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Sulfide functionalized covalent organic frame material and synthesis method thereof

A technology of covalent organic framework and synthesis method, applied in chemical instruments and methods, adsorption water/sewage treatment, water/sewage treatment, etc. The effect of high yield and good selective recognition

Active Publication Date: 2014-04-02
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, until now, functionalized hydrazone-linked COF materials have not been reported
In addition, other reported functionalized COF materials are difficult to control due to harsh synthesis reaction conditions, especially difficult to synthesize in large quantities, which limits the industrial application of functionalized COF materials.

Method used

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  • Sulfide functionalized covalent organic frame material and synthesis method thereof
  • Sulfide functionalized covalent organic frame material and synthesis method thereof
  • Sulfide functionalized covalent organic frame material and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add trimesaldehyde (32 mg, 0.20 mmol) and 2,5-bis(3-(ethylsulfide)propyl)-terephthalic hydrazide (130 mg, 0.30 mmol, compound 1) to 1, In the mixed solvent of 4-dioxane (1.0mL) and mesitylene (1.5mL), a white turbid solution was obtained, and 0.4mL of 6.0mol / L aqueous acetic acid solution was slowly added to the above mixed solution to obtain a white The turbid mixture, seal the tube, and then place it in an oven at 120°C for 3 days. After the reaction, the precipitate is washed with acetone (3×10mL), centrifuged, and then extracted by Soxhlet (with tetrahydrofuran, THF). After further purification and drying in a vacuum oven for 8 h, 122 mg of a thioether-functionalized covalent organic framework material (represented by COF-LZU8) was obtained with a yield of 80%.

[0024] The response is as follows:

[0025]

[0026] figure 1 Solid State NMR for COF-LZU8 13 C CP / MAS NMR spectrum.

[0027] figure 2 It is the X-ray powder diffraction pattern (PXRD) of COF-LZU8,...

Embodiment 2

[0031] Synthesis of compound 2,5-bis(3-(ethylthioether)propyl)-terephthalohydrazide【2,5-Bis(3-(ethylthio)propoxy)terephthalohydrazide】

[0032] Dissolve ethyl 2,5-dihydroxyterephthalate (2.0 g, 7.87 mmol), bromopropene (4 mL, 47.20 mmol), potassium carbonate (9.0 g), potassium iodide (160 mg) in 30 mL of dry acetone, and Placed in an oil bath and heated to reflux for reaction. After the reaction was monitored by TLC, the acetone was distilled off under reduced pressure and extracted with dichloromethane (3×40 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and separated by column chromatography (petroleum ether / ethyl acetate: 10 / 1, volume ratio) after vacuum distillation to obtain 2.47 g of 2,5-dipropyleneoxy Ethyl phthalate, yield: 95%. 1 H NMR (400MHz, CDCl 3 ):δ=7.38(s,2H),6.10-6.01(m,2H),5.51-5.45(m,2H),5.29-5.27(m,2H),4.60-4.58(m,4H),4.41-4.34 (m,4H),1.38(t,J=8.0Hz,6H). 13 C NMR (100MHz, CDCl 3 ):δ=165.6, 151....

Embodiment 3

[0035] Embodiment 3COF-LZU8 Selective recognition of mercury ions

[0036] The standard solution containing mercury ions was added dropwise to the solution containing COF-LZU8. It can be seen that the fluorescence intensity of COF-LZU8 will gradually weaken with the addition of mercury ions ( Figure 4 ). Under the same test conditions, the influence of other metal ions on the fluorescence intensity of COF-LZU8 solution is very small, far less than that of mercury ions (see Figure 5 ), indicating that COF-LZU8 has a good selective recognition of mercury ions. The same experiment was done with other existing COF materials, and no recognition effect on mercury ions was found.

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Abstract

The invention discloses a sulfide functionalized covalent organic frame material, The material has a structural unit shown in the specification, and is obtained by the following steps: adding 2,5-Bis(3-(ethylthio)propoxy)-terephthalohydrazide and benzenetricarboxaldehyde into a mixed solvent of 1,4-dioxane and mesitylene, adding an aqueous acetic acid solution into the above mixture and reacting at 120 DEG C for 1-3 days. The material has a mesoporous structure, has BET specific surface area of 470-480 m<2>?g<-1>, has good selective identification for mercury ions, and can be used for removal of the mercury ions.

Description

technical field [0001] The present invention is in the field of covalent organic frameworks (COFs). Specifically, it is a thioether functionalized covalent organic framework material and its synthesis method. Background technique [0002] In 2005, the Yaghi group reported a class of covalent organic frameworks (COFs) for the first time. Using the self-condensation of boric acid or the reversible reaction of boronate, they successfully designed and synthesized two covalent organic frameworks (COFs) containing boron. -1 and COF-5). Then they reported the design and synthesis of three-dimensional covalent organic framework materials. This kind of material is an organic porous material with crystalline structure connected by covalent bonds, and they have the advantages of definite structure, large specific surface area, and low relative density. Covalent organic framework materials have great potential application value in the fields of gas storage and separation, photoelectr...

Claims

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Application Information

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IPC IPC(8): C08G73/00C02F1/28C02F1/62
Inventor 王为丁三元
Owner LANZHOU UNIVERSITY
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