CN104804022A - Mixed ligand coordination compound of benzotriazole derivative and isophthalic acid - Google Patents
Mixed ligand coordination compound of benzotriazole derivative and isophthalic acid Download PDFInfo
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- CN104804022A CN104804022A CN201510156904.8A CN201510156904A CN104804022A CN 104804022 A CN104804022 A CN 104804022A CN 201510156904 A CN201510156904 A CN 201510156904A CN 104804022 A CN104804022 A CN 104804022A
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- China
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- title complex
- phthalic acid
- bmi
- coordination
- bdc
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 239000003446 ligand Substances 0.000 title claims abstract description 15
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 title abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 16
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012964 benzotriazole Substances 0.000 claims abstract description 4
- 239000000376 reactant Substances 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 3
- 239000010949 copper Substances 0.000 claims description 41
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 8
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 abstract 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 5
- 238000005352 clarification Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229910002480 Cu-O Inorganic materials 0.000 description 1
- 230000005536 Jahn Teller effect Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- ZHUXMBYIONRQQX-UHFFFAOYSA-N hydroxidodioxidocarbon(.) Chemical compound [O]C(O)=O ZHUXMBYIONRQQX-UHFFFAOYSA-N 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention discloses a mixed ligand copper (II) coordination compound of benzotriazole derivative and isophthalic acid. The structure of the coordination compound refers to the Specification. The coordination compound adopts the following technical scheme: CuCl2.2H2O, 1-(benzotriazole)-1-methyl-1-imidazole and isophthalic acid are used as reactants; methyl alcohol, water and DMF (N, N-dimethylformamide) are used as reactants, methyl alcohol, water, and DMF (N, N-dimethylformamide) are used as solvents; the the mixed ligand copper (II) coordination compound of benzotriazole derivative and isophthalic acid is synthesized at the temperature of 80 DEG C.
Description
Technical field
The present invention is specifically related to non-d
10the fluorescence of metal complexes to part has cancellation effect field and preparation method thereof.
Background technology
Although the title complex of many novel structures, excellent property is successfully synthesized, because the factor affecting complex structure is varied, cause the title complex synthesizing expected structure to be faced with heavy challenge, therefore emerged numerous synthesis strategies.As adopted known geometry and the secondary of fixed connection point to build unit, controlling the ratio of metal ion and part, the pH value of regulator solution, changing the temperature etc. of reaction system.Wherein, reasonably select the first part and assistant ligand to construct novel title complex and be proved to be a kind of method the most effective and important.Nitrogen heterocyclic 1-(benzotriazole)-1-methyl isophthalic acid-imidazoles is a kind of well organic ligand, containing three potential haptos, with multiple coordination mode and different metallic ion coordination, can obtain the title complex of novel structure.Simultaneously, in aromatic carboxylic acid, the coordination ability of carboxyl oxygen is also very strong, the coordination mode of carboxyl especially varied (as monodentate ligand, bidentate chelating or bridging coordination and tridentate ligand etc.), and partly or entirely can take off proton thus form the negatively charged ion of different valence state under different pH value condition, play the dual function not only meeting central metal coordination but also balancing charge.Therefore, utilizing nitrogen heterocyclic and fragrant carboxylic poly carboxylic acid jointly as part, is successful one of important method preparing title complex by constructing title complex with the self-assembly of different metal ion.
Summary of the invention
The object of the present invention is to provide a kind of Benzotriazole Derivative and m-phthalic acid mixed matching copper (II) title complex, and its preparation method is provided.The technical solution adopted in the present invention is: with CuCl
22H
2o, 1-(benzotriazole)-1-methyl isophthalic acid-imidazoles and m-phthalic acid as reactant, with methyl alcohol, water, DMF(N, dinethylformamide) be solvent, 80
oa kind of Benzotriazole Derivative and m-phthalic acid mixed matching copper (II) title complex is synthesized during C.
The structure of a kind of Benzotriazole Derivative of the present invention and m-phthalic acid mixed matching copper (II) title complex is:
Title complex of the present invention { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
nsynthetic method draw together following steps:
After the aqueous solution of the methanol solution of 2-8 mL bmi part (0.1-0.4 mmol) and 2-8 mL m-phthalic acid (0.05-0.2 mmol) being stirred, be dropwise added dropwise to 1 mL CuCl
22H
2in the aqueous solution of O (0.05 mmol), then instill 0.5-2 mL DMF(N, dinethylformamide), filter after stirring, the mixing solutions of clarification is incorporated with in the stainless steel cauldron of polytetrafluoroethylmaterial material liner, obturages and be placed in baking oven, be heated to 80
oc is also incubated 72-80 hour.Be down to room temperature with the speed of 5-10 DEG C/h, have good blue-tinted transparent rhabdolith to separate out, obtain title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
n, crystal is stable in the air.
Beneficial effect of the present invention is as follows: part has stronger coordination ability, flexible and changeable coordination mode, and 80
oc can synthesize title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
n, and its structure is unique, synthetic technology is simple, safety, product purity are high.
Accompanying drawing explanation
Fig. 1 title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
none-dimentional structure figure.
Fig. 2 title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
ncoordination environment figure.
Fig. 3 title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
nthree-dimensional packed structures.
Fig. 4 title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
nxRD figure spectrum.
Fig. 5 title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
ntG-DSC curve.
Fig. 6 title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
nand the solid state fluorescence of respective ligand.
Embodiment
The present invention is further described below with reference to embodiment:
Embodiment 1
The Benzotriazole Derivative of this enforcement and m-phthalic acid mixed matching copper (II) title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
npreparation method as follows:
After the methanol solution of 2 mL bmi parts (0.1 mmol) and the aqueous solution of 2 mL m-phthalic acids (0.05 mmol) being stirred, be dropwise added dropwise to 1 mL CuCl
22H
2in the aqueous solution of O (0.05 mmol), then instill 0.5mL DMF(N, dinethylformamide), filter after stirring, the mixing solutions of clarification is incorporated with in the stainless steel cauldron of polytetrafluoroethylmaterial material liner, obturages and be placed in baking oven, be heated to 80
oc is also incubated 72 hours.Be down to room temperature with the speed of 5-10 DEG C/h, have good blue-tinted transparent rhabdolith to separate out, obtain title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
n, crystal is stable in the air.Productive rate: 55% (based on Cu).
Embodiment 2
The Benzotriazole Derivative of this enforcement and m-phthalic acid mixed matching copper (II) title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
npreparation method as follows:
After the methanol solution of 4 mL bmi parts (0.2 mmol) and the aqueous solution of 4 mL m-phthalic acids (0.1 mmol) being stirred, be dropwise added dropwise to 1 mL CuCl
22H
2in the aqueous solution of O (0.05 mmol), then instill 1 mL DMF(N, dinethylformamide), filter after stirring, the mixing solutions of clarification is incorporated with in the stainless steel cauldron of polytetrafluoroethylmaterial material liner, obturages and be placed in baking oven, be heated to 80
oc is also incubated 75 hours.Be down to room temperature with the speed of 5-10 DEG C/h, have good blue-tinted transparent rhabdolith to separate out, obtain title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
n, crystal is stable in the air.Productive rate: 57% (based on Cu).
Embodiment 3
The Benzotriazole Derivative of this enforcement and m-phthalic acid mixed matching copper (II) title complex the preparation method of [Cu (bmi) 2 (m-bdc) (H2O)] 2H2O}n is as follows:
After the methanol solution of 6 mL bmi parts (0.3 mmol) and the aqueous solution of 8 mL m-phthalic acids (0.2 mmol) being stirred, be dropwise added dropwise to 2 mL CuCl
22H
2in the aqueous solution of O (0.05 mmol), then instill 1 mL DMF(N, dinethylformamide), filter after stirring, the mixing solutions of clarification is incorporated with in the stainless steel cauldron of polytetrafluoroethylmaterial material liner, obturages and be placed in baking oven, be heated to 80
oc is also incubated 80 hours.Be down to room temperature with the speed of 5-10 DEG C/h, have good blue-tinted transparent rhabdolith to separate out, obtain title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
n, crystal is stable in the air.Productive rate: 56% (based on Cu).
Advances in crystal X-ray diffraction shows, title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
nbelong to triclinic(crystalline)system,
p-1 spacer.Each asymmetric cell contains Cu (II) ion, two bmi parts, one
m-bdc
-negatively charged ion, the water molecules of a coordination, two free water moleculess.As shown in Figure 2, Cu (II) ion is in the tetragonal pyramid coordination environment of a distortion, two nitrogen-atoms (N1, N6) coming from bmi part, two come from
m-bdc
-the Sauerstoffatom (O1, O4#1) of part occupies cone position, the end, and the Sauerstoffatom (O5) coming from coordinated water is in the vertex of a cone.Title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
nin Cu-N and Cu-O bond distance all in normal range.Due to the existence of Jahn-Teller effect, the bond distance (2.399 (3)) of Cu (1)-O (5) is significantly than Cu (1)-O (4) #1, Cu (1)-N (6), Cu (1)-N (1), Cu (1)-O (1) bond distance (1.962 (3), 1.997 (3), 2.006 (3), 2.020 (2)) short.
As Fig. 1, { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
nin m-phthalic acid root be all of equal value, and two carboxyls of each m-phthalic acid root are all with the pattern of monodentate ligand and Cu (II) ion, form edge
athe one-dimensional catenary structure of the unlimited extension in direction is 10.1750 (21) by the distance between two Cu (II) ions of m-phthalic acid root bridging.At title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
nbmi parts different in middle existence two kinds of crystallography, and the both sides of chain are all hung on the pattern of monodentate ligand and Cu (II) ion, the bmi ligand conformational of the same side is identical.In addition, title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
nin also there is O (7)-H (6W) O (1), O (5)-H (2W) O (3) #1, O (6)-H (4W) O (3) #1, O (5)-H (1W) O (6) #3, O (6)-H (3W) N (10) #4 and O (7)-H (5W) O (7) #5 six kinds of hydrogen bonds.As shown in Figure 3, stable Magnetic Properties of Three-Dimensional Supramolecular Complex structure is further defined by these six kinds of hydrogen bonds and pi-pi accumulation effect between one-dimensional chain.
Powder x-ray diffraction (XRD) atlas analysis is carried out to characterize the purity of title complex to synthesized title complex.The XRD figure spectrum that the title complex obtained is tested in result display is coincide (Fig. 4) with the collection of illustrative plates of simulation, and this illustrates that the purity of title complex is higher.Be the TG-DSC curve of title complex shown in Fig. 5, as can be seen from the figure, title complex is from 80
oc starts weightlessness, to 179
oc is weightless 7.69 % altogether, corresponding to losing the good coordinated water of crystal water (in theory weightless 7.94%).Title complex continues the weightless decomposition corresponding to bmi part and m-phthalic acid root part at 239 ° of C to 517 ° of C, final residual 11.74 %, and resistates is that CuO(remains 11.69 % in theory).On DSC curve, the endotherm(ic)peak at 102.8 ° of C and 251.3 ° of C places and the exothermic peak at 274.0 ° of C and 474.1 ° of C places equally also have recorded the decomposition course of title complex.The solid state fluorescence of title complex and respective ligand shown in Fig. 6, free ligand bmi and m-phthalic acid respectively 389 nm (
λ ex=334 nm) and 386 nm (
λ ex=345 nm) there is stronger fluorescence peak in place, and title complex does not have fluorescence peak to occur in the scope of 350 ~ 500 nm, this may be due to non-d
10metal ion Cu (II) fluorescence to part has caused by cancellation effect.
Claims (2)
1. Benzotriazole Derivative and m-phthalic acid mixed matching copper (II) title complex, is characterized in that: the chemical formula of described title complex is { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
n, structure is:
Its feature is: described title complex is the one-dimensional catenary structure formed by m-phthalic acid root bridging Cu (II) center, three-dimensional structure is piled into by hydrogen bond between chain and chain, wherein, 1-(benzotriazole-1-methyl)-1-imidazoles is with the pattern of monodentate ligand and Cu (II) coordination, m-phthalic acid root is with bridging pattern and Cu (II) coordination, and two carboxyls of each m-phthalic acid root are all with the pattern of monodentate ligand and Cu (II) coordination, each Cu (II) center is in the coordination environment of the tetragonal pyramid of a distortion.
2. a kind of Benzotriazole Derivative according to patent requirements 1 and m-phthalic acid mixed matching copper (II) title complex, its feature is: adopt solution crystal process, by CuCl
22H
2o, 1-(benzotriazole)-1-methyl isophthalic acid-imidazoles and m-phthalic acid according to 1:2:1 ~ 1:6:4 mol ratio as reactant, with methyl alcohol, water, DMF(N, dinethylformamide) be solvent, its volume ratio is 4:5:1 ~ 6:10:1, with CuCl
22H
2o is benchmark, every 1 mmol CuCl
22H
2o needs methyl alcohol volume to be 40 ~ 50 ml, and filter after solution stirring, filtrate is 80
oc is also incubated 72 ~ 80 hours, is cooled to room temperature and obtains blue-tinted transparent rhabdolith, by this crystal separation out, successively through washing, drying treatment, obtains title complex { [Cu (bmi)
2(
m-bdc) (H
2o)] 2H
2o}
n.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510156904.8A CN104804022A (en) | 2015-04-04 | 2015-04-04 | Mixed ligand coordination compound of benzotriazole derivative and isophthalic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510156904.8A CN104804022A (en) | 2015-04-04 | 2015-04-04 | Mixed ligand coordination compound of benzotriazole derivative and isophthalic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104804022A true CN104804022A (en) | 2015-07-29 |
Family
ID=53689248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510156904.8A Pending CN104804022A (en) | 2015-04-04 | 2015-04-04 | Mixed ligand coordination compound of benzotriazole derivative and isophthalic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104804022A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106366328A (en) * | 2016-09-12 | 2017-02-01 | 桂林理工大学 | Isophthalic-acid cadmium polymer and preparing method thereof |
| CN106397784A (en) * | 2016-09-12 | 2017-02-15 | 桂林理工大学 | Isophthalic acid and copper coordination polymer and preparation method thereof |
| CN107022087A (en) * | 2017-03-08 | 2017-08-08 | 南京工业大学 | High-porosity and porous coordination polymer, preparation method and application thereof, and preparation method of membrane of high-porosity and porous coordination polymer |
| CN110818909A (en) * | 2019-11-07 | 2020-02-21 | 西北大学 | A kind of metal organic framework compound and its preparation method and application |
-
2015
- 2015-04-04 CN CN201510156904.8A patent/CN104804022A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106366328A (en) * | 2016-09-12 | 2017-02-01 | 桂林理工大学 | Isophthalic-acid cadmium polymer and preparing method thereof |
| CN106397784A (en) * | 2016-09-12 | 2017-02-15 | 桂林理工大学 | Isophthalic acid and copper coordination polymer and preparation method thereof |
| CN107022087A (en) * | 2017-03-08 | 2017-08-08 | 南京工业大学 | High-porosity and porous coordination polymer, preparation method and application thereof, and preparation method of membrane of high-porosity and porous coordination polymer |
| CN107022087B (en) * | 2017-03-08 | 2020-07-10 | 南京工业大学 | A kind of highly porous coordination polymer, preparation method, application and preparation method of membrane |
| CN110818909A (en) * | 2019-11-07 | 2020-02-21 | 西北大学 | A kind of metal organic framework compound and its preparation method and application |
| CN110818909B (en) * | 2019-11-07 | 2021-07-20 | 西北大学 | A kind of metal organic framework compound and its preparation method and application |
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