CN113845645B - Preparation method of carbon-carbon double bond connected two-dimensional conjugated organic framework material - Google Patents
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Abstract
The invention discloses a preparation method of a carbon-carbon double bond connected two-dimensional conjugated organic framework material, which comprises the following steps: step 1: in a glove box under argon atmosphere, adding reaction monomers of 2,4, 6-trimethyl-pyrylium tetrafluoroborate, 1,3, 5-tri (4-aldehyde biphenyl) -1,3, 5-triazine, solvent anhydrous n-butyl alcohol and o-dichlorobenzene and catalyst p-toluenesulfonic acid monohydrate into an ampoule bottle; step 2: sealing the ampoule bottle with butane combustible gas, transferring the ampoule bottle into a constant-temperature oven, and carrying out heating reaction; and step 3: and after the heating reaction is finished, cooling the ampoule bottle, carrying out suction filtration, collecting the precipitate, washing the precipitate, drying to obtain an organic framework material ivCOF-O, and further carrying out reaction to obtain vCOF-N. The COFs material has high crystallinity, high specific surface area, uniform pore channel structure, absorption in a visible light range, excellent thermal stability and uniform two-dimensional lamellar morphology.
Description
Technical Field
The invention relates to the technical field of covalent organic framework materials, in particular to a preparation method of a carbon-carbon double bond connected two-dimensional conjugated organic framework material.
Background
Conjugated Organic Frameworks (COFs) are porous organic materials which are formed by connecting light elements (C, H, O, N, B and the like) in two-dimensional or three-dimensional space through covalent bonds and have long-range ordered structures and regular pore channel structures through reversible polymerization under thermodynamic control. The Yaghi project group in 2005 reported the first two-dimensional COF based on boronate ester bond connection (Science,2005,310,1166-1170), which benefits from the rich designability of organic monomers, the ordering and regularity of crystalline materials and the diversity of covalent bond forms, and COFs have incomparable advantages of other traditional porous materials such as molecular sieves, porous polymers, metal organic framework Materials (MOFs), such as low density, high specific surface area, easy modification and functionalization, etc. Therefore, at present, COFs materials have been widely researched and show excellent application prospects in the fields of gas storage and separation, heterogeneous catalysis, energy storage materials, photoelectricity, sensing, drug delivery and the like. The dynamic covalent bond developed for COF synthesis at present mainly includes borate ester bond, imine bond, acylhydrazone bond, imide bond, etc., and such chemical bonds have good reversibility, but have great problems in aspects of stability, conjugation, semiconductor activity, etc.
In 2016, Zhang group reported a cyano-substituted carbon-carbon double bond bridged fully sp2 carbon conjugated COF material (Polymer. chem.,2016,7, 4176-4181). The novel COF material with carbon-carbon double bond connection shows ultrahigh stability different from the prior art, and has an all-carbon skeleton and effective pi electron delocalization. Recently, the formation of unsubstituted carbon-carbon double bonds by the brain venturi condensation (Knoevenagel condensation) reaction has become a sustainable and reliable method for extending covalent organic framework systems. Due to the large number of monomers available for brain wenger condensation polymerization, the geometry, electronics, and topology of such COFs connected by carbon-carbon double bonds can be carefully and rationally designed. In addition to excellent stability, several recently reported unsubstituted double-bonded COFs also exhibit some novel features. For example, the Yaghi project group reports vinyl-bridged COFs that can support strong boron-based Lewis acids to catalyze Diels-Alder reactions (J.Am.chem.Soc.,2019,141, 6848-6852). Thomas et al found the photocyclization of vinyl groups bridging vinyl bonds between adjacent layers of COFs (Angew. chem. int. Ed.2019,58, 14865-14870). Perepichka et al found that the synthetic polymers had high quantum yields (up to 50%), and that the photophysical properties of such COFs could be precisely adjusted by modification of the monomers (Angew. chem. int. Ed.2019,58, 13753-13757). However, the monomers that can be synthesized into two-dimensional COFs without a substituted carbon-carbon double bond are limited.
Accordingly, those skilled in the art have worked to develop more suitable monomers to synthesize such COF materials.
Disclosure of Invention
In view of the above-mentioned defects of the prior art, the technical problem to be solved by the present invention is to provide a method for preparing a two-dimensional covalent organic framework material with a carbon-carbon double bond linkage by using a pyrylium ion salt as a core and converting the pyrylium ion salt into a pyridine core, wherein 2,4, 6-trimethyl-pyrylium tetrafluoroborate is used as a core monomer, under the catalysis of an organic acid, a methyl group is activated to form an electron-rich vinyl ether structure, then nucleophilic attack is performed on aryl aldehyde, so that an unsubstituted carbon-carbon double bond is formed, and under the condition of solvothermal, two-dimensional COFs with a carbon-carbon double bond linkage are successfully synthesized. On this basis, the cationic skeleton is converted into a neutral skeleton by further reaction. The COFs material has a conjugated skeleton structure, high crystallinity, high specific surface area, good thermal stability and a two-dimensional layered structure.
In order to achieve the purpose, the invention provides a preparation method of a carbon-carbon double bond connected two-dimensional conjugated organic framework material, which comprises the following steps:
step 1: in a glove box under argon atmosphere, adding reaction monomers of 2,4, 6-trimethyl-pyrylium tetrafluoroborate, 1,3, 5-tri (4-aldehyde biphenyl) -1,3, 5-triazine, solvent anhydrous n-butanol and o-dichlorobenzene and catalyst p-toluenesulfonic acid monohydrate into a round-bottom solvent ampoule bottle;
step 2: sealing the ampoule bottle by using butane combustible gas, transferring the ampoule bottle into a constant-temperature oven, and carrying out heating reaction;
and step 3: and after the heating reaction is finished, naturally cooling the ampoule bottle to room temperature, collecting the precipitate by using a vacuum filtration method, washing the precipitate by using dichloromethane and methanol respectively, and then carrying out vacuum drying to finally obtain the organic framework material ivCOF-O.
Further, the method is characterized by also comprising the following steps:
and 4, step 4: adding the organic framework material ivCOF-O, anhydrous chloroform and ethanol into a thick-wall pressure-resistant bottle to obtain a mixed solution, adding ammonia water into the mixed solution under the nitrogen protection atmosphere, sealing the thick-wall pressure-resistant bottle by using a polytetrafluoroethylene spiral plug, transferring the thick-wall pressure-resistant bottle into a constant-temperature oil bath, and carrying out heating reaction.
And 5: and after the heating reaction is finished, naturally cooling the thick-wall pressure-resistant bottle to room temperature, collecting the precipitate by using a vacuum filtration method, washing the precipitate by using dichloromethane and methanol respectively, and then carrying out vacuum drying to finally obtain the organic framework material vCOF-N.
Further, in step 1, the 2,4, 6-trimethyl-pyrylium tetrafluoroborate, the 1,3, 5-tris (4-aldehydic biphenyl) -1,3, 5-triazine, the solvents anhydrous n-butanol and o-dichlorobenzene, and the p-toluenesulfonic acid monohydrate were used in amounts of 21mg, 62mg, 1.2mL, 2.8mL, and 50mg, respectively.
Further, in step 4, the organic framework material ivCOF-O, the anhydrous chloroform, the ethanol and the ammonia water were used in amounts of 20mg, 2mL, 6mL and 2mL, respectively.
Further, in step 2, the reaction temperature of the heating reaction is 120 ℃, and the reaction time is 72 hours.
Further, in step 3, the drying temperature of the vacuum drying is 60 ℃, and the drying time is 12 hours.
Further, in step 4, the reaction temperature of the heating reaction is 60 ℃, and the reaction time is 72 hours.
Further, in step 5, the drying temperature of the vacuum drying is 60 ℃, and the drying time is 12 hours.
Further, the pore size distribution of the organic framework material ivCOF-O and the vCOF-N are both concentrated at 2 nm.
Further, the visible light absorption band edge wavelengths of the organic framework material ivCOF-O and the vCOF-N are 590nm and 400nm respectively.
The invention uses 2,4, 6-trimethyl-pyrylium tetrafluoroborate as a core monomer for the first time, synthesizes the two-dimensional COFs material with carbon-carbon double bond connection under the condition of solvothermal, and converts the pyrylium cation framework into the pyridine nucleus neutral framework by a simple method. The COFs material obtained by the invention has high crystallinity, high specific surface area, uniform pore channel structure, good thermal stability and two-dimensional layered morphology. The COF prepared by the invention has abundant pyrylium ion salt units and two-dimensional layered morphology, thereby providing favorable conditions for the development and utilization of materials in the field of catalysis.
The conception, the specific structure and the technical effects of the present invention will be further described with reference to the accompanying drawings to fully understand the objects, the features and the effects of the present invention.
Drawings
FIG. 1 is a schematic diagram of the synthesis of carbon-carbon double bonded two-dimensional conjugated organic framework materials ivCOF-O and vCOF-N;
FIG. 2 is a powder X-ray diffraction pattern and a simulated X-ray diffraction pattern of a carbon-carbon double bonded two-dimensional covalent organic framework material ivCOF-O;
FIG. 3 is a powder X-ray diffraction pattern and a simulated X-ray diffraction pattern of a carbon-carbon double bonded two-dimensional covalent organic framework material vCOF-N;
FIG. 4 is a scanning electron micrograph of a carbon-carbon double bonded two-dimensional covalent organic framework material vCOF-N;
FIG. 5 is a scanning electron micrograph at another magnification of a carbon-carbon double bonded two-dimensional covalent organic framework material vCOF-N;
FIG. 6 is a scanning electron micrograph of a carbon-carbon double bonded two-dimensional covalent organic framework material ivCOF-O;
FIG. 7 is a scanning electron micrograph at another magnification of a carbon-carbon double bonded two dimensional covalent organic framework material ivCOF-O;
FIG. 8 is a transmission electron micrograph of a carbon-carbon double bonded two dimensional covalent organic framework material ivCOF-O;
FIG. 9 is a transmission electron micrograph of a carbon-carbon double bonded two dimensional covalent organic framework material vCOF-N;
FIG. 10 is a graph of a nitrogen adsorption-desorption isotherm spectrum and pore size distribution of a carbon-carbon double-bonded two-dimensional covalent organic framework material ivCOF-O;
FIG. 11 is a graph of a nitrogen adsorption-desorption isotherm spectrum and pore size distribution of a carbon-carbon double bonded two-dimensional covalent organic framework material vCOF-N;
FIG. 12 is a UV-VIS diffuse reflectance spectrum of carbon-carbon double bonded two-dimensional covalent organic framework materials ivCOF-O and vCOF-N;
FIG. 13 shows thermogravimetric analysis of carbon-carbon double-bonded two-dimensional covalent organic framework materials ivCOF-O and vCOF-N under nitrogen atmosphere.
Detailed Description
The technical contents of the preferred embodiments of the present invention will be more clearly and easily understood by referring to the drawings attached to the specification. The present invention may be embodied in many different forms of embodiments and the scope of the invention is not limited to the embodiments set forth herein.
The crystal structure of the two-dimensional covalent organic framework with two carbon-carbon double bonds connected is determined by powder X-ray diffraction and analyzed by theoretical simulation.
The porous structure of the two-dimensional covalent organic framework connected by the two carbon-carbon double bonds is characterized by a nitrogen adsorption and desorption test (Quantachrome autosorb iQ3 series full-automatic physical and chemical adsorption instrument): the obtained characterization results include nitrogen adsorption and desorption isotherms, BET specific surface areas and pore size distributions.
As shown in FIG. 1, in a glove box under argon atmosphere, 21mg of the reaction monomers 2,4, 6-trimethylpyranium tetrafluoroborate, 62mg of 1,3, 5-tris (4-formylbiphenyl) -1,3, 5-triazine, 1.2mL of anhydrous n-butanol and 2.8mL of o-dichlorobenzene, and 50mg of p-toluenesulfonic acid monohydrate were added to a round bottom solvent ampoule having a volume of 5 mL; sealing the ampoule bottle by using butane combustible gas, and transferring the ampoule bottle into a constant-temperature oven at 120 ℃ for reaction for 72 hours;
after the heating reaction is finished, naturally cooling the ampoule bottle to room temperature, collecting the precipitate by using a vacuum filtration method, washing the precipitate by using dichloromethane and methanol respectively, and then drying the precipitate in vacuum at 60 ℃ for 12 hours to finally obtain the cationic organic framework material ivCOF-O.
Adding 20mg of ivCOF-O, 2mL of anhydrous chloroform and 6mL of ethanol into a thick-wall pressure-resistant bottle with the volume of 15mL to obtain a mixed solution, adding 2mL of ammonia water into the mixed solution under the nitrogen protection atmosphere, sealing the thick-wall pressure-resistant bottle by using a polytetrafluoroethylene screw plug, transferring the thick-wall pressure-resistant bottle into a constant-temperature oil bath kettle at the temperature of 60 ℃, and heating and reacting for 72 hours. And after the heating reaction is finished, naturally cooling the thick-wall pressure-resistant bottle to room temperature, collecting the precipitate by using a vacuum filtration method, washing the precipitate by using dichloromethane and methanol respectively, and then carrying out vacuum drying to finally obtain the pyridine core organic framework material vCOF-N.
The resulting powder X-ray diffraction patterns of two carbon-carbon double bond-linked two-dimensional covalent organic frameworks, as shown in figures 2 and 3, are in agreement with the results of theoretical simulations. The results show that the prepared sample belongs to a hexagonal system and has good crystallinity.
Scanning electron micrographs of the two carbon-carbon double bond-linked two-dimensional covalent organic frameworks obtained are shown in fig. 4 to 7. The result shows that the prepared two-dimensional covalent organic frameworks connected by the carbon-carbon double bond have uniform two-dimensional layered morphology.
Transmission electron micrographs of the two carbon-carbon double bonds linked two-dimensional covalent organic frameworks obtained are shown in fig. 8 and 9. The result shows that the two prepared carbon-carbon double bond connected two-dimensional covalent organic frameworks have uniform lamellar morphology.
The resulting nitrogen adsorption isotherms and pore size distribution profiles for two carbon-carbon double bonds linking a two-dimensional covalent organic framework are shown in fig. 10 and 11. The result shows that the prepared two-dimensional covalent organic framework materials ivCOF-O and vCOF-N connected by the carbon-carbon double bond have porous structures, and the BET specific surface areas of the materials are 506m2g-1And 530m2g-1The pore size distribution is concentrated at 2 nm.
The resulting uv-vis diffuse reflectance spectra of two carbon-carbon double bond-linked two-dimensional covalent organic frameworks are shown in figure 12. The result shows that the absorption band edge wavelengths of the two prepared carbon-carbon double bonds connected with the two-dimensional covalent organic frameworks ivCOF-O and vCOF-N are 590nm and 400nm respectively, and a part of visible light wave bands are covered.
The resulting thermogravimetric plot of two carbon-carbon double bonds linked two-dimensional covalent organic framework materials is shown in fig. 13. The result shows that the residual mass of the prepared two carbon-carbon double bond connected two-dimensional covalent organic framework materials ivCOF-O and vCOF-N under the nitrogen atmosphere at 800 ℃ is respectively 62% and 54%, and the prepared organic framework materials have good thermal stability.
The foregoing detailed description of the preferred embodiments of the invention has been presented. It should be understood that numerous modifications and variations could be devised by those skilled in the art in light of the present teachings without departing from the inventive concept. Therefore, the technical solutions available to those skilled in the art through logic analysis, reasoning and limited experiments based on the prior art according to the concept of the present invention should be within the scope of protection defined by the claims.
Claims (12)
1. A preparation method of a carbon-carbon double bond connected two-dimensional conjugated organic framework material is characterized by comprising the following steps:
step 1: in a glove box under argon atmosphere, adding reaction monomers of 2,4, 6-trimethyl-pyrylium tetrafluoroborate, 2,4, 6-tri (4' -aldehyde biphenyl-4-yl) -1,3, 5-triazine, solvent anhydrous n-butyl alcohol and o-dichlorobenzene and catalyst p-toluenesulfonic acid monohydrate into a round-bottom solvent ampoule bottle;
step 2: sealing the ampoule bottle by using butane combustible gas, transferring the ampoule bottle into a constant-temperature oven, and carrying out heating reaction;
and step 3: and after the heating reaction is finished, naturally cooling the ampoule bottle to room temperature, collecting the precipitate by using a vacuum filtration method, washing the precipitate by using dichloromethane and methanol respectively, and then carrying out vacuum drying to finally obtain the organic framework material ivCOF-O.
2. The method for preparing a carbon-carbon double bond linked two-dimensional conjugated organic framework material according to claim 1, further comprising the steps of:
and 4, step 4: adding the organic framework material ivCOF-O, anhydrous chloroform and ethanol into a thick-wall pressure-resistant bottle to obtain a mixed solution, adding ammonia water into the mixed solution under the nitrogen protection atmosphere, sealing the thick-wall pressure-resistant bottle by using a polytetrafluoroethylene spiral plug, transferring the thick-wall pressure-resistant bottle into a constant-temperature oil bath, and carrying out heating reaction;
and 5: and after the heating reaction is finished, naturally cooling the thick-wall pressure-resistant bottle to room temperature, collecting the precipitate by using a vacuum filtration method, washing the precipitate by using dichloromethane and methanol respectively, and then carrying out vacuum drying to finally obtain the organic framework material vCOF-N.
3. The method for preparing a carbon-carbon double bond linked two-dimensional conjugated organic framework material according to claim 1, wherein in step 1, the 2,4, 6-trimethyl-pyrylium tetrafluoroborate, the 2,4, 6-tris (4' -aldenybiphenyl-4-yl) -1,3, 5-triazine, the solvents anhydrous n-butanol and o-dichlorobenzene, and the p-toluenesulfonic acid monohydrate are used in amounts of 21mg, 62mg, 1.2mL, 2.8mL, and 50mg, respectively.
4. The method for preparing a carbon-carbon double bonded two-dimensional conjugated organic framework material according to claim 2, wherein in the step 4, the amounts of the organic framework material ivCOF-O, the anhydrous chloroform, the ethanol and the ammonia water are 20mg, 2mL, 6mL and 2mL, respectively.
5. The method for preparing a carbon-carbon double bond linked two-dimensional conjugated organic framework material according to claim 1, wherein in the step 2, the heating reaction is carried out at a reaction temperature of 120 ℃ for a reaction time of 72 hours.
6. The method for preparing a carbon-carbon double bond linked two-dimensional conjugated organic framework material according to claim 1, wherein in the step 3, the drying temperature of the vacuum drying is 60 ℃ and the drying time is 12 hours.
7. The method for preparing a carbon-carbon double bond linked two-dimensional conjugated organic framework material according to claim 2, wherein in the step 4, the heating reaction is carried out at a reaction temperature of 60 ℃ for 72 hours.
8. The method for preparing a carbon-carbon double bond linked two-dimensional conjugated organic framework material according to claim 2, wherein in the step 5, the drying temperature of the vacuum drying is 60 ℃ and the drying time is 12 hours.
9. The method for preparing a carbon-carbon double bonded two-dimensional conjugated organic framework material according to claim 1, wherein the organic framework material ivCOF-O pore size distribution is concentrated at 2 nm.
10. The method according to claim 2, wherein the organic framework material vCOF-N has a pore size distribution centered at 2 nm.
11. The method according to claim 1, wherein the organic framework material ivCOF-O has a wavelength of 590nm at the visible light absorption band edge.
12. The method for preparing a carbon-carbon double bond linked two-dimensional conjugated organic framework material according to claim 2, wherein the visible light absorption band edge wavelength of the organic framework material vCOF-N is 400 nm.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111057221A (en) * | 2019-12-26 | 2020-04-24 | 上海交通大学 | Carbon-carbon double-bond connected organic framework ultra-long nanofiber material and preparation method thereof |
| CN111848897A (en) * | 2020-07-15 | 2020-10-30 | 上海交通大学 | Preparation method of covalent organic framework material formed by alternately connecting two types of octapole conjugated structural units through carbon-carbon double bonds |
| CN112500545A (en) * | 2020-11-27 | 2021-03-16 | 西安理工大学 | Preparation method of lamellar two-dimensional porous covalent organic framework material |
| CN112708090A (en) * | 2020-12-25 | 2021-04-27 | 上海交通大学 | Carbon-carbon double bond bridged covalent organic framework material and preparation method thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111057221A (en) * | 2019-12-26 | 2020-04-24 | 上海交通大学 | Carbon-carbon double-bond connected organic framework ultra-long nanofiber material and preparation method thereof |
| CN111848897A (en) * | 2020-07-15 | 2020-10-30 | 上海交通大学 | Preparation method of covalent organic framework material formed by alternately connecting two types of octapole conjugated structural units through carbon-carbon double bonds |
| CN112500545A (en) * | 2020-11-27 | 2021-03-16 | 西安理工大学 | Preparation method of lamellar two-dimensional porous covalent organic framework material |
| CN112708090A (en) * | 2020-12-25 | 2021-04-27 | 上海交通大学 | Carbon-carbon double bond bridged covalent organic framework material and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| Fancheng Meng,et al..Synthesis of Ionic Vinylene-Linked Covalent Organic Frameworks through Quaternization-Activated Knoevenagel Condensation.《Angew. Chem. Int. Ed.》.2021,13614-13620. * |
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