Preparation method and application of imine bond connected fluorescent covalent organic framework

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 effects of increasing adsorption capacity, reducing cost and high availability

Active Publication Date: 2022-01-14
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 imine bond connected fluorescent covalent organic framework
  • Preparation method and application of imine bond connected fluorescent covalent organic framework
  • Preparation method and application of imine bond connected fluorescent covalent organic framework

Examples

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Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Preparation and Characterization of Fluorescent Covalent Organic Framework Linked by Imine Bonds

[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) was loaded into a 20-mL Pyrex tube, and then 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 Heated under the conditions for 72 hours, cooled to room temperature, collected the solid product after filtration, washed several times with tetrahydrofuran (THF), and dried to obtain a solid, which was vacuum-dried at 80°C for 12 hours to prepare a fluorescent covalent organic compound linked by an imine bond. Framework (TFPPy-BDOH).

[0032] fig...

Embodiment 2

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

[0036] Make TFPPy-BDOH into 0.025mg mL -1 The N,N-dimethylacetamide (DMAC) dispersion liquid, take 360 ​​μL of the 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 fluorescent signal of the mixed solution was tested under the excitation wavelength of 325nm by a meter.

[0037] Figure 4 It is the fluorescence response diagram 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 increases, the fluorescence signal of TFPPy-BDOH decreases gradually, 25μM UO 2 2+ The fluorescence quenching rate of TFPPy-BDOH can reach more than 90%. Fluorescent signal of TFPPy-BDOH and UO 2 2+ Concentration is linear in the range of 0-25μM for UO 2 2+ The detection limit of 8.8nM. In addition, the...

Embodiment 3

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

[0039] Add 5mg of TFPPy-BDOH to a solution containing 10-300ppm uranyl ions, shake in a shaker at a constant temperature for 12h, take 1mL of the suspension, filter it with a 0.22μm microporous membrane, collect the filtrate, and use inductively coupled plasma mass spectrometry Measure remaining UO in filtrate 2 2+ content, the final calculation is 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. is 114.7 mg / g (R. Liu, Z.-Q. Wang, Q.-Y. Liu, F. Luo, Y.-L. Wang.A zinc MOF with carboxylate oxygen-functionalized pore channels for uranium(VI)sorption, Eur.J.Inorg.Chem., 2019, 735-739), Sun et al. have an adsorption capacity of 408 mg / g based on amidoxime-based COF materials (Q.Sun ,B.Aguila,L.D.Earl,C.W.Abney,L.Wojtas,P.K.Thallapally,S.Ma.Covalen...

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Abstract

The invention discloses a preparation method and application of an imine bond connected fluorescent covalent organic framework, and belongs to the technical field of environmental protection. The preparation method comprises the steps: carrying out a Schiff base reaction on 1,3,6,8-tetra (4-formyl phenyl) pyrene and 4,4'-diamino-[1,1'-biphenyl]-3,3'-diol to synthesize the imine bond connected fluorescent covalent organic framework. According to the fluorescent covalent organic framework, imine bonds serve as connecting units, a large number of hydroxyl functional groups exist around the connecting units, and uranyl ions can be selectively combined. Meanwhile, based on the excellent fluorescence characteristic of the pyrenyl unit, a rapid and sensitive detection method for uranyl ions is established. In addition, the phenolic hydroxyl group in the fluorescent covalent organic framework connected with the imine bond can also reduce soluble U (VI) into insoluble U (IV), so that the adsorption capacity of uranyl ions is greatly improved. The method for preparing the imine bond connected fluorescent covalent organic framework is simple, stable in structure and environment-friendly, can be used for high-sensitivity detection and selective recovery of the uranyl ions, and has a good application prospect.

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 an imine bond-linked fluorescent covalent organic framework. Background technique [0002] Nuclear energy is a clean energy that does not produce greenhouse gases, 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.Materials for the recovery of uranium from seawater , Chem. Rev. 2017, 117, 13935-14013). Uranium is a key element in the nuclear industry, and 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 has strong mobility, high radioactivity and high toxicity. In contrast, U(IV) has low solubi...

Claims

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Application Information

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Patent Type & Authority Applications(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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