CN117866160A - Ivt topological three-dimensional covalent organic framework compound, and preparation method and application thereof - Google Patents
Ivt topological three-dimensional covalent organic framework compound, and preparation method and application thereof Download PDFInfo
- Publication number
- CN117866160A CN117866160A CN202310597086.XA CN202310597086A CN117866160A CN 117866160 A CN117866160 A CN 117866160A CN 202310597086 A CN202310597086 A CN 202310597086A CN 117866160 A CN117866160 A CN 117866160A
- Authority
- CN
- China
- Prior art keywords
- organic framework
- ivt
- covalent organic
- framework compound
- dimensional
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000013310 covalent-organic framework Substances 0.000 title claims abstract description 69
- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title abstract description 7
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims abstract description 11
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims abstract description 10
- QBHWPVJPWQGYDS-UHFFFAOYSA-N hexaphenylbenzene Chemical compound C1=CC=CC=C1C(C(=C(C=1C=CC=CC=1)C(C=1C=CC=CC=1)=C1C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C1=CC=CC=C1 QBHWPVJPWQGYDS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000003115 biocidal effect Effects 0.000 claims abstract description 8
- 238000001917 fluorescence detection Methods 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- 239000002244 precipitate Substances 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000007810 chemical reaction solvent Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 229960000564 nitrofurantoin Drugs 0.000 claims description 7
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 claims description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- QRVQUBKLRBKFCG-UHFFFAOYSA-N 1-phenylpyrene Chemical compound C1=CC=CC=C1C1=CC=C(C=C2)C3=C4C2=CC=CC4=CC=C13 QRVQUBKLRBKFCG-UHFFFAOYSA-N 0.000 claims description 4
- CJTJLXCVRGMRTH-UHFFFAOYSA-N NC1C(C(C(C=C1)(C1=CC=CC=C1)N)(N)N)(N)N Chemical compound NC1C(C(C(C=C1)(C1=CC=CC=C1)N)(N)N)(N)N CJTJLXCVRGMRTH-UHFFFAOYSA-N 0.000 claims description 4
- 239000003242 anti bacterial agent Substances 0.000 claims description 4
- 229940088710 antibiotic agent Drugs 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- OGNSDRMLWYNUED-UHFFFAOYSA-N 1-cyclohexyl-4-[4-[4-(4-cyclohexylcyclohexyl)cyclohexyl]cyclohexyl]cyclohexane Chemical group C1CCCCC1C1CCC(C2CCC(CC2)C2CCC(CC2)C2CCC(CC2)C2CCCCC2)CC1 OGNSDRMLWYNUED-UHFFFAOYSA-N 0.000 claims description 3
- 238000000944 Soxhlet extraction Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000007710 freezing Methods 0.000 claims description 3
- 230000008014 freezing Effects 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- -1 pyrene aldehyde Chemical class 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000012046 mixed solvent Substances 0.000 claims 1
- 239000012264 purified product Substances 0.000 claims 1
- 230000004044 response Effects 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 238000005251 capillar electrophoresis Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 238000001144 powder X-ray diffraction data Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009360 aquaculture Methods 0.000 description 1
- 244000144974 aquaculture Species 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000001815 biotherapy Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 238000009432 framing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000011895 specific detection Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
- C08G12/08—Amines aromatic
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses a ivt topological three-dimensional covalent organic framework compound, a preparation method and application thereof, wherein the compound is formed by mutually connecting hexaphenyl benzene hexaamino connection nodes and pyrene aldehyde group four connection nodes in a three-dimensional plane; in at least one part of the three-dimensional covalent organic framework compound, each hexaphenyl benzene hexaamino connecting node is respectively connected with adjacent six pyrene aldehyde group four connecting nodes, each pyrene aldehyde group four connecting node is respectively connected with adjacent four hexaphenyl benzene hexaamino connecting nodes, and the connecting groups of the three-dimensional covalent organic framework compound contain dynamic covalent bonds-C=N-, so as to form a double interpenetrating three-dimensional structureivtThe novel covalent organic framework compound has good response in the field of water antibiotic fluorescence detection due to the high fluorescence emission characteristic of the covalent organic framework compound in solutionThe application prospect is good.
Description
Technical Field
The invention belongs to the technical field of covalent organic framework compounds, and particularly relates to a ivt topological three-dimensional covalent organic framework compound, a preparation method and application thereof.
Background
Antibiotics are often used as a solution to bacterial infections in aquaculture, but excessive use can result in too high a residual amount of antibiotics in the water system, which can be a serious organic contaminant. Antibiotics pose a serious threat to human life safety due to their high toxicity, numerous side effects and difficulty in natural degradation. Therefore, there is a need to develop an efficient and rapid antibiotic detection assay. In recent years, methods such as liquid chromatography-tandem mass spectrometry (LC-MS/MS), enzyme Immunoassay (EI), capillary Electrophoresis (CE), and fluorescence detection have been widely used. Fluorescence has received a great deal of attention in the fields of biological instrumentation and biological therapy, and has been applied to cancer diagnosis, inflammatory diseases, and the like. The fluorescence-based antibiotic analysis method has the advantages of convenient operation, low cost, quick response and the like.
Covalent Organic Frameworks (COFs) are emerging porous materials with the advantages of low density, high specific surface area, structural diversity, easy regulation and control of pore channel structures, easy functional modification and the like. COFs have great potential in the fields of gas storage/separation, catalysis, sensing, energy storage, photoelectricity and the like. A series of two-or three-dimensional COFs with borate and imine linkages achieve single photon fluorescence by introducing aggregation-induced emission groups or non-planar units and by altering the stacking mode. However, since conventional fluorescent chromophores emit only weak fluorescence or no luminescence at all in a high concentration or aggregation state, they are affected by a strong pi-pi stacking effect. And the three-dimensional COFs has a better fluorescence property due to the reduced pi-pi stacking effect of the unique three-dimensional framework.
Based on the characteristics, the invention designs a novel three-dimensional covalent organic framework material which is formed by combining a pyrene four-site derivative with a fluorescence emission function and a hexa-connection benzene derivative for topology regulation. The obtained three-dimensional covalent organic framework material has a ivt topological network structure, and has sensitive response and specific detection on nitrofurantoin.
Disclosure of Invention
Aiming at the problems in the prior art, the invention aims to provide a ivt topological three-dimensional covalent organic framework compound, a preparation method and application. The three-dimensional covalent organic framework compound has a pore structure with high crystallinity and specificity, and has good application prospect in the aspect of antibiotic detection.
The method is realized by the following technical scheme:
a ivt topological three-dimensional covalent organic framework compound, which is formed by interconnecting a hexaphenyl benzene hexaamino connection node shown in a formula (I) and a pyrene aldehyde tetraconnection node shown in a formula (II) in a three-dimensional plane; in at least one part of the three-dimensional covalent organic framework compound, each hexaphenyl benzene hexaamino connecting node is respectively connected with adjacent six pyrene aldehyde group four connecting nodes, each pyrene aldehyde group four connecting node is respectively connected with adjacent four hexaphenyl benzene hexaamino connecting nodes, the connecting groups of the three-dimensional covalent organic framework compound contain dynamic covalent bonds-C=N-, and form a double interpenetrating three-dimensional ivt topological structure,
further, in at least a part of the three-dimensional covalent organic framework compound having a ivt topology, the ratio of the number of moles of hexaphenyl hexaamino nodes and pyrenyl aldehyde group four-linked nodes is (0.8-1.2): (0.8-1.2).
Further, the ratio of the number of moles of hexaphenyl hexaamino node and pyrenyl aldehyde group four-connecting node is 1:1.
further, when the linkage is-c=n-, the three-dimensional covalent organic framework compound having a ivt topological network structure comprises a framework unit of formula (III):
a method of preparing a ivt topological three-dimensional covalent organic framework compound, comprising the steps of:
1) Adding hexaaminophenyl benzene hexajunction node molecule (I), tetra-aldehyde phenylpyrene tetra-junction node molecule (II), a reaction solvent and a catalyst into a reaction container, freezing with liquid nitrogen, vacuumizing and sealing;
the ratio of the amounts of substances of the hexaaminophenyl benzene hexajunction node molecule (I) and the tetra-aldehyde phenylpyrene tetra-junction node molecule (II) is (0.8-1.2): (0.8-1.2), preferably 1:1, a step of;
the volume ratio of the reaction solvent is 1:1-5:1, preferably the volume ratio of the o-dichlorobenzene to the n-butanol is 1:1;
the catalyst is 6-9mol/L acetic acid, preferably 6mol/L acetic acid; the ratio of the catalyst to tetra-aldehyde-group phenylpyrene four-connection node molecule (II) is 1-10:1mL/mmol, preferably 5:1mL/mmol; the volume of the catalyst is 10-20% of the volume of the reaction solvent;
2) Placing the sealed reaction container at 80-180deg.C (preferably 120deg.C) for 72-168h (preferably 96 h), generating solid precipitate, cooling to room temperature, and filtering to obtain precipitate;
3) Washing the obtained precipitate with organic solvent, and drying to obtain the three-dimensional covalent organic framework compound with ivt topological network structure
Specifically, the method for washing with the organic solvent comprises the following steps: sequentially soaking and washing with two or three of N, N-dimethylformamide, tetrahydrofuran and acetone, and then respectively Soxhlet extracting with tetrahydrofuran and acetone for 24-48h;
the specific drying method comprises the following steps: vacuum was applied to a vacuum oven at 80℃to 20mTorr and then dried for 24 hours.
The three-dimensional covalent organic framework compound with white light emission can be applied to the preparation of a light-induced fluorescence luminescent material, such as a white light emitting diode material.
The three-dimensional covalent organic framework with the ivt topological network structure can show fluorescence emission of different wavelengths in different solutions, has application potential in the aspect of antibiotic fluorescence detection, and particularly has sensitive specific response to the antibiotic nitrofurantoin.
Compared with the prior art, the invention has the following beneficial technical effects:
1) According to the invention, through reasonable structural design, a novel three-dimensional fluorescence covalent organic framework with a ivt topological structure is synthesized, and the covalent organic framework has higher crystallinity, larger specific surface area and good thermal stability;
2) The three-dimensional fluorescence covalent organic framework has simple synthesis steps, low price of required monomers and good industrialization potential;
3) The three-dimensional fluorescence covalent organic framework has excellent fluorescence performance, and the nitrofurantoin has a sensitive fluorescence detection effect in experiments and has great application potential.
Drawings
FIG. 1 is a schematic diagram of the topology of a 3D-ivt-COF three-dimensional covalent organic framework compound having a ivt topology in an embodiment of the present invention;
FIG. 2 is a schematic representation of the synthesis of a 3D-ivt-COF three-dimensional covalent organic framework compound having a ivt topology in an embodiment of the present invention;
FIG. 3 is a powder X-ray (PXRD) test pattern and a simulated pattern of a 3D-ivt-COF three-dimensional covalent organic framework compound having a ivt topology in an embodiment of the present invention;
FIG. 4 is an infrared (FT-IR) spectrum of a 3D-ivt-COF three-dimensional covalent organic framework compound having a ivt topology in an embodiment of the invention;
FIG. 5 is a fluorescence emission spectra of three-dimensional covalent organic framework compound 3D-ivt-COF with ivt topology prepared in example in different solutions;
FIG. 6 is a graph of the fluorescence change of nitrofurantoin titration of a three-dimensional covalent organic framework compound 3D-ivt-COF with ivt topology prepared in the examples.
Detailed Description
The invention is further described below with reference to the drawings and specific embodiments in order to better understand the technical scheme.
Examples
The preparation method of the three-dimensional covalent organic framework compound (called 3D-ivt-COF) with a ivt topological structure comprises the following steps:
referring to FIG. 2, hexaaminophenyl benzene (I) (18.7 mg,0.03 mmol) and 1,3,6, 8-tetrakis- (p-aldehydylphenyl) -pyrene (1 b) (11.8 mg,0.03 mmol) were added to a mixed reaction solvent of o-dichlorobenzene (0.8 mL) and n-butanol (0.8 mL) and dispersed ultrasonically in an amp-flask to give an orange-yellow cloudy solution. 6M acetic acid (0.20 mL) was added to the ampoules as catalyst. Quick freezing in liquid nitrogen bath at 77K, and degassing by freezing-vacuumizing-thawing three times, and sealing. The ampoules were placed in an oven at 120 ℃ for 4 days at constant temperature, cooled to room temperature after the reaction was completed and the yellow solid was collected by filtration. The collected solid was washed by soaking in N, N-dimethylacetamide (3X 10 mL) and acetone (3X 10 mL) in this order. After soxhlet extraction of the solid with tetrahydrofuran and acetone, respectively, for 48h, vacuum drying was performed at 80 ℃ for 24h, and the obtained 3D-ivt-COF was yellow powder. The topological structure schematic diagram of the 3D-ivt-COF of the prepared three-dimensional covalent organic framework compound with the ivt topological structure is shown in figure 1.
Characterization of the product
Referring to FIG. 3, the 3D-ivt-COF crystal structure was analyzed by structural simulation of the measured 3D-ivt-COF of PXRD at 7.0,7.1 and 18.8 and the Materials Studio software, and the corresponding simulated PXRD pattern generated by the three-dimensional ivt topology structure was well matched with the experimental PXRD pattern, thus proving the structural correctness.
Referring to FIG. 4, an infrared spectrum of the relevant monomer required for synthesis and the corresponding product 3D-ivt-COF was compared by Fourier transform infrared (FT-IR) spectroscopy at 1627cm -1 Characteristic stretching vibration of the c=n bond was generated, demonstrating successful synthesis of 3D-ivt-COF.
Referring to FIG. 5, fluorescence emission spectra of 3D-ivt-COF in different solutions were tested using a Hitachi F-4600 spectrometer at 298K and 365nm excitation wavelengths, indicating that it has strong fluorescence properties in a variety of organic solvents, with the longest emission wavelength at 500nm in dimethylformamide.
Antibiotic detection experiment
Referring to FIG. 6, 298K, 2mg of 3D-ivt-COF was sonicated in 3mL of dimethylformamide to form a suspension, after which 0.01mmol of nitrofurantoin was added to the suspension and its fluorescence emission spectra were measured using a fluorescence spectrometer (F-4600) at 298K and 365nm excitation wavelengths, and the fluorescence spectra showed that the framing material exhibited an aggregation quenching effect upon encountering nitrofurantoin.
Claims (10)
1. The ivt topological three-dimensional covalent organic framework compound is characterized in that the three-dimensional covalent organic framework compound is formed by interconnecting a hexaphenyl benzene hexaamino connection node shown in a formula (I) and a pyrene aldehyde tetraconnection node shown in a formula (II) in a three-dimensional plane; in at least one part of the three-dimensional covalent organic framework compound, each hexaphenyl benzene hexaamino connecting node is respectively connected with adjacent six pyrene aldehyde group four connecting nodes, each pyrene aldehyde group four connecting node is respectively connected with adjacent four hexaphenyl benzene hexaamino connecting nodes, the connecting groups of the three-dimensional covalent organic framework compound contain dynamic covalent bonds-C=N-, and form a double interpenetrating three-dimensional ivt topological structure,
2. a ivt topological three-dimensional covalent organic framework compound according to claim 1, wherein the ratio of the number of moles of hexaphenylsix amino-and pyrenyl aldehyde-tetrad-linked nodes in at least a portion of said three-dimensional covalent organic framework compound having a ivt topology is from (0.8 to 1.2): (0.8-1.2).
3. A ivt topological three-dimensional covalent organic framework compound according to claim 2, characterized in that the ratio of the number of moles of hexaphenyl hexaamino-and pyrenyl aldehyde-tetrad-ing-connecting nodes is 1:1.
4. a three-dimensional covalent organic framework compound of ivt topology according to claim 1, wherein when the means of attachment is-c=n-, the three-dimensional covalent organic framework compound having ivt topology network structure comprises a backbone unit of formula (III):
5. a method of preparing a ivt topological three-dimensional covalent organic framework compound according to claim 1, comprising the steps of:
1) Adding hexaaminophenyl benzene hexajunction node molecules shown in a formula (I), tetra-aldehyde phenyl pyrene tetra-junction node molecules shown in a formula (II), a reaction solvent and a catalyst into a reaction container, freezing with liquid nitrogen, vacuumizing and sealing;
2) Placing the sealed reaction container at 80-180 ℃ for reaction for 72-168 hours to generate solid precipitate, cooling to room temperature and filtering to obtain precipitate;
3) Washing the precipitate obtained in the step 2) with an organic solvent and drying to obtain the three-dimensional covalent organic framework compound with the ivt topology of white light emission.
6. The method for preparing a ivt topological three-dimensional covalent organic framework compound as claimed in claim 5, wherein the reaction solvent in the step 1) is a mixed solvent of o-dichlorobenzene and n-butanol in a volume ratio of 1:1-5:1, and the volume amount of the reaction solvent is 20mL/mmol based on the mass of tetra-aldehyde-phenylpyrene tetra-connection node molecules.
7. The method for preparing a ivt topological three-dimensional covalent organic framework compound according to claim 5, wherein in step 1), the catalyst is acetic acid with a concentration of 6-9mol/L and the catalyst volume is 10-0% of the volume of the reaction solvent.
8. The method for preparing a ivt topological three-dimensional covalent organic framework compound as claimed in claim 5, wherein the precipitate obtained in the step 3) is washed with an organic solvent, and after the completion of the drying, the solid precipitate is filtered, and is subjected to Soxhlet extraction with tetrahydrofuran and acetone for 12-48 hours, respectively, and after the Soxhlet extraction is completed, the precipitate is dried in vacuum at 80 ℃ for 12 hours to obtain the final purified product.
9. Use of a ivt topological three-dimensional covalent organic framework compound according to claim 1 for fluorescence detection of antibiotics.
10. The use according to claim 9, wherein the antibiotic is nitrofurantoin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310597086.XA CN117866160A (en) | 2023-05-24 | 2023-05-24 | Ivt topological three-dimensional covalent organic framework compound, and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310597086.XA CN117866160A (en) | 2023-05-24 | 2023-05-24 | Ivt topological three-dimensional covalent organic framework compound, and preparation method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117866160A true CN117866160A (en) | 2024-04-12 |
Family
ID=90595562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310597086.XA Pending CN117866160A (en) | 2023-05-24 | 2023-05-24 | Ivt topological three-dimensional covalent organic framework compound, and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117866160A (en) |
-
2023
- 2023-05-24 CN CN202310597086.XA patent/CN117866160A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111607051B (en) | Three-dimensional fluorescent covalent organic framework material and preparation method and application thereof | |
| CN105541660A (en) | Arylsalicylaldehyde-diphenyl-azine hydrazine compound as well as preparation and application | |
| CN109678897B (en) | Nd compound luminescent material containing phenanthroline and modified carboxylic acid ligand and preparation method thereof | |
| CN111234210B (en) | Covalent organic framework material with benzofuran structure, synthetic method and application | |
| CN115093526B (en) | Three-dimensional covalent organic framework compound with white light emission and preparation and application thereof | |
| CN103242298A (en) | 1,2,4-triazole derivative, preparation method and application thereof and organic electroluminescent device | |
| CN103468246A (en) | Organic luminescent material containing 1,2,4-tolyltriazole as well as preparation method and electroluminescent appliance of organic luminescent material containing 1,2,4-tolyltriazole | |
| CN107108812B (en) | Pure oxygen non-conjugated polymer with strong light emission and lyotropic discoloration performance for amine detection and preparation method thereof | |
| CN110903450A (en) | High-efficiency two-photon absorption-performance layered covalent organic framework material and preparation method thereof | |
| CN105801465A (en) | Water-soluble indole croconium cyanine colorimetric probe, preparation method and application | |
| CN105115953A (en) | Ratio type nanosphere sensor and preparation method and application thereof | |
| CN105061403B (en) | A kind of multifunctional groups pyridazinone compound, it is used as application of orange luminous organic material and preparation method thereof | |
| CN117866160A (en) | Ivt topological three-dimensional covalent organic framework compound, and preparation method and application thereof | |
| CN110330532B (en) | Novel phosphorescent iridium complex and preparation method and application thereof | |
| CN104152137A (en) | Fluorine-perylene bisimide molecule internal-energy transferring fluorescence split compound and preparation method thereof | |
| CN112391047B (en) | Temperature stimulation responsive perylene diimide supramolecular fluorescent gel, preparation method and application | |
| CN103755704B (en) | Responsive to temperature type poplar bundles and preparation method thereof | |
| CN106366041B (en) | It is a kind of it is continuous identification palladium ion, CO fluorescence probe and application | |
| CN112661922B (en) | Tetraphenyl ethylene fluorescent porous polyacetal amine, preparation method and application | |
| CN102942568A (en) | 2-[(N- alkyl carbazolyl) vinyl]-1, 8-naphthyridine derivative as well as preparation method and application thereof | |
| CN114773551B (en) | Two-dimensional covalent organic framework compound with high fluorescence quantum yield, and preparation and application thereof | |
| CN103864823A (en) | Cu (I) coordination polymer green light emitting material and synthesis method thereof | |
| CN116375959A (en) | Three-dimensional fluorescence covalent organic framework and preparation method and application thereof | |
| CN113234031A (en) | D-A type aggregation-induced emission compound and preparation method and application thereof | |
| CN106432170B (en) | A kind of rhodamine B base RAFT reagents and preparation method and the method that fluorescent microsphere is prepared based on this reagent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |