Metalloporphyrin@metal organic framework material heterogeneous photosensitizer as well as preparation method and application thereof

A metal-organic framework and metalloporphyrin technology, applied in the preparation of organic compounds, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve problems such as strong pollution, harsh conditions, and cumbersome preparation methods , achieving the effects of good repeatability, strong stability, and simple and easy-to-operate preparation method

Inactive Publication Date: 2021-05-28
PINGDINGSHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the disadvantages of cumbersome preparation methods, harsh conditions, and strong pollution of the above-mentioned porphyrin@MOFs composite materials, the present invention provides a simple "one-pot cooking" one-step self-assembly method to load metalloporphyrin organic photosensitizers In the ZIF-8 metal organic framework material, compared with the preparation method of porphyrin@MOFs heterogeneous photosensitizer reported so far, the preparation process provided by the present invention is not only simple and convenient to operate, environmentally friendly, fast, but also has strong universality. A variety of porphyrins with different structures can be loaded onto ZIF-8 by this method

Method used

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  • Metalloporphyrin@metal organic framework material heterogeneous photosensitizer as well as preparation method and application thereof
  • Metalloporphyrin@metal organic framework material heterogeneous photosensitizer as well as preparation method and application thereof
  • Metalloporphyrin@metal organic framework material heterogeneous photosensitizer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1. Preparation of zinc porphyrin@ZIF-8

[0036] Zinc porphyrin was prepared according to reference (D.W.Feng, Z.Y.Gu, J.R.Li, et al. Angew. Chem. Int. Ed., 2012, 51, 10307). Then, weigh 20.0 mg of zinc porphyrin and dissolve in 0.5 mL of N,N-dimethylformamide to prepare A solution. Weigh 0.3g Zn(NO 3 )·6H 2 O was dissolved in 1.5 mL distilled water. Weigh 2 g of 2-methylimidazole and dissolve in 4 mL of distilled water. Mix A solution and 2-methylimidazole solution well, then slowly add Zn(NO 3 )·6H 2 O solution, there will be precipitation soon, stir at room temperature for 10-20 minutes to stop the reaction, centrifuge, wash with distilled water, nitrogen nitrogen-dimethylformamide and ethanol several times in sequence until the supernatant becomes colorless, and then Vacuum drying to obtain the final target product zinc porphyrin @ZIF-8, the color is dark green.

Embodiment 2

[0037] Example 2. Preparation of manganese porphyrin@ZIF-8

[0038] Manganese porphyrins were prepared according to reference (D.W.Feng, Z.Y.Gu, J.R.Li, et al. Angew. Chem. Int. Ed., 2012, 51, 10307). Then, weigh 20.0 mg of manganese porphyrin and dissolve in 0.5 mL of N,N-dimethylformamide to prepare A solution. Weigh 0.3g Zn(NO 3 )·6H 2 O was dissolved in 1.5 mL distilled water. Weigh 2 g of 2-methylimidazole and dissolve in 4 mL of distilled water. Mix A solution and 2-methylimidazole solution well, then slowly add Zn(NO 3 )·6H 2 O solution, there will be precipitation soon, stir at room temperature for 10-20 minutes to stop the reaction, centrifuge, wash with distilled water, nitrogen nitrogen-dimethylformamide and ethanol several times in sequence until the supernatant becomes colorless, and then Vacuum drying to obtain the final target product manganese porphyrin @ZIF-8, the product color is light green.

Embodiment 4

[0042] Example 4. Application

[0043] The crystal structures of ZIF-8, zinc porphyrin @ZIF-8 and manganese porphyrin @ZIF-8 were studied by PXRD, and the results are attached image 3 shown. From attached image 3 It can be seen that the PXRD spectra of ZIF-8, zinc porphyrin@ZIF-8 and manganese porphyrin@ZIF-8 prepared by the present invention are completely consistent with the theoretically simulated ZIF-8, which shows that we have successfully prepared zinc porphyrin Phyrin@ZIF-8 and manganese porphyrin @ZIF-8, and the loading of zinc porphyrin and manganese porphyrin did not destroy the crystal structure integrity of ZIF-8.

[0044] The microscopic morphology and structure of zinc porphyrin @ZIF-8 and manganese porphyrin @ZIF-8 were characterized by scanning electron microscopy (SEM). The results are shown in the attached Figure 4 with 5 shown. It can be seen from the figure that both zinc porphyrin @ZIF-8 and manganese porphyrin @ZIF-8 exhibit a uniform spherical-li...

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Abstract

The invention discloses a heterogeneous photosensitizer based on a metal organic framework material as a carrier as well as a preparation method and application of the heterogeneous photosensitizer, and belongs to the technical field of preparation of environment-friendly functional composite materials. The heterogeneous photosensitizer disclosed by the invention is a metalloporphyrin@ZIF-8 composite material, wherein a metalloporphyrin compound which has strong absorption in a visible light region and can efficiently generate singlet oxygen (1O2) is loaded into a ZIF-8 metal organic framework material pore channel through a simple "one-pot" self-assembly method. Finally, the prepared heterogeneous photosensitizer is used for catalytic oxidation of thioanisole, then the catalyst can be recycled through simple centrifugation, washing and drying, and the heterogeneous photosensitizer is circularly used for catalytic oxidation of thioanisole and degradation of bisphenol A. The preparation method is simple, easy to operate, environmentally friendly, low in cost, good in repeatability and short in consumed time; the heterogeneous photosensitizer has strong absorption in a visible region, and 1O2 can be efficiently generated, so that thioether compounds can be selectively oxidized into sulfoxide under the condition of stirring at room temperature, the conversion rate is high, and the reusability is good.

Description

technical field [0001] The invention relates to the technical field of preparation of environment-friendly functional composite materials, and more specifically relates to a heterogeneous photosensitizer capable of efficiently catalyzing and oxidizing thioether compounds under visible light irradiation, as well as its preparation method and application. Background technique [0002] In recent years, metal-free pure organic photosensitizers, such as fluoroboron-dipyrrole (BODIPY), porphyrin, eosin, methylene blue, bengal red, etc., have been widely used as photocatalysts to catalyze various organic syntheses. The method requires only oxygen, a light source of the appropriate wavelength, and a triplet photosensitizer capable of absorbing light energy and transferring it to surrounding oxygen molecules. Its main process is as follows: when the photosensitizer is illuminated, the electrons absorb energy and transition from the ground state to the singlet excited state, and then ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22B01J31/18B01J35/08B01J35/10C07C46/08C07C50/32C07C315/02C07C317/14C07C317/22
CPCB01J31/1691B01J31/183B01J35/004B01J35/08B01J35/1076B01J2231/70B01J2231/763B01J2531/0213B01J2531/025B01J2531/26B01J2531/72C07C46/08C07C315/02C07C2602/10C07C50/32C07C317/14C07C317/22Y02P20/584
Inventor 周金风楚纯洁
Owner PINGDINGSHAN UNIVERSITY
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