CN113583029A - Two-dimensional supramolecular compound synthesized based on 1,3, 5-tri (4-carbonylphenoxy) benzene and method and application thereof - Google Patents
Two-dimensional supramolecular compound synthesized based on 1,3, 5-tri (4-carbonylphenoxy) benzene and method and application thereof Download PDFInfo
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- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1691—Coordination polymers, e.g. metal-organic frameworks [MOF]
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
- B01J31/2239—Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate ligands
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Abstract
The invention relates to treatment of dye-containing wastewater, in particular to a two-dimensional supramolecular compound synthesized based on 1,3, 5-tri (4-carbonyl phenoxy) benzene, a method and application thereof; the method comprises the steps of mixing 1,3, 5-tri (4-carbonyl phenyl oxy) benzene, phenol and Cu (NO)3)2·3H2Adding O into acetonitrile water solution, stirring, mixing, transferring into a reaction kettle with polytetrafluoroethylene lining, and heating to 11 deg.CKeeping the temperature at 0-130 ℃ for 60-84 hours, and then cooling to 20-30 ℃ at the speed of 3-8 ℃/h to obtain the two-dimensional supramolecular compound; compared with the prior art, the invention provides a simpler method for synthesizing the two-dimensional supramolecular compound and the two-dimensional supramolecular compound synthesized by the method has better degradation efficiency on the dye in water; in addition, the two-dimensional supermolecule compound synthesized by the invention is tested to be a stable and recyclable photocatalyst.
Description
Technical Field
The invention relates to treatment of dye-containing wastewater, in particular to a two-dimensional supramolecular compound synthesized based on 1,3, 5-tri (4-carbonylphenoxy) benzene, a method thereof and application of the two-dimensional supramolecular compound in degradation of dyes in water.
Background
Azo dyes containing-N ═ N-groups are the major pollutants in wastewater, and most dyes are difficult to degrade by microorganisms due to high stability and may induce carcinogenic effects in living systems. At present, treatment technologies such as adsorption, membrane separation and electrochemical degradation are applied to the removal and treatment of dye wastewater to eliminate and reduce the lasting influence of dyes on biological systems. Photocatalysis is considered to be the most promising approach to solve environmental problems. Since the discovery of photocatalytic properties of TiO2 in 1972, techniques for photocatalytic water decomposition and photocatalytic degradation of organic pollutants were developed in order to explore the application of photocatalysts. Dyes containing rhodamine B (Rh B), Methylene Blue (MB), Methylene Orange (MO) and the like are common target pollutants in the advanced oxidation process.
Coordination polymers are widely known for their aesthetic network structure and important potential application areas. In a wide variety of applications, coordination polymer-based photocatalytic technology has received extensive attention and advancement, mainly due to the fundamental need to deal with the contamination problem. In addition, an increasing number of transition metal complexes and coordination polymers have been extensively studied and discussed as photocatalysts, including their diverse network structures and controlled synthesis methods.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a method for synthesizing a two-dimensional supramolecular compound based on 1,3, 5-tri (4-carbonylphenoxy) benzene, wherein the two-dimensional supramolecular compound synthesized based on the method has better degradation efficiency on dyes in water, and is a stable and recyclable photocatalyst.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for synthesizing two-dimensional supramolecular compounds based on 1,3, 5-tri (4-carbonylphenoxy) benzene, which comprises reacting 1,3, 5-tri (4-carbonylphenoxy) benzene, phenol and Cu (NO)3)2·3H2Adding O into acetonitrile water solution, stirring and mixing uniformly, transferring into a reaction kettle with a polytetrafluoroethylene lining, heating to 110-130 ℃, preserving heat for 60-84 hours, and then cooling to 20-30 ℃ at the speed of 3-8 ℃/h to obtain the two-dimensional supramolecular compound.
In a further embodiment, the 1,3, 5-tris (4-carbonylphenoxy) benzene, phenol and Cu (NO)3)2·3H2The mass ratio of O is 1: (0.5-1): (1.2-1.8).
In a further technical scheme, in the acetonitrile water solution, the volume ratio of acetonitrile to water is 1: (0.8-1.5).
The invention also provides a two-dimensional supramolecular compound synthesized by the method.
The invention also provides the application of the two-dimensional supramolecular compound in degradation of dyes in water.
Compared with the prior art, the invention provides a simpler method for synthesizing the two-dimensional supramolecular compound and the two-dimensional supramolecular compound synthesized by the method has better degradation efficiency on the dye in water; in addition, the two-dimensional supermolecule compound synthesized by the invention is tested to be a stable and recyclable photocatalyst.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Drawings
FIG. 1 shows the structure of Compound 1 synthesized in example 1 of the present invention; FIG. 1(a) coordination geometry of the Cu (II) center in Compound 1; (b) perspective view 1 of three-dimensional supramolecular network in compound 1; (c) hydrogen bonding interactions between non-coordinating carboxyl groups of adjacent subunits and coordinating water molecules; (d) pi-pi interactions between phenol linkers on different chains;
FIG. 2 is a thermogravimetric analysis plot of Compound 1 synthesized in example 1 of the present invention;
FIG. 3 shows a UV-visible Diffuse Reflectance Spectrum (DRS) of Compound 1 synthesized in example 1 of the present invention;
FIG. 4 shows the photocatalytic performance of compound 1 synthesized in example 1 according to the present invention for different dyes; FIGS. 4(a) - (c) adsorption capacities of MO, Rh B and MB solutions, respectively; (d) the control group opinion, the adsorption capacity and the catalytic efficiency of the three dyes; (e) the degradation efficiency of the three dyes is compared; (f) ln (C)0Fitted data of/C) and t;
FIG. 5 shows a PXRD pattern under different conditions for Compound 1 synthesized in example 1 of the present invention;
FIG. 6 shows N as Compound 1 synthesized in example 1 of the present invention2Adsorption-desorption isotherms;
FIG. 7 shows a study of the catalytic reaction mechanism of Compound 1 synthesized in example 1 of the present invention; FIG. 7(a), (b) characteristics of concentration change and catalytic change in the presence of scavenger; (c) ln (C)0Fitted data for/c) and time (t); (d) influence on MB degradation after 4 cycles of operation;
FIG. 8 is a diagram showing the molecular skeleton of the dye in water in scheme 1 of the present invention.
FIG. 9 shows the analysis of possible switching paths of MB using LC-MS in scheme 2 of the present invention.
Detailed Description
In order to make the technical means, the creation features, the achievement purposes and the effects of the invention easy to understand, the invention is further clarified with the specific embodiments.
In the present invention, by selecting a tricarboxylic acid ligandBulk and nitrogen-containing ligands with Cu (NO)3)2Under mild conditions, a new two-dimensional compound is synthesized, namely: [ Cu ]2(HL)2(H2O)2(phen)2·H2O]n(H3L ═ 1,3, 5-tris (4-carbonylphenoxy) benzene, phen ═ 1, 10-phenanthroline) (1).
In the following examples of the invention, all other reagents were purchased and used without further purification. Elemental analysis of C, H and N was performed on a Perkin-Elmer 240C analyzer.
FT-IR spectra were obtained on a VERTEX 70FT-IR spectrophotometer in the 4000-600cm-1 region.
On a D/MAX-3C diffractometer, in Cu-Ka radiation
And powder x-ray diffraction (PXRD) experiments were performed at room temperature.
Luminescence measurements were performed at room temperature and spectral acquisitions were performed on a Perkin-Elmer LS50B fluorescence spectrometer.
The uv-vis spectrum is measured on a spectrophotometer.
The ultraviolet-visible diffuse reflectance spectrum of the solid sample is BaSO4Collected for reflectance standards on a Cary 500 spectrophotometer.
Example 1
This example provides a method for the synthesis of two-dimensional supramolecular compounds based on 1,3, 5-tris (4-carbonylphenyloxy) benzene, in particular 1,3, 5-tris (4-carbonylphenyloxy) benzene (0.05mmol, 0.024g), phenol (0.10mmol, 0.018g) and Cu (NO)3)2·3H2O (0.15mmol, 0.036g) was added to 10mL of an aqueous acetonitrile solution (acetonitrile to water volume ratio of 1: 1); stirring and mixing for 30 minutes, then putting the mixture into a 25mL reaction kettle with a polytetrafluoroethylene lining, heating to 120 ℃, keeping the temperature and reacting for 72 hours, and then cooling to 25 ℃ at the speed of 5 ℃/h to obtain a product.
For convenience of description, the above product is defined as compound 1.
The crystallographic data for compound 1 are shown in table 1 below: IR (cm-1):3466 (v); 3060 (m); 2583 (m); 2132 (m); 1712 (v); 1589 (v); 1496 (vs); 1384 (v); 1240 (vs); 1137 (m); 1004 (m); 840 (v); 727 (m).
TABLE 1 Crystal data for Compound 1
*R＝∑(Fo–Fc)/∑(Fo),**wR2＝{∑[w(Fo 2–Fc 2)2]/∑(Fo 2)2}1/2.
Structural description of compound 1:
in Compound 1, there is one Cu (II) cation, one HL in each asymmetric subunit2-Negative ions, one coordinated water molecule, one phenol molecule and one semi-free water molecule (as shown in FIG. 1 a);
each Cu (II) center in Compound 1 coordinates to two adjacent HL2-Two O atoms and two N atoms in the linker come from phen, and the other oxygen atom comes from a coordinated water molecule to form a { CuN2O3The tetrahedral geometry of the. The basal plane is fixed by two carboxyl oxygen atoms and two N atoms of phenol molecules, and the vertex position is occupied by one coordinated water molecule (O10).
In Compound 1, partially deprotonated HL2-The anion is combined with two metal ions on the carboxyl side in a coordination mode of mu 1-eta 1: eta 0, and COO in the middle of the two metal ions-The radicals are not coordinated. The dihedral angles between the two side benzene rings and the middle benzene ring were 21.5 ° and 18.1 °, respectively. In this connection, HL2-Monodentate coordination mode formation of anions and phenols [ Cu2(HL)2(H2O)2(phen)2]A ring (as in fig. 1 a); in addition, adjacent subunits of compound 1 are further connected by O-H-O interactions, creating parallel new layers along the bc plane (fig. 1 c). These layers are extended into 3D supramolecular structures by the interaction of adjacent phenol ligands (shown in fig. 1b and fig. 1D).
Thermogravimetric analysis of compound 1:
the thermal stability of compound 1 was investigated by thermogravimetric analysis (TGA), as shown in figure 2, for compound 1 the first step weight loss in the temperature range 25-197 ℃ is due to the release of one lattice water molecule and two coordinated water molecules; weight loss above 240 ℃ can be attributed to collapse of the lattice structure and decomposition of the organic ligands.
Measurement of photocatalytic reaction:
compound 1(40mg) was added to 100mL of Methylene Blue (MB)/Methylene Orange (MO)/rhodamine B (Rh B) solution (10 mg/L). The suspension was stirred in the dark for about 30 minutes and then continuously stirred under irradiation with visible light from a 300W Xe lamp with an ultraviolet cut-off filter (visible light. lambda. Xe lamp)>400 nm). The light intensity of the liquid surface is 3850W/m measured by a PL-MW2000 photoelectric radiometer2. At regular intervals, aliquots of the reaction mixture were taken periodically and analyzed with a uv-vis spectrophotometer at the absorption wavelengths of MB, MO and RhB.
Photocatalytic performance of compound 1:
diffuse reflection UV-vis data of Compound 1 was collected to give a band gap (Eg). Since the intersection between the x-axis and the line is inferred from the line position of the absorption edge, the final calculation results are obtained, and Eg is estimated to be about 2.78eV, as shown in fig. 3.
The decomposition of MB, MO and Rh B was measured by exposure to ultraviolet radiation. First, the product components of MB, MO and Rh B were extracted in the presence of a photocatalyst, the degradation efficiencies of which are listed (as shown in a, B, c and e in fig. 4);
in FIG. 4 of the present invention, FIGS. 4a, B, c show the absorbance per 10 minute illumination time under different wavelength conditions, the lower the absorbance, the more the dye is degraded, when compound 1 is allowed to act on MO, Rh B and MB, respectively. In fig. 4a, b, c, the curves correspond to absorbance curves for different treatment times, respectively, wherein for MO, the absorbance curves do not significantly shift downward with increasing treatment time, corresponding to a degradation rate of 10.17% in fig. 4 d; for MB, the absorbance curve was closer to the x-axis as the treatment time was extended, i.e. there was a significant decrease in absorbance, corresponding to a degradation rate of 46.87% in fig. 4 d; for Rh B, the absorbance curve decreased less than MB with increasing treatment time, corresponding to a degradation rate of 22.86% in FIG. 4 d.
That is, from the results, compound 1 showed photocatalytic performance for MO, Rh B and MB, with degradation rates of 10.17%, 22.86% and 46.87% in 100 minutes, respectively (see fig. 4 d).
Notably, compound 1 exhibited selective photocatalytic ability for MB. Moreover, the inventors have found that there is a significant variation in catalytic oxidation reactions at different catalyst dosages, dye concentrations, metal effects, light sources and irradiation times.
All data were fitted using a quasi-first order kinetic equation to obtain and explore the catalytic reaction rate profile (fig. 4 d). The kinetic rate constant (k) is calculated using a conventional linear plot. ln (C)0The reaction time (t) is preferably linear. The k values of MO, Rh B and MB in the presence of photocatalyst are 0.00107min respectively-1，0.00247min-1And 0.0610min-1(FIG. 4f and Table 2). In addition, the inventors also explored the cycling performance characteristics of compound 1. Even after four cycles of the experiment, it was found that the catalytic performance of the catalyst did not significantly decrease (fig. 7 d). PXRD of compound 1 did not change significantly over 4 cycles (fig. 5). The present results indicate that compound 1 can act as a stable, recyclable photocatalyst.
Table 2: different fitting parameters of a quasi-first order kinetic equation
Furthermore, the inventors investigated N of Compound 12Adsorption-desorption isotherms (FIG. 6) gave a Brunauer-Emmett-Teller surface area of 7.44m for Compound 12 g-1。
By analyzing the structural characteristics (0.22nm for 1), as shown in FIG. 8, the size of MO dye is 1.54nm × 0.48nm × 0.28nm, the size of MB dye is 1.38nm × 0.64nm × 0.21nm, and the size of Rh B dye is 1.56nm × 1.35nm × 0.42nm (scheme 1), which are larger than the pore result of crystal and thus cannot enter the pores of compound 1. Based on the correlation between the structural characteristics of the material channels and the size of the dye molecules, we hypothesize that the catalytic reaction occurs primarily at the surface of the catalyst.
To explore and monitor the mechanism of the catalytic reaction, the inventors performed a series of capture and trapping experiments. Three scavengers, Benzoquinone (BQ), tert-butanol (TBA) and Ammonium Oxalate (AO), were selected in each degradation process (FIGS. 7a-7 b). The data indicate that the scavenger can effectively induce and reduce the process of the catalytic reaction. The performance drop for MB was significant, from 93.64% to 68.38% (fig. 7 c). During the catalytic process, the OH-radical captures H + and becomes OH in compound 1. The results show that: OH is a major active oxidative radical in MB photolysis systems.
In order to further explore the possible decomposition intermediates generated during MB degradation, LC-MS method was adopted to study them. Based on current profiling analysis, a possible degradation mechanism was postulated in scheme 2. In the first route, the MB molecule starts from the amination reaction and intermediate products are formed at m/ z 269 and 255. The intermediate of formula 227 is produced by demethylation and/or oxidation of intermediate 241. Based on its strong oxidizing power for. OH, N/S heterocycles were produced and many subsequent decomposition products were detected. Scheme 2 (shown in figure 9) lists and discusses the most similar degradation pathways.
The foregoing shows and describes the general principles, essential features, and inventive features of this invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (5)
1. A method for synthesizing two-dimensional supramolecular compounds based on 1,3, 5-tri (4-carbonylphenoxy) benzene, characterized in that the method comprises the steps of mixing 1,3, 5-tri (4-carbonylphenoxy) benzene, phenol and Cu (NO)3)2·3H2Adding O into acetonitrile water solution, stirring and mixing uniformly, transferring into a reaction kettle with a polytetrafluoroethylene lining, heating to 110-130 ℃, preserving heat for 60-84 hours, and then cooling to 20-30 ℃ at the speed of 3-8 ℃/h to obtain the two-dimensional supramolecular compound.
2. The method of claim 1, wherein the 1,3, 5-tris (4-carbonylphenoxy) benzene, phenol and Cu (NO)3)2·3H2The mass ratio of O is 1: (0.5-1): (1.2-1.8).
3. The method according to claim 1, wherein the volume ratio of acetonitrile to water in the aqueous solution of acetonitrile is 1: (0.8-1.5).
4. A two-dimensional supramolecular compound synthesized according to the method of any one of claims 1-3.
5. Use of two-dimensional supramolecular compounds according to claim 4 for the degradation of dyes in water.
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| PCT/CN2021/142808 WO2023005143A1 (en) | 2021-07-30 | 2021-12-30 | Two-dimensional supramolecular compound synthesized on the basis of 1,3,5-tri(4-carbonylphenyloxy)benzene, method therefor, and application thereof |
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