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A kind of fluorene vinyl derivative and its synthetic method

A synthesis method and derivative technology, applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of hydroxyl compounds, etc., can solve the problems of poor optoelectronic properties and poor energy level matching of devices, and achieve the advantages of easy regulation and avoidance of optoelectronic properties. Reduce and avoid the effect of poor solubility

Inactive Publication Date: 2019-04-23
SHENYANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The test found that the energy level matching between the fluorene group and the benzene ring in the polymer shown in the above structural formula is poor, and the photoelectric performance of the device is poor.

Method used

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  • A kind of fluorene vinyl derivative and its synthetic method
  • A kind of fluorene vinyl derivative and its synthetic method
  • A kind of fluorene vinyl derivative and its synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Synthesis of 2-iodo-9,9-dibutylfluorene

[0048] Add 1.46g of 2-iodofluorene, 2ml of n-bromobutane, 0.5ml of DMSO, 0.03g of tetrabutylammonium bromide, and 2ml of 50% NaOH solution in a 25ml round bottom flask. React at 80°C for 6 hours. After the reaction, add 10 milliliters of water and 10 milliliters of petroleum ether, vibrate and separate the liquids, take the upper petroleum ether phase, and extract the water phase with 10 milliliters of petroleum ether once more. Petroleum ether was used as the mobile phase and separated by a chromatographic column. After drying in a vacuum oven at 50°C, the product was a light green solid. Yield 80%. 1 H NMR (ppm) (400MHz CDCl 3 ):7.65-7.24(m,7H).1.95-1.90(m,4H).1.10-1.04(m,4H).0.68-0.54(m,10H).

Embodiment 2

[0049] Example 2: Synthesis of 2-iodo-9,9-dibutylfluoreneacetyl

[0050] Add 0.73 g of anhydrous aluminum trichloride to 20 ml of dichloromethane, stir, and cool in an ice bath for 10 minutes, then slowly drop in acetic anhydride to make the mixture transparent. After sufficient cooling, 1.01 g of 9,9-dibutylfluorene was added in batches and reacted for 12 hours. The mixture was poured into 50 ml of ice water, separated, the aqueous phase was washed twice with 50 ml of dichloromethane, the oil phase was combined, the solvent was spin-dried, and purified by column chromatography to obtain 0.95 g of a light yellow solid. Yield 85%. The eluent is petroleum ether:dichloromethane=5:1. 1 H NMR (ppm) (400MHz CDCl 3 ):7.96-7.94(d,2H).7.74-7.69(m.3H).7.51-7.49(d.1H).2.67(s.3H).2.04-1.92(m.4H).1.10-1.04 (m.4H).0.68-0.65(m.6H).0.57-0.51(m.4H).

Embodiment 3

[0051] Example 3: Synthesis of 2-(2-methyl-3-butyn-2-ol)-9,9-dibutylfluoreneacetyl

[0052] Add 2.23 g of 2-iodo-9,9-dibutylfluoreneacetyl, 2 ml of 2-methyl-3-butynyl-2-ol, 25 ml of tetrahydrofuran, and 5 ml of triethylamine into a 50 ml three-necked flask. After exhausting oxygen with argon, 0.12 g tetrakistriphenylphosphine palladium and 0.06 g cuprous iodide were added. Under the protection of argon, react at 45°C for 6 hours. After the reaction, the mixture was poured into a beaker, 3g of ammonium chloride, 20ml of water and 20ml of dichloromethane were added, the liquid was separated by shaking, and the organic phase was taken and dried with anhydrous magnesium sulfate. Petroleum ether: ethyl acetate 2:1 as mobile phase, column chromatography separation and purification. Yield 80%. 1 H NMR (ppm) (400MHz CDCl 3 ):7.97-7.95(m.2H).7.74-7.68(m.2H).7.44-7.43(d.2H).2.67(s.3H).2.07-1.93(m.4H).1.67(s.6H ).1.11-1.02(m.4H).0.67-0.63(m.6H).0.53-0.47(m.4H).

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Abstract

The invention discloses fluorene ethylene derivatives and a synthesis method thereof; acetyl is generated on fluorene groups by a Fourier reaction, and after reduction is performed, a double bond is obtained through a toluene distillation dehydration method. The fluorene groups are coupled by a Sonogashira method. Monomers of the fluorene ethylene derivatives are used for obtaining a large number of semiconductor polymers with different properties through homopolymerization, copolymerization and other methods, and have quite high scientific research value and application prospects.

Description

technical field [0001] This patent belongs to the field of polymer materials, and specifically relates to a class of fluorene vinyl derivatives and typical synthetic routes of such compounds. Background technique [0002] Conductive polymers are a class of polymer materials that are converted from insulators to conductors by chemically or electrochemically "doping" polymers with conjugated π-bonds. In 2000, American scientists A.G.McDiarmid and A.Heeger and Japanese scientist Hideki Shirakawa won the Nobel Prize in Chemistry for their pioneering work in this field. [0003] Conductive polymer is a new type of functional material with excellent performance, and its research progressed rapidly in the 1980s and 1990s, and it became the research center of materials science, prompting scientists from all over the world to devote themselves to the practical application of conductive polymers. Since the conductive polymer has a π-conjugated structure, it has a fast response (10 -...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/567C07C1/24C08F38/04
CPCC07C1/20C07C1/24C07C17/266C07C17/269C07C29/00C07C29/143C07C29/34C07C45/46C07C45/68C08F38/04C07C13/567C07C33/38C07C49/835C07C49/813C07C25/22
Inventor 胡小丹王宁刘勇何佳音
Owner SHENYANG UNIV
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