CN114369230B - Eutectic solvent modified alkaline amino conjugated microporous polymer and preparation method thereof - Google Patents
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Abstract
The invention provides a eutectic solvent modified alkaline amino conjugated microporous polymer and a preparation method thereof, the preparation method mainly relates to a Sonogashira-Hagihara cross coupling chemistry catalyzed by tetra (triphenylphosphine) palladium and copper iodide, and a conjugated microporous polymer (NH) containing alkaline amino functional groups is synthesized 2 -CMP); then through eutectic solvent modification, a eutectic solvent modified alkaline amino conjugated microporous polymer (DESs-NH) is synthesized 2 -CMP). The preparation method has the advantages of simple process, readily available raw materials, easy implementation and capability of preparing DESs-NH 2 CMP, improved hydrophobicity. And by modification of DESs, to NH 2 CMP is multi-element doped. The obtained eutectic solvent modified alkaline amino conjugated microporous polymer has high application value in adsorption, electrochemistry and the like.
Description
Technical Field
The invention relates to the technical field of preparation of conjugated microporous polymers, in particular to an alkaline amino conjugated microporous polymer modified by a eutectic solvent and a preparation method thereof.
Background
The microporous material is focused on the surface and can interact with atoms, ions and molecules in the whole pores, and has potential application prospect in the fields of adsorption and separation, environmental protection, heterogeneous catalysis and the like. Since 2007, conjugated Microporous Polymers (CMP) have been an important class of microporous materials. CMP is a unique class of microporous materials, formed solely by covalent bonds of light elements (carbon, hydrogen, etc.), which combine pi-pi conjugation with a permanent microporous framework. However, in the prior art, a wide range of synthetic building blocks and network formation reactions provide a variety of CMP with different properties and structures, but the vast majority of CMP produced are hydrophobic powders. Because of its hydrophobic nature, it has less application in adsorption and extraction. In addition, the elements of CMP are relatively single, and CMP materials are more limited in their application.
Disclosure of Invention
The invention aims to provide an alkaline amino conjugated microporous polymer modified by a eutectic solvent and a preparation method thereof, which are used for solving the problems that a CMP material is single and less in adsorption and extraction aspects in the prior art.
The technical scheme adopted by the invention is as follows: the eutectic solvent modified alkaline amino conjugated microporous polymer is prepared by uniformly mixing a eutectic solvent and an alkaline amino conjugated microporous polymer, heating at 70-90 ℃ for 6-10 hours, separating a solid-liquid mixture after the reaction is finished, and washing and drying the obtained solid to obtain the eutectic solvent modified alkaline amino conjugated microporous polymer; wherein the eutectic solvent is ethylene glycol and choline chloride, phenol and choline chloride, urea and choline chloride or methylsulfonic acid and choline chloride; the structural formula of the basic amino conjugated microporous polymer is shown as follows:
the molar ratio of the eutectic solvent to the basic amino conjugated microporous polymer is 10-12:1.
The basic amino conjugated microporous polymer is prepared by the following method:
placing 1,3, 5-triacetylene benzene, 2,4, 6-tribromoaniline, tetra (triphenylphosphine) palladium and copper iodide in a reaction vessel, adding N, N-dimethylformamide and 2, 6-diisopropylaniline, introducing circulating argon after air is removed, stirring the mixture for 20-28h under 70-90 ℃ oil bath, separating solid and liquid mixture after the reaction is finished, washing the obtained solid, performing Soxhlet extraction on methanol, and drying to obtain the alkaline amino conjugated microporous polymer.
The reaction formula for preparing the basic amino conjugated microporous polymer is shown as follows:
the mass ratio of the 1,3, 5-triacetylene benzene to the 2,4, 6-tribromoaniline is 0.4-0.5:1; the mass ratio of the 1,3, 5-triacetylene benzene to the copper iodide is 9-10:1.
The mass ratio of the tetra (triphenylphosphine) palladium to the copper iodide is 4-6:1; the volume ratio of the solvent N, N-dimethylformamide to the 2, 6-diisopropylaniline is 1-2:1.
The preparation method of the alkaline amino conjugated microporous polymer modified by the eutectic solvent comprises the steps of uniformly mixing the eutectic solvent and the alkaline amino conjugated microporous polymer, heating at 70-90 ℃ for 6-10 hours, separating a solid-liquid mixture after the reaction is finished, and washing and drying the obtained solid to obtain the alkaline amino conjugated microporous polymer modified by the eutectic solvent; wherein the eutectic solvent is ethylene glycol and choline chloride, phenol and choline chloride, urea and choline chloride or methylsulfonic acid and choline chloride; the structural formula of the basic amino conjugated microporous polymer is shown as follows:
the molar ratio of the eutectic solvent to the basic amino conjugated microporous polymer is 10-12:1.
The basic amino conjugated microporous polymer is prepared by the following method:
placing 1,3, 5-triacetylene benzene, 2,4, 6-tribromoaniline, tetra (triphenylphosphine) palladium and copper iodide in a reaction vessel, adding N, N-dimethylformamide and 2, 6-diisopropylaniline, introducing circulating argon after air is removed, stirring the mixture for 20-28h under 70-90 ℃ oil bath, separating solid and liquid mixture after the reaction is finished, washing the obtained solid, performing Soxhlet extraction on methanol, and drying to obtain the alkaline amino conjugated microporous polymer; the reaction formula for preparing the basic amino conjugated microporous polymer is shown as follows:
the mass ratio of the 1,3, 5-triacetylene benzene to the 2,4, 6-tribromoaniline is 0.4-0.5:1; the mass ratio of the 1,3, 5-triacetylene benzene to the copper iodide is 9-10:1; the mass ratio of the tetra (triphenylphosphine) palladium to the copper iodide is 4-6:1; the volume ratio of the solvent N, N-dimethylformamide to the 2, 6-diisopropylaniline is 1-2:1.
The preparation method mainly relates to a Sonogashira-Hagihara cross-coupling chemistry catalyzed by tetra (triphenylphosphine) palladium and copper iodide, and synthesizes a conjugated microporous polymer (NH) containing basic amino functional groups 2 -CMP); then modifying by eutectic solvent (Deep Eutectic Solvents) to synthesize the alkaline amino conjugated microporous polymer (DESs-NH) modified by the eutectic solvent 2 -CMP）。
The preparation method has simple process and easily obtained raw materialsEasy to implement, DESs-NH prepared 2 CMP, improved hydrophobicity. And by modification of DESs, to NH 2 CMP is multi-element doped. The obtained eutectic solvent modified alkaline amino conjugated microporous polymer has high application value.
The beneficial effects of the invention are as follows:
1) The invention ensures that the conjugated microporous polymer material is functionalized by amino, thereby providing a method for selecting hydrophilic functional groups from reaction monomers and providing a new way for improving the hydrophobic conjugated microporous polymer material;
2) Modifying by using different eutectic solvents to obtain a basic amino conjugated microporous polymer material, wherein the hydrophobicity of the basic amino conjugated microporous polymer material is changed through characterization data; and the alkaline amino conjugated microporous polymer is subjected to multielement doping through modification of the eutectic solvent; the element types of the basic amino conjugated microporous polymer are increased, and the application value of the basic amino conjugated microporous polymer is improved.
Drawings
FIG. 1 is a NH of the present invention 2 -scanning electron microscopy of CMP.
FIG. 2 is a NH of the present invention 2 -an infrared map of CMP.
FIG. 3 is a NH of the present invention 2 X-ray diffraction pattern of CMP.
FIG. 4 is a NH of the present invention 2 -nitrogen adsorption-desorption profile of CMP.
FIG. 5 is a NH of the present invention 2 Thermogravimetric analysis of CMP.
FIG. 6 is a DESs-NH of the invention 2 -scanning electron microscopy of CMP.
FIG. 7 is a DESs-NH of the invention 2 -an infrared map of CMP.
FIG. 8 is a DESs-NH of the invention 2 -nitrogen adsorption-desorption profile of CMP.
Detailed Description
The invention will be described in detail with reference to the following specific examples, in which reagents and procedures not mentioned are carried out as usual in the art.
Example 1:
NH 2 -a CMP preparation step: 1,3, 5-Triacetylenyl (189.22 mg), 2,4, 6-tribromophenol (415.56 mg), tetrakis (triphenylphosphine) palladium (100.45 mg) and copper iodide (20.00 mg) were placed in a 25.00 mL three-neck round bottom flask, 4.00 mL DMF and 4.00 mL DIPA were added, and after removal of air, recycle argon was introduced. The mixture was stirred at 80 ℃ in an oil bath for about 24h, after the reaction, the solid-liquid mixture was suction-filtered, the upper layer solid was taken out, and the mixture was washed with dichloromethane and methanol solvent by filtration for several times, respectively, to remove unreacted monomers and catalyst. Finally, soxhlet extraction with methanol was carried out for 3 days, and the resulting product was dried at 100℃for 24 hours until the weight was constant. The resulting product was characterized and the results are shown in FIGS. 1-5.
DESs-NH 2 -a CMP preparation step: the eutectic solvent based on the alcoholic hydroxyl group consists of glycol and choline chloride in a molar ratio of 1:3, mixing and heating at 80 ℃; DESs (ethylene glycol: choline chloride) and NH 2 CMP at a molar ratio of 10:1 mixing, placing into 25.00 mL single-neck round bottom flask, ultrasonic treating for 30 min, heating at 80deg.C for 8h, vacuum filtering the solid-liquid mixture, collecting upper solid, washing with purified water for several times, and vacuum drying at 80deg.C for 6 h to obtain DESs (ethylene glycol: choline chloride) -NH 2 -CMP material. And then scanning electron microscopy and infrared characterization are carried out. The results are shown in the graphs or curves labeled 1 in FIGS. 6 and 7.
Example 2:
NH 2 the CMP preparation procedure is the same as in example 1.
The phenolic hydroxyl-based eutectic solvent consists of phenol and choline chloride in a molar ratio of 1:2, mixing and heating at 80 ℃; DESs (phenol: choline chloride) and NH 2 CMP molar ratio 10:1 heating at 80deg.C 8h, filtering, washing, vacuum drying at 80deg.C 6 h to obtain DESs (phenol: choline chloride) -NH 2 -CMP material. And then scanning electron microscopy and infrared characterization are carried out. The results are shown in the graphs or curves labeled 2 in fig. 6 and 7.
Example 3:
NH 2 the CMP preparation procedure is the same as in example 1.
Amide-based eutectic solvents consist of urea and choline chloride in a molar ratio of 1:2, mixing and heating at 80 ℃; DESs (Urea: choline chloride) and NH 2 CMP molar ratio 10:1 heating at 80deg.C 8h, filtering, washing, vacuum drying at 80deg.C 6 h to obtain DESs (urea: choline chloride) -NH 2 -CMP material. And then scanning electron microscopy and infrared characterization are carried out. The results are shown in figures 6 and 7 with the reference number 3.
Example 4:
NH 2 the CMP preparation procedure is the same as in example 1.
The sulfonic group-based eutectic solvent consists of methylsulfonic acid and choline chloride in a molar ratio of 1:2, mixing and heating at 80 ℃; DESs (methylsulfonic acid: choline chloride) and NH 2 CMP molar ratio 10:1 heating at 80deg.C 8h, filtering, washing, vacuum drying at 80deg.C 6 h to obtain DESs (methylsulfonic acid: choline chloride) -NH 2 -CMP material. And then scanning electron microscopy and infrared characterization are carried out. The results are shown in figures 6 and 7, numbered 4, or curves.
Example 5:
analysis of DESs for NH modification by BET method 2 The change before and after CMP is as follows: the empty tube was first weighed and then 0.1 g of NH prepared in example 1 was taken separately 2 CMP and 0.1 g DESs-NH 2 CMP sample is placed in the tube and the tube weight after placement of the sample is weighed and recorded. And after weighing, sequentially installing the sample tubes. After the sample tube is assembled, vacuum pumping is started. After the vacuum pumping is completed and the heating window appears, changing the pressure in the pretreatment parameters to 10 MPa, setting the furnace temperature, opening a heating switch, and manually lifting the furnace. After heating, a prompt window is automatically popped up, after the temperature of the sample tube is reduced to room temperature for 2 seconds, a liquid nitrogen tank is arranged, a foam pad is covered, the liquid nitrogen tank automatically rises about 5 minutes, and adsorption and desorption curve measurement is started (12-24 hours). After the measurement is finished, a weight window of the input sample is popped up, the liquid nitrogen tank automatically falls down, and the residual liquid nitrogen is poured back. The sample was removed.
The results of the nitrogen adsorption-desorption curve show that NH 2 CMP materials belong to the class I and class II isotherm composite composition because of NH 2 The CMP material has very obvious adsorption capacity at the lower end of P/P0 and NH 2 CMP material micropore filling is relevant, and belongs to the class of activated carbon-containing narrow slit-hole materials. But after modification by DESs, DESs-NH 2 The CMP material belongs to the gas adsorption produced by non-porous or macroporous materials, since the type II isotherm reflects unrestricted single-layer-multi-layer adsorption, single-layer adsorption is complete and ends; this portion of the curve is a more gradual curve, indicating a superposition of the monolayer coverage and the onset of multilayer adsorption. When P/p0=1, no plateau has been formed yet, adsorption has not reached saturation, and the thickness of the multi-layered adsorption seems to increase without limitation.
Claims (7)
1. The method is characterized in that the eutectic solvent and the alkaline amino conjugated microporous polymer are uniformly mixed, then the mixture is heated for 6 to 10 hours at the temperature of 70 to 90 ℃, after the reaction is finished, the solid-liquid mixture is separated, and the obtained solid is washed and dried to obtain the alkaline amino conjugated microporous polymer modified by the eutectic solvent; wherein the eutectic solvent is ethylene glycol and choline chloride, phenol and choline chloride, urea and choline chloride or methylsulfonic acid and choline chloride;
the basic amino conjugated microporous polymer is prepared by the following method:
placing 1,3, 5-triacetylene benzene, 2,4, 6-tribromoaniline, tetra (triphenylphosphine) palladium and copper iodide in a reaction vessel, adding N, N-dimethylformamide and 2, 6-diisopropylaniline, introducing circulating argon after air is removed, stirring the mixture for 20-28h under 70-90 ℃ oil bath, separating solid and liquid mixture after the reaction is finished, washing the obtained solid, performing Soxhlet extraction on methanol, and drying to obtain the alkaline amino conjugated microporous polymer.
2. The eutectic solvent modified basic amino conjugated microporous polymer of claim 1, wherein the molar ratio of the eutectic solvent to the basic amino conjugated microporous polymer is 10-12:1.
3. The eutectic solvent modified basic amino conjugated microporous polymer according to claim 1, wherein the mass ratio of 1,3, 5-triacetoxybenzene to 2,4, 6-tribromoaniline is 0.4-0.5:1; the mass ratio of the 1,3, 5-triacetylene benzene to the copper iodide is 9-10:1.
4. The eutectic solvent modified basic amino conjugated microporous polymer of claim 1, wherein the mass ratio of tetrakis (triphenylphosphine) palladium to copper iodide is 4-6:1; the volume ratio of the solvent N, N-dimethylformamide to the 2, 6-diisopropylaniline is 1-2:1.
5. A preparation method of a eutectic solvent modified alkaline amino conjugated microporous polymer is characterized in that the eutectic solvent and the alkaline amino conjugated microporous polymer are uniformly mixed, then the mixture is heated for 6 to 10 hours at the temperature of 70 to 90 ℃, after the reaction is finished, the solid-liquid mixture is separated, and the obtained solid is washed and dried to obtain the eutectic solvent modified alkaline amino conjugated microporous polymer; wherein the eutectic solvent is ethylene glycol and choline chloride, phenol and choline chloride, urea and choline chloride or methylsulfonic acid and choline chloride;
the basic amino conjugated microporous polymer is prepared by the following method:
placing 1,3, 5-triacetylene benzene, 2,4, 6-tribromoaniline, tetra (triphenylphosphine) palladium and copper iodide in a reaction vessel, adding N, N-dimethylformamide and 2, 6-diisopropylaniline, introducing circulating argon after air is removed, stirring the mixture for 20-28h under 70-90 ℃ oil bath, separating solid and liquid mixture after the reaction is finished, washing the obtained solid, performing Soxhlet extraction on methanol, and drying to obtain the alkaline amino conjugated microporous polymer.
6. The method of claim 5, wherein the molar ratio of the eutectic solvent to the basic amino conjugated microporous polymer is 10-12:1.
7. The process according to claim 5, wherein the mass ratio of 1,3, 5-triacetoxybenzene to 2,4, 6-tribromoaniline is 0.4-0.5:1; the mass ratio of the 1,3, 5-triacetylene benzene to the copper iodide is 9-10:1; the mass ratio of the tetra (triphenylphosphine) palladium to the copper iodide is 4-6:1; the volume ratio of the solvent N, N-dimethylformamide to the 2, 6-diisopropylaniline is 1-2:1.
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| Linear Conjugated Polymers for Solar-Driven Hydrogen Peroxide Production: The Importance of Catalyst Stability.《J. Am. Chem. Soc.》.2021,第143卷第19287-19293页. * |
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