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Aminocarbazole bridged molecular tweezer, and preparation method and applications thereof

A technology of aminocarbazole bridge and aminocarbazole dibromide is applied in the field of preparation of aminocarbazole bridged molecular tweezers, which can solve the problems of poor stability and poor molecular solubility of carbon nanotube composites, and achieve cost Inexpensive, good alcohol solubility, strong practical effect

Inactive Publication Date: 2015-02-11
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, small molecules with fused rings have a rigid structure, resulting in poor solubility of such molecules and poor stability of the formed carbon nanotube complexes.

Method used

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  • Aminocarbazole bridged molecular tweezer, and preparation method and applications thereof
  • Aminocarbazole bridged molecular tweezer, and preparation method and applications thereof
  • Aminocarbazole bridged molecular tweezer, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of 3,6-dibromo-9-amino substituted carbazole

[0036] Take the preparation of 3,6-dibromo-9-(N,N-dimethylaminopropyl)carbazole as an example to illustrate.

[0037]

[0038] Under argon protection, add 100mL DMSO, 3,6-dibromocarbazole (6.5g, 20mmol), and 120mg tetrabutylammonium bromide to a 250ml flask respectively, stir well, add 12mL of 50% NaOH aqueous solution dropwise, continue After reacting for 30 minutes, 20 mL of an aqueous solution containing 6.3 g (40 mmol) of N,N-dimethylchlorpropylamine hydrochloride that had been neutralized with NaOH was added dropwise. After reacting for 6 hours, add 100 mL of water to the reaction system to dissolve the salt generated in the reaction, extract the reaction solution three times with 300 mL of ether, wash the organic phase with saturated brine three times, dry it with anhydrous sodium sulfate, and evaporate it under reduced pressure. The solvent was removed, and the crude product was recrystallized in a mi...

Embodiment 2

[0041] Preparation of 1-pinacol borate pyrene

[0042]

[0043]1-Bromopyrene (2.81g, 10mmol) was dissolved in dried tetrahydrofuran (THF, 100mL), and n-butyllithium (2.5M, 4.8mL, 12mmol) was added dropwise at -78°C. After reacting for 1 h, add 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.7 mL, 18 mmol), then gradually warm to room temperature, and react for 24 h . The reaction mixture was poured into water and extracted with ether. The organic layer was washed with brine and dried over anhydrous calcium chloride. After the solvent was removed under reduced pressure, it was separated with a silica gel column, and the eluent was a mixed solution of petroleum ether and dichloromethane to obtain 2.33 g of white crystals with a yield of 71%. H NMR analysis results, 1 H NMR (300MHz, CDCl 3 ): 1.47 (12H, s, -CH 3 ), 7.99 (1H, t, PyrH), 8.06 (1H, d, PyrH), 8.16 (5H, m, PyrH), 8.53 (1H, d, PyrH), 8.99 (1H, d, PyrH). NMR tests showed that it was the target product. ...

Embodiment 3

[0045] Preparation of 2-pinacol borate pyrene:

[0046]

[0047] Add the catalyst [Ir(COD)Cl] in a 100mL three-neck flask under the protection of argon 2 (80mg), the ligand dtbpy (140mg) and a small amount of diboronic acid pinacol ester and 10mL n-hexane were dissolved, stirred vigorously for about 5min until the solution turned blue-purple, then added 4.04g (20mmol) pyrene and 5.58g (22mmol ) pinacol diboronate and 30 mL of n-hexane. After stirring and reacting in an oil bath at 80° C. for 24 h, the reaction mixture was passed through a short silica gel column to filter out the residual metal iridium catalyst. After the solvent was removed by rotary evaporation, 3.4 g of white solid was obtained by column separation, with a yield of 51.8%. H NMR analysis results, 1 H NMR (300MHz, CDCl 3 ): 1.46 (12H, s, -CH 3 ), 7.01 (1H, t, PyrH), 8.06 (4H, dd, PyrH), 8.20 (2H, d, PyrH), 8.59 (2H, s, PyrH). NMR tests showed that it was the target product.

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Abstract

The invention relates to an aminocarbazole bridged molecular tweezer, and a preparation method thereof. The aminocarbazole bridged molecular tweezer has the chemical structural formula shown in the following general formula which is shown in the specification, wherein Ar is condensed ring pyrenyl; n is equal to 1-15; R1 and R2 are alkyl chains with C1-C6. The preparation method comprises the following steps: 1) by taking 3,6-dibromocarbazole as a reaction raw material, reacting with excessive amine compounds under basic condition to obtain different aminocarbazole dibromides; and 2) by taking the aminocarbazole dibromides as raw materials, introducing rigid condensed ring pyrenyl units through palladium-catalyzed coupling reaction to obtain different target products. The aminocarbazole bridged molecular tweezer and the preparation method and applications thereof have the following advantages and beneficial effects that the aminocarbazole bridged molecular tweezer is simple to synthesize, low in cost, good in separation effect, and beneficial in large-scale purification of carbon nanotubes, has better alcohol solubility, is capable of separating the carbon nanotubes in an environment-friendly type solvent medium of ethanol, propanol and the like, and has the characteristics of being environment-friendly, strong in practicability and the like.

Description

technical field [0001] The invention relates to a preparation method of carbazole-containing bridging molecular tweezers, and also relates to a method for selectively separating single-walled carbon nanotubes with narrow diameter distribution by using molecular tweezers. Background technique [0002] Single-walled carbon nanotubes (SWNTs) have excellent electrical properties and super strong mechanical properties, showing broad application prospects in optoelectronic devices, composite materials, sensors and other fields. [0003] Under the current conditions, the single-walled carbon nanotubes synthesized by graphite arc method and chemical vapor deposition (CVD) are all mixtures of different thicknesses and multiple (n,m) components. Moreover, various impurities, such as fullerenes, amorphous carbon, carbon nanospheres and catalyst particles, are mixed in the products obtained by some preparation methods. These impurities and multiple (n,m) components greatly limit the ph...

Claims

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Application Information

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IPC IPC(8): C07D209/86C01B31/02B01J20/22B01D43/00
CPCB01D43/00B01J20/22B82Y30/00B82Y40/00C01B32/172C07D209/86
Inventor 汪锋李昱达王迅昶
Owner WUHAN INSTITUTE OF TECHNOLOGY
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