A metal organic coordination compound of 5-methyl isophthalic acid mixed ligand and its preparation method and application

Abstract

The application belongs to the technical field of metal organic coordination compounds, and particularly relates to a metal organic coordination compound of 5-methyl isophthalic acid mixed ligand and a preparation method and application thereof. 39 H 30 ZnN2O5 or C 39 H 30 CdN2O5. On this basis, structure analysis and characterization are carried out on MOFs1 and MOFs2, and structural characteristics of the MOFs1 and MOFs2 are studied through infrared, thermogravimetric, X-ray powder diffraction and ultraviolet reflection tests. Research shows that the two MOFs have isomorphic properties and good photocatalytic activity.

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of metal organic coordination compounds, and particularly relates to a metal organic coordination compound of 5-methyl isophthalic acid mixed ligand and a preparation method and application thereof. BACKGROUND

[0002] Water is one of the most important energy sources for human beings. With the rapid growth of global population and economy, water pollution has been identified as a major worldwide problem that threatens aquatic and human health. In particular, wastewater generated in many industrial processes contains toxic organic pollutants, which are not suitable for direct biological treatment, thus leading to serious environmental problems. As one of the many organic pollutants, organic dyes often have strong chemical stability and non-biodegradability, and therefore, to solve the environmental pollution problem, exploring an economical and effective technology for degrading these organic dyes has always been a research hotspot.

[0003] In recent decades, metal-organic frameworks (MOFs) as a classic inorganic-organic hybrid porous material, due to its structural diversity and modifiability and potential application value, such as catalysis, separation, gas storage, sensing, fluorescence, magnetism, proton conduction, etc. Many MOF-based active catalysts photocatalytic processes can be considered as an effective method for degrading organic dyes, because these MOF-based catalysts can mineralize synthetic organic dyes into minimal components such as CO2, H2O, etc. However, an important prerequisite for these metal organic frameworks is that the photocatalyst is a property that exists when a semiconductor is exposed to light irradiation. SUMMARY

[0004] Therefore, the purpose of the present application is to provide a metal organic coordination compound using 5-methyl isophthalic acid and transition metal as mixed ligand in view of the problems existing in the prior art.

[0005] In order to achieve the above-mentioned purpose, the technical scheme adopted by the present application is as follows:

[0006] A metal organic coordination compound of 5-methyl isophthalic acid mixed ligand, the general formula is [M(L)(mipa)] n , wherein M represents a metal ion, the metal is Zn or Cd; L represents an N-donor organic ligand; mipa represents 5-methyl isophthalic acid; n represents the coordination number, n is an integer, 1≤n≤2.

[0007] Further, the N-donor organic ligand is 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone.

[0008] Still further, the metal organic coordination compound comprises C 39 H 30ZnN2O5 or C 39 H 30 CdN2O5.

[0009] The present application constructs two new MOFs materials by mixing using the main ligand 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone and the auxiliary ligand 5-methylisophthalic acid. They are isomorphic compounds 1 [Zn(L)(mipa)] n and compound 2 [Cd(L)(mipa)] n . By introducing the mixed ligand of bipyridine derivative and carboxylic acid, the compound 1 and the compound 2 present a novel 3,5-connected two-dimensional layered structure, the topological symbol is (4 2 ·6 7 ·8)(4 2 ·6), and the two compounds have a relatively narrow optical band gap, so that the compounds have a certain ability of photocatalytic degradation of dyes under ultraviolet light irradiation.

[0010] The second object of the present application is to provide a preparation method of the metal organic coordination compound of the mixed ligand 5-methylisophthalic acid.

[0011] In order to achieve the above object, the present application provides the following technical scheme:

[0012] The preparation method of the metal organic coordination compound of the mixed ligand 5-methylisophthalic acid, the steps comprising:

[0013] I. Synthesis of 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand: 4-(pyridin-3-yl)benzylidene is added to KOH solution and dissolved in ethanol to obtain a mixed solution, then cyclohexanone ethanol solution is slowly added to the mixed solution, stirred, and finally washed with a mixed solvent of 10 mL of water and 10 mL of ethanol to obtain the 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand;

[0014] II. Synthesis of metal organic coordination compound of mixed ligand 5-methylisophthalic acid: 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand, 5-methylisophthalic acid, metal salt, N,N-dimethylformamide, ethanol and water are heated at 80℃ in a stainless steel reactor for 48h, the product is filtered, the crystals are collected and washed with deionized water and dried, and the obtained crystals are the metal organic coordination compound.

[0015] Further, the metal salt in the step II is Zn(NO3)2·6H2O or Cd(NO3)2·4H2O.

[0016] Compound 1 Zn-MOF is yellow transparent block crystal, and compound 2 Cd-MOF is light yellow transparent block crystal.

[0017] Further, in the mixed solution, 4-(pyridin-3-yl) benzylidene:KOH:ethanol = 5 mmol:4 mL:30 mL.

[0018] Further, in the step I, the molar ratio of cyclohexanone:ethanol in the cyclohexanone ethanol solution is 2.5 mmol:20 mL.

[0019] Further, in the step II, the molar ratio of 2,6-bis((E)-4-(pyridin-3-yl) benzylidene) cyclohexanone ligand, 5-methyl isophthalic acid, metal salt is 1:1:1, the volume ratio of N,N-dimethylformamide, ethanol and water is 4:1:1, and the concentration of 2,6-bis((E)-4-(pyridin-3-yl) benzylidene) cyclohexanone ligand in the solvent is 0.05 mmol / 6 mL.

[0020] A third object of the present application is to provide the application of the metal organic coordination compound of the mixed ligand of 5-methyl isophthalic acid in the degradation of dyes.

[0021] Further, the metal organic coordination compound is used as a green photocatalyst for degrading methylene blue, pararosaniline hydrochloride, rhodamine B, methyl orange, rhodamine 6G, indigo carmine and basic red 2 in wastewater.

[0022] Compared with the prior art, the present application adopts a mixed strategy, uses the main ligand 2,6-bis((E)-4-(pyridin-3-yl) benzylidene) cyclohexanone and the auxiliary ligand 5-methyl isophthalic acid to construct two new MOFs, which are compound 1 Zn-MOF and compound 2 Cd-MOF. 39 H 30 ZnN2O5 or CdN2O5. 39 H 30 As an effective strategy for constructing MOFs, the present application introduces mixed ligands of bipyridine derivatives and carboxylic acids, and the compound 1 and the compound 2 exhibit novel 3,5-connected two-dimensional layered structures, and the topological symbols are (4 2 ·6 7 ·8)(4 2 ·6), and the two compounds have a relatively narrow optical band gap, so that the compounds have a certain photocatalytic degradation ability of dyes under ultraviolet light irradiation. BRIEF DESCRIPTION OF DRAWINGS

[0023] In order to make the technical solutions in the embodiments of the present application or the prior art clearer, the accompanying drawings needed in the embodiments or prior art description will be briefly introduced. Obviously, the accompanying drawings in the following description are only some embodiments of the present application, and for those skilled in the art, other drawings can be obtained based on the provided drawings without creative effort

[0024] Figure 1 Topological simplification diagram of compound 1 in experimental example 1 of the present application.

[0025] Figure 2 Structure of compound 1 in experimental example 1 of the present application: (a) asymmetric unit of 1. (b) coordination environment of Zn2+ion symmetry code: ii, 1-x, -y, 2-z; vi, x-1, y-1, 1+z; vii, x, 1+y, z. (c) ladder chain. (d) two-dimensional layer structure.

[0026] Figure 3 IR spectrum of L in experimental example 2 of the present application.

[0027] Figure 4 IR spectrum of MOF1 in experimental example 2 of the present application.

[0028] Figure 5 IR spectrum of MOF2 in experimental example 2 of the present application.

[0029] Figure 6 Solid-state ultraviolet-visible diffuse reflectance (DRS) spectrum of compound 1 and compound 2 in experimental example 3 of the present application.

[0030] Figure 7 Photocatalytic degradation performance results in experimental example 3 of the present application.

[0031] Figure 8 PXRD diagram of compound 1 in experimental example 4 of the present application.

[0032] Figure 9 PXRD diagram of compound 2 in experimental example 4 of the present application.

[0033] Figure 10 Thermogravimetric analysis results of MOF1 in experimental example 5 of the present application.

[0034] Figure 11 Thermogravimetric analysis results of MOF2 in experimental example 5 of the present application.

[0035] Figure 12 NMR spectrum of compound 1 disclosed in experimental example 1 of the present application.

[0036] Figure 13 NMR spectrum of compound 2 disclosed in experimental example 2 of the present application. DETAILED DESCRIPTION

[0037] The technical solutions in the embodiments of the present application will be clearly and completely described below. Obviously, the described embodiments are only some of the embodiments of the present application, but not all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work fall within the scope of the present application.

[0038] Herein the term "embodiment" as used in the description of any embodiment is not necessarily an embodiment that is "preferred" over other embodiments. Performance indicators in the embodiments of the present application are tested by using conventional test methods in the art, unless otherwise specified. It should be understood that the terms used in the present application are merely used to describe particular embodiments and are not intended to limit the disclosure of the present application.

[0039] Unless otherwise defined, technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. As used herein, the term "comprising" is intended to mean that the compositions and methods include the recited elements, but not excluding others. "Consisting essentially of" when used herein in relation to a composition or method, shall mean excluding other elements of any essential significance to the composition or method. "Consisting of" shall mean excluding any element other than those identified.

[0040] The terms "substantially" and "approximately," as used herein, are used to describe small fluctuations. For example, they can mean less than or equal to ± 5%, such as less than or equal to ± 2%, such as less than or equal to ± 1%, such as less than or equal to ± 0.5%, such as less than or equal to ± 0.2%, such as less than or equal to ± 0.1%, such as less than or equal to ± 0.05%. Numerical data may, in some instances, be presented in a range format. It is to be understood that such a range format is used only for convenience and brevity and should be understood as a precision of the number of significant figures used and / or the accuracy of the measuring instrument. Unless otherwise stated, the numerical values are to be understood as approximations that are aimed merely at teaching the broadest interpretation of the terms to be used in the claims. Therefore, unless otherwise stated, each numerical value should be construed in light of the number of significant figures and / or the accuracy of the measuring instrument.

[0041] In order to better illustrate the present application, numerous specific details are given in the following specific embodiments. Those skilled in the art should understand that the present application can also be implemented without some specific details. In the embodiments, some methods, means, instruments, devices and the like that are well known to those skilled in the art are not described in detail in order to highlight the main idea of the present application.

[0042] The technical features disclosed in the embodiments of the present application can be combined arbitrarily without conflict, and the resulting technical solutions belong to the disclosure of the present application.

[0043] Embodiment 1

[0044] A metal organic coordination compound of 5-methyl isophthalic acid mixed ligand and a preparation method thereof:

[0045] I. Synthesis of 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand: accurately weigh and add 4-(pyridin-3-yl)benzylidene (0.9 g, 5 mmol) in 4 mL KOH solution, dissolve in 30 mL ethanol to form a mixed solution, then dissolve cyclohexanone (0.25 g, 2.5 mmol) in 20 mL ethanol solution and slowly drop into the mixed solution, stir, and finally wash with 10 mL water and 10 mL ethanol solvent to obtain 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand (L);

[0046] II. Synthesis of metal organic coordination compound of 5-methyl isophthalic acid mixed ligand: heat 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand (0.02 g, 0.05 mmol), 5-methyl isophthalic acid (0.009 g, 0.05 mmol), Zn(NO3)2·6H2O (0.015 g, 0.05 mmol), DMF (4 mL), ethanol (1 mL) and water (1 mL) in a stainless steel reactor, heat at 80°C for 48 h, filter the product, collect the crystals, and dry after washing with deionized water to obtain yellow transparent block crystals, which are compound 1C 39 H 30 ZnN2O5. The structure characterization nuclear magnetic spectrum is shown in Figure 12

[0047] Embodiment 2

[0048] A metal organic coordination compound of 5-methyl isophthalic acid mixed ligand and a preparation method thereof:

[0049] I. Synthesis of 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand: accurately weigh and add 4-(pyridin-3-yl)benzylidene (0.9 g, 5 mmol) in 4 mL KOH solution, dissolve in 30 mL ethanol to form a mixed solution, then dissolve cyclohexanone (0.25 g, 2.5 mmol) in 20 mL ethanol solution and slowly drop into the mixed solution, stir, and finally wash with 10 mL water and 10 mL ethanol solvent to obtain 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand (L); ​

[0050] II. Synthesis of metal organic coordination compound of mixed ligand of 5-methyl isophthalic acid: 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand (0.02 g, 0.05 mmol), 5-methyl isophthalic acid (0.009 g, 0.05 mmol), Cd(NO3)2·4H2O (0.0154 mg, 0.05 mmol), DMF (4 mL), ethanol (1 mL) and water (1 mL) were heated in a stainless steel reactor at 80 °C for 48 h, the product was filtered, the crystals were collected and washed with deionized water and dried to obtain light yellow transparent block crystals of compound 2C 39 H 30 CdN2O5. The structure characterization nuclear magnetic spectrum is shown in Figure 13

[0051] In order to further prove the beneficial effects of the present application and better understand the present application, the properties and application performance of the series of mixed ligand metal organic coordination compounds according to the present application are further illustrated by the following determination tests, but it should not be understood as a limitation of the present application. The properties of the products obtained by other determination experiments of those skilled in the art according to the above application content and the application according to the above properties are also regarded as falling within the protection scope of the present application.

[0052] Experimental Example 1

[0053] Crystal structure determination

[0054] X-ray powder diffraction (PXRD) data of metal organic coordination compound MOFs 1-2 were collected on an Oxford Diffraction Gemini R Ultra diffractometer using Cu-Kα radiation monochromated by a graphite monochromator The diffraction data were collected in a way at a temperature of 296 K. The diffraction data of part of the structure were corrected for absorption using the SADABS program. The crystal structure was solved by direct methods combined with difference Fourier synthesis. The coordinates and anisotropic parameters of all non-hydrogen atoms were refined by full-matrix least squares, the positions of C-H atoms were calculated according to the theoretical model, the O-H atoms were first found according to the difference Fourier, and then the coordinates and isotropic parameters of the hydrogen atoms were refined by full-matrix least squares and participated in the final structure refinement.

[0055] Single crystal X-ray diffraction analysis shows that compounds 1 and 2 are crystallized in a triclinic space group P. Since compound 1 and compound 2 are isomorphic, only the structure of compound 1 is discussed in detail. The asymmetric unit of compound 1 contains one Zn 2+ ion, one L ligand and one mipa 2- ligand. Zn​2+ The ZnO4N2 ion has a six-coordinate coordination environment with an octahedral configuration, consisting of four O atoms (O2, O3ii, O4vii, and O5vii) from three mipa ligands and two N atoms (N1vi and N2) from two L ligands. The Zn-O bond lengths range from 2.012 to... The bond lengths of Zn and N range from 2.162 to 2.162. Completely deprotonated mip 2- The carboxylate groups of the ligands exhibit both chelating bidentate and bridging bidentate coordination modes. The two hexacoordinate Zn groups in the asymmetric unit... 2+ The ion consists of two mipa 2- The two carboxylates of the ligand are bridged to form a binuclear core, with a Zn…Zn distance of . A dual-core unit via two MIPAs 2- Connecting with two adjacent dual-core units, a ladder-like chain is generated, with the coordinated L-ligand fixed between the two chains, forming a two-dimensional layered network. Adjacent layers are further connected through several classical interactions to form a 3D framework. Figures 1-2 (Tables 1-3). A simplified network was obtained through topology analysis, in which all MIPAs... 2- The ligands can be viewed as 3-connector nodes, and each bridging L-ligand can be viewed as a connector. Therefore, the framework is an unusual 3,5-connector network, as indicated by the TOPOS 4.0 package 26-dot notation (4...). 2 ·6 7 ·8)(4 2 ·6).

[0056] Table 1. Crystallographic parameters of the target compound

[0057]

[0058]

[0059] Table 2 Selective bond lengths of Compound 1 Bond angle (°)

[0060]

[0061] Table 3 Selective bond lengths of Compound 2 Bond angle (°)

[0062]

[0063]

[0064] Symmetry codes: (i)x,y-1,z; (ii)x-1,1+y,1+z; (iii)1-x,2-y,2-z;

[0065] This indicates that the L ligand crystallizes in the monoclinic space group P21 / c. The asymmetric unit consists of only one L ligand; adjacent molecules are connected by hydrogen bonds (C16-H16A…N1ii and C29-H29…N2i) and stacked on top of each other via π…πiii interactions. The center-to-center distance is... A 3D supramolecular framework is formed.

[0066] Experiment Example 2

[0067] Infrared performance analysis

[0068] The IR spectrum of L is as follows Figure 3 As shown, with 3427cm -1 The mid-band width centered at this point is attributed to the stretching vibration of the OH radical in free water molecules. (3027 cm⁻¹) -1 The bands at these locations are attributed to the CH stretching vibration of the benzene ring. The asymmetric or symmetric stretching bands of the CH2 group on cyclohexanone are located at 2958, 2919, or 2834 cm⁻¹, respectively. -1 Nearby. 1658cm -1 The peaks at 1598, 1567, and 1551 cm⁻¹ are attributed to the C=O stretching vibration of the carbonyl group. -1 The peak at 1473 cm⁻¹ is attributed to the C=C or C=N skeletal vibrations of the benzene and pyridine rings. -1 The band at 1157 cm⁻¹ is attributed to the in-plane deformation vibration of the CH₂ group. -1 The peak at 806 cm⁻¹ is attributed to the C-C stretching vibration of cyclohexanone. -1 The peak at 712 cm⁻¹ originates from the characteristic peak of para-substitution of the benzene ring, while the peak at 712 cm⁻¹ is... -1 This is attributed to the out-of-plane bending vibration of =CH. The IR spectra of compounds 1 and 2 are as follows: Figures 4-5 As shown, comparing them with L, the characteristic asymmetry and the symmetric stretching vibrations of the carboxylic acid ester group are at 1557 and 1383 cm⁻¹, respectively. -1 (For compound 1) and 1543 and 1377 cm -1 (Observed at compound 2).

[0069] Experimental Example 3

[0070] UV performance analysis

[0071] 30 mg of either compound 1 or compound 2 was added to an aqueous solution containing 50 mL of organic dye (6 mg / L). Before turning on the UV lamp (100 W, 365 nm), the resulting suspension was continuously stirred for 30 min without a light source to establish the catalyst adsorption / desorption equilibrium. Then, during the photocatalytic reaction, 4 mL of solution was taken from the reactor every 1 h for UV measurement.

[0072] To investigate photocatalytic activity, solid-state UV-Vis diffuse reflectance (DRS) experiments were conducted on compounds 1 and 2. Their band gaps (Eg) were studied using the Kubelka-Munk function: F = (1-R)² / 2R, where R is the reflectance from a given wavelength of the DRS set. Figure 6 As shown, compounds 1 and 2 exhibit significant light absorption at 310 nm. Furthermore, the band energies of compounds 1 and 2 are 2.50 eV and 2.52 eV, respectively, indicating that they possess suitable Eg for photocatalysis under ultraviolet light. Metal-organic frameworks can be used as green photocatalysts for the degradation of organic pollutants in wastewater. This study selected methylene blue (MB), pararosaniline hydrochloride (PH), rhodamine B (RhB), methyl orange (MO), rhodamine 6G (Rh6G), indigo (Isatin), and basic red 2 (BR2) as model pollutants to investigate their degradation processes in the presence of compounds 1 and 2.

[0073] Furthermore, the degradation process was monitored as a control in the absence of a catalyst. The photocatalytic effect of catalyst 1 in solutions of MB, PH, RhB, MO, Rh6G, Isatin, and BR2 dye molecules was clearly demonstrated. Figure 7 The left side illustrates the relationship between concentration ratio (C / C0) and irradiation time (h). The degradation rates of MB (60.3%), PH (71.1%), RhB (50.9%), MO (28.2%), Rh6G (24.9%), Isatin (19.3%), and BR2 (12.4%) were calculated for catalyst 1 after 7 hours. The photocatalytic activity order of catalyst 1 for the seven dyes was: PH > MB > RhB > MO > Rh6G > Isatin > BR2. The efficiency of catalyst 2 for the seven dyes is shown in the figure. The linear relationship between concentration ratio (C / C0) and irradiation time (h) is shown in the figure. Figure 7 As shown on the right. The degradation rates of MB (63.5%), PH (54.7%), RhB (49.6%), MO (31.9%), Rh6G (29.7%), Isatin (17.0%), and BR2 (10.5%) were calculated as those of compound 2 after 7 hours. The photocatalytic activity of compound 2 for the above dyes was in the order of MB > PH > RhB > MO > Rh6G > Isatin.

[0074] Experiment Example 4

[0075] Powder X-ray diffraction (PXRD)

[0076] The experimental results of the powder X-ray diffraction (PXRD) patterns of Compound 1 and Compound 2 are in good agreement with the simulated results, indicating that the bulk products of Compound 1 and Compound 2 have high phase purity. To prove that the two MOFs have good chemical stability, the PXRD patterns were recorded after they were immersed in different solvents (such as MeOH, MeCN, DMF, EtOH and water) for 7 days. As shown in the figures, both Compound 1 ( Figure 8 ) and Compound 2 ( Figure 9 ) show high stability in common solvents. At the same time, the skeleton of Compound 1 and Compound 2 can also be preserved in aqueous solution with pH = 2-13 for 3 days, which fully proves that both of the two MOFs have good acid and alkali resistance.

[0077] Experimental Example 5

[0078] Thermogravimetric analysis (TGA)

[0079] The TGA experiments of MOFs 1 and 2 were performed on a SDT 2960 differential thermal analyzer under nitrogen atmosphere, with a heating rate of 10 °C·min -1 . The UV-Vis measurements of the solutions were performed on a Thermo EV 201 CP. As shown in Figures Figure 10 (MOFs 1) and Figure 11 (MOFs 2), they show high thermal stability and the same one-step thermal decomposition behavior. With the temperature rising to 350 °C (1) and 360 °C (2) respectively, the skeleton of MOFs 1 and MOFs 2 starts to collapse due to the decomposition of the organic ligand. This further proves the evidence of the isomorphic properties of Compound 1 and Compound 2.

[0080] The above description of disclosed embodiments enables one skilled in the art to make or use the present application. Numerous modifications to these embodiments will be apparent to those skilled in the art, and the general principles defined herein can be applied to other embodiments without departing from the spirit or scope of the application. Therefore, the present application is not to be limited to the implementations illustrated herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. A metal-organic coordination compound containing a mixture of 5-methylisophthalic acid ligands, characterized in that the ligands... 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone, the structural formula of which is as follows: The topological symbols of compound 1 and compound 2 are (4 2 ·6 7 ·8)(4 2 ·6); The crystallographic parameters of the metal organic coordination compound are as follows:

2. A method for preparing a metal organic complex compound of 5-methylisophthalic acid mixed ligand as claimed in claim 1, characterized by the steps of The application further relates to a method for synthesizing the metal organic coordination compound of the 5-methyl isophthalic acid mixed ligand. I. Synthesis of a 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand: 4-(pyridin-3-yl)benzaldehyde is added into a KOH solution and dissolved in ethanol to obtain a mixed solution, then a cyclohexanone ethanol solution is slowly added into the mixed solution, stirring is performed, finally, the product is washed with a mixed solvent of 10 mL of water and 10 mL of ethanol to obtain the 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand; II. Synthesis of a metal organic coordination compound of a 5-methyl isophthalic acid mixed ligand: 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand, 5-methyl isophthalic acid, a metal salt, N,N-dimethylformamide, ethanol and water are heated in a stainless steel reactor at 80 DEG C for 48 h, the product is filtered, the crystals are collected and washed with deionized water and dried, and the obtained crystals are the metal organic coordination compound.

3. The method of producing a metal-organic coordination compound of a 5-methylisophthalic acid mixed ligand according to claim 2, characterized by, The metal salt in the step II is Zn(NO3)2.6H2O or Cd(NO3)2.4H2O.

4. The method for preparing the organometallic coordination compound of the 5-methylisophthalic acid mixed ligand according to claim 2, characterized in that, In the mixed solution, 4-(pyridin-3-yl)benzaldehyde: KOH: ethanol = 5 mmol: 4 mL: 30 mL.

5. The method for preparing the organometallic coordination compound of the 5-methylisophthalic acid mixed ligand according to claim 2, characterized in that, In the cyclohexanone ethanol solution in the step I, cyclohexanone: ethanol = 2.5 mmol: 20 mL.

6. The method for preparing the organometallic coordination compound of the 5-methylisophthalic acid mixed ligand according to claim 2, characterized in that, In the step II, the molar ratio of the 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand, 5-methyl isophthalic acid and the metal salt is 1:1:1, the volume ratio of N,N-dimethylformamide, ethanol and water is 4:1:1, and the concentration of the 2,6-bis((E)-4-(pyridin-3-yl)benzylidene)cyclohexanone ligand in the solvent is 0.05 mmol / 6 mL.

7. A metal organic coordination compound of a 5-methyl isophthalic acid mixed ligand according to claim 1 in the application of dye degradation.

8. Use of the metal-organic complex compound of 5-methylisophthalic mixed ligand according to claim 7, characterized in that, The metal organic coordination compound is used as a green photocatalyst for degrading methylene blue, pararosaniline hydrochloride, rhodamine B, methyl orange, rhodamine 6G, indigo carmine and basic red 2 in wastewater.

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