CN104370945A - Dinuclear zinc-containing three-dimensional compound containing dual flexible imidazole ligands and preparation method of compound - Google Patents
Dinuclear zinc-containing three-dimensional compound containing dual flexible imidazole ligands and preparation method of compound Download PDFInfo
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- CN104370945A CN104370945A CN201410558024.9A CN201410558024A CN104370945A CN 104370945 A CN104370945 A CN 104370945A CN 201410558024 A CN201410558024 A CN 201410558024A CN 104370945 A CN104370945 A CN 104370945A
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- zinc
- imidazoles
- compound
- flexible
- dimensional compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 40
- 239000011701 zinc Substances 0.000 title claims abstract description 30
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 229910052725 zinc Inorganic materials 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000003446 ligand Substances 0.000 title abstract description 19
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title abstract 9
- 230000009977 dual effect Effects 0.000 title abstract 3
- 239000000126 substance Substances 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 239000001273 butane Substances 0.000 claims description 17
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 17
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 17
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 17
- 239000011259 mixed solution Substances 0.000 claims description 16
- 150000002460 imidazoles Chemical class 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- 239000013110 organic ligand Substances 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 150000003751 zinc Chemical class 0.000 claims description 8
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004246 zinc acetate Substances 0.000 claims description 4
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 3
- 229960001763 zinc sulfate Drugs 0.000 claims description 3
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 238000010583 slow cooling Methods 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- VWSRHOIRMGHAPR-UHFFFAOYSA-N 2-methyl-1-[4-(2-methylimidazol-1-yl)butyl]imidazole Chemical compound CC1=NC=CN1CCCCN1C(C)=NC=C1 VWSRHOIRMGHAPR-UHFFFAOYSA-N 0.000 abstract 1
- JATKASGNRMGFSW-UHFFFAOYSA-N 5-bromobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(Br)=CC(C(O)=O)=C1 JATKASGNRMGFSW-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- WHLZPGRDRYCVRQ-UHFFFAOYSA-N 1-butyl-2-methylimidazole Chemical compound CCCCN1C=CN=C1C WHLZPGRDRYCVRQ-UHFFFAOYSA-N 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical group [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009466 transformation Effects 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
- C07F3/06—Zinc compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention relates to the field of coordination chemistry and in particular relates to a dinuclear zinc-containing three-dimensional compound containing dual flexible imidazole ligands and a preparation method of the compound. The chemical formula of the dinuclear zinc-containing three-dimensional compound containing dual flexible imidazole ligands is C29H27N4O9Br2Zn2; the compound is a triclinic system and belongs to the space group P-1; the cell parameters of the compound are as follows: a=9.031(1) angstroms, b=9.978(5) angstroms, c=17.072(7) angstroms, alpha=76.375(3) degrees, beta=88.841(4) degrees, gamma=79.774(8) degrees, and V=1538.21(1) cubic angstroms. The dinuclear zinc-containing three-dimensional compound is easy to prepare; besides, 5-bromoisophthalic acid is capable of regulating the structure, while the flexible ligand 1,4-bis(2-methyl-imidazol-1-yl)butane is capable of improving the dimensionality and the stability of the compound. The dinuclear zinc-containing three-dimensional compound has excellent potential application prospect in the fields of molecular fluorescence and molecular recognition.
Description
Technical field
The present invention relates to coordination chemistry field, particularly a kind of double-core containing the two part of flexible imidazoles is containing zinc three-dimensional compound and preparation method thereof.
Background technology
In recent years, ligand polymer obtains as a kind of novel functional materials and develops rapidly, not only due to its charming topological framework but also because of its unique potential using value.Affect a lot of because have of ligand polymer Structure and Properties, as metal ion, ligand structure, solvent, pH value and synthetic method etc., wherein the Structure and Properties of snappiness on ligand polymer of ligand structure plays vital impact, because flexible ligand with the process of metallic cation generation coordination in can there is distortion to a certain degree and distortion, add the prediction difficulty of its Structure and Properties, and then obtain the ligand polymer of novel structure unique properties.
Summary of the invention
A kind of double-core containing the two part of flexible imidazoles that technical problem to be solved by this invention is to provide with flexible ligand contains zinc three-dimensional compound.
Another object of the present invention is the preparation method providing above-mentioned three-dimensional compound.
Double-core containing the two part of flexible imidazoles is containing a zinc three-dimensional compound, and chemical formula is C
29h
27n
4o
9br
2zn
2, stating compound is triclinic(crystalline)system,
p-1spacer, unit cell parameters is
a=9.031 (1),
b=9.978 (5),
c=17.072 (7),
α=76.375 (3) o,
β=88.841 (4) o,
γ=79.774 (8) o, V=1538.21 (1)
3.
A kind of double-core containing the two part of flexible imidazoles is containing the preparation method of zinc three-dimensional compound, by organic ligand 5-bromine m-phthalic acid, 1,4-bis-(2-methyl-imidazoles-1-base) butane and soluble zinc salt are dissolved in methanol solvate, at room temperature stir formed mixed solution, then by described mixed solution under solvent thermal condition after reacting by heating slow cooling obtain described three-dimensional compound.
Wherein, the English formal name used at school of Isosorbide-5-Nitrae-two (2-methyl-imidazoles-1-base) butane is Isosorbide-5-Nitrae-bis (2-methyl-imidazol-1-yl) butane, and its chemical structural formula is as follows:
Further, described Heating temperature is 140 DEG C ~ 160 DEG C, and the reacting by heating time is 48 ~ 96 hours.
Further, described cooling is 2 DEG C/h ~ 5 DEG C/h and is down to room temperature.
Further, described soluble zinc salt is at least one in zinc nitrate, zinc chloride, zinc acetate, zinc sulfate.
Further, the mol ratio of described 5-bromine m-phthalic acid, Isosorbide-5-Nitrae-two (2-methyl-imidazoles-1-base) butane and soluble zinc salt is 0.8 ~ 1.2:0.8 ~ 1.2:1.
Further, the mol ratio of described 5-bromine m-phthalic acid, Isosorbide-5-Nitrae-two (2-methyl-imidazoles-1-base) butane and soluble zinc salt is preferably 1:1:1.
The present invention has following beneficial effect:
The double-core of the present invention's synthesis is easy to preparation containing zinc three-dimensional compound, and 5-bromine m-phthalic acid can carry out regulating and controlling effect to structure, and flexible ligand Isosorbide-5-Nitrae-two (2-methyl-imidazoles-1-base) butane improves dimension and the stability of compound.This double-core has extraordinary potential application prospect containing zinc three-dimensional compound in molecular fluorescence, molecular recognition field.
Accompanying drawing explanation
Fig. 1 is that double-core of the present invention is containing zinc three-dimensional compound C
29h
27n
4o
9br
2zn
2with the coordination environment figure of metal center Zn.
Fig. 2 is that double-core of the present invention is containing zinc three-dimensional compound C
29h
27n
4o
9br
2zn
2tomograph schematic diagram.
Embodiment
Below in conjunction with embodiment, the present invention will be described in detail, and embodiment is only the preferred embodiment of the present invention, is not limitation of the invention.
embodiment 1
By 1mmol organic ligand 5-bromine m-phthalic acid, 1mmol1,4-bis-(2-methyl-imidazoles-1-base) butane and 1mmol zinc nitrate are dissolved in the middle of 15mL methanol solvate, at room temperature stir and form mixed solution, then described mixed solution to be inserted in 25mL reactor reacting by heating under solvent thermal 150 DEG C of conditions to be down to room temperature with 5 DEG C/h after 72 hours and to obtain described three-dimensional compound, productive rate is 72.4% (based on Zn).
Then above-claimed cpd is carried out structural characterization.
The X ray diffracting data of this compound visits on diffractometer in Bruker Smart Apex CCD face, uses MoK
αradiation (λ=0.71073), collects with ω scan mode and carries out Lp factor correction, and absorption correction uses SADABS program.Use direct method solution structure, then obtain whole non-hydrogen atom coordinate by difference Fourier method, and obtain hydrogen atom position (C H 1.083) with theoretical hydrogenation method, by method of least squares, structure is revised.Evaluation work completes with SHELXTL routine package on PC.Compound crystal mathematic(al) parameter is in table 1.Structure is shown in Fig. 1, Fig. 2.
table 1. crystallographic parameter and structure elucidation
From crystalline structure, this compound belongs to triclinic(crystalline)system,
p-1spacer, comprises two independent Zn (II) atoms in asymmetric cell, although two Zn atoms are all hexa-coordinate patterns, and its coordination structure difference (as shown in Figure 1).Wherein, two Sauerstoffatoms on a Zn1 and 5-bromine m-phthalic acid take the pattern of double coordination, the pattern of monodentate ligand is then adopted with two atoms on two other 5-bromine m-phthalic acid and the Sauerstoffatom in methanol molecules, Isosorbide-5-Nitrae-two (2-methyl-imidazoles-1-base) butane is then as a kind of bridge ligand and Zn1 coordination; In addition, two Sauerstoffatoms on a Zn2 and 5-bromine m-phthalic acid take the pattern of double coordination, the pattern of monodentate ligand is then adopted with three atoms on other three 5-bromine m-phthalic acids, Isosorbide-5-Nitrae-two (2-methyl-imidazoles-1-base) butane is then as a kind of bridge ligand and Zn2 coordination; Zn1 and Zn2 forms a kind of dual-core architecture by the effect of 5-bromine m-phthalic acid monodentate ligand.This dual-core architecture utilizes Isosorbide-5-Nitrae-two (2-methyl-imidazoles-1-base) butane as the three-dimensional structure formed under the effect of bridge ligand as shown in Figure 2.
embodiment 2
By 1.2mmol organic ligand 5-bromine m-phthalic acid, 1.2mmol1,4-bis-(2-methyl-imidazoles-1-base) butane and 1mmol zinc sulfate are dissolved in the middle of 15mL methanol solvate, at room temperature stir and form mixed solution, then described mixed solution to be inserted in 25mL reactor reacting by heating under solvent thermal 155 DEG C of conditions to be down to room temperature with 3 DEG C/h after 60 hours and to obtain described three-dimensional compound, productive rate is 67.4% (based on Zn).
embodiment 3
By 0.8mmol organic ligand 5-bromine m-phthalic acid, 1.2mmol1,4-bis-(2-methyl-imidazoles-1-base) butane and 1mmol zinc chloride are dissolved in the middle of 15mL methanol solvate, at room temperature stir and form mixed solution, then described mixed solution to be inserted in 25mL reactor reacting by heating under solvent thermal 145 DEG C of conditions to be down to room temperature with 4 DEG C/h after 84 hours and to obtain described three-dimensional compound, productive rate is 59.4% (based on Zn).
embodiment 4
By 1.2mmol organic ligand 5-bromine m-phthalic acid, 0.8mmol1,4-bis-(2-methyl-imidazoles-1-base) butane and 1mmol zinc acetate are dissolved in the middle of 15mL methanol solvate, at room temperature stir and form mixed solution, then described mixed solution to be inserted in 25mL reactor reacting by heating under solvent thermal 160 DEG C of conditions to be down to room temperature with 4 DEG C/h after 84 hours and to obtain described three-dimensional compound, productive rate is 47.8% (based on Zn).
embodiment 5
By 0.08mmol organic ligand 5-bromine m-phthalic acid, 0.08mmol1,4-bis-(2-methyl-imidazoles-1-base) butane and 0.1mmol zinc acetate are dissolved in the middle of 15mL methanol solvate, at room temperature stir and form mixed solution, then described mixed solution to be inserted in 25mL reactor reacting by heating under solvent thermal 140 DEG C of conditions to be down to room temperature with 5 DEG C/h after 84 hours and to obtain described three-dimensional compound, productive rate is 64.3% (based on Zn).
embodiment 6
By 0.9mmol organic ligand 5-bromine m-phthalic acid, 0.8mmol1,4-bis-(2-methyl-imidazoles-1-base) butane and 1mmol zinc nitrate are dissolved in the middle of 15mL methanol solvate, at room temperature stir and form mixed solution, then described mixed solution to be inserted in 25mL reactor reacting by heating under solvent thermal 150 DEG C of conditions to be down to room temperature with 3 DEG C/h after 84 hours and to obtain described three-dimensional compound, productive rate is 58.1% (based on Zn).
The above embodiment only have expressed embodiments of the present invention; it describes comparatively concrete and detailed; but therefore can not be interpreted as the restriction to the scope of the claims of the present invention; in every case the technical scheme adopting the form of equivalent replacement or equivalent transformation to obtain, all should drop within protection scope of the present invention.
Claims (8)
1. the double-core containing the two part of flexible imidazoles, containing a zinc three-dimensional compound, is characterized in that: chemical formula is C
29h
27n
4o
9br
2zn
2.
2. a kind of double-core containing the two part of flexible imidazoles according to claim 1 is characterized in that containing zinc three-dimensional compound, and described compound is triclinic(crystalline)system,
p-1spacer, unit cell parameters is
a=9.031 (1),
b=9.978 (5),
c=17.072 (7),
α=76.375 (3) o,
β=88.841 (4) o,
γ=79.774 (8) o, V=1538.21 (1)
3.
3. a kind of double-core containing the two part of flexible imidazoles according to claim 1 is containing the preparation method of zinc three-dimensional compound, it is characterized in that: by organic ligand 5-bromine m-phthalic acid, 1,4-bis-(2-methyl-imidazoles-1-base) butane and soluble zinc salt are dissolved in methanol solvate, at room temperature stir formed mixed solution, then by described mixed solution under solvent thermal condition after reacting by heating slow cooling obtain described three-dimensional compound.
4. a kind of double-core containing the two part of flexible imidazoles stated according to claim 3 contains the preparation method of zinc three-dimensional compound, it is characterized in that: described Heating temperature is 140 DEG C ~ 160 DEG C, and the reacting by heating time is 48 ~ 96 hours.
5. a kind of double-core containing the two part of flexible imidazoles stated according to claim 3 contains the preparation method of zinc three-dimensional compound, it is characterized in that: described cooling is 2 DEG C/h ~ 5 DEG C/h and is down to room temperature.
6. a kind of double-core containing the two part of flexible imidazoles stated according to claim 3 contains the preparation method of zinc three-dimensional compound, it is characterized in that: described soluble zinc salt is at least one in zinc nitrate, zinc chloride, zinc acetate, zinc sulfate.
7. a kind of double-core containing the two part of flexible imidazoles stated according to claim 3 contains the preparation method of zinc three-dimensional compound, it is characterized in that: the mol ratio of described 5-bromine m-phthalic acid, Isosorbide-5-Nitrae-two (2-methyl-imidazoles-1-base) butane and soluble zinc salt is 0.8 ~ 1.2:0.8 ~ 1.2:1.
8. a kind of double-core containing the two part of flexible imidazoles stated according to claim 7 contains the preparation method of zinc three-dimensional compound, it is characterized in that: the mol ratio of described 5-bromine m-phthalic acid, Isosorbide-5-Nitrae-two (2-methyl-imidazoles-1-base) butane and soluble zinc salt is preferably 1:1:1.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410558024.9A CN104370945A (en) | 2014-10-21 | 2014-10-21 | Dinuclear zinc-containing three-dimensional compound containing dual flexible imidazole ligands and preparation method of compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410558024.9A CN104370945A (en) | 2014-10-21 | 2014-10-21 | Dinuclear zinc-containing three-dimensional compound containing dual flexible imidazole ligands and preparation method of compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104370945A true CN104370945A (en) | 2015-02-25 |
Family
ID=52550171
Family Applications (1)
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|---|---|---|---|
| CN201410558024.9A Withdrawn CN104370945A (en) | 2014-10-21 | 2014-10-21 | Dinuclear zinc-containing three-dimensional compound containing dual flexible imidazole ligands and preparation method of compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104370945A (en) |
-
2014
- 2014-10-21 CN CN201410558024.9A patent/CN104370945A/en not_active Withdrawn
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Application publication date: 20150225 |