like, the materials are particularly concerned by relevant academic workers, however, more and better synthetic strategies are developed to solve the problems existing in the existing preparation of the materials, and for example, how to utilize the conventional organic building block one-pot multi-component reaction to efficiently realize the preparation of the materials and the like. In addition, the functionalization of the existing Covalent Organic Frameworks (COFs) requires the synthesis of functional monomers with relatively complex structures, and the synthesis price is high; the stability problem of mainstream covalent organic framework materials, namely Schiff base COFs needs to be improved urgently; the sulfur element introduced into the COFs framework can only be introduced in a physical adsorption mode, so that the stability is extremely poor, and the performance of the material is greatly influenced.
Disclosure of Invention
An object of the present invention is to solve at least the above problems or disadvantages and to provide at least the advantages described hereinafter.
The invention also aims to provide a preparation method of the sulfur-rich covalent organic framework of thiazolyl, which comprises the following steps of firstly, utilizing the specificity of the activity of organic building blocks and the difference of the reaction activity activation energy to realize that the thiazolyl is introduced into the COFs framework by one step, and simultaneously, the stability of the thiazolyl is superior to that of Schiff base COFs; furthermore, the fixation of the sulfur element is realized by introducing a vinyl unit into the initial unit. Secondly, the invention economically and efficiently synthesizes the COFs with high stability (acid resistance, alkali resistance, high temperature resistance and illumination resistance) by a general method so as to solve the problem that the COFs are difficult to have practical application value due to high synthesis cost and poor stability. And the synthesized difunctional COFs material with thiazolyl and sulfur fixation solves the problem that the current COFs are difficult to be multifunctional.
The invention not only solves the problems of single synthesis method, poor stability, single function, limited application and the like of the COFs serving as the photoelectric material, but also promotes the progress of the COFs in the photoelectric field through the systematic research of the immobilization of thiazolyl and sulfur elements.
It is a further object of the present invention to provide a thiazolyl sulfur-rich covalent organic framework.
It is also an object of the present invention to provide the use of thiazolyl rich covalent organic frameworks in electrically conducting materials.
In order to achieve these objects and other advantages and in accordance with the purpose of the invention, as embodied and broadly described herein, there is provided a method for preparing a thiazolyl sulfur-rich covalent organic framework, comprising the steps of dissolving an amino-phenyl-substituted aromatic compound, a vinyl-containing aromatic aldehyde, and sulfur powder as raw materials in a mixed organic solvent, performing a one-pot reaction under the action of an oxidant and a catalyst, and purifying to obtain the thiazolyl sulfur-rich covalent organic framework after the reaction is completed.
Preferably, the aminophenyl-substituted aromatic compound is 1,3, 5-tris (3-aminophenyl) benzene.
Preferably, the vinyl-containing aromatic aldehyde is 2, 5-divinylterephthalaldehyde.
Preferably, the mixed organic solvent is ortho-dichlorobenzene and an alcohol.
Preferably, the molar ratio of the aminophenyl-substituted aromatic compound, the vinyl-containing aromatic aldehyde, and the sulfur powder is 1: 1.5.
Preferably, the oxidizing agent is dimethyl sulfoxide and the catalyst is 6M aqueous acetic acid.
Preferably, the amino phenyl substituted aromatic compound, the vinyl-containing aromatic aldehyde and the sulfur powder are placed in a Pyrex tube, a mixed organic solvent is added, an acidic aqueous solution is added after ultrasonic homogenization, the system is subjected to vacuum treatment after ultrasonic homogenization again, finally the Pyrex tube is placed in a 120 ℃ oven to be subjected to static reaction for 3 days to obtain solid powder, and the solid powder is purified to obtain the sulfur-rich covalent organic framework of the thiazolyl.
Preferably, the purification comprises: and washing the solid powder with water, ethanol and tetrahydrofuran for three times respectively, wherein the dosage of the water, the ethanol and the tetrahydrofuran is 20mL each time, and performing Soxhlet extraction on the tetrahydrofuran for 48 hours to obtain the sulfur-rich covalent organic framework of the thiazolyl.
The object of the present invention can be further achieved by a thiazolyl sulfur-rich covalent organic framework obtained by the above preparation method.
The object of the invention is further achieved by the use of a thiazolyl sulfur-rich covalent organic framework in electrically conducting materials.
The invention at least comprises the following beneficial effects:
1. according to the preparation method of the thiazolyl sulfur-rich covalent organic framework, cheap sulfur powder, amine and aldehyde compounds are selected as raw materials, and the thiazolyl sulfur-rich covalent organic framework is prepared by a one-pot method, so that the technical problems that the existing Covalent Organic Frameworks (COFs) polymer preparation is high in production cost, complex in route and unstable in product properties are solved;
2. the preparation method of the thiazolyl sulfur-rich covalent organic framework prepares difunctional COFs polymers with thiazolyl and sulfur-fixing functions, and solves the problem that the COFs are difficult to be multifunctional at present;
3. the preparation method of the sulfur-rich covalent organic framework of thiazolyl prepared by the invention utilizes the specificity of the activity of the organic building blocks and the difference of the reaction activity activation energy to introduce thiazolyl into the COFs organic framework in one step, thereby improving the stability of the COFs polymers; the vinyl unit is introduced into the initial unit, so that the fixation of the sulfur element through a chemical bond is realized, and the problems that the sulfur element introduced into the conventional COFs framework can only be introduced in a physical adsorption mode, the stability is extremely poor, and the performance of the material is greatly influenced are solved.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention.
Drawings
FIG. 1 is a graph of nitrogen adsorption-desorption for a thiazolyl sulfur-rich covalent organic framework in example 1 of the present invention;
FIG. 2 is a plot of the pore size distribution of thiazolyl sulfur-rich covalent organic frameworks in example 1 of the present invention;
FIG. 3 is an XRD pattern of a sulfur-rich covalent organic framework of thiazolyl in example 1 of the present invention;
FIG. 4 is a graph showing the adsorption-desorption of nitrogen from a thiazolyl sulfur-rich covalent organic framework in example 2 of the present invention;
FIG. 5 is a plot of the pore size distribution of thiazolyl sulfur-rich covalent organic frameworks in example 2 of the present invention;
FIG. 6 is an XRD pattern of a sulfur-rich covalent organic framework of thiazolyl in example 2 of the present invention;
FIG. 7 is a graph of hydrogen sorption-desorption for thiazolyl sulfur-rich covalent organic frameworks in example 2 of the present invention;
FIG. 8 is a graph of nitrogen adsorption-desorption for thiazolyl sulfur-rich covalent organic frameworks in example 3 of the present invention;
FIG. 9 is a plot of pore size distribution of thiazolyl sulfur-rich covalent organic frameworks in example 3 of the present invention;
FIG. 10 is a graph of the adsorption-desorption of hydrogen for the sulfur-rich covalent organic framework of the thiazolyl group in example 3 of the present invention.
Detailed Description
The present invention is further described in detail below with reference to the attached drawings so that those skilled in the art can implement the invention by referring to the description text.
It will be understood that terms such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
< example 1>
A thiazolyl, sulfur-rich covalent organic framework, wherein said thiazolyl, sulfur-rich covalent organic framework has the structure shown below:
the specific synthetic route of the sulfur-rich covalent organic framework of the thiazolyl is as follows:
the specific synthesis steps are as follows:
1,3,5-tris (3-aminophenyl) benzene (17.57mg, 0.05mmol), terephthalaldehyde (10.06mg, 0.075mmol) and sulfur powder (14.43mg, 0.075mmol) were placed in a 10mL Pyrex tube (tube length about 18cm, neck length 9 cm) at room temperature. Then adding 1mL of methanol, 1mL of mesitylene and 0.05mL of dimethyl sulfoxide into the mixture, carrying out ultrasonic homogenization, adding 0.1mL of 6M acetic acid aqueous solution, carrying out ultrasonic homogenization again, carrying out vacuum treatment on the system, and finally placing the Pyrex tube in a 120 ℃ oven for standing reaction for 3 days to obtain brick red solid powder. The powder was washed with water (3X 20 mL), ethanol (3X 20 mL) and tetrahydrofuran (3X 20 mL) in this order to remove unreacted monomers and oligomers, and then subjected to Soxhlet extraction with tetrahydrofuran for 48 hours to obtain a tan powder, COF-2D for short.
The adsorption-desorption profile of nitrogen of the thiazolyl sulfur-rich covalent organic framework COF-2D synthesized in the embodiment is shown in a figure 1, the pore size distribution profile is shown in a figure 2, and the XRD pattern is shown in a figure 3.
In the invention, the adsorption-desorption test, the pore size distribution test and the XRD test of nitrogen adopt the conventional test methods in the field.
The specific surface area of the thiazolyl sulfur-rich covalent organic framework synthesized in the example is 46m 2 The COFs material has a certain ordered structure in a small range, and the pore diameter is mainly distributed in a mesoporous region and a macroporous region.
< example 2>
A thiazolyl, sulfur-rich, covalent organic framework, wherein said thiazolyl, sulfur-rich, covalent organic framework has the structure shown below:
wherein n is a positive integer greater than or equal to 1.
The specific synthetic route of the sulfur-rich covalent organic framework of the thiazolyl is as follows:
the specific synthesis steps are as follows:
1,3, 5-tris (3-aminophenyl) benzene (17.57mg, 0.05mmol), 2, 5-divinylterephthalaldehyde (13.97mg, 0.075mmol) and sulfur powder (14.43mg, 0.075mmol) were placed in a 10mL Pyrex tube (tube length about 18cm, neck length 9 cm) at room temperature. And then adding 1mL of o-dichlorobenzene, 1mL of n-butanol and 0.05mL of dimethyl sulfoxide into the mixture, performing ultrasonic homogenization, adding 0.1mL of 6M acetic acid aqueous solution, performing ultrasonic homogenization again, performing vacuum treatment on the system, and finally placing the Pyrex tube in a 120 ℃ oven for standing reaction for 3 days to obtain brick red solid powder. The powder is washed by (3X 20 mL) water, (3X 20 mL) ethanol and (3X 20 mL) tetrahydrofuran solvents in sequence, unreacted monomers and oligomers are removed, and then Soxhlet extraction is carried out for 48 hours by adopting tetrahydrofuran, so that brown yellow powder, namely COF-2D-S2, is obtained.
In the invention, the adsorption-desorption test of nitrogen, the pore size distribution test, the XRD test and the adsorption-desorption test of hydrogen adopt the conventional test methods in the field.
The adsorption-desorption graph of nitrogen gas, the pore size distribution graph of figure 5, the XRD graph of figure 6 and the adsorption-desorption graph of hydrogen gas of the thiazolyl sulfur-rich covalent organic framework COF-2D synthesized in the example are shown in figure 4, and figure 7 respectively.
The thiazolyl, sulfur-rich, covalent organic framework COF-2D-S2 synthesized in this example has a specific surface area of 848m 2 The specific surface area is high, the pore size distribution is narrow, and the pore size distribution is narrow and is mainly distributed in a micropore area, so that the order of the material is greatly improved; the hydrogen adsorption capacity can reach 1.93wt%, and compared with other existing organic porous materials, the performance has certain competitiveness。
< example 3>
Example 3 the same starting material as example 2, except for the specific synthesis steps:
1,3, 5-tris (3-aminophenyl) benzene (17.57mg, 0.05mmol), 2, 5-divinylterephthalaldehyde (13.97mg, 0.075mmol) and sulfur powder (14.43mg, 0.075mmol) were placed in a 10mL Pyrex tube (tube length about 18cm, neck length 9 cm) at room temperature. And then adding 1.2mL of o-dichlorobenzene, 0.81mL of ethanol and 0.05mL of dimethyl sulfoxide into the mixture, performing ultrasonic homogenization, adding 0.1mL of 6M acetic acid aqueous solution, performing ultrasonic homogenization, performing vacuum treatment on the system, and finally placing the Pyrex tube in a 120 ℃ oven for standing reaction for 3 days to obtain brick red solid powder. The powder is washed by (3X 20 mL) water, (3X 20 mL) ethanol and (3X 20 mL) tetrahydrofuran solvents in sequence, unreacted monomers and oligomers are removed, and then Soxhlet extraction is carried out for 48 hours by adopting tetrahydrofuran, so that brown yellow powder, namely COF-2D-S1, is obtained.
The adsorption-desorption graph of nitrogen, the pore size distribution graph of the sulfur-rich covalent organic framework COF-2D of the thiazolyl synthesized in the embodiment is shown in FIG. 8, and the adsorption-desorption graph of hydrogen is shown in FIG. 10.
The specific surface area of the thiazolyl sulfur-rich covalent organic framework COF-2D-S1 synthesized in the example is 572m 2 The specific surface area is reduced compared with COF-2D-S2, but the specific surface area is still higher and the pore size distribution is narrower, so that the COFs material has high orderliness and narrower pore size distribution, and the pore size is mainly distributed in a micropore area and a part of a macroporous area; the hydrogen adsorption capacity can reach 0.77wt%, which shows that the material has certain adsorption performance to hydrogen.
As can be seen from examples 2 and 3, the solvents used in the synthesis are different, the properties of the resulting sulfur-rich covalent organic frameworks of the thiazolyl are different, and COF-2D-S2 has a high specific surface area and a high hydrogen adsorption capacity compared to COF-2D-S1.
In conclusion, the preparation method of the thiazolyl sulfur-rich covalent organic framework provided by the invention has the advantages of cheap raw materials, simplicity and easy obtainment, and no synthesis (in the prior art, a monomer with a special functional group or a monomer with a complex structure is needed, the preparation process is complex, and the price is high); the synthetic process and the condition are simple; in the initial unit, a vinyl unit is introduced, and a sulfur chain is linked in a COFs framework by adopting a weak bond to obtain sulfur-rich COFs (in the prior art, sulfur element can be physically adsorbed in the framework only by post-treatment, and the stability is poor).
While embodiments of the invention have been disclosed above, it is not intended to be limited to the uses set forth in the specification and examples. It can be applied to all kinds of fields suitable for the present invention. Additional modifications will readily occur to those skilled in the art. It is therefore intended that the invention not be limited to the exact details and illustrations described and illustrated herein, but fall within the scope of the appended claims and equivalents thereof.
Claims (8)
1. A preparation method of a thiazolyl sulfur-rich covalent organic framework comprises the steps of dissolving an amino phenyl substituted aromatic compound, vinyl-containing aromatic aldehyde and sulfur powder serving as raw materials into a mixed organic solvent, carrying out one-pot reaction under the action of an oxidant and a catalyst, and purifying after the reaction is finished to obtain the thiazolyl sulfur-rich covalent organic framework;
wherein the aromatic compound substituted by the aminophenyl is 1,3, 5-tri (3-aminophenyl) benzene, and the aromatic aldehyde containing the vinyl is 2, 5-divinyl terephthalaldehyde.
2. The method according to claim 1, wherein the mixed organic solvent is o-dichlorobenzene and an alcohol.
3. The method according to claim 1, wherein the molar ratio of the aminophenyl-substituted aromatic compound, the vinyl-containing aromatic aldehyde, and the sulfur powder is 1: 1.5.
4. The method according to claim 1, wherein the oxidizing agent is dimethyl sulfoxide, and the catalyst is 6M aqueous acetic acid.
5. The preparation method according to claim 1, wherein the amino phenyl substituted aromatic compound, the vinyl-containing aromatic aldehyde and the sulfur powder are placed in a Pyrex tube, the mixed organic solvent is added, the mixture is ultrasonically homogenized, the oxidant and the catalyst are added, the mixture is ultrasonically homogenized again, the system is subjected to vacuum treatment, finally the Pyrex tube is placed in an oven at 120 ℃ for standing reaction for 3 days to obtain solid powder, and the solid powder is purified to obtain the sulfur-rich covalent organic framework of the thiazolyl group.
6. The method of claim 5, wherein purifying comprises: and washing the solid powder with water, ethanol and tetrahydrofuran for three times respectively, wherein the dosage of the water, the ethanol and the tetrahydrofuran is 20mL each time, and performing Soxhlet extraction on the tetrahydrofuran for 48 hours to obtain the sulfur-rich covalent organic framework of the thiazolyl.
7. A thiazolyl, sulfur-rich, covalent organic framework obtainable by the process according to any one of claims 1 to 6.
8. Use of the thiazolyl sulfur-rich covalent organic framework of claim 7 in conductive materials.
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