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Improved methods and related compositions for the synthesis of conjugated polymers by oxidative polymerization

A technology of conjugated polymers and compositions, applied in ultrasonic/acoustic/infrasonic diagnosis, diagnostics, surgical system user interface, etc., can solve the problem of difficult to produce a large amount of processable pure substances, increase costs, development, manufacturing and commercial Complicated process and other issues

Active Publication Date: 2017-10-31
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although these polymerization methods can be used for the synthesis of conjugated polymers, they still have many limitations, including (a) difficulty in producing large quantities of processable, pure species; (b) polymerization of many polymers with sensitive / reactive functional groups problems with monomers; and (c) multiple intermediate steps (synthesis and / or purification) in the synthetic route, which increases the cost of the final product and complicates the development, manufacturing and commercialization process

Method used

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  • Improved methods and related compositions for the synthesis of conjugated polymers by oxidative polymerization
  • Improved methods and related compositions for the synthesis of conjugated polymers by oxidative polymerization
  • Improved methods and related compositions for the synthesis of conjugated polymers by oxidative polymerization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0185] Example 1. Synthesis of poly{3-[2-(2-methoxyethoxy)ethoxy]thiophene}[PMEET]

[0186]

[0187] A dry 100-mL three-neck flask equipped with an addition funnel was filled with N 2 Rinse and charge 3-[2-(2-methoxyethoxy)ethoxy]thiophene (0.20 g, 1.0 mmol), boron trifluoride etherate (BF 3 ·O(Et) 2 ) (0.5mL, 4.0mmol) and anhydrous CHCl 3 (20 mL, 0.05M). The reaction flask was cooled to 0°C, and 0.05M 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in CHCl was added dropwise via a deoxygenated syringe 3 (80 mL, 4.0 mmol) suspension. Formation of a black precipitate was observed within 1 hour of addition of DDQ. After the addition was complete, stirring was continued for 24 hours, at which point the reaction mixture was poured into 200 mL of hexane, forming fine black particles. The combined organic solids were washed twice with hexane and dried. The crude product was redissolved in a minimum amount of methanol and precipitated in water. The polymer was collected by filt...

Embodiment 2

[0190] Example 2. Solvent-free synthesis of poly{3-[2-(2-methoxyethoxy)ethoxy]thiophene}[PMEET]

[0191]

[0192] A dry 250-mL three-neck flask equipped with a mechanical stirrer and a thermocouple was filled with N 2 Rinse and charge 3-[2-(2-methoxyethoxy)ethoxy]thiophene (20 g, 0.099 mol) and boron trifluoride etherate (BF 3 ·O(Et) 2 ) (50 mL, 0.41 mol). 2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) (27.86 g, 0.123 mol) was added in five portions. The reaction was exothermic and DDQ was added in such a way that the reaction temperature was allowed to stabilize and / or begin to decrease before each successive addition. The formation of a black precipitate was observed when the first portion of DDQ was added. After the addition was complete, the temperature was set at 60°C and stirring was continued for 24 hours, at which point most of the material solidified. The reaction mixture was quenched by adding zinc dust (16.1 g, 0.246), and the reaction mixture was stirred for an a...

Embodiment 3

[0194] Example 3. Synthesis of poly{3,4-bis[2-(2-butoxyethoxy)ethoxy]thiophene}[PdiBEET]

[0195]

[0196] Fill a dry 100-mL three-neck flask with N 2 Rinse, and charge 3,4-bis[2-(2-butoxyethoxy)ethoxy]thiophene (1.83 g, 4.50 mmol), boron trifluoride etherate (BF 3 ·O(Et) 2 ) (1.40mL, 11.1mmol) and anhydrous CHCl 3 (20 mL, 0.23M). 2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) (3.1 g, 13.6 mol) was added in small portions. Polymerization was performed at room temperature (approximately 25°C). The formation of a black precipitate was observed within 1 hour of adding DDQ. After the addition was complete, stirring was continued for 24 hours and the reaction mixture was poured into 200 mL of a water:methanol (50:50) mixture to quench and precipitate the polymer. The organic solid was separated and washed well with hot water. The residue was dedoped by stirring in 100 mL of water containing 2 mL of hydrazine monohydrate for 1 hour. Redissolve the polymer in a minimal amount ...

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Abstract

An improved polymerization process comprising a process comprising providing a reaction mixture comprising a first monomer, an organic oxidizing agent and at least one Lewis acid or Bronsted acid, wherein the first monomer comprises at least one an optionally substituted heterocycle, wherein the heterocycle contains at least one heteroatom; and reacting the reaction mixture to obtain a conjugated polymer. The method can reduce the content of undesired entities such as halogens and metals in polymers, which can be used in organic electronic device applications. Purification methods are also suitable for removing organic and inorganic impurities.

Description

[0001] related application [0002] This application claims priority to US Provisional Application 61 / 550,322, filed October 21, 2011. Background technique [0003] As the field of conducting polymers develops, it should be understood that, in addition to a good balance of conductivity, processability, and stability, commercially successful intrinsically conducting polymers (ICPs) also require cost-effective Synthesis. Over the past few years, researchers have used synthetic methods and techniques to attempt to control all three properties together. The synthesis of conjugated polymers, including important polymers of the polythiophene family, is generally divided into three polymerization techniques: electrochemical polymerization, oxidative chemical polymerization using metal-based oxidants, and transition metal-promoted crossover of organic dihalide groups. coupling. For example, the application of these polymerization techniques to the synthesis of polythiophenes is des...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F4/32C08G61/12
CPCA61B8/0841A61B8/4455A61B2017/3413A61B8/0891A61B8/465A61B34/25C08G61/124C08G61/125C08G61/126C08G2261/1424C08G2261/3222C08G2261/3223C08G2261/3241C08G2261/3243C08G2261/43A61B8/4427C08G75/06
Inventor 埃琳娜·E·舍伊娜查德·兰迪斯文卡塔拉曼南·塞沙德里克里斯托弗·T·布朗塞缪尔·M·马扎
Owner NISSAN CHEM IND LTD
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