CN110590817A - 3, 4-ethylenedioxy group thiophene-2, 5-dicarboxylic acid cadmium complex and preparation method thereof - Google Patents
3, 4-ethylenedioxy group thiophene-2, 5-dicarboxylic acid cadmium complex and preparation method thereof Download PDFInfo
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- CN110590817A CN110590817A CN201910889454.1A CN201910889454A CN110590817A CN 110590817 A CN110590817 A CN 110590817A CN 201910889454 A CN201910889454 A CN 201910889454A CN 110590817 A CN110590817 A CN 110590817A
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- dicarboxylic acid
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- -1 3, 4-ethylenedioxy group Chemical group 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 238000010668 complexation reaction Methods 0.000 title description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 26
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000012153 distilled water Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 7
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical group [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 abstract description 4
- 239000000243 solution Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- NWIYUAISDYJVMZ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid Chemical compound O1CCOC2=C(C(=O)O)SC(C(O)=O)=C21 NWIYUAISDYJVMZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 5
- 238000002447 crystallographic data Methods 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 239000003446 ligand Substances 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- 230000002194 synthesizing effect Effects 0.000 abstract description 4
- 229910052723 transition metal Inorganic materials 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 2
- YCGAZNXXGKTASZ-UHFFFAOYSA-N thiophene-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)S1 YCGAZNXXGKTASZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 description 7
- 229910052793 cadmium Inorganic materials 0.000 description 5
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000004729 solvothermal method Methods 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000005389 magnetism Effects 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000012621 metal-organic framework Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention discloses a 3, 4-ethylenedioxy group thiophene-2, 5-dicarboxylic acid cadmium complex and a preparation method thereof. 3, 4-ethylenedioxy group thiophene-2, 5-dicarboxylic acid is taken as a ligand, and reacts with cadmium chloride in distilled water and N, N-Dimethylformamide (DMF) solution to prepare the 3, 4-ethylenedioxy group thiophene-2, 5-dicarboxylic acid cadmium complex. The complex is tetragonal system, and the space group isI41/amdUnit cell parameters are a =20.6409(3) Å, b =20.6409(3) Å, c =14.2126(4) Å, α =90.00 °, β =90.00 °, γ =90.00 °, V =6055.2(2) Å3And Z = 16. The preparation method has the advantages of simple process, good repeatability, environmental protection and the like, successfully synthesizes the 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid cadmium complex, and provides a certain theoretical basis for synthesizing the nitrogen heterocyclic carboxylic acid transition metal complex.
Description
Technical Field
The invention belongs to the technical field of metal organic complex synthesis, and particularly relates to a 3, 4-ethylenedioxy group thiophene-2, 5-dicarboxylic acid cadmium complex and a preparation method thereof.
Background
The metal organic complex is an organic-inorganic hybrid material with intramolecular pores, which is assembled by an organic ligand and metal ions or metal clusters through coordination bonds. The arrangement of organic ligand, metal ion and metal cluster has obvious directivity, so that it can form several frame structures, and has the characteristics of both organic matter and inorganic matter. And the MOFs material also has the advantages of very high specific surface area and high porosity, and also has the structural characteristics of controllability, decorativeness and the like. The material has excellent performances in the aspects of light, electricity, magnetism, adsorption, catalysis, ion exchange and the like, and attracts the attention of scientific researchers. The metal ions are easy to coordinate with lone pair electron atoms such as N, S, O, P and the like to form a complex with one-dimensional, two-dimensional and three-dimensional structures. The nitrogen heterocyclic carboxyl ligand combines the characteristics of nitrogen heterocycles and carboxyl groups, and the carboxylic acid groups can show various coordination modes such as monodentate coordination, bidentate coordination, asymmetric coordination, tridentate coordination, tetradentate coordination and the like when being coordinated with metal ions, so that the complex with complex and various configurations, novel structure and different functions can be derived. The current methods commonly used for synthesizing the complex are as follows: normal temperature solution method, hydrothermal method, solvothermal method, evaporation method, diffusion method, electrochemical method, and the like.
The metal ions are important factors influencing the complex structure, and different metal ions have different coordination numbers, so that the properties of the formed complexes are different. The transition metal complex has wide application in the aspects of magnetism, catalysis, luminescence, gas adsorption and the like. The application provides a method for synthesizing a compound with a chemical formula of [ C ] by taking 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid and transition metal salt as raw materials through a solvothermal method10H10ClCdN2O7.5S]nA structure of cadmium complex and a preparation method thereof.
Disclosure of Invention
The invention aims to provide a 3, 4-ethylenedioxy group thiophene-2, 5-dicarboxylic acid cadmium complex and a preparation method thereof.
The idea of the invention is as follows: the 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid cadmium complex is obtained by using 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid as a ligand and cadmium chloride salt through a solvothermal method.
The molecular formula of the complex is as follows: c10H10ClCdN2O7.5S, molecular weight is: 457.92, the complex belongs to tetragonal system and has space group I41Unit cell parameter of α＝90.00°，β＝90.00°，γ＝90.00°，The crystallographic data of Z-16 are shown in Table 1, and the partial bond lengths and bond angles are shown in Table 2.
TABLE 1 crystallographic data for cadmium 3, 4-ethylenedioxythiophene-2, 5-dicarboxylate complexes
TABLE 2 partial bond length of cadmium 3, 4-ethylenedioxythiophene-2, 5-dicarboxylate complexesAngle of harmony key (°)
The preparation method of the 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid cadmium complex comprises the following specific steps:
(1) weigh 0.25mmol (0.0570g) of CdCl2·2.5H2Dissolving O in 6mL of distilled water to prepare a cadmium chloride solution.
(2) 0.2mmol (0.0460g) of 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid and 4mL of DMF were weighed out and added to a 25mL beaker and stirred until dissolved to prepare a 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid solution.
(3) Dropwise adding the cadmium chloride solution prepared in the step (1) into the 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid solution prepared in the step (2), magnetically stirring at room temperature for 30min, adjusting the pH value to 5-7 with ammonia water to clarify the solution, and continuously stirring for 20min to prepare a mixed solution.
(4) And (3) transferring the mixed solution prepared in the step (3) into a 25mL reaction kettle with a polytetrafluoroethylene bottle, putting the reaction kettle into an oven, heating the mixture to 100 ℃ for reaction for 72h, then cooling the mixture to 60 ℃ at the speed of 5 ℃/h, keeping the temperature for 12h, closing the oven, naturally cooling the mixture to room temperature, taking the mixture out of the reaction kettle, generating milky blocky crystals, alternately washing the milky blocky crystals for 3 times by using DMF and distilled water, wherein the amount of DMF is 5mL each time, the amount of distilled water is 5mL, and then putting the mixture into a 50 ℃ vacuum drying oven for drying for 12h to obtain the 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid cadmium complex.
The preparation method has the advantages of simple process, good repeatability, environmental protection and the like, successfully synthesizes the 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid cadmium complex, and provides a certain basis for synthesizing the nitrogen heterocyclic carboxylic acid transition metal complex.
Drawings
FIG. 1 shows an example of the present invention in which the chemical formula is [ C ]10H10ClCdN2O7.5S]nThe crystal structure diagram of the cadmium complex.
FIG. 2 shows an example of the present invention in which the chemical formula is [ C ]10H10ClCdN2O7.5S]nThe crystal three-dimensional stacking diagram (a direction) of the cadmium complex of (1).
Detailed Description
Example (b):
(1) weigh 0.25mmol (0.0570g) of CdCl2·2.5H2Dissolving O in 6mL of distilled water to prepare a cadmium chloride solution.
(2) 0.2mmol (0.0460g) of 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid and 4mL of DMF were weighed out and added to a 25mL beaker and stirred until dissolved to prepare a 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid solution.
(3) Dropwise adding the solution prepared in the step (1) into the solution prepared in the step (2), magnetically stirring for 30min at room temperature, adjusting the pH value to 6 by using ammonia water to clarify the solution, and continuously stirring for 20 min.
(4) And (4) transferring the mixed solution prepared in the step (3) into a 25mL reaction kettle with a polytetrafluoroethylene bottle, and putting the reaction kettle into an oven to be heated to 100 ℃ for reaction for 72 hours. Cooling to 60 ℃ at the speed of 5 ℃/h after 72h, preserving heat for 12h, closing the oven to cool to room temperature in a natural state, taking out the reaction kettle, generating milky massive crystals, alternately washing with DMF (dimethyl formamide) and distilled water for 3 times, wherein the amount of DMF is 5mL and the amount of distilled water is 5mL each time, then putting the reaction kettle into a vacuum drying oven at 50 ℃, and drying for 12h to obtain the product with the chemical formula [ C ]10H10ClCdN2O7.5S]nCadmium complex, yield 69%. Theoretical value of elemental analysis (%): c, 26.20; n, 6.11; h, 2.18; test value (%) C, 26.03; n, 6.38; h, 2.07.
The obtained chemical formula is [ C ]10H10ClCdN2O7.5S]nAnalyzing the crystal structure of the cadmium complex: selecting crystal with proper size, and using Agilent CCD plane-probing monocrystal diffractometer at 293(2) K and Mo-K alpha rayDiffraction points were collected in an omega scan fashion. All crystal data are subjected to Lp factor correction and empirical absorption correction by adopting an SADABS program, non-hydrogen atoms are corrected by using a full matrix least square method, and hydrogen atom coordinates are given by theoretical values. Structural analysis was performed with Olex2, structural refinement and all calculations were performed with Olex 2. All hydrogen atoms are theoretically hydrogenated. The relevant crystallographic data are listed in table 1, and the main bond lengths and bond angles are listed in table 2.
As can be seen from Table 1, the complex belongs to the tetragonal system and has the space group I41Unit cell parameter ofα＝90.00°，β＝90.00°，γ＝90.00°，Z ═ 16, the complex contains, as essential units, the anion of 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid, one Cd ion and one water molecule, one dimethylamine molecule. In the complex, a central metal ion Cd is respectively coordinated with an oxygen atom of a carboxyl group on two 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid ligands, a chloride ion and a water molecule. Cd-O bond length is inIn the meantime. The crystal structure diagram of the complex is shown in figure 1, and the direction a stacking diagram is shown in figure 2.
Claims (2)
1. A3, 4-ethylenedioxy group thiophene-2, 5-dicarboxylic acid cadmium complex is characterized in that the molecular formula of the complex is as follows: c10H10ClCdN2O7.5S, molecular weight is: 457.92, the complex belongs to tetragonal system and has space group I41Unit cell parameter ofα＝90.00°，β＝90.00°，γ＝90.00°， The crystallographic data of Z is shown in Table 1, and the partial bond length and the bond angle are shown in Table 2;
TABLE 1 crystallographic data for cadmium 3, 4-ethylenedioxythiophene-2, 5-dicarboxylate complexes
TABLE 2 partial bond length of cadmium 3, 4-ethylenedioxythiophene-2, 5-dicarboxylate complexesAngle of harmony key (°)
2. A method for preparing the cadmium 3, 4-ethylenedioxythiophene-2, 5-dicarboxylate complex according to claim 1, comprising the steps of:
(1) weigh 0.25mmol of CdCl2·2.5H2Dissolving O in 6mL of distilled water to prepare a cadmium chloride solution;
(2) weighing 0.2mmol of 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid and 4mL of N, N-Dimethylformamide (DMF), adding into a 25mL beaker, and stirring until the mixture is dissolved to obtain a 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid solution;
(3) dropwise adding the cadmium chloride solution prepared in the step (1) into the 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid solution prepared in the step (2), magnetically stirring at room temperature for 30min, adjusting the pH value to 5-7 with ammonia water to clarify the solution, and continuously stirring for 20min to prepare a mixed solution;
(4) and (3) transferring the mixed solution prepared in the step (3) into a 25mL reaction kettle with a polytetrafluoroethylene bottle, putting the reaction kettle into an oven, heating the mixture to 100 ℃ for reaction for 72h, then cooling the mixture to 60 ℃ at the speed of 5 ℃/h, keeping the temperature for 12h, closing the oven, naturally cooling the mixture to room temperature, taking the mixture out of the reaction kettle, generating milky blocky crystals, alternately washing the milky blocky crystals for 3 times by using DMF and distilled water, wherein the amount of DMF is 5mL each time, the amount of distilled water is 5mL, and then putting the mixture into a 50 ℃ vacuum drying oven for drying for 12h to obtain the 3, 4-ethylenedioxythiophene-2, 5-dicarboxylic acid cadmium complex.
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| CN112409249A (en) * | 2020-10-28 | 2021-02-26 | 桂林理工大学 | 6-methylpyridine-2, 3-dicarboxylic acid zinc complex and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106589395A (en) * | 2016-10-26 | 2017-04-26 | 桂林理工大学 | Metal-organic framework compound with chemical formula of [CdC16H10N2O4S]n, and preparation method and applications thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106589395A (en) * | 2016-10-26 | 2017-04-26 | 桂林理工大学 | Metal-organic framework compound with chemical formula of [CdC16H10N2O4S]n, and preparation method and applications thereof |
Non-Patent Citations (2)
| Title |
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| CUI-LIAN GUO ET AL.: "Synthesis, crystal structures, and fluorescence properties of six complexes with thiophene derivative carboxylic acid ligand", 《INORGANICA CHIMICA ACTA》 * |
| 梁楚欣等: "基于杂环羧酸配体的金属有机骨架化合物的合成、表征及性质研究", 《化学通报》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112409249A (en) * | 2020-10-28 | 2021-02-26 | 桂林理工大学 | 6-methylpyridine-2, 3-dicarboxylic acid zinc complex and preparation method thereof |
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