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Preparation method and application of a fluorescent covalent organic framework linked by imine bonds

A technology of covalent organic framework and imine bond, which is applied in the field of preparation of fluorescent covalent organic framework, can solve the problems of reducing porosity and crystallinity, and achieve the effect of improving adsorption capacity, good selectivity and efficient adsorption

Active Publication Date: 2022-07-12
NANCHANG UNIV
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Problems solved by technology

[0004] Aiming at the problems that the current amidoxime-based COF has a higher affinity for vanadium, and the complicated post-modification process will reduce porosity and crystallinity, the present invention provides a preparation of a fluorescent covalent organic framework linked by imine bonds Method and application to detection and adsorption of uranyl ions

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  • Preparation method and application of a fluorescent covalent organic framework linked by imine bonds
  • Preparation method and application of a fluorescent covalent organic framework linked by imine bonds
  • Preparation method and application of a fluorescent covalent organic framework linked by imine bonds

Examples

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Embodiment 1

[0030] Example 1: Preparation and characterization of imine-linked fluorescent covalent organic frameworks

[0031] 1,3,6,8-Tetrakis(4-formylphenyl)pyrene (TFPPy) (24.7 mg, 40 μmol) and 4,4'-diamino-[1,1'-biphenyl]-3,3 '-Diol (BDOH) (17.3 mg, 80 μmol) into a 20 mL Pyrex tube, followed by addition of 1,4-dioxane (800 μL), benzyl alcohol (800 μL), mesitylene (1334 μL) and acetic acid solution ( 200 μL, 6M); the suspension was sonicated for 10 min, then frozen in a 77K liquid nitrogen bath, and after degassing through three freeze pump-thaw cycles, the tube was evacuated and flame sealed; the tube was placed in an oven at 120 °C Heating for 72h under conditions, cooling to room temperature, collecting the solid product after filtration, washing with tetrahydrofuran (THF) for several times, vacuum drying to obtain a solid, vacuum drying at 80°C for 12h to prepare imine-bonded fluorescent covalent organic Framework (TFPPy-BDOH).

[0032] figure 1 Schematic diagram of the synthet...

Embodiment 2

[0035] Example 2: Detection of uranyl ions by TFPPy-BDOH

[0036] Make up TFPPy-BDOH to 0.025mg mL -1 of N,N-dimethylacetamide (DMAC) dispersion liquid, take 360 ​​μL of dispersion liquid, add 40 μL of uranyl ions of different concentrations, so that the final concentration of uranyl ions is 0-25 μM, after shaking evenly, use fluorescence spectrophotometry The fluorescence signal of the mixture was measured under the condition of excitation wavelength of 325nm.

[0037] Figure 4 Fluorescence response of TFPPy-BDOH to different concentrations of uranyl ions. Depend on Figure 4 It can be seen that with the uranyl ion (UO 2 2+ ) concentration, the fluorescence signal of TFPPy-BDOH gradually decreased, and 25 μM UO 2 2+ The fluorescence quenching rate of TFPPy-BDOH can reach more than 90%. Fluorescence signal of TFPPy-BDOH and UO 2 2+ Concentration is linear in the range 0-25 μM, with respect to UO 2 2+ The detection limit was 8.8 nM. In addition, TFPPy-BDOH has no ...

Embodiment 3

[0038] Example 3: Adsorption capacity of TFPPy-BDOH for uranium

[0039] Add 5 mg of TFPPy-BDOH to the solution containing 10-300 ppm uranyl ions, shake at constant temperature in a shaker for 12 h, take 1 mL of the suspension, filter it with a 0.22 μm microporous membrane, collect the filtrate, and use inductively coupled plasma mass spectrometry. Measure the remaining UO in the filtrate 2 2+ content, the final calculation of TFPPy-BDOH to UO 2 2+ The adsorption capacity of 982.6 mg / g is higher than that of most existing materials. For example, the adsorption capacity of the carboxyl-functionalized zinc MOF material developed by Liu et al. zinc MOF with carboxylate oxygen-functionalized pore channels for uranium(VI)sorption, Eur.J.Inorg.Chem., 2019, 735-739), Sun et al. based on amidoxime-based COF material adsorption capacity 408mg / g (Q.Sun ,B.Aguila,L.D.Earl,C.W.Abney,L.Wojtas,P.K.Thallapally,S.Ma.Covalent organic frameworks as adecorating platform for utilization and ...

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Abstract

The invention discloses a preparation method and application of a fluorescent covalent organic framework connected by imine bonds, and belongs to the technical field of environmental protection. Reaction of 1,3,6,8-tetrakis(4-formylphenyl)pyrene and 4,4'-diamino-[1,1'-biphenyl]-3,3'-diol via Schiff base Synthesis of imine-linked fluorescent covalent organic frameworks. The fluorescent covalent organic framework uses imine bonds as connecting units, surrounded by a large number of hydroxyl functional groups, which can selectively bind uranyl ions. Meanwhile, based on the excellent fluorescence properties of pyrene-based units, a rapid and sensitive detection method for uranyl ions was established. In addition, the phenolic hydroxyl groups in the imine-bonded fluorescent covalent organic framework can also reduce soluble U(VI) to insoluble U(IV), which greatly improves the adsorption capacity for uranyl ions. The method of the invention has the advantages of simple method, stable structure and environmental friendliness for preparing the imine bond-linked fluorescent covalent organic framework, which can be used for highly sensitive detection and selective recovery of uranyl ions, and has good application prospects.

Description

technical field [0001] The invention belongs to the technical field of environmental protection, and in particular relates to a preparation method and application of a fluorescent covalent organic framework connected by imine bonds. Background technique [0002] Nuclear energy is a clean energy that does not produce greenhouse gases and has extremely high energy density, and is expected to become one of the main clean energy sources in the future (C.W.Abney, R.T.Mayes, T.Saito, S.Dai. , Chem. Rev. 2017, 117, 13935-14013). Uranium is a key element in the nuclear industry. Extracting uranium from the environment is beneficial to the sustainable development of the energy industry. However, uranium is also a radioactive and chemically toxic global environmental pollutant. The main valence state of uranium in the environment is U(VI), which is highly mobile, highly radioactive and highly toxic. In contrast, U(IV) is less soluble and toxic. The chemical reduction of soluble U(...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/02B01J20/26B01J20/30C02F1/28G01N27/626C02F101/20
CPCC08G73/02B01J20/262C02F1/285G01N21/643G01N27/626C02F2101/20Y02P10/20
Inventor 邱建丁牛成鹏张程蓉梁汝萍
Owner NANCHANG UNIV
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