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Organic monomer 1, 3, 6, 8-tetrapyridylpyrene and synthetic method thereof

A synthetic method, the technology of pyridine pyrene, applied in the direction of organic chemistry, etc., can solve the problems of low product solubility, difficulty in product separation and structure analysis, and many by-products, and achieve simple synthesis method, good light absorption capacity, and easy separation and the effect of representation

Pending Publication Date: 2021-04-13
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to solve the problem that there are many by-products in the existing synthesis process, the solubility of the product is low, and the difficulty of product separation and structure analysis is relatively large, and it provides a synthesis of organic monomer 1,3,6,8-tetrapyridine pyrene Methods and Characterization

Method used

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  • Organic monomer 1, 3, 6, 8-tetrapyridylpyrene and synthetic method thereof
  • Organic monomer 1, 3, 6, 8-tetrapyridylpyrene and synthetic method thereof
  • Organic monomer 1, 3, 6, 8-tetrapyridylpyrene and synthetic method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0021]Synthesis of 1,3,6,8-tetrapyridine: 30 mL of dioxane and 10 ml of water in three bottles, and then deprive with argon bubbles, 4-pyridine boric acid, 1, 3,6,8-tetraromomatoids and potassium carbonate are added to the mixed solvent in 6 mmol: 1 mmol: 4 mmol of material, and the catalyst thloride and four (triphenylphosphine) palladium are 0.07: 0.15 equivalent ratio. In the above suspension, the mixture was stirred at 90 ° C and stirred under an argon atmosphere, and the reaction was 4 days. The resulting yellow powder crude product was washed with a large amount of methanol solution and filtered, dried at 100 ° C for 6 hours.

[0022]The dry yellow powder and N, N-dimethylformamide were mixed in a hydrothermal reaction kettle in a hydrothermal reaction kettle, and the temperature was 100 ° C, the temperature was 15 hours, fell to room temperature. Filter, the resulting large amount of yellow crystal is the product 1,3,6,8-tetrapyridine 芘 (figure 1 ).

[0023]The synthetic routes of ...

Embodiment 2

[0026]Synthesis of 1,3,6,8-tetrapyridine: 30 mL of dioxane and 10 ml of water in three bottles, and then deprive with argon bubbles, 4-pyridine boric acid, 1, 3,6,8-tetraromomatoids and potassium carbonate were added to the mixed solvent in 5 mmol: 1 mmol: 4 mmol, and the catalyst tetra (triphenylphosphine) palladium was added to the above-mentioned suspension in an equivalent of 0.18. The mixture was refluxed under 93 ° C under the argon atmosphere, and the reaction was reacted for 3.5 days. The resulting yellow powder crude product was washed with a large amount of methanol solution and filtered, dried at 100 ° C for 6 hours.

[0027]The dry yellow powder crude product and N, N-dimethylformamide were mixed in a hydrothermal reaction kettle in a hydrothermal reaction kettle, and the temperature was 90 ° C, the heating reaction time was 12 hours, down to room temperature. Filtration, a large amount of yellow crystals, i.e., product 1,3,6,8-tetrapyridine.

Embodiment 3

[0029]Synthesis of 1,3,6,8-tetrapyridine: 30 mL of dioxane and 10 ml of water in three bottles, and then deprive with argon bubbles, 4-pyridine boric acid, 1, 3,6,8-tetraromomatoids and potassium carbonate were added to the mixed solvent in 4 mmol: 1 mmol: 4 mmol of material, and the catalyst tetra (triphenylphosphine) palladium was added to the above-mentioned suspension in an equivalent of 0.15. The mixture was stirred at 90 ° C under the argon atmosphere, and the reaction was 4 days. The resulting yellow powder crude product was washed with a large amount of methanol solution and filtered, dried at 100 ° C for 6 hours.

[0030]The rough product and N, N-dimethylformamide were mixed in a hydrothermal reaction kettage, and the temperature was 100 ° C, the heating reaction time was 24 hours, and the heated reaction time was filtered after 5 mg. The resulting large amount of yellow crystals, i.e., product 1,3,6,8-tetrapyridine.

[0031]Structural assay and characterization of three, 3, 6, ...

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Abstract

The invention discloses an organic monomer 1, 3, 6, 8-tetrapyridylpyrene and a synthetic method thereof. The molecular formula of the organic monomer is C36N4H22, and the organic monomer is a fused ring compound which is formed by respectively connecting four pyridines to positions 1, 3, 6 and 8 by taking a pyrene ring as a center. The method comprises the following steps: in an argon atmosphere, adding 4-pyridylboronic acid, 1, 3, 6, 8-tetrabromo pyrene and potassium carbonate into a mixed solvent of dioxane and water, adding palladium chloride and tetrakis (triphenylphosphine) palladium to catalyze the system to catalyze the reaction system, and carrying out solvothermal recrystallization on the crude product to obtain the crystalline product 1, 3, 6, 8-tetrapyridylpyrene. The organic monomer obtained in the invention has high crystallinity, so that the accurate structure of the compound is characterized by an X-monocrystalline diffraction instrument, the original powder diffraction peak is simulated, the synthesis method is simple, the product is easy to separate and characterize, the light absorption range can reach the visible light region, the method has potential application value in the aspects of synthesis of functional materials and photoelectrocatalysis.

Description

Technical field[0001]The present invention belongs to the field of organic synthesis, and more particularly to the synthesis method and characterization of SUZUKi coupling reaction organic monomers, 1,3,6,8-tetrapyridine.Background technique[0002]The anthracene is a four-ring-horn-raw aromatic hydrocarbon compound that has been proven to have excellent optical properties, and various types of derivatives based on the anthracene have also aroused extensive attention in the field of optics. application. So far, various natural products, pesticides, and fine chemicals have been synthesized by the classic Suzuki coupling, which has been synthesized, and the reaction is to cross the aryl boric acid and the halogenated aromatic or olefin under the catalysis of palladium. The combined compound is generated. However, based on the SUZUKi coupling reaction for the synthesis and study of 1,3,6,8-tetrapyridine, the relevant reaction methods currently involved can only isolate the paratimental p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/127C07D213/06
CPCC07D213/127C07D213/06
Inventor 赵斌杨国利
Owner NANKAI UNIV
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