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Carbazole-based carborane derivative material, and preparation method and application thereof

A technology of carborane and its derivatives, which is applied in the field of photoelectric materials, can solve the problems of complex preparation and achieve the effects of simple preparation method, high purity and high yield

Inactive Publication Date: 2017-11-17
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Provides a method for preparing carborane derivatives of carbazole based on high-strength, high-stability electrochemiluminescence emitters, which is easy to prepare, and solves the complicated problem of preparing ECL emitter materials at present

Method used

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  • Carbazole-based carborane derivative material, and preparation method and application thereof
  • Carbazole-based carborane derivative material, and preparation method and application thereof
  • Carbazole-based carborane derivative material, and preparation method and application thereof

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preparation example Construction

[0031] The preparation method includes: 9-(4-bromophenyl)-9-carbazole, 9-(3-bromophenyl)-9-carbazole obtains 9-(4-ethynylbenzene) through alkynylation of the head coupling reaction -9-carbazole, 9-(3-ethynylbenzene)-9-carbazole, and then react with carborane to synthesize compounds I and II. The carborane derivatives have good applications in electrochemiluminescence, and can be used as small molecule bioluminescent probes. The carborane derivatives have high electrochemiluminescence intensity and good stability.

[0032]

[0033] The preparation method of the carborane derivative material of this type of carbazole comprises the following steps:

[0034] Step 1: Preparation of 9-(4-ethynylbenzene)-9-carbazole and 9-(3-ethynylbenzene)-9-carbazole, with 9-(4-ethynylbenzene)-9-carbazole The preparation of the method is an example: under nitrogen atmosphere and light-shielding conditions, the catalyst of 1 mmol of 9-(4-bromobenzene)-9-carbazole, 0.05-0.1 mmol of tetrakis (trit...

Embodiment 1

[0039]

[0040] Reaction condition 1: under nitrogen and protection from light, 9-(4-bromobenzene)-9-carbazole (322.6 mg, 1.0 mmol), tetrakis(trityl)phosphine palladium (57 mg, 0.05 mmol), cuprous iodide (19 mg, 0.1 mmol) and ethynylbenzene (112 mg, 1.0 mmol) were dissolved in 10 mL of triethylamine (Et 3 N), reflux at 110° C. for 12 hours. After terminating the reaction and cooling to room temperature, the reaction mixture was added to water and extracted with dichloromethane. The remaining organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was dried by rotary evaporation, and the solid was purified by silica gel column chromatography. Finally, 9-(4-ethynylbenzene)-9-carbazole was obtained as slightly yellow powder (265 mg), with a yield of 61%

[0041] Reaction condition 2: under nitrogen and protection from light, 9-(4-bromobenzene)-9-carbazole (322.6 mg, 1.0 mmol), tetrakis(trityl)phosphine palladium (104 mg, 0.01 mmol), cuprous iodid...

Embodiment 2

[0045]

[0046] Reaction condition one: under the condition of nitrogen protection, decaborane (121.3 mg, 1.0 mmol) and nitrogen, nitrogen-dimethylaniline (181.4 mg, 1.5 mmol) were dissolved in 5 mL of dry distilled toluene solvent, at 35 °C and stirred for 30 minutes. Then 10 mL of the compound 9-(4-ethynylbenzene)-9-carbazole (345 mg, 1.0 mmol) dissolved in distilled toluene was injected, and the reaction mixture was refluxed at 100° C. for 10 hours. After terminating the reaction, the mixture was cooled to room temperature and quenched with methanol. The solvent was removed using rotary evaporation, the residue was added to water, the organic layer was extracted with dichloromethane, dried over anhydrous magnesium sulfate and filtered. The solvent was dried by rotary evaporation and the solid was purified by silica gel column chromatography. Compound I was obtained as a yellow powder, which was recrystallized from methanol to obtain 107 mg of purer Compound I with a yi...

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Abstract

The invention discloses a carbazole-based carborane derivative material, and preparation and application methods thereof. The preparation method comprises the following steps: performing alkynylation on 9-(4-bromophenyl)-9-carbazole or 9-(3-bromophenyl)-9-carbazole by a Sonogashira coupling reaction to obtain 9-(4-acetenylphenyl)-9-carbazole or 9-(3-acetenylphenyl)-9-carbazole, and performing a reaction with carborane to synthesize a compound I or compound II. The invention gives out the specific conditions and illustrations on the reaction between the alkynyl derivatives of carbazole and the carborane, and the results show a high yield of the target products. The compounds are simple to prepare, the intermediates are low in cost, and the reaction processes are easy to control; and the products are easy to separate, have the advantages of high yield and high purity, and have potential application values in the aspects of sensors, electroluminescent devices, organic solar cells, organic field-effect transistors and the like. The carborane derivatives can be well applied to electrochemiluminescence (ECL), and can be used as a small-molecule biological fluorescent probe.

Description

technical field [0001] The invention relates to a carbazole-based carborane derivative material and a preparation method and application thereof, belonging to the technical field of photoelectric materials. Background technique [0002] Organic molecules have structural diversity and ease of tailoring, and molecular design and organic synthesis can be combined to obtain new compounds with certain specific properties. Due to the good designability and easy functionalization of organic molecules, in recent years, with the development of molecular engineering and organic synthesis, the research on electrochemiluminescence (ECL) materials of organic molecules has been widely developed. They are used in the detection of environmental pollutants. , biological detection and other aspects have played a significant role. [0003] Electrochemiluminescence is a unique type of luminescence in which electron transfer between electrogenerated ionic radicals produces electronically excite...

Claims

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Application Information

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IPC IPC(8): C07F5/05C09K11/06C09K9/02
CPCC07F5/05C09K9/02C09K11/06C09K2211/1029C09K2211/1096
Inventor 赖文勇万一李军峰黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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