CN106220655A - The double triazole trimesic acid Zn complex monocrystalline of 1,2,4,5 durols and application - Google Patents
The double triazole trimesic acid Zn complex monocrystalline of 1,2,4,5 durols and application Download PDFInfo
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- CN106220655A CN106220655A CN201610602281.7A CN201610602281A CN106220655A CN 106220655 A CN106220655 A CN 106220655A CN 201610602281 A CN201610602281 A CN 201610602281A CN 106220655 A CN106220655 A CN 106220655A
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- triazole
- tma
- trimesic acid
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- monocrystalline
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- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 150000003852 triazoles Chemical class 0.000 title claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000013078 crystal Substances 0.000 claims abstract description 15
- 229910001868 water Inorganic materials 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 239000000706 filtrate Substances 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000011232 storage material Substances 0.000 claims abstract description 5
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 claims description 8
- 238000001179 sorption measurement Methods 0.000 claims description 8
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 230000005260 alpha ray Effects 0.000 claims description 2
- 238000004364 calculation method Methods 0.000 claims description 2
- 238000012937 correction Methods 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000011701 zinc Substances 0.000 description 17
- 238000003860 storage Methods 0.000 description 10
- 239000012621 metal-organic framework Substances 0.000 description 7
- JMUZONWUVWBPSJ-UHFFFAOYSA-N NCC1=C(C(=C(C(=C1C)C)NC)C)C Chemical compound NCC1=C(C(=C(C(=C1C)C)NC)C)C JMUZONWUVWBPSJ-UHFFFAOYSA-N 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 4
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- -1 metals hydride Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical group C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 description 1
- POTIFVZPGGZBBA-UHFFFAOYSA-N 4-[2,3,5,6-tetramethyl-4-(1,2,4-triazol-4-ylmethyl)phenyl]-1,2,4-triazole Chemical compound N=1N=CN(C=1)CC1=C(C(=C(C(=C1C)C)N1C=NN=C1)C)C POTIFVZPGGZBBA-UHFFFAOYSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000013132 MOF-5 Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- AJSMFLLYPNSHIV-UHFFFAOYSA-N [4-(aminomethyl)-2,5-dimethylphenyl]methanamine Chemical compound CC1=CC(CN)=C(C)C=C1CN AJSMFLLYPNSHIV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229920001795 coordination polymer Polymers 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
- C01B3/0005—Reversible uptake of hydrogen by an appropriate medium, i.e. based on physical or chemical sorption phenomena or on reversible chemical reactions, e.g. for hydrogen storage purposes ; Reversible gettering of hydrogen; Reversible uptake of hydrogen by electrodes
- C01B3/001—Reversible uptake of hydrogen by an appropriate medium, i.e. based on physical or chemical sorption phenomena or on reversible chemical reactions, e.g. for hydrogen storage purposes ; Reversible gettering of hydrogen; Reversible uptake of hydrogen by electrodes characterised by the uptaking medium; Treatment thereof
- C01B3/0015—Organic compounds; Solutions thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/32—Hydrogen storage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Inorganic Chemistry (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Hydrogen, Water And Hydrids (AREA)
Abstract
The invention discloses 1, the double triazole trimesic acid Zn complex monocrystalline of 2,4,5 durols and application, its structure: [Zn (L) (tma)] H2O, wherein, L=4 (4 ((4H 1,2,4 triazole 4 base) methyl) 2,3,5,6 tetramethylphenyls) 4H 1,2,4 triazole；Tma=trimesic acid.Also disclose the preparation method of monocrystalline simultaneously.It is to use " room temperature volatility process ", i.e. L, tma and Zn (NO3)2·6H2O filters after stirring half an hour in water, and filtrate room temperature obtains being suitable for the colourless bulk crystals of X ray single crystal diffraction after volatilizing two weeks.Wherein L:tma:Zn (NO3)2·6H2The mol ratio of O is 1:1:1.The present invention further discloses the double triazole trimesic acid Zn complex monocrystalline of 1,2,4,5 durols as hydrogen storage material application in terms of adsorbed hydrogen.
Description
The present invention obtains the subsidy of Tianjin innovation team of Education Commission (TD12-5037).
Technical field
The present invention relates to the preparation method and applications of triazole organic acid cadmium complex hydrogen storage material, be one in particular
Plant the double triazole trimesic acid Zn complex monocrystalline of 1,2,4,5-durol and application.
Background technology
The synthesis of metal-organic framework (MOFs) and character research are the nothings that nineteen nineties Later development gets up
One of important field of research in chemical machine and materials chemistry.Owing to open metal-organic coordination polymer density is little, it is only
/ 3rd of conventional metals hydride, use MOFs can be substantially reduced the weight of hydrogen storage device as hydrogen storage media.This feature
Especially meet the hydrogen-feeding system requirement of hydrogen cell automobile.In addition such material also has that specific surface area is big, pore volume is big
Feature, be therefore a kind of novel high-capacity light hydrogen occluding material, the hydrogen storage method the most having become a kind of novel simplicity should
Transport and give birth to.It is, in general, that hydrogen storage mechanism can be divided into chemisorbed and physical absorption, and the hydrogen storage mechanism of coordination compound is mostly physics
Absorption.The Kitagawa etc. of Japan in 1997 reports the metal-organic framework that 4,4 '-bipyridyl constructs, and to have adsorbed gas little
After the character of molecule [S. Kitagawa etc.,Angew. Chem. Int. Ed.1997, 36, 1725], correlational study draws
Play the extensive attention of countries in the world.American scientist Yaghi in 2003 etc. report micropore metal-organic frame MOF-5 tool
After having good hydrogen storage property [O. M. Yaghi etc.,Science2003, 300, 1127], metal-organic framework hydrogen storage skill
Art is increasingly becoming 21st century international emerging research frontier.
Summary of the invention
The present invention is i.e. to select Zn (NO3)2·6H2O, tma and L filter after stirring half an hour in water, and filtrate room temperature volatilizees
Obtain being suitable for water white transparency bulk crystals [Zn (L) (the tma)] H of X-ray single crystal diffraction after one week2O (1), (L=4-
(4-((4H-1,2,4-triazole-4-yl) methyl)-2,3,5,6-tetramethylphenyl)-4H-1,2,4-triazole；Tma=equal benzene three
Acid).Hydrogen can be adsorbed by this complex monocrystal as hydrogen storage material.
Following technical scheme is current inventor provides for this:
Its structure is as follows:
[Zn(L)(tma)]·H2O, wherein
L=4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,3,5,6-tetramethylphenyl)-4H-1,2,4-triazole；
Tma=trimesic acid.
The present invention further discloses the preparation side of the double triazole trimesic acid Zn complex monocrystalline of 1,2,4,5-durol
Method, it is characterised in that it is to use room temperature volatility process, by L, tma and Zn (NO3)2·6H2O filters after stirring half an hour in water,
Filtrate room temperature obtains being suitable for the colourless bulk crystals of X-ray single crystal diffraction after volatilizing two weeks；Wherein L:tma:Zn (NO3)2·
6H2The mol ratio of O is 1:1:1；
The structure of the double triazole trimesic acid Zn complex monocrystalline of 1,2,4,5-durol is [Zn (L) (tma)] H2O；Wherein L
=4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,3,5,6-tetramethylphenyl)-4H-1,2,4-triazole；Tma=all
Benzenetricarboxylic acid；
L tma。
The present invention further discloses the double triazole trimesic acid Zn complex monocrystalline of 1,2,4,5-durol as storage
Hydrogen material is in preparation to the application in terms of hydrogen adsorption, and experimental result shows: the double triazole trimesic acid of 1，2，4，5-tetramethylbenzene
Zn complex monocrystalline two dimension coordination frame complex monocrystalline is under about 3.4 MPa, when 298 and 77 K, this hydrogen storage Porous materials
Hydrogen adsorption amount has respectively reached 0.87 and 1.38 wt%.
It is excellent that the double triazole trimesic acid Zn complex monocrystalline of a kind of 1,2,4,5-durol disclosed by the invention is had
Point and feature are:
(1) operation is simple and easy to do.
(2) reaction yield is high, and the purity of products obtained therefrom is high.
(3) the double triazole trimesic acid Zn complex monocrystalline of the 1，2，4，5-tetramethylbenzene prepared by the present invention, production cost
Low, method is easy, is suitable for large-scale production.The double triazole trimesic acid Zn complex monocrystalline of 1,2,4,5-durol is as hydrogen storage
Material has good application effect in terms of storing hydrogen.
Accompanying drawing explanation
The crystal structure figure of Fig. 1: complex monocrystal；
The two-dimensional structure figure of Fig. 2: complex monocrystal；
Fig. 3: inhale hydrogen curve.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described further, and embodiment is only explanatory, is in no way intended to it
Limit the scope of the present invention by any way.All of raw material (4-(aminomethyl)-2,3,5,6-tetramethylphenyl) methylamine, 1H-
1,2,4-triazole, potassium carbonate, copper oxide, zinc nitrate and trimesic acid etc. are commercially available.
Embodiment 1
(4-(aminomethyl)-2,3,5,6-tetramethylphenyl) methylamine: the mol ratio of double formylhydrazines is 1:4
Be separately added in equipped with 50 mL three neck round bottom flasks of magneton, reflux condenser and thermometer (4-(aminomethyl)-2,
3,5,6-tetramethylphenyls) methylamine (1 mmol) and double formylhydrazine (4 mmol), start stirring 150oC, reacts 24 hours.
After reaction terminates, reactant liquor is down to room temperature, the precipitation obtained is added 100 mL hot methanols, after stirring and dissolving, filter, filtrate
Slowly volatilization obtains white solid, yield 85%.Elementary analysis (C16N6H20) theoretical value (%): C, 64.84；H, 6.80；N,
28.36.Measured value: C, 64.88；H, 6.85；N, 28.05.
The double formylhydrazine of (4-(aminomethyl)-2,3,5,6-tetramethylphenyl) methylamine.
The mol ratio of the present invention preferably (4-(aminomethyl)-2,3,5,6-tetramethylphenyl) methylamine and double formylhydrazine is 1:4；
Reaction temperature 150 DEG C, 24 hours response time.Use " one kettle way ", by (4-(aminomethyl)-2，3，5，6-tetramethylphenyl) first
Amine and double formylhydrazine prepare 4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,3,5,6-durol in a heated condition
Base)-4H-1,2,4-triazole (L).
Embodiment 2
4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,3,5,6-tetramethylphenyl)-4H-1,2,4-triazole (L) (0.1
Mmol), trimesic acid (tma) (0.1 mmol) and Zn (NO3)2·6H2O (0.1 mmol) is stirring half in water (10 mL)
Filtering after hour, filtrate room temperature obtains being suitable for the colourless bulk crystals of X-ray single crystal diffraction after volatilizing two weeks.Productivity: 40%.Unit
Element analyzes (C12.5H13N3O3.5Zn0.5) theoretical value (%): C, 50.95；H, 5.04；N, 14.86.Measured value: C, 51.05；H,
4.99；N, 14.82.
Embodiment 3
Crystal structure determination uses APEX II CCD single crystal diffractometer, uses through graphite monochromatised Mok alpha ray, and λ=
0.71073 is incident radiation, withω-2θScan mode collects point diffraction, obtains structure cell ginseng through least square refinement
Number, utilizes software to solve crystal structure from difference Fourier electron density map, and through Lorentz lorentz and polarity effect correction.All of
H atom is synthesized by difference Fourier and determines through preferable position calculation.Detailed axonometry data:
Embodiment 4
The suction hydrogen curve of metal-organic framework hydrogen storage Porous materials is as shown in Figure 3.The hydrogen adsorption carried out under 298 and 77 K is real
Testing is an adsorption process quickly, has reached thermodynamical equilibrium, it is believed that this is physical adsorption process within several seconds.
This adsorption process belongs to first kind gas absorption type, and this is also the MOFs most typical one of poromerics adsorption gas molecule.
Hydrogen is located in duct, and the adsorbance that size limit in duct is one layer or which floor hydrogen molecule.At about 3.4 MPa
During with 77 K, the adsorbance of hydrogen has reached 1.38 wt%.
After the preferred embodiment described in detail, it is familiar with this skilled worker and is clearly understood that, without departing from above-mentioned
Can carry out various change and amendment under claim and spirit, all technical spirit according to the present invention are to above example institute
Any simple modification, equivalent variations and the modification made, belongs to the scope of technical solution of the present invention.And the present invention is not illustrated
The restriction of example embodiment in book.
Claims (3)
1. the monocrystalline of the double triazole trimesic acid Zn complex of 1，2，4，5-tetramethylbenzene, it is characterised in that this mono-crystalline structures is adopted
With APEX II CCD single crystal diffractometer, using through graphite monochromatised Mok alpha ray, λ=0.71073 is incident radiation,
Withω-2θScan mode collects point diffraction, obtains cell parameter through least square refinement, close from difference Fourier electronics
Degree is desired to make money or profit and is solved crystal structure with software, and through Lorentz lorentz and polarity effect correction；All of H atom is synthesized by difference Fourier
And determine through preferable position calculation, detailed axonometry data:
Its structure is as follows:
[Zn(L)(tma)]·H2O, wherein
L=4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,3,5,6-tetramethylphenyl)-4H-1,2,4-triazole；
Tma=trimesic acid.
2. the preparation method of the double triazole trimesic acid Zn complex monocrystalline of 1，2，4，5-tetramethylbenzene described in claim 1, it is special
Levy and be that it is to use room temperature volatility process, by L, tma and Zn (NO3)2·6H2O filters after stirring half an hour in water, and filtrate is normal
Temperature volatilization obtains being suitable for the colourless bulk crystals of X-ray single crystal diffraction after two weeks；Wherein L:tma:Zn (NO3)2·6H2O rubs
That ratio is 1:1:1；
The structure of the double triazole trimesic acid Zn complex monocrystalline of 1,2,4,5-durol is [Zn (L) (tma)] H2O, wherein, L
=4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,3,5,6-tetramethylphenyl)-4H-1,2,4-triazole；Tma=all
Benzenetricarboxylic acid；
L tma。
3. the double triazole trimesic acid Zn complex monocrystalline of 1,2,4,5-durol described in claim 1 is being made as hydrogen storage material
Standby to the application in terms of hydrogen adsorption.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101092434A (en) * | 2007-06-12 | 2007-12-26 | 南开大学 | Hydrogen stored porus material of iso metals, prepartion method and application |
| CN104610293A (en) * | 2015-02-26 | 2015-05-13 | 天津师范大学 | Naphthalene bistriazole trimesic acid zinc complex with potential fluorescent material and preparation method thereof |
| CN105622650A (en) * | 2016-01-05 | 2016-06-01 | 天津师范大学 | 1,2,4,5-tetramethyl benzene bistriazole two-dimensional zinc complex single crystal and application thereof |
| CN105669718A (en) * | 2016-01-05 | 2016-06-15 | 天津师范大学 | 1,2,4,5-Tetramethylphenylbistriazol zinc complex monocrystal and application thereof |
-
2016
- 2016-07-28 CN CN201610602281.7A patent/CN106220655A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101092434A (en) * | 2007-06-12 | 2007-12-26 | 南开大学 | Hydrogen stored porus material of iso metals, prepartion method and application |
| CN104610293A (en) * | 2015-02-26 | 2015-05-13 | 天津师范大学 | Naphthalene bistriazole trimesic acid zinc complex with potential fluorescent material and preparation method thereof |
| CN105622650A (en) * | 2016-01-05 | 2016-06-01 | 天津师范大学 | 1,2,4,5-tetramethyl benzene bistriazole two-dimensional zinc complex single crystal and application thereof |
| CN105669718A (en) * | 2016-01-05 | 2016-06-15 | 天津师范大学 | 1,2,4,5-Tetramethylphenylbistriazol zinc complex monocrystal and application thereof |
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Application publication date: 20161214 |