CN111234214B - Triazine-based Schiff base conjugated microporous polymer and preparation method thereof - Google Patents
Triazine-based Schiff base conjugated microporous polymer and preparation method thereof Download PDFInfo
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- CN111234214B CN111234214B CN202010252947.7A CN202010252947A CN111234214B CN 111234214 B CN111234214 B CN 111234214B CN 202010252947 A CN202010252947 A CN 202010252947A CN 111234214 B CN111234214 B CN 111234214B
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
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Abstract
The invention provides a triazine-based Schiff base conjugated microporous polymer and a preparation method thereof. The average pore diameter of the prepared triazine-based Schiff base conjugated microporous polymer is 1-50 nm, and the specific surface area is 100m2/g～2500m2(ii)/g; under the nitrogen atmosphere, the 5 wt% thermal weight loss temperature is 200-500 ℃. The triazine-based Schiff base conjugated microporous polymer prepared by the invention has higher nitrogen content and higher specific surface area than the previous triazine-based nitrogen-rich conjugated microporous polymer, and the synthesis process is a molecular level reaction, so that the product is more ordered and stable, and the pi electron delocalization is more stable, so that the triazine-based Schiff base conjugated microporous polymer has outstanding application prospects in the fields of charge transfer and separation, semiconductors, gas adsorption, catalysis and the like.
Description
Technical Field
The invention relates to the technical field of organic polymer preparation, in particular to a triazine-based Schiff base conjugated microporous polymer and a preparation method thereof.
Background
Conjugated Microporous Polymers (CMPs) are an attractive porous solid material, and the structure of the CMPs is formed by connecting a plurality of C-C bonds and aromatic rings, has a conjugated system, a tunable topological structure and inherent nanopores, and has excellent photoelectric properties compared with graphene. Since the discovery and the report, the conjugated microporous polymer attracts extensive research attention due to the characteristics of high specific surface area, a programmable structure, tunable performance, adjustable performance and the like. The conjugated microporous polymer has great application potential in the aspects of gas adsorption and separation, luminescence, heterogeneous catalysis, supercapacitors, light capturing, packaging, hydrogen production, electrodes and the like.
Disclosure of Invention
In order to solve the technical problems, the first aspect of the present invention provides a triazine-based schiff base conjugated microporous polymer, wherein the structural formula of the triazine-based schiff base conjugated microporous polymer is:
wherein the content of the first and second substances,
represents a repeating structural unit;
a is any one of the following structural units:
b is any one of the following structural units:
wherein the average pore diameter of the triazine-based Schiff base conjugated microporous polymer is 1-50 nm.
Wherein the triazine-based Schiff base conjugated microporous polymer material is in a powder or block shape, and the specific surface area of the material is 100m2/g～2500m2/g。
Wherein, the 5 wt% thermal weight loss temperature of the triazine-based Schiff base conjugated microporous polymer material is 200-500 ℃ in a nitrogen atmosphere.
The preparation method of the triazine-based Schiff base conjugated microporous polymer provided by the invention comprises the following steps:
the first step is as follows: dissolving a triazinyl arylamine compound and a benzaldehyde compound in any one or a mixture of several of dimethyl sulfoxide, tetrahydrofuran, dioxane and toluene in a sealed and vacuum pyrex tube, and reacting for 4-72 hours at the temperature of 80-200 ℃ by using a weak acid as a catalyst to obtain the triazinyl Schiff base conjugated microporous polymer, wherein the reaction formula is as follows:
the second step is that: washing the triazine-based Schiff base conjugated microporous polymer prepared in the first step by distilled water and dimethyl sulfoxide in sequence, performing Soxhlet extraction by tetrahydrofuran, acetone and methanol, and drying and activating under a vacuum condition to obtain the triazine-based Schiff base conjugated microporous polymer material.
The invention provides a preparation method of a triazine-based Schiff base conjugated microporous polymer, which is characterized in that a triazine-based arylamine compound and a benzaldehyde compound are dissolved in an organic solvent in a closed vacuum pyrex tube, then a catalyst is added, and the triazine-based Schiff base conjugated microporous polymer is synthesized by a solvothermal method.
Wherein, the triazinyl arylamine compound is any one of the following structural formulas:
wherein, the benzaldehyde compound is any one of the following structural formulas:
wherein the organic solvent is any one or a mixture of several of dimethyl sulfoxide, tetrahydrofuran, dioxane and toluene.
The catalyst is weak acid, and the weak acid can be organic carboxylic acid compounds or inorganic weak acid compounds.
The reaction temperature for synthesizing the triazine-based Schiff base conjugated microporous polymer by the solvothermal method is 80-200 ℃, and the reaction time is 4-72 hours.
The invention has the beneficial effects that:
the invention has the advantages that the triazine group-rich conjugated microporous polymer is introduced, the polymer has higher nitrogen content and higher specific surface area than the previous triazine group nitrogen-rich conjugated microporous polymer, the synthesis process is a molecular level reaction, the product is more ordered and stable, and the pi electron delocalization is more stable, so that the triazine group nitrogen-rich conjugated microporous polymer has outstanding application prospect in the organic fields of charge transfer and separation, semiconductors, gas adsorption, catalysis and the like.
Drawings
In order to more clearly illustrate the technical solution of the present invention, the drawings used in the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it should be obvious for those skilled in the art that other drawings can be obtained according to these drawings without creative efforts.
FIG. 1 shows the CO of triazine-based Schiff base conjugated microporous polymer CMP-100 prepared in example 1 under 273K and 298K2Adsorption isotherms;
FIG. 2 is a graph of iodine weight absorption versus time at 350K for the triazine-based Schiff base conjugated microporous polymer CMP-100 prepared in example 1 of the present invention.
Detailed Description
The following is a preferred embodiment of the present invention, and it should be noted that it is obvious to those skilled in the art that various modifications and improvements can be made without departing from the principle of the present invention, and these modifications and improvements are also considered to be within the scope of the present invention.
Example 1
The invention provides a preparation method of triazine-Schiff base conjugated microporous polymer, which comprises the steps of sequentially adding 4,4'- (benzene-1, 3, 5-triyl-tri (benzene-4, 1-diyl)) -6,6' -tri (1,3, 5-triazane-2, 4-diamine) (0.2mmol) and terephthalaldehyde (0.8mmol) in a molar ratio of 1:4 into a closed vacuum pyrex tube, adding an organic solvent dimethyl sulfoxide and a catalyst acetic acid, and stirring and refluxing for reaction for 72 hours at 120 ℃ under the protection of argon; cooling the reaction liquid to room temperature to obtain precipitate, washing with distilled water and dimethyl sulfoxide, performing Soxhlet extraction with tetrahydrofuran, acetone and methanol, and drying under 10kPaAnd reacting to obtain the triazine-based Schiff base conjugated microporous polymer material CMP-100. TGA and BET were measured separately, and the specific surface area was 724m2(ii)/g, average pore diameter of 1.97nm, 5% thermal weight loss temperature of 388 ℃ under nitrogen, I2The adsorption capacity at 350K was 4.43 g/g.
Example 2
The invention provides a preparation method of a triazinyl Schiff base conjugated microporous polymer, which comprises the steps of sequentially adding 4,4' - (benzene-1, 3, 5-triyl-tri (benzene-4, 1-diyl)) -6,6' -tri (1,3, 5-triazane-2, 4-diamine) (0.2mmol) and 4,4' -biphenyldicarboxaldehyde (0.8mmol) in a molar ratio of 1:4 into a closed and vacuum pyrex tube, adding an organic solvent tetrahydrofuran and a catalyst acetic acid, and stirring and refluxing for 50 hours at 150 ℃ under the protection of argon; cooling the reaction liquid to room temperature to obtain a precipitate, washing the precipitate by distilled water and dimethyl sulfoxide in sequence, performing Soxhlet extraction by tetrahydrofuran, acetone and methanol, and drying and activating the precipitate under the vacuum condition of 10kPa to obtain the triazine-based Schiff base conjugated microporous polymer material. The obtained triazine-based Schiff base conjugated microporous polymer has the specific surface area of 758m2/g, the average pore diameter of 1.83nm, the 5 percent thermal weight loss temperature of 390 ℃ under the nitrogen condition, I2The adsorption capacity at 350K was 5.54 g/g.
Example 3
The invention provides a preparation method of a triazine-based Schiff base conjugated microporous polymer, which comprises the steps of sequentially adding 4,4' - (benzene-1, 3, 5-triyl-tri (benzene-4, 1-diyl)) -6,6' -tri (1,3, 5-triazane-2, 4-diamine) (0.2mmol) and 4,4' -diphenyloxymethylene ethylene (0.8mmol) in a molar ratio of 1:4 into a closed and vacuum pyrex tube, then adding an organic solvent dioxane, toluene and a catalyst acetic acid, and stirring and refluxing for reaction for 60 hours at 180 ℃ under the protection of argon; cooling the reaction liquid to room temperature to obtain a precipitate, washing the precipitate by distilled water and dimethyl sulfoxide in sequence, performing Soxhlet extraction by tetrahydrofuran, acetone and methanol, and drying and activating the precipitate under the vacuum condition of 10kPa to obtain the triazine-based Schiff base conjugated microporous polymer material. The specific surface area of the obtained triazine-based Schiff base conjugated microporous polymer is 690m2(g), average pore diameter of 1.92nm, 5% thermal weight loss temperature of 412 ℃ under nitrogen, I2At 350KThe adsorption capacity was 5.11 g/g.
Example 4
The invention provides a preparation method of a triazine-based Schiff base conjugated microporous polymer, which comprises the steps of sequentially adding 1:4 benzene-1, 3, 5-triyl-tri (1,3, 5-triazane-2, 4-diamine) (0.2mmol) and terephthalaldehyde (0.8mmol) in a closed and vacuum pyrex tube, adding an organic solvent dioxane, toluene and a catalyst acetic acid, and stirring and refluxing for reaction for 72 hours at 120 ℃ under the protection of argon; cooling the reaction liquid to room temperature to obtain a precipitate, washing the precipitate by distilled water and dimethyl sulfoxide in sequence, performing Soxhlet extraction by tetrahydrofuran, acetone and methanol, and drying and activating the precipitate under the vacuum condition of 10kPa to obtain the triazine-based Schiff base conjugated microporous polymer material. The specific surface area of the obtained triazine-based Schiff base conjugated microporous polymer is 773m2Per g, average pore diameter of 1.63nm, 5% thermal weight loss temperature of 403 ℃ under nitrogen, I2The adsorption capacity at 350K was 5.88 g/g.
Example 5
The invention provides a preparation method of a triazine-based Schiff base conjugated microporous polymer, which comprises the steps of sequentially adding 1:4 benzene-1, 3, 5-triyl-tri (1,3, 5-triazane-2, 4-diamine) (0.2mmol) and 4,4' -biphenyldicarboxaldehyde (0.8mmol) in a closed and vacuum pyrex tube, adding an organic solvent dioxane, toluene and a catalyst acetic acid, and stirring and refluxing for reaction for 50 hours at 150 ℃ under the protection of argon; cooling the reaction liquid to room temperature to obtain a precipitate, washing the precipitate by distilled water and dimethyl sulfoxide in sequence, performing Soxhlet extraction by tetrahydrofuran, acetone and methanol, and drying and activating the precipitate under the vacuum condition of 10kPa to obtain the triazine-based Schiff base conjugated microporous polymer material. The specific surface area of the obtained triazine-based Schiff base conjugated microporous polymer is 621m2Per g, average pore diameter of 1.59nm, 5% thermal weight loss temperature of 354 ℃ under nitrogen, I2The adsorption capacity at 350K was 5.47 g/g.
Example 6
The invention provides a preparation method of a triazinyl Schiff base conjugated microporous polymer, which comprises the steps of sequentially adding 1:4 benzene-1, 3, 5-triyl-tri (1,3, 5-triazane-2, 4-diamine) (0.2mmol) and4,4' -diphenylformaldehyde vinyl (0.8mmol), then adding an organic solvent dioxane, toluene and a catalyst acetic acid, and stirring and refluxing for reaction for 60 hours at 180 ℃ under the protection of argon; cooling the reaction liquid to room temperature to obtain a precipitate, washing the precipitate by distilled water and dimethyl sulfoxide in sequence, performing Soxhlet extraction by tetrahydrofuran, acetone and methanol, and drying and activating the precipitate under the vacuum condition of 10kPa to obtain the triazine-based Schiff base conjugated microporous polymer material. The specific surface area of the obtained triazinyl Schiff base conjugated microporous polymer is 721m2Per g, average pore diameter of 1.80nm, 5% thermal weight loss temperature of 381 ℃ under nitrogen, I2The adsorption capacity at 350K was 5.36 g/g.
The above examples only express the specific embodiments of the present invention, and the description thereof is more specific and detailed, but not to be construed as limiting the scope of the present invention. It should be noted that, for those skilled in the art, various changes and modifications can be made without departing from the spirit of the present invention, and these changes and modifications are all within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (8)
1. A triazine-based Schiff base conjugated microporous polymer is characterized in that the structural formula of the triazine-based Schiff base conjugated microporous polymer is as follows:
wherein the content of the first and second substances,
represents a repeating structural unit;
a is any one of the following structural units:
wherein, the symbol in the A structural formula represents the position connected with other groups;
b is any one of the following structural units:
wherein, the symbol in the structural formula B represents the position connected with other groups.
2. The triazine-based schiff base conjugated microporous polymer according to claim 1, wherein: the average pore diameter of the triazine-based Schiff base conjugated microporous polymer is 1-50 nm.
3. The triazine-based schiff base conjugated microporous polymer according to claim 1, wherein: the triazine-based Schiff base conjugated microporous polymer material is in a powder shape or a block shape, and the specific surface area of the material is 100m2/g～2500m2/g。
4. The triazine-based schiff base conjugated microporous polymer according to claim 1, wherein: the triazine-based Schiff base conjugated microporous polymer material has a 5 wt% thermal weight loss temperature of 200-500 ℃ in a nitrogen atmosphere.
5. A preparation method of a triazine-based Schiff base conjugated microporous polymer is characterized by comprising the following steps: dissolving triazine-based arylamine compounds and benzaldehyde compounds in an organic solvent in a closed and vacuum pyrex tube, adding a catalyst, and synthesizing a triazine-based Schiff base conjugated microporous polymer by a solvothermal method;
the triazine arylamine compound is any one of the following structural formulas:
the benzaldehyde compound is any one of the following structural formulas:
6. the method of claim 5, wherein the triazine-based Schiff base conjugated microporous polymer comprises: the organic solvent is any one or a mixture of several of dimethyl sulfoxide, tetrahydrofuran, dioxane and toluene.
7. The method of claim 5, wherein the triazine-based Schiff base conjugated microporous polymer comprises: the catalyst is weak acid which is organic carboxylic acid compounds or inorganic weak acid compounds.
8. The method for preparing the triazine-based schiff base conjugated microporous polymer according to any one of claims 5 to 7, wherein: the reaction temperature for synthesizing the triazine-based Schiff base conjugated microporous polymer by the solvothermal method is 80-200 ℃, and the reaction time is 4-72 hours.
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