CN110790877A - Covalent organic framework material, preparation thereof and application thereof in identification of chiral polysaccharide - Google Patents
Covalent organic framework material, preparation thereof and application thereof in identification of chiral polysaccharide Download PDFInfo
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- CN110790877A CN110790877A CN201810864482.3A CN201810864482A CN110790877A CN 110790877 A CN110790877 A CN 110790877A CN 201810864482 A CN201810864482 A CN 201810864482A CN 110790877 A CN110790877 A CN 110790877A
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Abstract
The invention discloses a covalent organic framework material and a preparation method and application thereof in chiral polysaccharide identification, wherein the covalent organic framework material is synthesized by taking a compound A and a compound B as monomers, the compound A is a compound shown in a formula I or a compound shown in a formula II, and the compound B is a compound shown in a formula III or a compound shown in a formula IV or a compound shown in a formula V; selecting a formula III or a formula IV as a covalent organic framework material of a compound B, wherein the molar ratio of the compound A to the compound B is 1: 0.5; the formula V is selected as the covalent organic framework material of the compound B, the molar ratio of the compound A to the compound B is 1:0.6, and the chiral polysaccharide compound can be rapidly identified.
Description
Technical Field
The invention relates to the field of chiral polysaccharide recognition, in particular to a covalent organic framework material, a preparation method thereof and application thereof in chiral polysaccharide recognition.
Background
Chirality (Chirality) is one of the essential attributes of nature. Biological macromolecules, such as proteins, polysaccharides, nucleic acids, enzymes and the like, which are important bases of life activities, are almost all chiral, and these small molecules often have important physiological functions in vivo. Most of the currently used drugs are organic small molecules consisting of less than 50 atoms, most of the drugs have chirality, and the pharmacological action of the drugs is realized through strict chiral matching and molecular recognition with macromolecules in vivo. The enantiomers of chemical drugs containing chiral factors have significant differences in pharmacological activity, metabolic processes and toxicity in the human body. The study of chiral drugs has become one of the major directions in the international research of new drugs.
Chiral pharmacy is a leading field of the pharmaceutical industry, and the nuebel chemical prize in 2001 awards a major contributor to molecular chiral catalysis. There are many chiral compounds in nature, which have two enantiomers. Enantiomers are very similar to the human right and left hands, but they do not look exactly the same. When a chiral compound enters a living organism, its two enantiomers often exhibit different biological activities. For chiral drugs, one isomer may be effective, while the other isomer may be ineffective or even harmful. The chiral pharmaceutical is based on the principle of compound, and can develop medicine with high curative effect and less side effect.
In view of the importance of chiral drugs, the identification and separation of chiral compounds is also important. Covalent Organic Framework (COF) materials are one of the hot spots in the field of functional materials. COF has the advantages of highly ordered pore channel structure, adjustable pore diameter, larger specific surface area, various synthetic methods, easy functional modification and the like, is a new high polymer material, and has no report in the chiral recognition neighborhood at present.
Disclosure of Invention
The first purpose of the invention is to provide a covalent organic framework material which has the advantage of fast recognition of chiral polysaccharide compounds.
The technical purpose of the invention is realized by the following technical scheme:
a covalent organic framework material is synthesized by taking a compound A and a compound B as monomers, wherein the compound A is a compound shown in a formula I or a compound shown in a formula II, and the compound B is a compound shown in a formula III or a compound shown in a formula IV or a compound shown in a formula V;
selecting a formula III or a formula IV as a covalent organic framework material of a compound B, wherein the molar ratio of the compound A to the compound B is 1: 0.5; selecting a formula V as a covalent organic framework material of a compound B, wherein the molar ratio of the compound A to the compound B is 1: 0.6;
formula I:
formula II:
formula III:
formula IV:
formula V:
the second purpose of the invention is to provide a preparation method of the covalent organic framework material.
The technical purpose of the invention is realized by the following technical scheme:
a method of preparing a covalent organic framework material, comprising the steps of: mixing the compound A, the compound B, a catalyst glacial acetic acid and an organic solvent C, repeatedly freezing and thawing by liquid nitrogen for three times, sealing, standing at 100-120 ℃ until the reaction is complete, taking out the solid, purifying and drying; the organic solvent C is 1, 4-dioxane, tetrahydrofuran or toluene;
when a formula III or a formula IV is selected as a compound B, the molar amount of the compound A, the compound B and glacial acetic acid is 1: 0.45-0.55: 0.03-0.04; when the formula V is selected as the compound B, the molar consumption of the compound A, the compound B and glacial acetic acid is 1: 0.54-0.66: 0.03-0.04.
The organic solvent C is used as a solvent for the reaction, and the amount thereof does not greatly affect the reaction. The organic solvent C mainly plays a role in dissolving the reaction substrate and the catalyst, the dosage of the organic solvent C can be adjusted according to the dosage of the reaction substrate, the dosage of the catalyst, the solubility of the reaction substrate, the solubility of the catalyst and the size of the reaction container, the minimum dosage of the organic solvent C is just dissolving the reaction substrate and the catalyst, and the maximum dosage of the organic solvent C is 2/3 of the reaction container.
More preferably: the purification adopts Soxhlet extraction, which adopts tetrahydrofuran, ethyl acetate, ethanol and/or acetone as solvent for extraction.
More preferably: the purification is performed by soxhlet extraction, which is sequentially performed by using tetrahydrofuran, ethyl acetate and ethanol as solvents.
The third purpose of the invention is to provide the application of the covalent organic framework material in the rapid recognition of the chiral polysaccharide compound.
The technical purpose of the invention is realized by the following technical scheme:
an application of covalent organic framework material in rapidly identifying chiral polysaccharide compound.
More preferably: gradually adding a solution of chiral polysaccharide compound into the solution of the covalent organic framework material, recording the fluorescence intensity in the process, and calculating a fluorescence quenching selectivity factor K, thereby rapidly identifying the chiral polysaccharide compound.
In conclusion, the invention has the following beneficial effects:
(1) the chiral polysaccharide compound can be rapidly identified: because the monomer cyclohexanediamine synthesized according to the organic framework material COF has chirality, the synthesized covalent organic framework also has chirality, and the chiral framework can perform the specific recognition function with chiral polysaccharide molecules;
(2) the synthesis method is a common tube sealing reaction in a laboratory, is simple and convenient to operate, easy to amplify, high in yield and capable of quickly identifying various chiral polysaccharide compounds.
Drawings
FIG. 1 is an infrared spectrum of R-CCOF-1;
FIG. 2 is a PXRD pattern for R-CCOF-1;
FIG. 3 is a PXRD pattern for S-CCOF-1;
FIG. 4 is an infrared spectrum of R-CCOF-2;
FIG. 5 is a PXRD pattern for R-CCOF-2;
FIG. 6 is a PXRD map of S-CCOF-2;
FIG. 7 is an infrared spectrum of R-CCOF-3;
FIG. 8 is a PXRD pattern for R-CCOF-3;
FIG. 9 is a PXRD pattern for S-CCOF-3.
Detailed Description
The present embodiment is only for explaining the present invention, and it is not limited to the present invention, and those skilled in the art can make modifications of the present embodiment without inventive contribution as needed after reading the present specification, but all of them are protected by patent law within the scope of the present invention.
The instrument used for X-ray powder diffraction (PXRD) was a Bruker D8advanced diffractometer using KaX-radiation with a copper target wavenumber of 1.54nm, a theta-2 theta goniometer, a Mo monochromator, a Lynxeye detector under operating conditions of 40kV and 40 mA. The instrument was calibrated with silicon carbide prior to use. The acquisition software is DiffracPlusXRDCommander. The samples were tested at room temperature and the sample to be tested was placed on a non-reflective plate. The detailed detection conditions are as follows, the angle range is 2-30 degrees 2 theta, the step length is 0.02 degrees 2 theta, and the speed is 0.2 seconds per step.
Fourier Infrared Spectroscopy (FT-IR) data was taken from Bruker sensor 27, with both instrument control software and data analysis software being OPUS. An ATR device is generally adopted and is 500-4000cm-1Within the range, the infrared absorption spectrum is collected, the scanning time of the sample and the blank background are both 16 seconds, and the resolution of the instrument is 4cm-1。
Example 1 a: one method is to put 114mg of (R, R) cyclohexanediamine and 222mg of tetraphenylethylenealdehyde into a 25mL sealed tube and add 2mL of glacial acetic acid and 6mL of 1, 4-dioxane. Freezing and thawing with liquid nitrogen for three times, sealing the tube, and standing for 72h at 120 ℃. The solid was taken out, subjected to respective Soxhlet extraction with tetrahydrofuran, ethyl acetate and ethanol for 24 hours, and vacuum-dried at 100 ℃ for 10 hours to obtain 280mg of R-CCOF-1 with a yield of 95%.
The infrared spectrum of R-CCOF-1 is shown in figure 1.
The PXRD spectrum of R-CCOF-1 is shown in FIG. 2.
Example 1 b: one method is to put 114mg of (R, R) cyclohexanediamine and 244mg of tetraphenylethylenealdehyde into a 25mL lock tube and add 2.3mL of glacial acetic acid and 6mL of tetrahydrofuran. Freezing and thawing with liquid nitrogen for three times, sealing the tube, and standing for 68h at 120 ℃. Taking out the solid, performing Soxhlet extraction with tetrahydrofuran, ethyl acetate and acetone respectively for 24h, and vacuum drying at 120 ℃ for 8h to obtain R-CCOF-1.
Example 1 c: one method is to put 114mg of (R, R) cyclohexanediamine and 200mg of tetraphenylethylenealdehyde into a 25mL lock tube, and add 1.7mL of glacial acetic acid and 6mL of toluene. Freezing and thawing with liquid nitrogen for three times, sealing the tube, and standing for 80h at 110 ℃. Taking out the solid, performing Soxhlet extraction with tetrahydrofuran, acetone and ethanol for 24h respectively, and vacuum drying at 80 ℃ for 18h to obtain R-CCOF-1.
Example 2
114mg of (S, S) cyclohexanediamine and 222mg of tetraphenylethylenealdehyde were placed in a 25mL stoppered tube, and 2mL of glacial acetic acid and 6mL of 1, 4-dioxane were added. Freezing and thawing with liquid nitrogen for three times, sealing the tube, and standing for 72h at 120 ℃. Taking out the solid, performing Soxhlet extraction with tetrahydrofuran, ethyl acetate and ethanol for 24h respectively, and vacuum drying at 100 deg.C for 10 h. 278mgS-CCOF-1 was obtained with a yield of 95%.
The IR spectrum of S-CCOF-1 was consistent with that of R-CCOF-1 of example 1.
PXRD of S-CCOF-1 is shown in FIG. 3.
Example 3
114mg of (R, R) cyclohexanediamine and 310mg of pyrene tetra-aldehyde were placed in a 25mL stoppered tube, and 2mL of glacial acetic acid and 6mL of 1, 4-dioxane were added. Freezing and thawing with liquid nitrogen for three times, sealing the tube, and standing for 72h at 120 ℃. Taking out the solid, performing Soxhlet extraction with tetrahydrofuran, ethyl acetate and ethanol for 24h respectively, and vacuum drying at 100 deg.C for 10 h. 371mgR-CCOF-2 was obtained in 96% yield.
The infrared spectrum of R-CCOF-2 is shown in FIG. 4.
PXRD of R-CCOF-2 is shown in FIG. 5.
Example 4
114mg of (S, S) cyclohexanediamine and 310mg of pyrene tetra-aldehyde were placed in a 25mL stoppered tube, and 2mL of glacial acetic acid and 6mL of 1, 4-dioxane were added. Freezing and thawing with liquid nitrogen for three times, sealing the tube, and standing for 72h at 120 ℃. Taking out the solid, performing Soxhlet extraction with tetrahydrofuran, ethyl acetate and ethanol for 24h respectively, and vacuum drying at 100 deg.C for 10 h. 374mgS-CCOF-2 was obtained with a yield of 96%.
The IR spectrum of S-CCOF-2 was consistent with that of R-CCOF-2 of example 3.
PXRD of S-CCOF-2 is shown in FIG. 6.
Example 5
114mg of (R, R) cyclohexanediamine and 102mg of trimesic aldehyde were placed in a 25mL stoppered tube and 2mL of glacial acetic acid, 6mL of 1, 4-dioxane were added. Freezing and thawing with liquid nitrogen for three times, sealing the tube, and standing for 72h at 120 ℃. Taking out the solid, performing Soxhlet extraction with tetrahydrofuran, ethyl acetate and ethanol for 24h respectively, and vacuum drying at 100 deg.C for 10 h. 175mgR-CCOF-3 was obtained in 96% yield.
The infrared spectrum of R-CCOF-3 is shown in FIG. 7.
PXRD of R-CCOF-3 is shown in FIG. 8.
Example 6
114mg of (S, S) cyclohexanediamine and 102mg of trimesic aldehyde were placed in a 25mL stoppered tube and 2mL of glacial acetic acid, 6mL of 1, 4-dioxane were added. Freezing and thawing with liquid nitrogen for three times, sealing the tube, and standing for 72h at 120 ℃. Taking out the solid, performing Soxhlet extraction with tetrahydrofuran, ethyl acetate and ethanol for 24h respectively, and vacuum drying at 100 deg.C for 10 h. 173mgS-CCOF-3 was obtained with a yield of 96%.
The IR spectrum of S-CCOF-3 was consistent with that of R-CCOF-3 of example 5.
PXRD of S-CCOF-3 is shown in FIG. 9.
Fluorescence titration experiment: the (R) -CCOF and (S) -CCOF after the thorough grinding were dispersed and suspended in an acetonitrile solution to prepare a solution having a concentration of 1.0X 10-5mol/L solution. Separately prepare 1.0X 10-3And (3) acetonitrile solution of glucose, fructose, galactose, maltose and sorbitol in mol/L dextrorotation. Add 20. mu.l of sugar solution to 2.0mL of sample solution at 10 min intervals, add a total of 200. mu.l of sugar solution, and keep the mixture well stirred, and record the fluorescence intensity of each time. And the light source is immediately turned off every time the scanning is carried out, so that the influence on the sample caused by too long exposure time is prevented. The excitation wave number for the fluorescence titration experiment was set at 390nm and the slit width was set at 4nm × 4 nm. According to the Stern-Volmer (SV) equation, a fluorescence quenching selectivity factor K is calculated, and chiral polysaccharide compounds are identified according to Table 1.
TABLE 1 fluorescence quenching selectivity factor K of chiral polysaccharide compounds in different covalent organic framework materials
The above description should not be taken as limiting the invention to the specific embodiments, but rather, as will be readily apparent to those skilled in the art to which the invention pertains, numerous simplifications or substitutions may be made without departing from the spirit of the invention, which should be construed to fall within the scope of the invention as defined in the claims appended hereto.
Claims (6)
1. A covalent organic framework material is characterized by being synthesized by taking a compound A and a compound B as monomers, wherein the compound A is a compound shown in a formula I or a compound shown in a formula II, and the compound B is a compound shown in a formula III or a compound shown in a formula IV or a compound shown in a formula V;
selecting a formula III or a formula IV as a covalent organic framework material of a compound B, wherein the molar ratio of the compound A to the compound B is 1: 0.5; selecting a formula V as a covalent organic framework material of a compound B, wherein the molar ratio of the compound A to the compound B is 1: 0.6;
formula I:
formula II:
formula III:
formula IV:
formula V:
2. a method of preparing a covalent organic framework material, comprising the steps of:
mixing the compound A, the compound B, a catalyst glacial acetic acid and an organic solvent C, repeatedly freezing and thawing by liquid nitrogen for three times, sealing, standing at 100-120 ℃ until the reaction is complete, taking out the solid, purifying and drying; the organic solvent C is 1, 4-dioxane, tetrahydrofuran or toluene;
when a formula III or a formula IV is selected as a compound B, the molar amount of the compound A, the compound B and glacial acetic acid is 1: 0.45-0.55: 0.03-0.04; when the formula V is selected as the compound B, the molar consumption of the compound A, the compound B and glacial acetic acid is 1: 0.54-0.66: 0.03-0.04.
3. The method according to claim 2, wherein the purification is performed by Soxhlet extraction using tetrahydrofuran, ethyl acetate, ethanol and/or acetone as a solvent.
4. The method according to claim 3, wherein the purification is performed by Soxhlet extraction using tetrahydrofuran, ethyl acetate and ethanol as solvents in this order.
5. Use of a covalent organic framework material according to claim 1 or prepared by the preparation method according to any one of claims 2 to 4 for the rapid recognition of chiral polysaccharide compounds.
6. Use according to claim 5, characterized in that: gradually adding a solution of chiral polysaccharide compound into the solution of the covalent organic framework material, recording the fluorescence intensity in the process, and calculating a fluorescence quenching selectivity factor K, thereby rapidly identifying the chiral polysaccharide compound.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108129669A (en) * | 2016-12-01 | 2018-06-08 | 中国科学院大连化学物理研究所 | A kind of salen porous organic polymers and metal complex and application |
| CN108276574A (en) * | 2018-03-27 | 2018-07-13 | 台州学院 | A kind of cyclohexanediamine Quito hole covalent organic framework compound and preparation method thereof |
| CN110790939A (en) * | 2018-08-01 | 2020-02-14 | 孝感市思远新材料科技有限公司 | Metal organic framework material, preparation thereof and application thereof in identification of chiral polysaccharide |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108129669A (en) * | 2016-12-01 | 2018-06-08 | 中国科学院大连化学物理研究所 | A kind of salen porous organic polymers and metal complex and application |
| CN108276574A (en) * | 2018-03-27 | 2018-07-13 | 台州学院 | A kind of cyclohexanediamine Quito hole covalent organic framework compound and preparation method thereof |
| CN110790939A (en) * | 2018-08-01 | 2020-02-14 | 孝感市思远新材料科技有限公司 | Metal organic framework material, preparation thereof and application thereof in identification of chiral polysaccharide |
Non-Patent Citations (2)
| Title |
|---|
| XING HAN ET AL.: "Chiral Covalent Organic Frameworks with High Chemical Stability for Heterogeneous Asymmetric Catalysis", 《J.AM.CHEM.SOC.》 * |
| 路振宇等: "手性荧光传感器的研究进展", 《分析测试学报》 * |
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