CN115678032B - Preparation method and application of olefin-linked cationic three-dimensional covalent organic framework - Google Patents
Preparation method and application of olefin-linked cationic three-dimensional covalent organic framework Download PDFInfo
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Abstract
The invention discloses a preparation method and application of an olefin-linked cationic three-dimensional covalent organic framework, and belongs to the technical field of environmental protection. The invention directly synthesizes the three-dimensional covalent organic framework linked with porous olefin with positive charges through the aldol condensation reaction promoted by quaternization, the positive charge framework with regular porosity is beneficial to the rapid transmission of perrhenate ions, and the local hydrophobic environment can also improve the adsorption selectivity of the perrhenate ions. The preparation method of the olefin-linked cation three-dimensional covalent organic framework is simple, clear in structure, good in stability, high in adsorption capacity to perrhenate ions, rapid in adsorption kinetics and good in selectivity.
Description
Technical Field
The invention relates to the technical field of environmental protection, in particular to a preparation method and application of an olefin-linked cationic three-dimensional covalent organic framework.
Background
Technetium is a long life (t) 1/2 ＝2.13×10 5 Annual) radioisotope, the high content of nuclear waste, is one of the sources of strong radioactive pollution. Due to pertechnetate (TcO) 4 - ) And perrhenate (ReO) 4 - ) With similar thermodynamic parameters, electron distribution and spatial configuration, researchers often employ non-radioactive ReO 4 - As TcO 4 - Alternatives to chemical behavior have been the subject of research. The ion exchange method is the most promising capture of ReO at present due to the simple process, environmental protection and low cost 4 - /TcO 4 - One of the methods of (a). Many cationic materials have been used to capture ReO 4 - /TcO 4 - But still has the problems of slow adsorption kinetics, poor chemical stability and the like; in particular in natural waste systems, in which large amounts of SO are present 4 2- And NO 3 - In the case of (a), selective capture of ReO 4 - /TcO 4 - Is a major scientific problem and technical challenge (D.Banerjee, D.Kim, M.J.Schweiger, A.A.Kruger, P.K.Thallapally, remote of TcO) 4 - ions from solution:materials and future outlook,Chem.Soc.Rev.2016,45,10,2724-2739)。
Covalent Organic Frameworks (COFs) are a novel porous crystalline material linked by strong covalent bonds between light atoms. Unlike conventional polymers, COFs can precisely link different types of molecules into two-or three-dimensional networks with structural periodicity and intrinsic porosity (P.J.Waller, F.Gandara and o.m. yaghi, acc, chemistry of covalent organic frameworks, chem.res.,2015,48,3053). To date, COFs research has mostly focused on two-dimensional structures with overlapping AA or staggered AB stacking patterns. Generally, two-dimensional COFs only contain one-dimensional channels, while three-dimensional COFs have more complex pore structures and more void frames, which are more beneficial for applications such as separation and catalysis. Furthermore, due to the more empty frames, high specific surface area, low density and abundant readily available active sites are often observed in three-dimensional COFs, which is difficult to achieve in two-dimensional COFs. In three-dimensional COFs synthesis strategies, the most commonly used dynamic covalent bonds rely on imine and borate linkages, are relatively poor in stability and weak in electron delocalization, and are difficult to apply practically (Ding H, li J, xie G, lin G, chen R, peng Z, yang C, wang B, sun J, wang c.an AIEgen-based 3D covalent organic framework for white light-patterning diodes, nat.Commun,2018,9,5234). Thus, recognition of structures and development of novel linking covalent bonds remain major challenges facing three-dimensional COFs.
The advent of olefin-linked COFs overcomes the limitations of current dynamic covalent bonds. The irreversibility of the c=c bond allows the framework to have excellent stability under severe conditions and provides extended pi conjugation throughout the framework to achieve efficient electron transfer, showing great potential for application in the field of photocatalysis. Furthermore, synthesis of ion-functionalized three-dimensional COFs is also a great challenge due to the limitations of building blocks and complex post-modification processes, where almost all three-dimensional COFs are neutral backbones.
Disclosure of Invention
The invention aims to provide a preparation method and application of an olefin-linked cationic three-dimensional covalent organic framework. According to the invention, the olefin-linked cationic three-dimensional covalent organic framework is synthesized by taking 1,2, 5-trimethyl pyrazinium iodide and tetra (4-formylphenyl) methane as raw materials, and the material can adsorb perrhenate ions without post-modification, so that the problems that the distribution of the sites cannot be controlled and the adsorption capacity is low and dynamics is slow due to less functional group load caused by combining the binding sites into holes through a post-modification strategy are solved. The olefin-linked cationic three-dimensional covalent organic framework prepared by the invention has the advantages of open three-dimensional hydrophobic channel, large specific surface area and good stability, has high adsorption capacity, quick adsorption kinetics and good selectivity on perrhenate ions, and realizes the efficient removal of perrhenate ions in simulated waste liquid. In addition, the olefin-linked cationic three-dimensional covalent organic framework prepared by the method has good reusability, is favorable for economic saving and sustainable development of ecological environment, and has good application prospect.
The invention is realized by the following technical scheme:
the invention provides a preparation method of an olefin-linked cationic three-dimensional covalent organic framework, which comprises the following steps:
1) 1,2, 5-trimethyl pyrazinium iodide and tetra (4-formylphenyl) methane are taken as reaction raw materials, and then a catalyst and an organic solvent are added, and the mixture is uniformly mixed by ultrasonic to obtain a reaction mixed solution;
2) The obtained reaction mixed solution is subjected to freeze-thawing cycle degassing, is subjected to flame sealing and then is subjected to reaction at 120-180 ℃ for 3-6 days, cooling, filtering, collecting precipitate, neutralizing, washing and drying to obtain the olefin-linked cation three-dimensional covalent organic framework.
Further, the molar ratio of 1,2, 5-trimethylpyrazinium iodide to tetrakis (4-formylphenyl) methane in step 1) is (1-3): 1.
Further, the catalyst in the step 1) is trifluoroacetic acid.
Further, the organic solvent in the step 1) is one or more of mesitylene, 1, 4-dioxane or acetonitrile.
The invention also provides the method for adsorbing the ReO by using the olefin-linked cationic three-dimensional covalent organic framework 4 - Is used in the field of applications.
Further, the olefin-linked cationic three-dimensional covalent organic framework is capable of selectively removing ReO under conditions of coexistence of multiple competing anions 4 - The method comprises the steps of carrying out a first treatment on the surface of the The plurality of competing anions includes SO 4 2- 、NO 3 - 、PO 4 3- And CO 3 2- 。
Further, the olefin-linked cationic three-dimensional covalent organic framework undergoes 5 adsorption/desorption cycles followed by a reaction for ReO 4 - The removal rate of the catalyst can still reach more than 97 percent.
Compared with the prior art, the invention has the beneficial effects that:
(1) The synthesized olefin-linked cationic three-dimensional covalent organic framework can adsorb ReO without post-modification 4 - The problems of low adsorption capacity and slow kinetics caused by the inability to control the distribution of the binding sites and less functional group loading due to the binding sites incorporated into the network by post-modification strategies are overcome.
(2) The irreversibility of the c=c bond allows the olefinic-linked cationic three-dimensional covalent organic framework prepared according to the invention to have excellent stability under extreme conditions.
(3) The olefin-linked cationic three-dimensional covalent organic framework prepared by the invention has positive charge framework with regular porosity, is favorable for rapid transmission of perrhenate ions, and has high adsorption capacity and rapid adsorption kinetics.
(4) The olefin-linked cation three-dimensional covalent organic framework prepared by the invention has a three-dimensional hydrophobic channel and has good adsorption selectivity on perrhenate ions.
(5) The olefin-linked cationic three-dimensional covalent organic framework prepared by the invention can be reused, and is beneficial to economic saving and sustainable development of ecological environment.
(6) The olefin-linked cation three-dimensional covalent organic framework prepared by the method has the advantages of open three-dimensional channel, large specific surface area and good stability, and has high adsorption capacity, rapid adsorption kinetics and good selectivity for perrhenate ions, and the efficiency of removing perrhenate ions from simulated waste liquid is high.
Drawings
FIG. 1 is a schematic diagram of the synthetic route to TFPM-PZI.
Fig. 2 is a fourier transform infrared spectrum of TFPM, PZI and TFPM-PZI.
Fig. 3 is a PXRD pattern of TFPM-PZI.
FIG. 4 shows TFPM-PZI vs. ReO under different pH conditions 4 - Is drawn from the figure.
FIG. 5 is a diagram of TFPM-PZI versus ReO 4 - Adsorption isotherm plot of (c).
FIG. 6 is a diagram of TFPM-PZI versus ReO 4 - Adsorption kinetics of (c) are described.
FIG. 7 is a graph of TFPM-PZI versus ReO in the presence of competing anions 4 - Adsorption selectivity graph of (2).
Fig. 8 is a cyclic usage diagram of TFPM-PZI.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be clearly and completely described in the following examples. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
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. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and/or" as used herein includes any and all combinations of one or more of the associated listed items.
Example 1: preparation and characterization of an olefin-linked cationic three-dimensional covalent organic framework
1,2, 5-trimethylpyrazinium iodide (PZI, 12.75 mg) and tetrakis (4-formylphenyl) methane (TFPM, 11.03 mg) were added to a Pyrex tube, trifluoroacetic acid (0.30 mL), mesitylene (0.67 mL), 1, 4-dioxane (0.67 mL) and acetonitrile (0.037 mL) were further added, the mixture was sonicated for 10 minutes to mix it uniformly, and degassed by three freeze-pump-thaw cycles, the Pyrex tube flame sealed and placed in an oven to react at 150 ℃ for 72 hours, cooled to room temperature, the reaction product was isolated by vacuum filtration to remove acid by neutralization with a methanol solution containing aqueous ammonia, and acetone, methanol, ethanol were sequentially washed to precipitate, and after pumping to dryness, the obtained solid was dried under vacuum at 120 ℃ for 12 hours to obtain an olefin-linked cationic three-dimensional covalent organic framework (TFPM-ppm).
FIG. 1 is a schematic diagram of the synthetic route to TFPM-PZI.
Fig. 2 is a fourier transform infrared spectrum of TFPM, PZI and TFPM-PZI. As can be seen from FIG. 2, the Fourier transform infrared spectrum (FT-IR) of TFPM and PZI is compared with that of 1594cm for TFPM-PZI -1 A new absorption band corresponding to C=C stretching vibration occurs at the same time of 1702cm -1 The c=o tensile vibration absorption peak corresponding to TFPM disappeared, indicating that aldol condensation reaction between TFPM and PZI occurred to prepare an olefin-linked three-dimensional covalent organic framework.
The crystallinity of TFPM-PZI was characterized by X-ray powder diffraction (PXRD). FIG. 3 is a PXRD pattern of TFPM-PZI measured experimentally and simulated by Material studio software. As can be seen from FIG. 3, TFPM-PZI shows a strong diffraction peak at 7.41 degrees, indicating that the three-dimensional covalent organic framework synthesized by the method of the invention has good crystallinity.
Example 2: pH to TFPM-PZI adsorption ReO 4 - Influence of (2)
The effect of pH on the adsorbent performance was investigated. Regulation of ReO with nitric acid or sodium hydroxide solution 4 - The pH of the aqueous solution is 2-10, 10mg of TFPM-PZI is added to 20mL of ReO with a concentration of 28mg/L 4 - Oscillating for 12 hours at constant temperature in the aqueous solution, filtering with a 0.22 mu m microporous filter membrane, collecting filtrate, and measuring ReO in the filtrate by adopting inductively coupled plasma mass spectrometry 4 - Content, calculate TFPM-PZI vs. ReO 4 - Is used as a catalyst. The adsorption capacity is calculated by the following formula: q e ＝(C o -C e ) M×v; wherein V is the volume of the solution, unit L, m is the amount of the olefin-linked cationic three-dimensional covalent organic framework, unit g, C o Is ReO 4 - Initial concentration in mg/L, C e Is ReO 4 - Equilibrium concentration in mg/L.
FIG. 4 is a graph of TFPM-PZI versus ReO at different pH conditions 4 - Is drawn from the figure. As can be seen from FIG. 4, TFPM-PZI is specific to ReO in the pH range of 2-10 4 - Is very high even at pH 2 for TFPM-PZI to ReO 4 - The removal rate of (2) is still more than 90%, probably due to the irreversibility of the C=C bond, so that the synthesized TFPM-PZI has excellent stability under extreme conditions, and positive charges on the framework can effectively capture ReO 4 - 。
Example 3: TFPM-PZI pair ReO 4 - Adsorption of (3)
Study of ReO 4 - The effect of initial concentration on TFPM-PZI adsorption performance. Regulation of ReO with nitric acid or sodium hydroxide solution 4 - The aqueous solution has a pH of 7, 5mg of TFPM-PZI is added to 10mL of aqueous solution containing different concentrations (0-700 mg/L) of ReO 4 - Oscillating for 12 hours at constant temperature, filtering with a 0.22 μm microporous filter membrane, collecting filtrate, and measuring ReO in the filtrate by inductively coupled plasma mass spectrometry 4 - Content, calculate TFPM-PZI vs. ReO 4 - Is plotted against ReO for TFPM-PZI 4 - Is a solid phase, and is a solid phase. FIG. 5 is a TFPM-PZI versus ReO 4 - Adsorption isotherm plot of (c). As can be seen from FIG. 5, TFPM-PZI pair ReO 4 - With the adsorption capacity of ReO 4 - The increase in concentration increases rapidly until an equilibrium state is reached. The isothermal adsorption process is found to be in accordance with Langmuir model through fitting, which shows that TFPM-PZI pair ReO 4 - Is a single layer adsorption.
Study of ReO 4 - Adsorption kinetics at pH 7. Will 10mgTFPM-PZI was added to 20mL of ReO at a concentration of 28mg/L 4 - Stirring in water solution for desired time (30 s,1min,2min,5min,10min,20min,40min,60 min), taking out 0.5 ml sample, filtering with 0.22 microporous filter membrane, collecting filtrate, and measuring ReO in filtrate by inductively coupled plasma mass spectrometry 4 - Content, calculate TFPM-PZI vs. ReO 4 - Mapping TFPM-PZI versus ReO under different contact time conditions 4 - Is a removal efficiency map of (2). FIG. 6 is a TFPM-PZI versus ReO 4 - Adsorption kinetics of (c) are described. As can be seen from FIG. 6, TFPM-PZI pair ReO 4 - The adsorption capacity of (2) increases with the adsorption time, and over 95% of ReO can be removed after 2min 4 - . This is because the TFPM-PZI synthesized by the invention has positive charge framework with regular porosity and is beneficial to ReO 4 - And the adsorption kinetics are fast.
10mg of TFPM-PZI was added to 10mL of a mixture containing 25mg/L of ReO 4 - 25mg/L competing anion (SO 4 2- 、NO 3 - 、PO 4 3- And CO 3 2- ) Oscillating for 12 hours at constant temperature, filtering with a 0.22 μm microporous filter membrane, collecting filtrate, and measuring ReO in the filtrate by inductively coupled plasma mass spectrometry 4 - Content investigation of TFPM-PZI vs. ReO 4 - Selectivity of adsorption. FIG. 7 is a graph of TFPM-PZI versus ReO in the presence of competing anions 4 - Adsorption selectivity graph of (2). As can be seen from FIG. 7, in SO 4 2- 、NO 3 - 、PO 4 3- And CO 3 2- TFPM-PZI pair ReO in the presence of anions 4 Has excellent removal efficiency, indicating that TFPM-PZI pair ReO 4 - Has good selectivity. This may be due to ReO 4 - The three-dimensional hydrophobic channel environment of the synthesized TFPM-PZI of the invention has stronger hydrophobicity than other coexisting anions with higher charge density, and the three-dimensional hydrophobic channel environment of the synthesized TFPM-PZI has the same charge density as the three-dimensional hydrophobic channel environment of the synthesized TFPM-PZI 4 - The adsorption selectivity of (C) is better.
When the adsorbent/solution ratio was 5mg/mL, the simulation was performedReO in waste liquid of Hanford 4 - The removal rate of the catalyst reaches 86.4 percent.
Example 4: recycling of TFPM-PZI
10mg of TFPM-PZI was added to 20mL of ReO at a concentration of 28mg/L 4 - Oscillating for 12 hours at constant temperature in the aqueous solution, filtering with a 0.22 mu m microporous filter membrane, collecting filtrate, and measuring ReO in the filtrate by adopting inductively coupled plasma mass spectrometry 4 - Content investigation of TFPM-PZI vs. ReO 4 - Is not limited, and the removal rate of the catalyst is not limited. Will adsorb ReO 4 - The TFPM-PZI of (C) was regenerated in 3M NaCl solution at 80 ℃, washed with absolute ethanol and water and dried under vacuum at 120℃overnight to give regenerated TFPM-PZI. Fig. 8 is a cyclic usage diagram of TFPM-PZI. As can be seen from FIG. 8, after 5 adsorption/desorption cycles, TFPM-PZI pair ReO 4 - The removal rate of the catalyst can still reach more than 97%, which shows that the TFPM-PZI prepared by the method has good recycling property.
According to the invention, the olefin-linked cationic three-dimensional covalent organic framework with high crystallinity and good stability is synthesized by a solvothermal method, and positive charge framework with regular porosity and local hydrophobic environment are favorable for selectively capturing relatively hydrophobic ReO 4 - /TcO 4 - The method comprises the steps of carrying out a first treatment on the surface of the Its open three-dimensional channels, large specific surface area and readily accessible binding sites contribute to ReO 4 - /TcO 4 - To accelerate the ion exchange process; the 5 adsorption/desorption cycle results show that the TFPM-PZI prepared by the invention has good recycling performance. The olefin-linked cationic three-dimensional covalent organic framework prepared by the invention has the advantages of definite structure, high adsorption capacity, rapid adsorption kinetics and good selectivity, and can be used for simulating ReO in waste liquid 4 - Has good application prospect.
The embodiments described above represent only a few preferred embodiments of the present invention, which are described in more detail and are not intended to limit the present invention. It should be noted that various changes and modifications can be made to the present invention by those skilled in the art, and any modifications, equivalent substitutions, improvements, etc. which are within the spirit and principle of the present invention are included in the scope of the present invention.
Claims (7)
1. A method for preparing an olefin-linked cationic three-dimensional covalent organic framework, comprising the steps of:
1) 1,2, 5-trimethyl pyrazinium iodide and tetra (4-formylphenyl) methane are taken as reaction raw materials, and then a catalyst and an organic solvent are added, and the mixture is uniformly mixed by ultrasonic to obtain a reaction mixed solution;
2) The obtained reaction mixed solution is subjected to freeze-thawing cycle degassing, is subjected to flame sealing and then is subjected to reaction at 120-180 ℃ for 3-6 days, cooling, filtering, collecting precipitate, neutralizing, washing and drying to obtain the olefin-linked cation three-dimensional covalent organic framework.
2. The method for preparing an olefin-linked cationic three-dimensional covalent organic framework according to claim 1, wherein the molar ratio of 1,2, 5-trimethylpyrazinium iodide to tetrakis (4-formylphenyl) methane in step 1) is (1-3): 1.
3. The method of preparing an olefin-linked cationic three-dimensional covalent organic framework according to claim 1, wherein the catalyst of step 1) is trifluoroacetic acid.
4. The method of preparing an olefin-linked cationic three-dimensional covalent organic framework according to claim 1, wherein the organic solvent of step 1) is one or more of mesitylene, 1, 4-dioxane, or acetonitrile.
5. The method according to any one of claims 1 to 4, wherein the olefin-linked cationic three-dimensional covalent organic framework is used for adsorbing ReO 4 - Is used in the field of applications.
6. The olefin-linked cationic three-dimensional covalent organic framework of claim 5 in adsorbing ReO 4 - Wherein the olefin-linked cation is three-dimensionalCovalent organic frameworks capable of selective removal of ReO under conditions of coexistence of multiple competing anions 4 - The method comprises the steps of carrying out a first treatment on the surface of the The plurality of competing anions includes SO 4 2- 、NO 3 - 、PO 4 3- And CO 3 2- 。
7. The olefin-linked cationic three-dimensional covalent organic framework of claim 5 in adsorbing ReO 4 - The application of the catalyst is characterized in that the olefin-linked cationic three-dimensional covalent organic framework is subjected to 5 adsorption/desorption cycles and then subjected to a reaction for ReO 4 - The removal rate of the catalyst can still reach more than 97 percent.
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