CN104356148B - Two triazole Cu-nitric acid title complex of isophthalic and preparation method thereof and application - Google Patents
Two triazole Cu-nitric acid title complex of isophthalic and preparation method thereof and application Download PDFInfo
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- CN104356148B CN104356148B CN201410623862.XA CN201410623862A CN104356148B CN 104356148 B CN104356148 B CN 104356148B CN 201410623862 A CN201410623862 A CN 201410623862A CN 104356148 B CN104356148 B CN 104356148B
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000003852 triazoles Chemical class 0.000 title abstract description 5
- 229910017604 nitric acid Inorganic materials 0.000 title abstract description 3
- 239000010949 copper Substances 0.000 claims abstract description 26
- 239000000463 material Substances 0.000 claims abstract description 9
- 239000000523 sample Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 238000001027 hydrothermal synthesis Methods 0.000 claims abstract description 4
- -1 triazole copper complex Chemical class 0.000 claims description 11
- HVMMGTLUNJNHFE-UHFFFAOYSA-N 4-[3-(1,2,4-triazol-4-yl)phenyl]-1,2,4-triazole Chemical compound N=1N=CN(C1)C=1C=C(C=CC1)N1C=NN=C1 HVMMGTLUNJNHFE-UHFFFAOYSA-N 0.000 claims description 10
- 239000013078 crystal Substances 0.000 claims description 10
- 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
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 abstract description 12
- 150000004699 copper complex Chemical class 0.000 abstract description 3
- 229910020366 ClO 4 Inorganic materials 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 238000002447 crystallographic data Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 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
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000009415 formwork Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
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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
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- General Health & Medical Sciences (AREA)
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Abstract
Two triazole Cu-nitric acid title complex of isophthalic and preparation method thereof and application.The invention discloses one { [Cu (L)] (NO
3)
2? (<b>1</bGreatT.Gr eaT.GT) (L=4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole) and preparation method.It adopts " hydrothermal method ", i.e. Cu (ClO
4)
2with L 100
oc hydrothermal condition gets off and prepares this title complex.The present invention further discloses copper complex { [Cu (L)] (NO
3)
2? (<b>1</bGreatT.Gr eaT.GT)? (L=4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole) as the application of potential ferroelectric material, fluorescent material aspect; Described fluorescent material refers to this compound as Mg
2+the application of ion fluorescence probe.
Description
The present invention obtains state natural sciences fund general project (21471113), and Tianjin Education Commission funded projects (20140506) and Tianjin innovation team of institution of higher education training plan subsidize (TD12-5038).
Technical field
The invention belongs to Inorganic synthese technical field, relate to copper complex { [Cu (L)] (NO
3)
2(1) (L=4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole) preparation method and as Mg
2+the application of fluorescent probe.
Background technology
1,2,4-triazole and derivative thereof have the coordination feature of pyrazoles and imidazoles concurrently, are the bridgingligands that coordination ability is stronger, have synthesized at present and have characterized a large amount of monokaryons, multinuclear and multidimensional compound.These parts can with 1, nitrogen-atoms on 2 and metallic ion coordination form N1, N2-bridging pattern, for 4 unsubstituted 1,2,4-triazole derivative is by 2, nitrogen-atoms on 4 forms N2, N4-bridging pattern, this N2, N4-bridging pattern is with the N1 of imidazoles in metalloenzyme, and N3-bridging mode class seemingly.Special purpose for triazole class compounds also shows in the design of molecular device, and the metal complexes that synthesis has different dimension has been the vital step of device.
The present invention selects Cu (NO
3)
2with 4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole (L) 160
ounder C hydrothermal condition, obtain three-dimensional copper coordination polymer.Fluorometric investigation result shows, this title complex can as Mg
2+ion fluorescence probe.
Summary of the invention
Another object of the present invention is to provide a kind of isophthalic two triazole copper complex { [Cu (L)] (NO
3)
2(1) (L=4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole) monocrystalline and preparation method thereof.
Current inventor provides following technical scheme for this reason:
Two triazole copper complex { [Cu (L)] (NO of isophthalic
3)
2}
n(1) structural motif of (L=4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole) as shown in Figure 1; L=4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole;
The present invention further discloses two triazole copper complex { [Cu (L)] (NO of isophthalic
3)
2(1) (L=4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole) monocrystalline, it is characterized in that this single crystal structure adopts APEXIICCD single crystal diffractometer, use through graphite monochromatised Mok alpha-ray (l=0.71073) be incident radiation, point diffraction is collected with w-2q scan mode, obtain unit cell parameters through least-squares refinement, utilize SHELXL-97 direct method to solve single crystal data from difference Fourier electron density map:
The crystallographic data of table 1. title complex 1
Two triazole copper complex { [Cu (L)] (NO of isophthalic of the present invention
3)
2the preparation method of (1) (L=4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole) monocrystalline, its feature in employing " hydrothermal method ", at CH
3cN and H
2in O, by Cu (NO
3)
2with 4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole (L) ligand 1 00
oreact under C hydrothermal condition after three days and be down to room temperature, obtain the yellow rhabdolith of applicable X-ray single crystal diffraction.Wherein CH
3cN and H
2the volume ratio of O is 4:6, Cu (NO
3)
2be 1:1 with the mol ratio of 4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole (L);
The more detailed preparation method of the present invention is as follows:
Two triazole copper complex { [Cu (L)] (NO of a kind of isophthalic
3)
2the preparation method of (1) (L=4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole) monocrystalline is characterized in that, at mixed solvent C H
3cN and H
2in O, by Cu (NO
3)
2with 4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole (L) ligand 1 00
oreact under C hydrothermal condition after three days and be down to room temperature, obtain the yellow rhabdolith of applicable X-ray single crystal diffraction.
Solvent of the present invention is mixed solvent, CH
3cN and H
2o.
Wherein Cu (NO
3)
2be 1:1 with the mol ratio of 4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole (L).
The present invention further discloses copper complex { [Cu (L)] (NO
3)
2(1) (L=4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole) be as the application of potential ferroelectric material, fluorescent material aspect; Described fluorescent material refers to this compound as Mg
2+the application of ion fluorescence probe.
Two triazole copper complex { [Cu (L)] (NO of isophthalic disclosed by the invention
3)
2the advantage and disadvantage that has of (1) (L=4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole) monocrystalline is:
(1) operation is simple and easy to do.
(2) reaction yield is high, and the purity of products obtained therefrom is high.
(3) { [Cu (L)] (NO prepared by the present invention
3)
2(1) (L=4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole) production cost is low, profit margin is large, is more suitable for large-scale industrial production.
Accompanying drawing explanation
Fig. 1: the crystalline structure primitive figure of title complex 1;
Fig. 2: the two-dirnentional structure figure of title complex 1;
Fig. 3: different ions is for the impact of title complex 1 fluorescence intensity.
Embodiment
Below in conjunction with embodiment, the present invention is described further, and embodiment is only indicative, never means that it limits the scope of the invention by any way.All raw materials are such as: anthracene nucleus etc. are all buy from chemical reagents corporation both domestic and external, through continuing to purify but directly use.The fusing point of product is X in model
4the melting point apparatus of Micro carries out measure.Used raw material is by commercially available.
Embodiment 1
The preparation of 4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole (L) part
In 50mL tri-mouthfuls of round-bottomed flasks that magneton, reflux exchanger and thermometer are housed, add mphenylenediamine (1mmol) respectively, two formyl hydrazine (2mmol), starts and is stirred in 160 DEG C, reacts 12 hours.After reaction terminates, reaction solution is down to room temperature, separates out and precipitate in a large number, by precipitation water and ethyl alcohol recrystallization, yield 86%.Ultimate analysis C
10h
8n
6theoretical value: C, 56.60; H, 3.80; N, 39.60.Experimental value: C, 56.56; H, 3.75; N, 39.56.Mphenylenediamine, the mol ratio of two formyl hydrazine is 1:2.
Embodiment 2
Cu (NO
3)
2be 1:1 with the mol ratio of 4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole (L).
L (0.0424g, 0.2mmol), Cu (NO
3)
2(0.0691g, 0.2mmol), H
2o (6mL), CH
3cN (4mL), hydro-thermal 100
oc is slowly down to room temperature in tri-days afterwards.The yellow rhabdolith that applicable X-ray single crystal diffraction is analyzed is had after driving still.Productive rate: 35% (calculating based on L).Ultimate analysis (C
10h
8cuN
7o
3) theoretical value (%): C, 35.56; H, 2.39; N, 29.03.Measured value: C, 35.63; H, 2.36; N, 29.09.
Embodiment 3
Crystal structure determination adopts APEXIICCD single crystal diffractometer, use through graphite monochromatised Mok alpha-ray (l=0.71073) be incident radiation, point diffraction is collected with w-2q scan mode, unit cell parameters is obtained through least-squares refinement, software is utilized to solve crystalline structure from difference Fourier electron density map, and through Lorentz lorentz and polarizing effect correction.All H atom are synthesized by difference Fourier and are determined through desirable position calculation.Detailed axonometry data are in table 1.Structural motif is shown in Fig. 1, and inclusion anthracene nucleus molecule is shown in Fig. 2 as the two-dimensional layered structure of organic formwork.
The crystallographic data of table 1 title complex 1
Embodiment 4
Wherein Cu (NO
3)
2be 1:1 with the mol ratio of 4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole (L);
We also attempted other ratios, such as Cu (NO
3)
2be 2:1 with the mol ratio of L, then the length of no matter hydro-thermal reaction time, all can not get crystalline compound.Therefore Cu (NO
3)
2be 2:1 with the mol ratio of L be optimum response proportioning.
Embodiment 5
Mg
2+ion fluorescence probe
As shown in Figure 3, as the Mg adding 1-3 times of equivalent in the DMSO solution at title complex 1
2+ion, the maximum emission peak that 441nm place occurs is by force do not add Mg
2+the twice of ion.Work as Ni
2+ion and Co
2+ion joins in this system, and it is launched light intensity and weakens to some extent relative to 1.And add Ca
2+after ion, luminous intensity is almost constant.Above experimental result shows, the luminous intensity of 1 shows Mg
2+the selectivity of height, therefore can be used as Mg
2+ion fluorescence probe.As far as we know, this is the Mg of first case based on triazole derivative
2+ion fluorescence probe.
After the preferred embodiment described in detail, be familiar with this technology personage can be well understood to, do not departing under above-mentioned claim and spirit and can carry out various change and amendment, all above embodiment is done according to technical spirit of the present invention any simple modification, equivalent variations and modification, all belong to the scope of technical solution of the present invention.And the present invention is not also by the restriction of example embodiment in specification sheets.
Claims (4)
1. the two triazole copper complex monocrystalline of isophthalic, it is characterized in that this single crystal structure adopts APEXIICCD single crystal diffractometer, use through graphite monochromatised Mok alpha-ray, λ=0.71073 is incident radiation, point diffraction is collected with ω-2 θ scan mode, obtain unit cell parameters through least-squares refinement, utilize software to solve single crystal data from difference Fourier electron density map:
The molecular formula of the two triazole copper complex monocrystalline of described isophthalic: [Cu (L)] (NO
3)
2, wherein L=4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole.
2. the preparation method of the two triazole copper complex monocrystalline of isophthalic described in claim 1, is characterized in that adopting " hydrothermal method ", i.e. Cu (NO
3)
2with 4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole (L) 100
oc hydrothermal condition gets off and prepares this complex monocrystal;
Described solvent is mixed solvent is CH
3cN and H
2o; Wherein Cu (NO
3)
2be 1:1 with the mol ratio of 4-(3-(4H-1,2,4-triazole-4-yl) phenyl)-4H-1,2,4-triazole (L).
3. the two triazole copper complex monocrystalline of isophthalic described in claim 1 has using value as luminescent material.
4. the application in fluorescent material prepared by the two triazole copper complex monocrystalline of isophthalic described in claim 1; Described fluorescent material refers to this compound as Mg
2+the application of ion fluorescence probe.
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| CN104610376B (en) * | 2015-02-26 | 2017-07-07 | 天津师范大学 | Double triazole iron complexes of oxygen ether with potential fluorescent material and preparation method thereof |
| CN104610378B (en) * | 2015-02-26 | 2017-08-11 | 天津师范大学 | Double triazole nickel complexes of oxygen ether with potential fluorescent material and preparation method thereof |
| CN105524081A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | Anthracycline bistriazole two-dimensional copper complex single crystal and application thereof |
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|---|---|---|---|---|
| US3141023A (en) * | 1961-08-23 | 1964-07-14 | Du Pont | Certain nu-carbamylurazoles |
| CN87104294A (en) * | 1986-06-23 | 1988-04-13 | 鲁布里佐尔公司 | The Urazole compositions of useful as additives for functional fluids |
| CN103130841A (en) * | 2013-03-25 | 2013-06-05 | 南京工业大学 | Transition metal coordination compound of 5-(naphthyridine-4-base) triazole derivative and luminescence application |
| CN103539805A (en) * | 2013-11-03 | 2014-01-29 | 安庆师范学院 | Flexible dual-triazole ligand based CuCN complex and preparation method thereof |
| CN103755620A (en) * | 2014-01-13 | 2014-04-30 | 阜阳师范学院 | Magnesium ion fluorescent probe and preparation method and application thereof |
-
2014
- 2014-11-10 CN CN201410623862.XA patent/CN104356148B/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3141023A (en) * | 1961-08-23 | 1964-07-14 | Du Pont | Certain nu-carbamylurazoles |
| CN87104294A (en) * | 1986-06-23 | 1988-04-13 | 鲁布里佐尔公司 | The Urazole compositions of useful as additives for functional fluids |
| CN103130841A (en) * | 2013-03-25 | 2013-06-05 | 南京工业大学 | Transition metal coordination compound of 5-(naphthyridine-4-base) triazole derivative and luminescence application |
| CN103539805A (en) * | 2013-11-03 | 2014-01-29 | 安庆师范学院 | Flexible dual-triazole ligand based CuCN complex and preparation method thereof |
| CN103755620A (en) * | 2014-01-13 | 2014-04-30 | 阜阳师范学院 | Magnesium ion fluorescent probe and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| "Synthesis, Crystal Structure, and Properties of a 3D Cu(I) Coordination Polymer Based on Cu3(CN)2 Clusters and 1,3-Di-(1,2,4-Triazole-4-yl)Benzene";Shao-Bin Miao等;《J Clust Sci》;20140228;第25卷;1137-1145 * |
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