CN106188109A - The double triazole two dimension cadmium complex monocrystalline of 1,4 dibromo 2,5 dimethylenes and application - Google Patents
The double triazole two dimension cadmium complex monocrystalline of 1,4 dibromo 2,5 dimethylenes and application Download PDFInfo
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- CN106188109A CN106188109A CN201610602762.8A CN201610602762A CN106188109A CN 106188109 A CN106188109 A CN 106188109A CN 201610602762 A CN201610602762 A CN 201610602762A CN 106188109 A CN106188109 A CN 106188109A
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- triazole
- btca
- cadmium complex
- monocrystalline
- bromo
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- 229910052793 cadmium Inorganic materials 0.000 title claims abstract description 18
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 150000003852 triazoles Chemical class 0.000 title claims abstract description 18
- -1 dimethylenes Chemical class 0.000 title abstract description 3
- 125000000950 dibromo group Chemical group Br* 0.000 title abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000013078 crystal Substances 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 230000008569 process Effects 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 239000000706 filtrate Substances 0.000 claims abstract description 6
- 239000011232 storage material Substances 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000001179 sorption measurement Methods 0.000 claims description 8
- GCAIEATUVJFSMC-UHFFFAOYSA-N benzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1C(O)=O GCAIEATUVJFSMC-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 230000005260 alpha ray Effects 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 abstract 2
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000005997 bromomethyl group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000003860 storage Methods 0.000 description 10
- 239000012621 metal-organic framework Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- QENIALCDPFDFHX-UHFFFAOYSA-N 1,4-dibromo-2,5-dimethylbenzene Chemical compound CC1=CC(Br)=C(C)C=C1Br QENIALCDPFDFHX-UHFFFAOYSA-N 0.000 description 2
- QXISTPDUYKNPLU-UHFFFAOYSA-N 2-bromo-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(Br)=C1 QXISTPDUYKNPLU-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000005855 radiation Effects 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
- 239000013132 MOF-5 Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229920001795 coordination polymer Polymers 0.000 description 1
- 238000012937 correction Methods 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
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 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
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 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
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- 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 the double triazole two dimension cadmium complex monocrystalline of Isosorbide-5-Nitrae dibromo 2,5 dimethylene and application, its structure: [Cd (L)]2+[btca]2‑·H2O, wherein, L=4 (4 ((4H 1,2,4 triazole 4 base) methyl) 2,5 two bromomethyls) 4H 1,2,4 triazole；Btca=PMA.Also disclose the preparation method of monocrystalline simultaneously.It is to use room temperature volatility process, i.e. L, btca and Cd (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:btca:Cd (NO3)2·6H2The mol ratio of O is 1:1:1.The present invention further discloses the double triazole two dimension cadmium complex monocrystalline of 1,4 dibromo 2,5 dimethylenes 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 two dimension cadmium complex monocrystal coordination compound monocrystalline of 1,4-bis-bromo-2,5-dimethylene 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 use room temperature volatility process, i.e. L, btca and Cd (NO3)2·6H2O stirs mistake after half an hour in water
Filter, filtrate room temperature obtains being suitable for the colourless bulk crystal structure of X-ray single crystal diffraction after volatilizing two weeks be [Cd (L)]2+[btca
]2-·H2O, wherein, L=4-(4-((4H-1,2,4-triazole-4-yls) methyl)-2,5-bis-bromomethyl)-4H-1,2,4-triazoles；
Btca=PMA.Hydrogen can be adsorbed by this complex monocrystal as hydrogen storage material.
To this end, the invention discloses a kind of Isosorbide-5-Nitrae-two bromo-2, the monocrystalline of the double triazole two dimension cadmium complex of 5-dimethylene, its
It is characterised by that this mono-crystalline structures uses APEX II CCD single crystal diffractometer, uses 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,
Software is utilized to solve single crystal data from difference Fourier electron density map:
Its structure is as follows:
[Cd(L)]2+[btca]2-·H2O, wherein
L=4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-two bromomethyl)-4H-1,2,4-triazole；
Btca=PMA.
The present invention further discloses the preparation side of the double triazole two dimension cadmium complex monocrystalline of 1,4-bis-bromo-2,5-dimethylene
Method, it is characterised in that it is to use room temperature volatility process, by L, btca and Cd (NO3)2·6H2O stirs mistake after half an hour in water
Filter, filtrate room temperature obtains being suitable for the colourless bulk crystals of X-ray single crystal diffraction after volatilizing two weeks；Wherein L:btca:Cd
(NO3)2·6H2The mol ratio of O is 1:1:1；
The structure of the double triazole two dimension cadmium complex monocrystalline of 1,4-bis-bromo-2,5-dimethylene is [Cd (L)]2+[btca]2-·H2O；
Wherein L=4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-two bromomethyl)-4H-1,2,4-triazole；Btca=all
Benzenetetracarboxylic acid；
L btca。
The present invention further discloses the double triazole two dimension cadmium complex monocrystalline of 1,4-bis-bromo-2,5-dimethylene as storage
Hydrogen material is in preparation to the application in terms of hydrogen adsorption, and experimental result shows: anthracene nucleus double triazole two dimension cadmium coordination frame complex
Monocrystalline is under about 3.4 MPa, and when 298 and 77 K, the hydrogen adsorption amount of this hydrogen storage Porous materials has respectively reached 0.87 and 1.38
wt%。
It is excellent that the double triazole two dimension cadmium complex monocrystalline of a kind of 1,4-bis-disclosed by the invention bromo-2,5-dimethylene 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) Isosorbide-5-Nitrae-two bromo-2 prepared by the present invention, the double triazole two dimension cadmium complex monocrystalline of 5-dimethylene, produce into
This is low, and method is easy, is suitable for large-scale production.The double triazole two dimension cadmium complex monocrystalline conduct of 1,4-bis-bromo-2,5-dimethylene
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.Raw materials used it is commercially available.All raw materials are all public from chemical reagent both domestic and external
The raw materials such as department buys, such as Isosorbide-5-Nitrae-two bromo-2,5-dimethyl benzene, through continuation purification but directly do not use.
Embodiment 1
The preparation of 4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-two bromomethyl)-4H-1,2,4-triazole (L)
1,4-bis-bromo-2,5-dimethyl benzene: the mol ratio of double formylhydrazines is 1:4
The bromo-2,5-of 1,4-bis-bis-it is separately added in equipped with 50 mL three neck round bottom flasks of magneton, reflux condenser and thermometer
Methylbenzene (1 mmol) and double formylhydrazine (4 mmol), start stirring 150oC, reacts 24 hours.After reaction terminates, will be anti-
Answer liquid to be down to room temperature, the precipitation obtained added 100 mL hot methanols, after stirring and dissolving, filter, filtrate slowly volatilize obtain white
Color solid, yield 85%.Elementary analysis (C12N6H10Br2) theoretical value (%): C, 36.21；H, 2.53；N, 21.11.Measured value: C,
36.24；H, 2.55；N, 21.05；
The double formylhydrazine of 1,4-bis-bromo-2,5-dimethyl benzene.
The preferred Isosorbide-5-Nitrae of the present invention-two bromo-2,5-dimethyl benzene: the mol ratio of double formylhydrazines is 1:4, reaction temperature 150 DEG C,
24 hours response time.Using " one kettle way ", by bromo-for Isosorbide-5-Nitrae-two 2,5-dimethyl benzene and double formylhydrazine are prepared in a heated condition
4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-two bromomethyl)-4H-1,2,4-triazole (L).
Embodiment 2
4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-two bromomethyl)-4H-1,2,4-triazole (L) (0.1
Mmol), PMA (btca) (0.1 mmol) and Cd (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 (C46H36Br6CdN18O9) theoretical value (%): C, 35.04；H, 2.30；N, 15.99.Measured value: C, 35.08；H, 2.34；
N, 15.89.
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 cell parameter through least square refinement,
Software is utilized to solve crystal structure from difference Fourier electron density map, and through Lorentz lorentz and polarity effect correction.All of H is former
Son 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. an Isosorbide-5-Nitrae-two bromo-2, the monocrystalline of the double triazole two dimension cadmium complex of 5-dimethylene, it is characterised in that this mono-crystalline structures
Using APEX II CCD single crystal diffractometer, use through graphite monochromatised Mok alpha ray, λ=0.71073 is incident spoke
Penetrate, withω-2θScan mode collects point diffraction, obtains cell parameter through least square refinement, from difference Fourier electronics
Density map utilizes software to solve single crystal data:
Its structure is as follows:
[Cd(L)]2+[btca]2-·H2O, wherein L=4-(4-((4H-1,2,4-triazole-4-yls) methyl)-2,5-dibromo first
Base)-4H-1,2,4-triazole；
Btca=PMA.
2. Isosorbide-5-Nitrae-two bromo-2 described in claim 1, the preparation method of the double triazole two dimension cadmium complex monocrystalline of 5-dimethylene, it is special
Levy and be that it is to use room temperature volatility process, by L, btca and Cd (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:btca:Cd (NO3)2·6H2O rubs
That ratio is 1:1:1；
The structure of the double triazole two dimension cadmium complex monocrystalline of 1,4-bis-bromo-2,5-dimethylene is [Cd (L)]2+[btca]2-·H2O；
Wherein L=4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-two bromomethyl)-4H-1,2,4-triazole；Btca=all
Benzenetetracarboxylic acid；
L btca。
3. the double triazole two dimension cadmium complex monocrystalline of 1,4-bis-bromo-2,5-dimethylene described in claim 1 is as hydrogen storage material
In preparation to the application in terms of hydrogen adsorption.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110358106A (en) * | 2019-08-02 | 2019-10-22 | 湖北师范大学 | A kind of anion frame metal-organic framework material and its preparation method and application of pair of nitro-aromatic explosive sensing |
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|---|---|---|---|---|
| CN105524094A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole inclusion N, N'-diethyl acetamide cadmium complex single crystal |
| CN105541881A (en) * | 2016-01-05 | 2016-05-04 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bis(triazole) three-dimensional cadmium complex single crystal and application |
| CN105566361A (en) * | 2016-01-05 | 2016-05-11 | 天津师范大学 | 1,4-dibromo-2,5-dimethylene bis(triazole) cadmium complex monocrystal and applications thereof |
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2016
- 2016-07-28 CN CN201610602762.8A patent/CN106188109A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105524094A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole inclusion N, N'-diethyl acetamide cadmium complex single crystal |
| CN105541881A (en) * | 2016-01-05 | 2016-05-04 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bis(triazole) three-dimensional cadmium complex single crystal and application |
| CN105566361A (en) * | 2016-01-05 | 2016-05-11 | 天津师范大学 | 1,4-dibromo-2,5-dimethylene bis(triazole) cadmium complex monocrystal and applications thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110358106A (en) * | 2019-08-02 | 2019-10-22 | 湖北师范大学 | A kind of anion frame metal-organic framework material and its preparation method and application of pair of nitro-aromatic explosive sensing |
| CN110358106B (en) * | 2019-08-02 | 2021-10-01 | 湖北师范大学 | Anion framework metal organic framework material for sensing p-nitroaromatic explosives and preparation method and application thereof |
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Application publication date: 20161207 |
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