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Preparation method of 4CzIPN type organic polymer and application of 4CzIPN type organic polymer in photocatalytic synthesis

A polymer and photocatalyst technology, applied in the field of material chemistry, can solve the problems of poor structural stability, easy photobleaching, high price, etc., achieve mild conditions, high catalytic efficiency, and overcome the effect of high price

Active Publication Date: 2022-03-22
XINYANG AGRI & FORESTRY UNIV
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Problems solved by technology

Although transition metal complexes have excellent optical properties, their inherent defects such as heavy metal residues, potential toxicity, and high price greatly limit their application in the field of medicine and chemical industry. Although organic dyes are cheap, they have poor structural stability and are easy to catalyze reactions. photobleaching

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  • Preparation method of 4CzIPN type organic polymer and application of 4CzIPN type organic polymer in photocatalytic synthesis
  • Preparation method of 4CzIPN type organic polymer and application of 4CzIPN type organic polymer in photocatalytic synthesis
  • Preparation method of 4CzIPN type organic polymer and application of 4CzIPN type organic polymer in photocatalytic synthesis

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Embodiment Construction

[0019] The present invention will be further described in detail below through the specific examples, the following examples are only descriptive, not restrictive, and cannot limit the protection scope of the present invention with this.

[0020] A preparation method of 4CzIPN polymer CPP3, the steps are as follows:

[0021] In a nitrogen atmosphere, 9.5 g of 3,5-dibromocarbazole was added to 60 ml of dry tetrahydrofuran, and after it was completely dissolved, 1.0 g of sodium hydride was slowly added. After stirring for 30 minutes, 130 mg of 2,4,5,6-tetrafluoroisophthalonitrile was added to the reaction system, and stirring was continued at room temperature for 12 hours. Subsequently, 2 ml of water was added to quench the reaction, and after the solvent was spin-dried, the residue was recrystallized from n-hexane / dichloromethane to obtain 3,6-bromo-4CzIPN as a yellow solid. Add 564 mg of 3,6-bromo-4CzIPN, 12 mg of bistriphenylphosphinepalladium dichloride, 6 mg of ketone iodi...

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Abstract

The invention relates to a preparation method of a 4CzIPN type organic polymer and an application of the 4CzIPN type organic polymer in photocatalytic synthesis, and provides a preparation method of the 4CzIPN type organic polymer based on a 2, 4, 5, 6-tetra (9H-carbazole-9-yl) isophthalonitrile (4CzIPN) fluorescent molecule, which comprises the following steps: taking 2, 4, 5, 6-tetrafluoroisophthalonitrile and 3, 6-dibromo-9H-carbazole or 3, 6-dibromo-9H-carbazole as initial raw materials, and reacting at the temperature of 60-80 DEG C to obtain the 4CzIPN type organic polymer based on the 2, 4, 5, 6-tetra (9H-carbazole-9-yl) isophthalonitrile (4CzIPN) fluorescent molecule. The preparation method comprises the following steps: carrying out a nucleophilic substitution reaction to generate a brominated 4CzIPN monomer in one step, then carrying out a palladium-catalyzed Sonogashira-Hagihara coupling reaction to enable the brominated 4CzIPN monomer to respectively react with 1, 4-phenylenediyne, 1, 3, 5-benzene triyne or 1, 2, 4, 5-benzene tetrayne to sequentially construct six polymers with different skeletons, and taking the synthesized polymers as a heterogeneous photocatalyst to catalyze visible light induced C (sp3)-H bond functionalization reaction, so as to obtain the polymer with the high molecular weight. The method has the advantages of mild conditions, wide substrate application range, greenness, sustainability and the like, and proven that the method has a huge application prospect in organic photochemical reactions.

Description

technical field [0001] The invention belongs to the field of material chemistry and relates to organic synthesis technology, in particular to a preparation method of 4CzIPN type organic polymer and its application in photocatalytic synthesis. Background technique [0002] Visible light-induced synthesis reaction is one of the greenest synthesis methods at present. Unfortunately, most organic compounds do not absorb in the visible light region, and cannot directly use visible light to realize the conversion of light energy into chemical energy. Additional photocatalysts can act as absorbers of visible light. The medium that transitions from the ground state to the excited state promotes subsequent reactions. According to the dispersion state in the reaction system, photocatalysts can be divided into homogeneous and heterogeneous, and homogeneous photocatalysts can be further divided into: transition metal complexes and organic dyes. Although transition metal complexes have e...

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Application Information

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IPC IPC(8): C08G61/12B01J31/06B01J35/00C07F9/62
CPCC08G61/124B01J31/06C07F9/62B01J2231/46C08G2261/415C08G2261/12C08G2261/3241C08G2261/312B01J35/39
Inventor 商天奕刘琰董翠陈重罗伟
Owner XINYANG AGRI & FORESTRY UNIV
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