CN111499668A - Anderson-based polyacid type cobalt complex for electrostatic adsorption of gentian violet and application thereof - Google Patents
Anderson-based polyacid type cobalt complex for electrostatic adsorption of gentian violet and application thereof Download PDFInfo
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- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 title claims abstract description 41
- 229960001235 gentian violet Drugs 0.000 title claims abstract description 41
- 238000001179 sorption measurement Methods 0.000 title claims abstract description 38
- 150000004700 cobalt complex Chemical class 0.000 title claims abstract description 16
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229960003966 nicotinamide Drugs 0.000 claims abstract description 8
- 235000005152 nicotinamide Nutrition 0.000 claims abstract description 8
- 239000011570 nicotinamide Substances 0.000 claims abstract description 8
- 238000001027 hydrothermal synthesis Methods 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000008367 deionised water Substances 0.000 claims abstract description 6
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 239000013078 crystal Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000004140 cleaning Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- -1 polytetrafluoroethylene Polymers 0.000 claims description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 3
- 238000002791 soaking Methods 0.000 claims description 3
- 239000011148 porous material Substances 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 description 11
- 239000000975 dye Substances 0.000 description 8
- 239000002184 metal Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 150000004696 coordination complex Chemical group 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000002447 crystallographic data Methods 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 108010077805 Bacterial Proteins Proteins 0.000 description 2
- 239000000981 basic dye Substances 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 231100000357 carcinogen Toxicity 0.000 description 2
- 239000003183 carcinogenic agent Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 229910001429 cobalt ion Inorganic materials 0.000 description 2
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 2
- 239000011365 complex material Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000012621 metal-organic framework Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006385 ozonation reaction Methods 0.000 description 1
- 238000013033 photocatalytic degradation reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- 238000000373 single-crystal X-ray diffraction data Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
- B01J20/28011—Other properties, e.g. density, crush strength
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- Analytical Chemistry (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
An Anderson type polyacid type cobalt complex for electrostatic adsorption of gentian violet and application thereof are disclosed, wherein the molecular formula of the complex is as follows: { Co2(3‑bpah)4[CrMo6(OH)6O18]}·4H2O, wherein 3-bpah is N, N' -bis (3-pyridinecarboxamide) -1,2 cyclohexane. The preparation method comprises the following steps: mixing Co (NO)3)2N, N' -bis (3-pyridinecarboxamide) -1, 2-cyclohexane and Na3[CrMo6(OH)6O18]Dissolving in deionized water, and hydrothermal reactionAnd (4) synthesizing. The organic molecules of the gentian violet can be simply obtained through a simple one-step hydrothermal method, the gentian violet organic molecules can be efficiently degraded through an electrostatic adsorption mode, the gentian violet molecules with positive charges can be fully attracted through a high negative charge structure of polyacid in the complex, and the problem that the porous material is excessively relied on in the aspect of organic drug adsorption at present is solved.
Description
Technical Field
The invention relates to an Anderson type polyacid type cobalt complex for electrostatic adsorption of gentian violet and application thereof.
Background
Gentian violet is a well-known external medicine because the cation of gentian violet can be combined with the carboxyl of bacterial protein to influence the metabolism of the bacterial protein to generate an antibacterial effect. Intensive research on gentian violet (gentian violet) by foreign medical scientists has resulted in the finding that the gentian violet has extremely strong carcinogenicity. British pharmacologists confirmed by repeated experiments with animals that gentian violet in the purple water is a cationic basic dye. This basic dye is a carcinogen and is a potential carcinogen. Thus, how to effectively degrade and handle gentian violet during use is an urgent issue facing today.
Currently, various methods have been developed, such as photocatalytic degradation, chemical degradation, Fenton-based oxidation, ozonation, and the like. However, the above techniques have problems of poor selectivity, high cost, non-reusability, and the like. And materials such as activated carbon, metal organic framework and the like have the characteristics of high specific surface area, high porosity, environmental friendliness and the like, and are considered to be ideal candidate materials for adsorbing organic dyes. However, at present, most of the adsorption materials rely on porous materials, the preparation requirement conditions are high, and the materials are difficult to desorb.
The main problems at present are: how to prepare a material capable of adsorbing organic drugs and further meet different requirements on the adsorption activity of the dye when the material is used as a drug adsorption material.
Disclosure of Invention
The invention aims to solve the technical problem of providing an Anderson type polyacid type cobalt complex for electrostatically adsorbing gentian violet and application thereof, wherein the complex can be simply obtained by a simple one-step hydrothermal method, gentian violet molecules can be efficiently degraded by an electrostatic adsorption mode, and the problem that a porous material is difficult to desorb when dye is adsorbed is solved.
The technical scheme of the invention is as follows:
an Anderson type polyacid-based cobalt complex for electrostatically adsorbing gentian violet is prepared by selecting polyacid anions and organic ligands and using metal cobalt ions as construction units by a hydrothermal method, and the structure of the complex is represented by X-ray single crystal diffraction.
The molecular formula of the complex is as follows:
{Co2(3-bpah)4[CrMo6(OH)6O18]}·4H2O；
wherein the 3-bpah is N, N' -bis (3-pyridine carboxamide) -1,2 cyclohexane.
An Anderson type polyacid type cobalt complex for electrostatic adsorption of gentian violet is prepared by the following specific steps:
mixing Co (NO)3)2N, N' -bis (3-pyridinecarboxamide) -1, 2-cyclohexane and Na3[CrMo6(OH)6O18]Dissolving in deionized water, said Co (NO)3)2N, N' -bis (3-pyridinecarboxamide) -1, 2-cyclohexane and Na3[CrMo6(OH)6O18]Adjusting the pH value to 4.35 by using HCl solution, stirring for 30 minutes, transferring to the inner liner of a polytetrafluoroethylene high-temperature reaction kettle, pouring into a high-pressure reaction kettle, carrying out hydrothermal reaction at 120 ℃, keeping the temperature for 4 days, gradually cooling to obtain a purple crystal product, cleaning and drying to obtain { Co } crystal product2(3-bpah)4[CrMo6(OH)6O18]}·4H2O。
Further, said Co (NO)3)2The molar ratio to deionized water was 0.04 mol/L.
Further, the concentration of the HCl solution is 1 mol/L.
Further, the cooling speed is 10 ℃/h.
An application of an Anderson-based polyacid type cobalt complex in electrostatic adsorption of gentian violet.
An application of an Anderson-based polyacid type cobalt complex in electrostatic adsorption of gentian violet is specifically operated as follows:
taking the complex { Co2(3-bpah)4[CrMo6(OH)6O18]}·4H2And O, soaking the sample in a solution containing gentian violet in a dark environment, and stirring for 8-10 min.
The invention has the beneficial effects that:
1. inventive complexes { Co }2(3-bpah)4[CrMo6(OH)6O18]}·4H2The cobalt ions in the O are in a six-coordination mode, the polyacid is in a four-coordination mode, the polyacid and the central metal form a one-dimensional chain structure, the 3-bpah is in a two-coordination mode and is coordinated with the central metal, and then the adjacent one-dimensional chain structures are connected to form a two-dimensional layer; and the high negative charge of polyacid in the polyacid coordination complex structure is utilized to realize electrostatic adsorption of gentian violet. The problem of to the adsorption of organic dyestuff, to the dependence of porous material is solved, has also broken through the limitation in aspects such as present organic dyestuff adsorbing material in weight, adsorption efficiency simultaneously.
2. The coordination complex can be simply obtained by a simple one-step hydrothermal method, can be directly used without any post-treatment, and has the characteristics of light weight, high adsorption efficiency and high-batch preparation.
Drawings
FIG. 1 is a diagram of the coordination mode and two-dimensional layer structure of the polyacid-based complex of the present invention;
FIG. 2 is an infrared image of a polyacid-based metal organic complex of the present invention;
FIG. 3 is an X-ray powder diffraction pattern of a polyacid-based metal-organic complex of the present invention;
FIG. 4 is a flow chart of an experiment for dye adsorption of the polyacid-based metal organic complex of the present invention;
FIG. 5 is a diagram of the UV-VIS absorption spectrum of the complex after adsorbing gentian violet for different times;
FIG. 6 is a comparison graph of the color of a gentian violet solution before and after adsorption by the polyacid-based metal-organic complex of the present invention.
Detailed Description
Examples
1mmol of Co (NO)3)2,1mmol 3-bpah,1mmol Na3[CrMo6(OH)6O18]Dissolving the materials into 25m L deionized water in sequence, adjusting the pH value to 4.35 by using 1 mol/L HCl solution, stirring the solution for 30 minutes, transferring the solution into a lining of a polytetrafluoroethylene high-temperature reaction kettle, pouring the lining into a high-pressure reaction kettle to perform hydrothermal reaction at 120 ℃, keeping the temperature for four days, gradually cooling the temperature at a speed of 10 ℃/h to obtain a purple crystal product, cleaning and drying the purple crystal product to obtain { Co2(3-bpah)4[CrMo6(OH)6O18]}·4H2O。
For prepared { Co2(3-bpah)4[CrMo6(OH)6O18]}·4H2Performing single crystal X-ray diffraction, infrared and X-ray powder diffraction structure characterization on the O coordination complex sample; the complete powder diffraction data were collected on a Rigaku Ultima IV powder X-ray diffractometer operating at 40mA and 40 kV. Copper target X-rays were used. Scanning was fixed and the receiving slit was 0.1mm wide. Density data collection uses a 2 theta/theta scan pattern with a scan range of 5 deg. to 50 deg., a scan speed of 5 deg./s, and a span of 0.02 deg./time. Data fitting Using the program Cerius2, single crystal structure powder diffraction Spectrum simulation transformation was tested on an Ultima IV X-ray powder diffractometer using Mercury 1.4.1X-ray powder diffraction (PXRD). By infrared and XRD characterization (fig. 2 and 3), the homogeneity and high crystallinity of the composition of the material was demonstrated,
the crystal structure determination is that single crystals with proper size are selected by a microscope, diffraction data are collected by a Bruker SMART APEXII diffractometer (graphite monochromator, Mo-Ka) at room temperature, the diffraction data in a scanning mode are absorbed and corrected by an SADABS program, data reduction and structure analysis are completed by SAINT and SHE L XT L programs respectively, a least square method is used for determining all non-hydrogen atom coordinates, a theoretical hydrogenation method is used for obtaining hydrogen atom positions, a least square method is used for refining the crystal structure, and partial parameters of the collection of the data of the crystal diffraction points and the refining of the structure are shown in Table 1:
TABLE 1
The complex { Co ] is analyzed and known through single crystal X-ray diffraction data2(3-bpah)4[CrMo6(OH)6O18]}·4H2The metal ions in O are in a six-coordination mode, the polyacid is in a four-coordination mode, the polyacid and the central metal form a one-dimensional chain structure, and 3-bpah is in a two-coordination mode, and is coordinated with the central metal, so that the adjacent one-dimensional chain structures are connected, and a two-dimensional layer is formed (figure 1).
Adsorption performance of coordination complex: taking 50mg of { Co ] from the polyacid coordination complex material obtained in the step2(3-bpah)4[CrMo6(OH)6O18]}·4H2Testing an O sample, soaking the sample in 100m L0.3.3 mmol/L gentian violet solution in a dark environment, taking 10m L gentian violet solution samples every 1 minute for ultraviolet adsorption testing, transferring the taken gentian violet solution to an ultraviolet spectrophotometer for ultraviolet absorption spectrogram testing, and scanning the wave number range of 400-700 cm--1. A total of 8 solutions were taken before and after the adsorption reaction time was 8 minutes. FIG. 5 is a graph of the relative UV absorbance peaks of gentian violet for a sample over time. The ultraviolet peak value and the concentration of the gentian violet solution form a positive linear relation. Therefore, the concentration value of the gentian violet solution before and after adsorption can be indirectly obtained, and the concentration of the solution before adsorption is CoAnd after adsorption, the concentration is CtAnd the formula for calculating the adsorption quantity of the gentian violet is qt(mmol g-1)＝(C0-Ct) V/W, wherein V is the volume of the solution and W is the mass of the complex. In this embodiment, Co0.3 mmol/L, Ct0.048 mmol/L, V100 m L, and W50 mg, which are substituted into the formula, the adsorption amount is calculated to be 0.504mmol g-1Average adsorption rate of 0.063mmol g-1min-1
FIG. 6 is a comparison graph of the color of a gentian violet solution before and after adsorption by the polyacid-based metal-organic complex of the present invention. The left part is before adsorption, and the right part is after adsorption, and the complex material can generate obvious adsorption effect on the gentian violet through naked eyes.
The result shows that the polyacid complex-based adsorbing material prepared by the invention can efficiently adsorb gentian violet through electrostatic action by virtue of the high negative charge of polyacid. The method solves the problem of dependence on porous materials in the existing dye adsorption technology, and further improves the rate of adsorbing the dye by non-porous materials.
The above description is only exemplary of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. An Anderson type polyacid type cobalt complex for electrostatic adsorption of gentian violet, which is characterized in that:
the molecular formula of the complex is as follows:
{Co2(3-bpah)4[CrMo6(OH)6O18]}·4H2O；
wherein the 3-bpah is N, N' -bis (3-pyridine carboxamide) -1,2 cyclohexane.
2. An Anderson-based polyacid-type cobalt complex for the electrostatic adsorption of gentian violet according to claim 1, characterized by:
the preparation method comprises the following specific steps:
mixing Co (NO)3)2N, N' -bis (3-pyridinecarboxamide) -1, 2-cyclohexane and Na3[CrMo6(OH)6O18]Dissolving in deionized water, said Co (NO)3)2N, N' -bis (3-pyridinecarboxamide) -1, 2-cyclohexane and Na3[CrMo6(OH)6O18]Adjusting the pH value to 4.35 by using HCl solution, stirring for 30 minutes, transferring to the inner liner of a polytetrafluoroethylene high-temperature reaction kettle, pouring into a high-pressure reaction kettle, carrying out hydrothermal reaction at 120 ℃, keeping the temperature for 4 days, gradually cooling to obtain a purple crystal product, cleaning and drying to obtain { Co } crystal product2(3-bpah)4[CrMo6(OH)6O18]}·4H2O。
3. The Anderson-based polyacid-type cobalt complex for the electrostatic adsorption of gentian violet according to claim 3, characterized by: the Co (NO)3)2The molar ratio to deionized water was 0.04 mol/L.
4. The Anderson-based polyacid-type cobalt complex for electrostatic adsorption of gentian violet according to claim 3, wherein the concentration of HCl solution is 1 mol/L.
5. The Anderson-based polyacid-type cobalt complex for the electrostatic adsorption of gentian violet according to claim 3, characterized by: the cooling speed is 10 ℃/h.
6. Use of the Anderson-based polyacid-type cobalt complex of claim 1 for electrostatically adsorbing gentian violet.
7. The use of the Anderson-based polyacid-type cobalt complex of claim 6, wherein:
the specific operation is as follows:
taking the complex { Co2(3-bpah)4[CrMo6(OH)6O18]}·4H2And O, soaking the sample in a solution containing gentian violet in a dark environment, and stirring for 8-10 min.
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Citations (4)
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|---|---|---|---|---|
| CN103709182A (en) * | 2013-12-06 | 2014-04-09 | 渤海大学 | Transition metal compounds based on semi-rigid, synthetic method and applications |
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| CN103992338A (en) * | 2014-03-22 | 2014-08-20 | 渤海大学 | Copper complex based on dipyridine piperazine ligand and Anderson type polyacid, and synthetic method and application thereof |
| CN106277159A (en) * | 2016-08-09 | 2017-01-04 | 渤海大学 | A kind of methylene blue and the processing method of Congo red organic pollution |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103709182A (en) * | 2013-12-06 | 2014-04-09 | 渤海大学 | Transition metal compounds based on semi-rigid, synthetic method and applications |
| CN103724365A (en) * | 2013-12-18 | 2014-04-16 | 渤海大学 | Transition metal complex based on semirigid bipyridine bisamide organic ligand and terephthalic acid as well as synthetic method and application of transition metal complex |
| CN103992338A (en) * | 2014-03-22 | 2014-08-20 | 渤海大学 | Copper complex based on dipyridine piperazine ligand and Anderson type polyacid, and synthetic method and application thereof |
| CN106277159A (en) * | 2016-08-09 | 2017-01-04 | 渤海大学 | A kind of methylene blue and the processing method of Congo red organic pollution |
Non-Patent Citations (1)
| Title |
|---|
| XIU-LI WANG等: "Metal(II)–Organic Coordination Polymers Modulated by Two Isomeric Semirigid Bis-Pyridyl-Bis-Amide Ligands: Structures, Fluorescent Sensing Behavior, and Selective Photocatalysis", 《CHEMPLUSCHEM》 * |
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