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Hyperbranched polyaromatic hydrocarbon containing pyridine rings and method for producing the same

A technology of pyridine ring and polyaromatic hydrocarbon is applied in the field of hyperbranched polymers to achieve the effects of good wave absorption performance, good electron transmission performance and high luminous efficiency

Inactive Publication Date: 2008-07-16
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of hyperbranched polyaromatic hydrocarbons containing pyridine rings by ring trimerization has not been reported in the literature so far.

Method used

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  • Hyperbranched polyaromatic hydrocarbon containing pyridine rings and method for producing the same
  • Hyperbranched polyaromatic hydrocarbon containing pyridine rings and method for producing the same
  • Hyperbranched polyaromatic hydrocarbon containing pyridine rings and method for producing the same

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: Biphenyls

[0038] Synthesis principle equation:

[0039]

[0040] (1) Synthesis of 1,4-diol base biphenyl (2):

[0041] 1,4-Dibromobiphenyl (5g, 16.02mmol), Pd(Ph 3 P) 2 Cl 2 (11.2mg, 0.016mmol), cuprous iodide (3mg, 0.016mmol), triphenylphosphine (10mg, 0.016mmol) were added to a 100mL (19#) single-necked round bottom flask, and under nitrogen protection, toluene (20mL ), triethylamine (20mL), 2-methyl-3-butyn-2-ol (2.4mL, 24.6mmol), the temperature was maintained between 90-100°C, and the reaction was carried out under nitrogen atmosphere for 36h. The product was filtered and washed with anhydrous ether. The solvent was distilled off under atmospheric pressure, and purified by column chromatography (developer: petroleum ether / ethyl acetate=3 / 1) to obtain 4.0 g of yellow viscous liquid with a yield of 80%.

[0042] (2) Synthesis of 1,4-diynylbiphenyl (3):

[0043] Add 1,4-diol-based biphenyl (2) (3g, 12.2mmol), sodium hydroxide (0.48g, 12.2mmol...

Embodiment 1-1

[0044] Example 1-1: Synthesis of biphenyl conjugated polymer P1

[0045] Put 1,4-(diynyl)biphenyldiyne (50mg, 0.25mmol) into a thoroughly dried test tube, dissolve valeronitrile (26 μL, 0.25mmol) in (0.2mL) toluene, and add it to the test tube; Add dissolved CpCo(CO) 2 (4.5mg, 0.025mmol) of toluene (1.0mL); the mixture was stirred under the irradiation of a 300w Hg lamp, the lamp was 25cm away from the center of the test tube, and the irradiation was continued at 65°C for 10h; a small amount of methanol was added to stop the polymerization reaction. Stir well to precipitate the polymer, pour the polymer solution into 100 mL of methanol through a cotton filter, collect a light yellow powder, and dry it to constant weight under vacuum. Yield: 36 mg (77%) 13 C NMR analysis of its structure showed that it was the target product.

Embodiment 1-2

[0046] Example 1-2: Synthesis of biphenyl conjugated polymer P2

[0047] 1,4-(diynyl)biphenyldiyne (50mg, 0.25mmol) was put into a thoroughly dried test tube, valeronitrile (12 μL, 1.24mmol) was dissolved in (0.2mL) toluene, and added to the test tube; Add dissolved CpCo(CO) 2 (4.5mg, 0.025mmol) of toluene (1.0mL); the mixture was stirred under the irradiation of a 300w Hg lamp, the lamp was 25cm away from the center of the test tube, and the irradiation was continued at 65°C for 10h; a small amount of methanol was added to stop the polymerization reaction. Stir well to precipitate the polymer, pour the polymer solution into 100 mL of methanol through a cotton filter, collect a light yellow powder, and dry it to constant weight under vacuum. Yield: 36 mg (75%) 13 C NMR analysis of its structure showed that it was the target product.

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Abstract

The invention discloses a ring type hyperbranched polyarylenes containing pyridine and a preparation method thereof. The synthesizing of the polymer of the method is that newly distilled toluene solvent is added with a mixture containing end double alkyne monomers and nitrile monomers and then added with transition metal catalyzer CpCo(CO)2; each gram of a monomer which contains the end double alkyne is added with 10-100ml toluene solvent, 3-8ml nitrile monomer and 0.06-0.1g transition metal catalyst, and then the mixture is irradiated under 300w ultraviolet for reacting for 2 to 20h to obtain the hyperbranched polyarylenes containing pyridine ring. The alkyne-nitrile ring trimerization is a new method for constructing hyperbranched polyarylenes containing pyridine ring. By adopting one step synthesizing method, the polymerization of directly aroma cyclizing of alkyne and nitrile is simple. The hyperbranched polyarylenes shows high brightness and high irradiance efficiency, which is characterized by high temperature resistance, corrosion resistance, light specific weight and high strength, etc. and is hopeful to be taken as a high capacity material in spaceflight.

Description

technical field [0001] The invention relates to the field of hyperbranched polymers, in particular to a pyridine ring-containing hyperbranched polyaromatic hydrocarbon and a preparation method thereof. Background technique [0002] Compared with dendrimers, hyperbranched polymers are relatively simple to synthesize due to their unique molecular shape, molecular size, branching pattern and surface functionality endowing them with chemical and physical properties different from linear polymers. , can be completed in one step and is more practical, so it has been applied in a wide range of fields. [0003] How to prepare hyperbranched polymers by using monomers with simple synthesis methods and existing organic compound synthesis methods is of great significance both in terms of basic theoretical research and practical application. The reaction of alkyne ring trimerization to benzene derivatives was first discovered by Berthelot. It is an ancient reaction of this century, and...

Claims

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Application Information

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IPC IPC(8): C08G61/12
CPCC08G83/005
Inventor 彭汉张娜
Owner SOUTH CHINA UNIV OF TECH
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