Heterogeneous photosensitizer based on metal organic framework material as carrier as well as preparation method and application of heterogeneous photosensitizer

A metal-organic framework and photosensitizer technology, applied in the preparation of organic compounds, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve the problems of strong pollution, cumbersome preparation methods, harsh conditions, etc. Achieve the effect of strong universality, simple and convenient operation, and strong stability

Inactive Publication Date: 2021-04-30
PINGDINGSHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to overcome the shortcomings of the above-mentioned organic photosensitizer@MOFs composite materials, which are cumbersome, harsh conditions, and strong pollution, the present invention provides a simple "one-pot cooking" one-step self-assembly method to synthesize iodo-BODIPY organic photosensitive The agent is loaded into the ZIF-8 metal organic framework material. Compared with the preparation method of the organic photosensitizer @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, and universal Strong, a variety of iodo-BODIPY with different structures can be loaded onto ZIF-8 by this method

Method used

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  • Heterogeneous photosensitizer based on metal organic framework material as carrier as well as preparation method and application of heterogeneous photosensitizer
  • Heterogeneous photosensitizer based on metal organic framework material as carrier as well as preparation method and application of heterogeneous photosensitizer
  • Heterogeneous photosensitizer based on metal organic framework material as carrier as well as preparation method and application of heterogeneous photosensitizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1. Preparation of iodo-BODIPY@PVP

[0022]Iodo-BODIPY-1, Iodo-BODIPY-2 and Iodo-BODIPY-3 were prepared according to reference (HarrisJ.,Optical limiting properties of 3,5-dithienylenevinylene BODIPY dyes at532nm.Chem.Eur.J.2017,23 , 14507-14514). Weigh 20.0mg iodo-BODIPY-1, iodo-BODIPY-2 and iodo-BODIPY-3 and dissolve them in 5.0mL tetrahydrofuran, weigh 250.0mg polyvinylpyrrolidone and dissolve them in 5.0mL chloroform, and dissolve the iodo-BODIPY solution Mix it with polyvinylpyrrolidone solution and stir at room temperature for 24 hours. At the end of the reaction, add n-hexane to precipitate iodo-BODIPY@PVP, filter it with suction, wash it with n-hexane, and then directly use it in the next reaction.

Embodiment 2

[0023] Example 2. Preparation of iodo-BODIPY@ZIF-8

[0024] Dissolve the iodo-BODIPY@PVP prepared above in 5.0 mL of distilled water. Weigh 0.5g Zn(NO 3 ).6H 2 O was dissolved in 1.0 mL distilled water. Weigh 1g of 2-methylimidazole and dissolve in 4mL of distilled water. Mix iodo-BODIPY@PVP aqueous 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 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 dry , to obtain the final target product iodo-BODIPY@ZIF-8.

Embodiment 3

[0025] Example 3. Application

[0026] Using thioanisole as the reaction substrate and iodo-BODIPY-1@ZIF-8 as the catalyst, the catalytic performance, stability and recyclability of the iodo-BODIPY@ZIF-8 prepared above were studied. The specific experimental process is as follows: Add 10.0 mg of iodo-BODIPY-1@ZIF-8 catalyst, sulfide anisole (0.5 mmol) and methanol solvent (2 mL) into a 10 mL glass vial equipped with a magnetic stirrer, and mix well by ultrasonic , Air bubbling for 10 minutes under dark conditions. Then, stir at room temperature and irradiate with a green LED light, take a small amount of the mixture every 2 hours 1 H NMR analysis, using the ratio of substrate and product 1 The conversion was calculated from the ratio of the integrated areas of the HNMR peaks.

[0027] After the catalysis is completed, the iodo-BODIPY-1@ZIF-8 catalyst is recovered by centrifugation, washing and drying with ethanol, and the same experimental operation as above is used to cata...

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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 an iodo-BODIPY-coated ZIF-8 composite material prepared by loading iodo-BODIPY which has strong absorption in a visible light region and can efficiently generate singlet oxygen (1O2) into a ZIF-8 metal organic framework material pore passage through a simple one-pot boiling self-assembly method. The prepared heterogeneous photosensitizer is used for catalytically oxidizing diphenyl sulfide, and then the catalyst can be recovered through simple centrifugation, washing and drying, and can be recycled for catalytic oxidation of diphenyl sulfide. The preparation method is simple, easy to operate, environmentally friendly, cheap, good in repeatability and short in consumed time; and the heterogeneous photosensitizer has strong absorption in a visible light region, can efficiently generate 1O2, can selectively oxidize thioether compounds into sulfoxide under the condition of stirring at room temperature, and has high conversion rate and good reusability.

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] As a safe, cheap and abundant sustainable energy source, visible light can provide enough energy to effectively promote chemical reactions. Visible light-driven photocatalysts have attracted more and more attention from researchers because of their efficient use of sunlight. In recent years, although the discovery of ruthenium, iridium, platinum and other common transition metal complexes such as copper, chromium and iron has greatly promoted the development of organic synthesis, such catalysts contain precious rare metals or toxic heavy metal ions, not only the price Expensive, and there are st...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22B01J31/02B01J35/10C07C315/02C07C317/14
CPCB01J31/0275B01J31/1691B01J31/1815B01J35/004B01J35/1004B01J2231/70C07C315/02C07C317/14
Inventor 周金风楚纯洁
Owner PINGDINGSHAN UNIVERSITY
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