CN105418661A - Double-penetration coordination polymer, and preparation method and application thereof - Google Patents
Double-penetration coordination polymer, and preparation method and application thereof Download PDFInfo
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- CN105418661A CN105418661A CN201610038107.4A CN201610038107A CN105418661A CN 105418661 A CN105418661 A CN 105418661A CN 201610038107 A CN201610038107 A CN 201610038107A CN 105418661 A CN105418661 A CN 105418661A
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- 239000013256 coordination polymer Substances 0.000 title abstract description 9
- 229920001795 coordination polymer Polymers 0.000 title abstract description 9
- 238000002360 preparation method Methods 0.000 title abstract description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000013078 crystal Substances 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 239000002360 explosive Substances 0.000 claims abstract description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000001914 filtration Methods 0.000 claims abstract description 5
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000007789 sealing Methods 0.000 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims abstract 2
- 230000035515 penetration Effects 0.000 claims description 36
- 239000003446 ligand Substances 0.000 claims description 33
- 229920000642 polymer Polymers 0.000 claims description 31
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000013110 organic ligand Substances 0.000 claims description 3
- 125000006850 spacer group Chemical group 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 230000000694 effects Effects 0.000 abstract description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000012621 metal-organic framework Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- ZHUXMBYIONRQQX-UHFFFAOYSA-N hydroxidodioxidocarbon(.) Chemical group [O]C(O)=O ZHUXMBYIONRQQX-UHFFFAOYSA-N 0.000 description 2
- 229910001449 indium ion Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000013384 organic framework Substances 0.000 description 1
- JDFUJAMTCCQARF-UHFFFAOYSA-N tatb Chemical compound NC1=C([N+]([O-])=O)C(N)=C([N+]([O-])=O)C(N)=C1[N+]([O-])=O JDFUJAMTCCQARF-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
The invention relates to a double-penetration coordination polymer, and a preparation method and application of the double-penetration coordination polymer. The technical scheme adopted by the invention is characterized by adding In(NO3)3, an organic ligand-H3TATB, DMF (Dimethyl Formamide), acetonitrile and HNO3 into a container, and stirring under room temperature; putting the container in a drying oven after sealing the container, and keeping the container for 3 to 4 days under 355 K; slowly cooling the container to room temperature, obtaining white crystals, and obtaining a target product by washing, filtering and drying the white crystals. The In<III>-based double-penetration coordination polymer prepared by the invention has fluorescence activity and can be used for detecting an explosive solvent.
Description
Technical field
The present invention relates to a kind of metal-organic framework materials, specifically, relate to a kind of coordination polymer material based on two-fold penetration with fluorescence activity.
Background technology
In the past few decades, metallic organic framework (MOFs) is widely studied as a kind of functional material, and it is more various that MOFs has large specific surface area, higher porosity, structure and function, as: be separated, ion-exchange, atmosphere storage and fluorescent optical sensor.And its function can be changed by rational rear synthetic modification.The structures and characteristics of the coordination polymer material interted also result in people and pays close attention to widely.In order to the coordination polymer material of two-fold penetration is applied to productive life widely, the further development and utilization of its active needs.
Summary of the invention
The object of the invention is to utilize In as metal node, utilize 4,4 ', 4 "-s-triazine-2,4,6-tri-phenylformic acid (H
3tATB) as organic ligand, at a certain temperature, the method for solvent thermal is utilized to synthesize the coordination polymer material with two-fold penetration structure.
The technical solution used in the present invention is as follows: a kind of ligand polymer of two-fold penetration, comprises following synthesis step:
1) by In (NO
3)
3, organic ligand 4,4 ', 4 " and-s-triazine-2,4,6-tri-phenylformic acid (H
3tATB), DMF (DMF), acetonitrile and HNO
3join in container, stir under normal temperature;
2) by after container sealing, be placed in baking oven, under 353-363K, keep 3-4 days;
3) progressively cool to room temperature, obtain white crystal; The described room temperature that progressively cools to is: rate of temperature fall is 3-8Kh
-1.
4) wash, filter and drying, obtain target product.
The structure of the ligand polymer of the two-fold penetration that the present invention synthesizes is: it belongs to oblique system, and spacer is P2/c, in its elementary cell, has three indium ions, two 4,4 ', 4 "-s-triazine-2,4; 6-tri-phenylformic acid part, three formic acid, a DMF, the In of this title complex
iIIby 4,4 ', 4 " carboxyl in-s-triazine-2,4,6-tri-phenylformic acid, takes O, O-chelating ligands, each In
iIIion center is all 7 coordinations, wherein has 4 carboxyl oxygen atoms to come from two independently 4,4 '; 4 "-s-triazine-2,4,6-tri-phenylformic acid part, two Sauerstoffatoms come from two formic acid, another one Sauerstoffatom is from the Sauerstoffatom of DMF solvent molecule, each 4,4 ', 4 "-s-triazine-2; 4,6-tri-phenylformic acid part is all connected to three In
iIIion center, forms unlimited chain-like structure, and the unlimited chain-like structure extended is by 4,4 ', 4 "-s-triazine-2,4,6-tri-phenylformic acid part constitutes the ligand polymer of two-fold penetration further.
The invention has the beneficial effects as follows: the ligand polymer of the two-fold penetration prepared by the present invention has good fluorescence activity, preparation method is simple, has great application prospect.
Accompanying drawing explanation
Fig. 1 is the structure iron of the ligand polymer basic structural unit based on two-fold penetration prepared by embodiment 1.
Fig. 2 is the tomograph of the ligand polymer based on two-fold penetration prepared by embodiment 1.
Fig. 3 is the two-fold penetration structure iron of the ligand polymer based on two-fold penetration prepared by embodiment 1.
Fig. 4 is the fluorescence spectrum figure of the ligand polymer that the present invention is based on two-fold penetration.
Fig. 5 is the detection of fluorescence activity to different solvents of the ligand polymer that the present invention is based on two-fold penetration.
Embodiment
The ligand polymer of embodiment 1 one kinds of two-fold penetration
By the In (NO of 0.05mmol
3)
3, 4,4 ', 4 of 0.02mmol " and-s-triazine-2,4,6-tri-phenylformic acid, the DMF of 0.75mL, the acetonitrile of 0.75mL and the nitric acid of 0.15mL3M add in the vial of 5mL.And stir 20 minutes under normal temperature condition, then by its good seal, put into baking oven, heating makes oven temperature reach 355K, and keeps 3 days with this understanding, and (rate of temperature fall is 3-8Kh to be then slowly cooled to room temperature
-1), obtain white crystal, washing, filtration are also dry, and obtain the ligand polymer of two-fold penetration, productive rate is 70%.
The coordination polymer material (examination of X-ray single crystal diffraction instrument obtains data, and the structure iron of acquisition as depicted in figs. 1 and 2) of the two-fold penetration obtained.Based on the basic structural unit figure of the ligand polymer of two-fold penetration.This compound belongs to oblique system, and spacer is P2/c, in its elementary cell, have three indium ions, two 4,4 ', 4 "-s-triazine-2,4,6-tri-phenylformic acid part, three formic acid, a DMF, the In of this title complex
iIIby 4,4 ', 4 " carboxyl in-s-triazine-2,4,6-tri-phenylformic acid takes O, O-chelating ligands, each In
iIIion center is all 7 coordinations, wherein has 4 carboxyl oxygen atoms to come from two independently 4,4 '; 4 "-s-triazine-2,4,6-tri-phenylformic acid part, two Sauerstoffatoms come from two formic acid, another one Sauerstoffatom carrys out the Sauerstoffatom of DMF solvent molecule, each 4,4 ', 4 "-s-triazine-2; 4,6-tri-phenylformic acid part is all connected to three In
iIIion center, forms unlimited chain-like structure, and the unlimited chain-like structure extended is by 4,4 ', 4 "-s-triazine-2,4,6-tri-phenylformic acid part constitutes the ligand polymer [In (TATB) of two-fold penetration further
2(HCOO)
3(DMF)
3] 2DMFH
2o, as shown in Figure 2.
The ligand polymer of embodiment 2 one kinds of two-fold penetration
By the In (NO of 0.05mmol
3)
3, 4,4 ', 4 of 0.02mmol " and-s-triazine-2,4,6-tri-phenylformic acid, the DMF of 0.75mL, the acetonitrile of 0.75mL and the nitric acid of 0.13mL3M add in the vial of 5mL.And stir 20 minutes under normal temperature condition, then by its good seal, put into baking oven, heating makes oven temperature reach 355K, and keeps 3 days with this understanding, and (rate of temperature fall is 3-8Kh to be then slowly cooled to room temperature
-1), obtain white crystal, washing, filtration are also dry, and obtain the ligand polymer of two-fold penetration, productive rate is 60%.
The ligand polymer of embodiment 3 one kinds of two-fold penetration
By the In (NO of 0.05mmol
3)
3, 4,4 ', 4 of 0.02mmol " and-s-triazine-2,4,6-tri-phenylformic acid, the DMF of 0.75mL, the acetonitrile of 0.75mL and the nitric acid of 0.14mL3M add in the vial of 5mL.And stir 20 minutes under normal temperature condition, then by its good seal, put into baking oven, heating makes oven temperature reach 355K, and keeps 3 days with this understanding, and (rate of temperature fall is 3-8Kh to be then slowly cooled to room temperature
-1), obtain white crystal, washing, filtration are also dry, and obtain the ligand polymer of two-fold penetration, productive rate is 65%.
The fluorescence activity of the ligand polymer of embodiment 4 two-fold penetration
The ligand polymer DMF of two-fold penetration embodiment 1 prepared cleans, and under 60 DEG C of conditions, vacuum-drying 8 hours, is ground.
Method: the ethanol adding 4mL in the vial of 5mL, then the sample (ligand polymer of two-fold penetration prepared by embodiment 1) adding 10mg in ethanol, by ultrasonic for the ethanolic soln containing sample, make it be uniformly dispersed.Finely dispersed solution is joined in fluorescence cuvette, utilizes fluorescence spectrophotometer to detect.As shown in Figure 4, this sample has stronger fluorescence activity to detected result, and its excitation wavelength is 242nm, and wavelength of transmitted light is 380nm.
Embodiment 5 utilizes the fluorescence activity of the ligand polymer of two-fold penetration to detect explosive organic solvent
Method: the organic solvent adding 4mL in the vial of 5mL, wherein organic solvent is respectively toluene, o-Xylol, bromobenzene, chlorobenzene and oil of mirbane, in organic solvent, add the sample (ligand polymer of two-fold penetration prepared by embodiment 1) of 10mg again, by ultrasonic for the solution containing sample, make it be uniformly dispersed.Finely dispersed solution is joined in fluorescence cuvette, utilizes fluorescence spectrophotometer to detect.Result as shown in Figure 5, can find out the toluene containing sample, o-Xylol, bromobenzene, the fluorescence intensity of chlorobenzene solution is all very strong, and the fluorescence intensity of nitrobenzene solution is very weak, therefore can reach a conclusion: the ligand polymer of two-fold penetration of the present invention can detect explosive solvent oil of mirbane.
Claims (7)
1. a ligand polymer for two-fold penetration, is characterized in that, comprises following synthesis step:
1) by In (NO
3)
3, organic ligand 4,4 ', 4 " and-s-triazine-2,4,6-tri-phenylformic acid, DMF, acetonitrile and HNO
3join in container, stir under normal temperature;
2) by after container sealing, be placed in baking oven, under 353-363K, keep 3-4 days;
3) progressively cool to room temperature, obtain crystal;
4) wash, filter and drying, obtain target product.
2. the ligand polymer of two-fold penetration according to claim 1, is characterized in that, the ligand polymer of described two-fold penetration, and its crystal belongs to oblique system, and spacer is P2/c.
3. the ligand polymer of two-fold penetration according to claim 1, is characterized in that, comprises following synthesis step:
1) by the In (NO of 0.05mmol
3)
3, 4,4 ', 4 of 0.02mmol " and-s-triazine-2,4,6-tri-phenylformic acid, the DMF of 0.75mL, the acetonitrile of 0.75mL and the nitric acid of 0.15mL3M add in container, stir under normal temperature;
2) by after container sealing, be placed in baking oven, under 355K, keep 3 days;
3) also dry with DMF washing, filtration, obtain target product.
4. the ligand polymer of two-fold penetration according to claim 1, is characterized in that, the described rate of temperature fall progressively cooling to room temperature is 3-8Kh
-1.
5. the ligand polymer of the two-fold penetration described in claim 1,2,3 or 4 is detecting the application in explosive solvent.
6. application according to claim 5, is characterized in that method is as follows: the ligand polymer adding the two-fold penetration described in claim 1,2,3 or 4 in the solution containing explosive solvent, carries out fluoroscopic examination.
7. the application according to claim 5 or 6, is characterized in that: described explosive solvent is oil of mirbane.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610038107.4A CN105418661B (en) | 2016-01-20 | 2016-01-20 | A kind of coordination polymer of two-fold penetration and its preparation method and application |
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|---|---|---|---|
| CN201610038107.4A CN105418661B (en) | 2016-01-20 | 2016-01-20 | A kind of coordination polymer of two-fold penetration and its preparation method and application |
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|---|---|
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| CN105418661B CN105418661B (en) | 2017-06-16 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108912337A (en) * | 2018-06-01 | 2018-11-30 | 中山大学 | A kind of rare earth metal organic framework materials of high quantum production rate and preparation method thereof |
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| WO2009011545A2 (en) * | 2007-07-16 | 2009-01-22 | Insilicotech Co., Ltd. | Compound or solvate thereof with mesoporous metal-organic framework |
| CN103613555A (en) * | 2013-11-26 | 2014-03-05 | 中国科学院福建物质结构研究所 | Porous indium-organic framework material for adsorption and separation and preparation and application thereof |
| CN105131025A (en) * | 2015-07-24 | 2015-12-09 | 郑州轻工业学院 | Micro-pore aluminum-based metal-organic framework material and preparation method thereof |
-
2016
- 2016-01-20 CN CN201610038107.4A patent/CN105418661B/en active Active
Patent Citations (3)
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|---|---|---|---|---|
| WO2009011545A2 (en) * | 2007-07-16 | 2009-01-22 | Insilicotech Co., Ltd. | Compound or solvate thereof with mesoporous metal-organic framework |
| CN103613555A (en) * | 2013-11-26 | 2014-03-05 | 中国科学院福建物质结构研究所 | Porous indium-organic framework material for adsorption and separation and preparation and application thereof |
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|---|
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108912337A (en) * | 2018-06-01 | 2018-11-30 | 中山大学 | A kind of rare earth metal organic framework materials of high quantum production rate and preparation method thereof |
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