CN112409249A - 6-methylpyridine-2, 3-dicarboxylic acid zinc complex and preparation method thereof - Google Patents

6-methylpyridine-2, 3-dicarboxylic acid zinc complex and preparation method thereof Download PDF

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CN112409249A
CN112409249A CN202011174407.8A CN202011174407A CN112409249A CN 112409249 A CN112409249 A CN 112409249A CN 202011174407 A CN202011174407 A CN 202011174407A CN 112409249 A CN112409249 A CN 112409249A
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methylpyridine
dicarboxylic acid
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刘峥
孙丹
魏润芝
韦文厂
梁楚欣
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Guilin University of Technology
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Abstract

The invention discloses a 6-methylpyridine-2, 3-dicarboxylic acid zinc complex and a preparation method thereof. The method is characterized in that 6-methylpyridine-2, 3-dicarboxylic acid is used as a ligand, zinc acetate is used as a metal salt, and the 6-methylpyridine-2, 3-dicarboxylic acid zinc complex is prepared in an aqueous solution of N, N-dimethylformamide through a solvothermal method. The complex belongs to an orthorhombic system and has a space group of Pna21Cell parameter of
Figure DDA0002748302300000011
α＝90°，β＝90°，γ＝90°，
Figure DDA0002748302300000012
Figure DDA0002748302300000013
And Z is 4. The preparation method disclosed by the invention has the advantages of simple process, good repeatability, environmental friendliness and the like. The invention can provide a certain theoretical basis for synthesizing the nitrogen heterocyclic carboxylic acid transition metal complex.

Description

6-methylpyridine-2, 3-dicarboxylic acid zinc complex and preparation method thereof
Technical Field
The invention belongs to the technical field of metal organic complex preparation, and particularly relates to a 6-methylpyridine-2, 3-dicarboxylic acid zinc complex and a preparation method thereof.
Background
Metal-Organic Frameworks (MOFs) are a group of inorganic metals (M)n+) Inorganic-organic hybrid crystalline materials constructed from organic ligands (L) through Coordination bonds, intermolecular forces, hydrogen bonds, or the like are also generally called Porous Coordination Polymers (PCPs). The organic ligand is generally used as a bridging in the framework structure, and can form a coordination network which can be infinitely extended in one dimension, two dimensions or three dimensions in space.
MOFs were defined in 1995 by the american professor Omar Yaghi, and have attracted much attention from researchers due to their structural diversity, permanent porosity, high specific surface area, high stability, and the like. The MOFs material with changeable structure can be prepared by changing the acting force of metal ions, organic ligands or the acting force between the metal ions and the organic ligands. The preparation methods of the MOFs materials are various, and the common methods mainly include a volatilization method, a diffusion method, a hydrothermal/solvothermal method, an ultrasonic method, a microwave method and the like. With the increasing variety and number of MOFs, MOFs materials are widely used in various fields such as gas storage or separation, catalysis, optics, magnetics, drug delivery, electrochemical sensing, etc.
The 6-methylpyridine-2, 3-dicarboxylic acid belongs to a nitrogen heterocyclic polycarboxylic acid compound, is a commonly used ligand, is easy to coordinate with transition metal ions to form a stable coordination bond, is easy to obtain a topological structure, and brings excellent performance to a complex; and meanwhile, the partially or completely deprotonated carboxyl can be used as a hydrogen bond donor and a hydrogen bond acceptor, so that structures with different dimensions are easily formed. In addition, the azacyclic polycarboxylic acid compound has good fluorescence performance due to the conjugated double bonds and the aromatic groups.
The application provides a method for preparing a compound by using 6-methylpyridine-2, 3-dicarboxylic acid and transition metal zinc salt as raw materials through a solvothermal methodThe chemical formula [ Zn (6-Me-2,3-pydc) (H) is prepared2O)2·2H2O]nA zinc complex of (1).
Disclosure of Invention
The purpose of the invention is as follows: provides a structure, properties and a preparation method of a 6-methylpyridine-2, 3-dicarboxylic acid zinc complex.
The idea of the invention is as follows: 6-methylpyridine-2, 3-dicarboxylic acid (6-Me-2,3-pydc) is used as a ligand and zinc acetate is used as a zinc source, and the 6-methylpyridine-2, 3-dicarboxylic acid zinc complex is obtained by a solvothermal method.
The zinc complex has the structural characteristics that: belongs to the orthorhombic system and has a space group of Pna21Cell parameter of
Figure BDA0002748302280000021
α＝90°，β＝90°，γ＝90°，
Figure BDA0002748302280000022
Figure BDA0002748302280000023
The crystallographic data are shown in table 1, and the part and bond angle are shown in table 2.
TABLE 1 crystallographic data for zinc 6-methylpyridine-2, 3-dicarboxylate complexes
Figure BDA0002748302280000024
Figure BDA0002748302280000031
TABLE 2.6 partial bond length of Zinc 6-methylpyridine-2, 3-dicarboxylate complexes
Figure BDA0002748302280000032
Angle of harmony key (°)
Figure BDA0002748302280000033
Symmetry codes:A:x+1/2,-y+1/2,z
The preparation method of the 6-methylpyridine-2, 3-dicarboxylic acid zinc complex comprises the following steps:
(1) 0.5mmol (0.1131g) of Zn (CH) was weighed3COO)2·H2O, 0.5mmol (0.0909g) 6-methylpyridine-2, 3-dicarboxylic acid (6-Me-2,3-pydc) was dissolved in a beaker containing 10mL distilled water and 2mL N, N-Dimethylformamide (DMF).
(2) And (3) stirring the solution in the beaker in the step (1) for 30min by using a magnetic stirrer at room temperature to prepare a mixed solution.
(3) And (3) transferring the mixed solution prepared in the step (2) into a 25mL reaction kettle with a polytetrafluoroethylene bottle, putting the reaction kettle into an oven, heating the mixture to 80 ℃, reacting at a constant temperature for 72 hours, cooling the mixture to 60 ℃ at a speed of 5 ℃/h, closing the oven, naturally cooling the mixture to room temperature, taking the reaction kettle out, and generating light white transparent blocky crystals to obtain the 6-methylpyridine-2, 3-zinc dicarboxylate complex.
The preparation method has the advantages of simple process, good repeatability, environmental protection and the like, and the successful preparation of the 6-methylpyridine-2, 3-dicarboxylic acid zinc complex provides a new way for preparing the nitrogen heterocyclic carboxylic acid transition metal complex.
Drawings
FIG. 1 shows the chemical formula of [ Zn (6-Me-2,3-pydc) (H) according to the present invention2O)2·2H2O]nThe molecular structure of the zinc complex is an ellipsoid diagram.
FIG. 2 shows the chemical formula of [ Zn (6-Me-2,3-pydc) (H) according to the present invention2O)2·2H2O]nThree-dimensional stacking diagram of Zinc Complex (in the a-direction)
FIG. 3 shows the chemical formula of [ Zn (6-Me-2,3-pydc) (H) according to the present invention2O)2·2H2O]nThermogram of zinc complex
FIG. 4 shows the chemical formula of [ Zn (6-Me-2,3-pydc) (H) according to the present invention2O)2·2H2O]nFluorescence diagram of Zinc Complex
Detailed Description
Example 1:
(1) 0.5mmol (0.1131g) of Zn (CH) was weighed3COO)2·H2O, 0.5mmol (0.0909g) 6-methylpyridine-2, 3-dicarboxylic acid (6-Me-2,3-pydc) was dissolved in a beaker of distilled water containing 10mL and 2mL N, N-Dimethylformamide (DMF).
(2) Stirring the solution in the beaker in the step (1) for 30min by using a magnetic stirrer at room temperature to prepare a mixed solution;
(3) and (3) transferring the mixed solution prepared in the step (2) into a 25mL reaction kettle with a polytetrafluoroethylene bottle, putting the reaction kettle into an oven, heating the mixture to 80 ℃, reacting for 72 hours, cooling the mixture to 60 ℃ at the speed of 5 ℃/h, closing the oven, naturally cooling the mixture to room temperature, taking the reaction kettle out, and generating light white transparent blocky crystals to obtain the 6-methylpyridine-2, 3-zinc dicarboxylate complex.
(4) Structure analysis of 6-methylpyridine-2, 3-dicarboxylic acid zinc complex
The molecular structure ellipsoid of the zinc complex is shown in figure 1, and the a-direction three-dimensional stacking diagram is shown in figure 2. The crystallographic data are shown in Table 1, and the key bond lengths and angles are shown in Table 2.
Theoretical value of elemental analysis as C8H13NO8Zn calculation (%): c, 30.35; n, 4.42; h, 4.14; found (%): c, 32.87; n, 4.82; h, 3.76.
As can be seen from Table 1, the zinc complex belongs to the orthorhombic system with the space group of Pna21Cell parameter of
Figure BDA0002748302280000051
α＝90°，β＝90°，γ＝90°，
Figure BDA0002748302280000052
Figure BDA0002748302280000053
Z＝4。
As can be seen from the crystal structure diagram of the zinc complex (figure 1), each asymmetric unit consists of 1 Zn (II) central ion and 1 ligand (6-Me-2,3-pydc)2-2 coordinated water molecules and 7 guest water molecules (figure 1). Each Zn (II) ion is bound to a ligand (6-Me-2,3-pydc)2-2 carboxy oxygen atoms ofThe atoms (O1, O4A) are coordinated with 1 nitrogen atom (N8) and 2 oxygen atoms (O5, 96) of the coordinating water molecule to form a penta-coordinated structure (symmetry code: A: x +1/2, -y +1/2, z). Each of the coordinating atoms O1, O4A, O5 lies in the equatorial plane and the sum of the bond angles with the central Zn (ii) ion is 359.8 °, approaching 360 °, N8 on the ligand and O6 on the coordinating water are located at axial positions and the axial bond angles N8-Zn1-O6(169.65 °), constituting a modified trigonal bipyramidal configuration. As can be seen from Table 2, the coordinate Zn-O bond length is 0.2015-0.2078 nm, and the Zn-N bond length is 0.2137nm, which is consistent with the Zn-X (X ═ O, N) bond length (0.1957-0.2149 nm) range of the reported complex. The bond angles O — Zn — X (X ═ O, N) are in the normal range from 78.56(7) to 161.81(7) °.
The zinc complex is Zn2+Is a metal node, (6-Me-2,3-pydc)2-The connecting bodies are connected with each other to form an infinitely extending one-dimensional chain structure. As can be seen from the b-direction stacking diagram (figure 2) of the zinc complex, the molecules are connected through Zn-O coordination bonds and Zn-N coordination bonds to form one-dimensional chains, the chains form two-dimensional planes with layered structures through O-H … O intermolecular hydrogen bonds, and the layers are orderly stacked through the O-H … O intermolecular hydrogen bonds and van der Waals forces to form three-dimensional structures.
Example 2:
(1) 0.5mmol (0.1131g) of Zn (CH) was weighed3COO)2·H2Dissolving O and 0.5mmol (0.0909g) of 6-methylpyridine-2, 3-dicarboxylic acid (6-Me-2,3-pydc) in a beaker containing 10mL and 2mL of N, N-Dimethylformamide (DMF) distilled water, then placing the beaker in a magnetic stirrer to stir for 35min, transferring the prepared mixed solution into a 25mL reaction kettle with a polytetrafluoroethylene bottle, placing the reaction kettle in an oven to heat to 80 ℃, after reacting for 72h, cooling to 60 ℃ at the speed of 5 ℃/h, closing the oven, naturally cooling to room temperature, taking out the reaction kettle, and generating light white transparent blocky crystals to obtain the 6-methylpyridine-2, 3-dicarboxylic acid zinc complex.
(2) Grinding the crystal sample obtained in the step (1) into powder by using an agate mortar, and then carrying out thermogravimetric analysis test on the powder, wherein the result is shown in figure 3, and the analysis on the figure 3 shows that the zinc complex starts to be gradually decomposed after 150 ℃, and a platform appears after 420 ℃, the residue is ZnO, which indicates that the complex is continuously decomposed along with the rise of temperature until stable ZnO is generated, and the synthesized complex has certain thermal stability.
(3) Grinding the crystal sample obtained in the step (1) into powder by using an agate grinding mortar, dissolving the complex powder by using DMF (dimethyl formamide) as reference solution to prepare the complex powder with the concentration of 1.0 multiplied by 10-4mol·L-1The fluorescence spectrum of the zinc complex solution is tested under the room temperature condition by utilizing a fluorescence spectrometer F-4600 of Hitachi, Japan, and the result is shown in figure 4. analysis of figure 4 shows that the zinc complex has certain fluorescence property when the emission wavelength is 340nm, the excitation wavelength is 335nm and the fluorescence intensity is 204a.u.

Claims (1)

1. A6-methylpyridine-2, 3-dicarboxylic acid zinc complex is characterized in that the chemical formula is [ Zn (6-Me-2,3-pydc) (H)2O)2·2H2O]n6-Me-2,3-pydc is 6-methylpyridine-2, 3-dicarboxylic acid having the molecular formula C8H13NO8Zn with molecular weight of 316.56, belonging to orthorhombic system with space group of Pna21Cell parameter of
Figure FDA0002748302270000011
α＝90°，β＝90°，γ＝90°，
Figure FDA0002748302270000012
Z is 4, the crystallographic data is shown in Table 1, the part and the bond angle are shown in Table 2,
TABLE 1 crystallographic data for zinc 6-methylpyridine-2, 3-dicarboxylate complexes
Figure FDA0002748302270000013
TABLE 2.6 partial bond length of Zinc 6-methylpyridine-2, 3-dicarboxylate complexes
Figure FDA0002748302270000014
Angle of harmony key (°)
Figure FDA0002748302270000015
Figure FDA0002748302270000021
The preparation method of the 6-methylpyridine-2, 3-dicarboxylic acid zinc complex is characterized by comprising the following specific steps:
(1) 0.1131g of Zn (CH) were weighed out3COO)2·H2Dissolving O and 0.0909g 6-methylpyridine-2, 3-dicarboxylic acid in a beaker containing 10mL and 2mLN, N-Dimethylformamide (DMF) distilled water, and stirring for 30min by a magnetic stirrer at room temperature to prepare a mixed solution;
(2) and (2) transferring the mixed solution prepared in the step (1) into a 25mL reaction kettle with a polytetrafluoroethylene bottle, putting the reaction kettle into an oven, heating the mixture to 80 ℃, reacting for 72 hours, cooling the mixture to 60 ℃ at the speed of 5 ℃/h, keeping the temperature for 6 hours, closing the oven, naturally cooling the mixture to room temperature, taking the mixture out of the reaction kettle, and generating light white transparent blocky crystals to obtain the 6-methylpyridine-2, 3-zinc dicarboxylate complex.
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