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Macrocyclic compound as well as preparation method and application thereof

A macrocyclic compound and compound technology, applied in electrodes, electrolysis processes, electrolysis components, etc., can solve the problems of catalyst electrochemical activity decline, content loss, uneven distribution of the microenvironment of the active site, etc., and achieve excellent hydrogen peroxide production performance. , the effect of improving selectivity, high concentration production potential

Active Publication Date: 2020-05-29
SHANGHAI ADVANCED RES INST CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of the reported carbon-based materials, as electrocatalysts, need to be pyrolyzed at high temperature (400-1000 °C), which will lead to the loss of active heteroatom content and uneven distribution of active site microenvironment, resulting in Decrease in the electrochemical activity of the catalyst

Method used

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  • Macrocyclic compound as well as preparation method and application thereof
  • Macrocyclic compound as well as preparation method and application thereof
  • Macrocyclic compound as well as preparation method and application thereof

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preparation example Construction

[0051] The first aspect of the present invention provides a method for preparing a macrocyclic compound, comprising: preparing a first macrocyclic compound by reacting a monomer with a benzyl bromide compound having a symmetrical structure;

[0052] Wherein, the monomer has the structure shown in formula I:

[0053]

[0054] The structure shown in Formula I is 2,5-bis(4-pyridine)thiazo[5,4-d]thiazole, denoted as Py 2 TTz.

[0055] In the preparation method provided by the present invention, usually, the reaction needs to be carried out in the presence of a solvent, and the solvent is selected from one or more of chloroform, dioxane, acetonitrile and N-methylpyrrolidone combination of species. In a specific embodiment, the monomer is dissolved in a solvent, and then mixed with a benzyl bromide compound having a symmetrical structure, reacted at a reaction temperature of 30-120°C, filtered after the reaction, and the precipitate is collected, and then soaked with an organic...

Embodiment 1

[0090] Step (1): Synthesis of 2,5-bis(4-pyridine)thiazo[5,4-d]thiazole monomer

[0091] In a reaction flask, 4-pyridinecarbaldehyde (0.58ml, 6.15mmol) and dithiooxamide (0.25g, 2.08mmol) were added and dissolved in N,N-dimethylformamide (10ml), nitrogen Reflux at 150°C for 6 hours under atmosphere, cool, filter, and wash the precipitate with water to obtain a light yellow powder (0.30 g, 49%), which is 2,5-bis(4-pyridine)thiazo[5,4-d]thiazole, denoted as Py 2 TTz.

[0092] Such as figure 1 Shown, the proton nuclear magnetic resonance spectrum of product is characterized as follows: 1 H-NMR (500MHz, CDCl3 ): δ8.71(d, J=6.0Hz, 4H), 7.81(d, J=6.4Hz, 4H);

[0093] Such as figure 2 As shown, the high-resolution mass spectrometry characterization data of the product are as follows: HRMS (ESI) m / z: 297.0262.

[0094] Step (2) Preparation of the first macrocyclic compound

[0095] In a 250ml reaction vial, Py 2 TTz (0.24g, 0.81mmol) and chloroform (17mL) were added, 1,3,5-tri...

Embodiment 2

[0099] Step (1): Synthesis of 2,5-bis(4-pyridine)thiazo[5,4-d]thiazole monomer

[0100] In a reaction flask, 4-pyridinecarbaldehyde (0.58ml, 6.15mmol) and dithiooxamide (0.25g, 2.08mmol) were added and dissolved in N,N-dimethylformamide (10ml), nitrogen Reflux at 150°C for 6 hours under atmosphere, cool, filter, and wash the precipitate with water to obtain a light yellow powder (0.30 g, 49%), which is 2,5-bis(4-pyridine)thiazo[5,4-d]thiazole, denoted as Py 2 TTz.

[0101] Step (2) Preparation of the first macrocyclic compound

[0102] In a 250ml reaction vial, Py 2 TTz (0.24g, 0.81mmol) and chloroform (17mL) were added, 1,3,5-tris(bromomethyl)benzene (0.19g, 0.54mmol) was dissolved in chloroform (7ml) and added dropwise The above solution was protected by nitrogen, stirred at 30°C for 72 hours, filtered, and the precipitate was collected. Rinse with dichloromethane, repeat three times, and dry in a vacuum oven at 60° C. for 12 hours to obtain a yellow powder (0.35 g, yie...

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Abstract

The invention relates to the field of organic chemical synthesis, and in particular, relates to a macrocyclic compound as well as a preparation method and application thereof. The preparation method of the macrocyclic compound comprises the steps: carrying out a reaction on a monomer with a benzyl bromide compound with a symmetrical structure to prepare a first macrocyclic compound, wherein the monomer has a structure represented by a formula I. The material disclosed by the invention is synthesized at normal temperature, reaction conditions are mild, and amplification synthesis can be easilyrealized; the material is not subjected to high-temperature pyrolysis and is free of metal doping, and the material is directly used for oxygen cathode reduction of a fuel cell and has excellent hydrogen peroxide generation performance. The material is an ionic carbon material, so that the selectivity of hydrogen peroxide is improved. The material provided by the invention can be made into a membrane electrode with a sandwich structure, has relatively large current and good stability, and has high-concentration hydrogen peroxide production potential.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a macrocyclic compound, a preparation method and an application thereof. Background technique [0002] Hydrogen peroxide, chemical formula H 2 o 2 , its aqueous solution is commonly known as hydrogen peroxide, is a strong oxidant, the biggest use is the bleaching of paper and cotton fabrics. It can also be used in chemical synthesis, water treatment, metal polishing, pharmaceuticals, disinfection, sterilization, food processing and rocket combustion aids, etc. (Inorganic Salt Industry, 2013, 45(9): 1), and hydrogen peroxide is also a Potential energy carrier, an environmentally friendly oxidant. Wide application makes hydrogen peroxide one of the most important hundred substances in the world today (J.Chem.Edu., 2007,86(5):1182-1182). However, the current commercially available hydrogen peroxide content in my country is up to 30%. Existing technologies limit our prod...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/06C25B1/30C25B11/06
CPCC08G73/0627C25B1/30C25B11/075
Inventor 文珂李文茜邹志青陈涛王焯郭运哲杨杰强慧肖光俊高飞
Owner SHANGHAI ADVANCED RES INST CHINESE ACADEMY OF SCI
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