WO2023005143A1 - Composé supramoléculaire bidimensionnel synthétisé sur la base de 1,3,5-tri(4-carbonylphényloxy)benzène, procédé associé et son application - Google Patents

Composé supramoléculaire bidimensionnel synthétisé sur la base de 1,3,5-tri(4-carbonylphényloxy)benzène, procédé associé et son application Download PDF

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WO2023005143A1
WO2023005143A1 PCT/CN2021/142808 CN2021142808W WO2023005143A1 WO 2023005143 A1 WO2023005143 A1 WO 2023005143A1 CN 2021142808 W CN2021142808 W CN 2021142808W WO 2023005143 A1 WO2023005143 A1 WO 2023005143A1
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benzene
dimensional supramolecular
compound
supramolecular compound
carbonylphenyloxy
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PCT/CN2021/142808
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English (en)
Chinese (zh)
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金俊成
吴红敏
姜陪陪
孙传伯
谢成根
刘真
蔡循
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皖西学院
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Priority to MYPI2022001790A priority Critical patent/MY197243A/en
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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
    • 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
    • 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
    • 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]
    • 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
    • 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
    • B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • 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
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B01J35/39—Photocatalytic properties
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/30—Treatment of water, waste water, or sewage by irradiation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/008—Supramolecular polymers
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
    • B01J2531/16—Copper
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/30—Organic compounds
    • C02F2101/308—Dyes; Colorants; Fluorescent agents
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2305/00—Use of specific compounds during water treatment
    • C02F2305/10—Photocatalysts
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W10/00—Technologies for wastewater treatment
    • Y02W10/30—Wastewater or sewage treatment systems using renewable energies
    • Y02W10/37—Wastewater or sewage treatment systems using renewable energies using solar energy

Definitions

  • the invention relates to the treatment of dye-containing wastewater, in particular to a two-dimensional supramolecular compound synthesized based on 1,3,5-tris(4-carbonylphenyloxy)benzene and a method thereof, and a two-dimensional supramolecular compound based on the two-dimensional supramolecular compound Application to the degradation of dyes in water.
  • Rh B rhodamine B
  • MB methylene blue
  • MO methylene orange
  • coordination polymers have been widely used because of their beautiful network structure and important potential application fields.
  • coordination polymer-based photocatalysis has received extensive attention and improvements, mainly due to the fundamental need to deal with pollution problems.
  • transition metal complexes and coordination polymers have been widely studied and discussed as photocatalysts, including their diverse network structures and controlled synthesis methods.
  • the purpose of the present invention is to overcome the deficiencies in the prior art, and to provide a method for synthesizing two-dimensional supramolecular compounds based on 1,3,5-tris(4-carbonylphenyloxy)benzene, based on the synthesis of two
  • the dimensional supramolecular compound has a good degradation efficiency for dyes in water and is a stable and recyclable photocatalyst.
  • the present invention adopts the following technical solutions to achieve:
  • a method for synthesizing a two-dimensional supramolecular compound based on 1,3,5-tris(4-carbonylphenyloxy)benzene comprising 1,3,5-tris(4-carbonylphenyloxy) ) benzene, phenol and Cu(NO 3 ) 2 ⁇ 3H 2 O into the aqueous solution of acetonitrile, stir and mix evenly, transfer to a reaction kettle with Teflon lining, heat to 110-130°C and keep it warm 60-84 hours, then cooling down to 20-30°C at a rate of 3-8°C/h to obtain the two-dimensional supramolecular compound.
  • the mass ratio of 1,3,5-tris(4-carbonylphenyloxy)benzene, phenol and Cu(NO 3 ) 2 ⁇ 3H 2 O is 1:(0.5-1) : (1.2-1.8).
  • the volume ratio of acetonitrile to water is 1:(0.8-1.5).
  • Another aspect of the present invention provides a two-dimensional supramolecular compound synthesized by the above method.
  • Another aspect of the present invention also provides an application of the above-mentioned two-dimensional supramolecular compound to the degradation of dyes in water.
  • the present invention provides a relatively simple method for synthesizing two-dimensional supramolecular compounds, and the two-dimensional supramolecular compounds synthesized by this method have better degradation efficiency for dyes in water; in addition, after Tests show that the two-dimensional supramolecular compound synthesized by the present invention is a stable and recyclable photocatalyst.
  • Fig. 1 shows the structure of compound 1 synthesized in Example 1 of the present invention
  • Fig. 1 (a) coordination geometry of Cu(II) center in compound 1; (b) three-dimensional supramolecular network perspective view 1 in compound 1 ; (c) hydrogen bond interactions between non-coordinating carboxyl groups of adjacent subunits and coordinated water molecules; (d) ⁇ - ⁇ interactions between phenol linkers on different chains;
  • Fig. 2 shows the thermogravimetric analysis curve diagram of compound 1 synthesized in Example 1 of the present invention
  • FIG. 3 shows the ultraviolet-visible diffuse reflectance spectrum (DRS) of compound 1 synthesized in Example 1 of the present invention
  • Figure 4 shows the photocatalytic properties of compound 1 synthesized in Example 1 of the present invention to different dyes;
  • Figure 4 (a)-(c) MO, the respective adsorption capacities of Rh B and MB solutions;
  • Figure 5 shows the PXRD patterns of compound 1 synthesized in Example 1 of the present invention under different conditions
  • Figure 6 shows the N adsorption-desorption isotherm of compound 1 synthesized in Example 1 of the present invention
  • Fig. 7 shows the research of the catalytic reaction mechanism of the compound 1 that is synthesized in the embodiment of the present invention 1;
  • Fig. 7 (a), (b) concentration change characteristic and catalytic change when scavenger exists; (c) ln (C 0 /c) and time(t) fitting data; (d) the effect on MB degradation after 4 cycles of running;
  • Fig. 8 shows the molecular skeleton diagram of the dye in water in scheme 1 of the present invention.
  • FIG. 9 shows possible conversion paths for analyzing MB by LC-MS in Scheme 2 of the present invention.
  • FT-IR spectra were obtained on a VERTEX 70FT-IR spectrophotometer in the region 4000-600 cm-1.
  • Luminescence measurements were performed at room temperature, and spectra were collected on a Perkin-Elmer LS50B fluorescence spectrometer.
  • UV-Vis spectra were measured on a spectrophotometer.
  • UV-Vis diffuse reflectance spectra of solid samples were collected on a Cary 500 spectrophotometer using BaSO4 as reflectance standard.
  • This example provides a method for synthesizing two-dimensional supramolecular compounds based on 1,3,5-tris(4-carbonylphenyloxy)benzene, specifically, 1,3,5-tris(4-carbonylphenyloxy)benzene oxy)benzene (0.05mmol, 0.024g), phenol (0.10mmol, 0.018g) and Cu(NO 3 ) 2 ⁇ 3H 2 O (0.15mmol, 0.036g) were added to 10mL of acetonitrile in water (acetonitrile and water The volume ratio is 1:1); Stir and mix for 30 minutes, then put it into a 25mL reactor with a polytetrafluoroethylene liner, heat it to 120°C and keep it warm for 72 hours, then at a speed of 5°C/h The temperature was lowered to 25°C to obtain the product.
  • the following table 1 shows the crystallographic data of compound 1: 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).
  • Each Cu(II) center in compound 1 coordinates to two O atoms in two adjacent HL 2- linkers, two N atoms from phen, and another oxygen atom from a coordinated water molecule, forming A tetrahedral geometry of ⁇ CuN 2 O 3 ⁇ .
  • the basal plane is fixed by two carboxyl oxygen atoms and the N atoms of two phenol molecules, and the apex position is occupied by a coordinated water molecule (O10).
  • the partially deprotonated HL 2- anion was bound to two metal ions on the carboxyl side in a ⁇ 1- ⁇ 1: ⁇ 0: ⁇ 0: ⁇ 0 coordination manner, while the COO - group in the middle was uncoordinated.
  • the dihedral angles between the two benzene rings and the middle benzene ring are 21.5° and 18.1°, respectively.
  • the monodentate coordination mode of HL 2- anion and phenol forms a [Cu 2 (HL) 2 (H 2 O) 2 (phen) 2 ] ring (as shown in Figure 1a); moreover, the phase of compound 1 Neighboring subunits are further connected by OHO interactions, generating parallel new layers along the bc plane (Fig. 1c). These layers are extended into a 3D supramolecular structure by the interaction of adjacent phenolic ligands (shown in Figures 1b and 1d).
  • thermogravimetric analysis TGA
  • the first step of weight loss in the temperature range of 25-197 °C is due to the release of a lattice water molecule and Two coordinated water molecules; the weight loss over 240 °C can be attributed to the collapse of the lattice structure and the decomposition of organic ligands.
  • the diffuse reflectance UV-vis data of compound 1 was collected to obtain the band gap (Eg). Since the point of intersection between the x-axis and the straight line is deduced from the straight line position of the absorption edge, the final calculation result, as shown in Fig. 3, Eg is estimated to be about 2.78eV.
  • Fig. 4a, b, c show respectively when compound 1 acts on MO, Rh B and MB, under different wavelength conditions, the absorbance of every 10 minutes illumination time, the absorbance is lower, Indicates that the more the dye is degraded.
  • the multiple curves correspond to the absorbance curves of different processing times, among which, for MO, as the processing time prolongs, the absorbance curve does not move down significantly, corresponding to 10.17 in Figure 4d % degradation rate; for MB, as the processing time prolongs, the absorbance curve is closer to the x-axis, that is, the absorbance decreases significantly, corresponding to the degradation rate of 46.87% in Figure 4d; for Rh B, as the processing time The prolongation of the absorbance curve decreased less than that of MB, corresponding to a degradation rate of 22.86% in Fig. 4d.
  • compound 1 showed photocatalytic properties for MO, Rh B and MB, and the degradation rates were 10.17%, 22.86% and 46.87% within 100 minutes (as shown in Figure 4d).
  • compound 1 exhibited selective photocatalytic ability towards MB. Moreover, the inventors found that there are significant changes in the catalytic oxidation reaction with different catalyst dosage, dye concentration, metal effect, light source and irradiation time.
  • the size of the MO dye is 1.54nm ⁇ 0.48nm ⁇ 0.28nm
  • the size of the MB dye is 1.38nm ⁇ 0.64nm ⁇ 0.21nm
  • the Rh B dye The size of is 1.56nm ⁇ 1.35nm ⁇ 0.42nm (Scheme 1), they are larger than the crystal pores, so they cannot enter the pores of compound 1.

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Abstract

La présente invention concerne un composé supramoléculaire bidimensionnel à base de 1,3,5-tri(4-carbonylphényloxy)benzène, un procédé de préparation associé et une application de ce dernier. Le procédé consiste à ajouter 1,3,5-tri(4-carbonylphényloxy)benzène, de phen et Cu(NO3)2·3H2O dans une solution aqueuse d'acétonitrile, à agiter et à mélanger jusqu'à uniformité, à transférer le mélange formé dans une cuve de réaction ayant un revêtement intérieur en polytétrafluoréthylène, à mettre en œuvre un chauffage à 110-130 °C, à maintenir la température pendant 60 à 84 heures et à mettre en œuvre un refroidissement à 20 à 30 °C à une vitesse de 3 à 8 °C/h pour obtenir le composé supramoléculaire bidimensionnel. Par comparaison avec l'état de la technique, la présente invention fournit un procédé relativement simple de synthèse du composé supramoléculaire bidimensionnel, et le composé supramoléculaire bidimensionnel synthétisé par le procédé présente un rendement de dégradation relativement bon sur les colorants dans de l'eau ; et en outre, des essais montrent que le composé supramoléculaire bidimensionnel synthétisé par la présente invention est un photocatalyseur stable et récupérable.
PCT/CN2021/142808 2021-07-30 2021-12-30 Composé supramoléculaire bidimensionnel synthétisé sur la base de 1,3,5-tri(4-carbonylphényloxy)benzène, procédé associé et son application WO2023005143A1 (fr)

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CN117585647B (zh) * 2023-11-24 2024-05-31 天津大学 分子共晶材料在光催化合成过氧化氢中的应用

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