Chiral porphyrin complex nanotweezers and its preparation method and application in the separation of single-walled carbon nanotubes

A technology of carbon nanotubes and complexes, applied in the field of chiral porphyrin complex nanotweezers and its preparation, can solve the problems of complicated experimental steps, high separation cost, unfavorable separation of pure carbon nanotubes, etc.

Inactive Publication Date: 2011-12-07
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

First of all, the experimental steps are relatively complicated, and the utilization rate of carbon nanotubes is low; secondly, the separation cost is high, which is not conducive to the separation of a large number of high-purity carbon nanotubes and comes with surfactants, which affects its subsequent application and promotion.

Method used

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  • Chiral porphyrin complex nanotweezers and its preparation method and application in the separation of single-walled carbon nanotubes
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  • Chiral porphyrin complex nanotweezers and its preparation method and application in the separation of single-walled carbon nanotubes

Examples

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Effect test

Embodiment 1

[0030] Preparation of 3,6-dibromo-N-substituted carbazole

[0031] According to the method disclosed in Macromolecules, 2002, 35, 6080, the preparation of 3,6-dibromo-N-n-octylcarbazole is taken as an example to illustrate.

[0032]

[0033] Add 60% sodium hydride (1.104 g, 27.6 mmol) and 25 ml of anhydrous tetrahydrofuran into a 200 ml three-necked flask, and start to add dropwise 3,6-dibromocarbazole (5 g, 15.4 mg) dissolved in 30 ml of tetrahydrofuran mol), about 30 minutes dropwise. After dropping, the cooling device was removed, and the temperature was gradually raised to reflux temperature, 4.5 ml of 1-bromo-n-octane (4.16 g, 25.2 mmol) was added, and the reaction was refluxed overnight. Pour the reaction solution into clear water, filter, wash until neutral, dry over anhydrous magnesium sulfate, remove the solvent, and use ethyl acetate and n-hexane mixed solvent (1:10) as eluent for further purification by column chromatography to obtain white Crystals, 80% yield....

Embodiment 2

[0036] Preparation of 3,6-dibromo-9,9-disubstituted fluorene

[0037] According to the method disclosed in Adv. Mater., 2008, 20, 2359, the preparation of 3,6-dibromo-9,9-di-2-ethylhexylfluorene is taken as an example to illustrate.

[0038]

[0039] Under argon protection, 60% sodium hydride (2.1 g, 52.5 mmol) and 50 ml of tetrahydrofuran were added to a 100 ml flask, and 3,6-dibromofluorene (4 g, 12.3 mmol) solution was stirred at room temperature for 2 hours. 5.4 g (28 mmol) of 1-bromo-2-ethylhexylane was added dropwise within 1 hour, and after the addition was complete, it was heated to reflux for 24 hours. Cool, neutralize with dilute hydrochloric acid, then extract with dichloromethane (3×50), combine the organic phases, dry over anhydrous magnesium sulfate, concentrate, and then separate by column chromatography (silica gel, petroleum ether) to obtain 6.50 g of free Color oil, yield 96.0%. Proton NMR spectrum analysis results: 1 HNMR (CDCl3, 270MHz), 7.80 (d, 2H), ...

Embodiment 3

[0042] Preparation of 2,8-dibromodibenzothiophene

[0043]

[0044] Prepare according to the method disclosed in J.Mater.Chem., 2003, 13, 1351, add dibenzothiophene (5 g, 27.1 mmol) in a 100 ml three-necked flask, 50 ml of carbon trichloride, cool to 0 ° C, The dropwise addition of liquid bromine (3.1 mL, 60.5 mmol) dissolved in 30 mL of carbon trichloride was started and continued for about 30 minutes. After dropping, the cooling device was removed, and the temperature was gradually raised to room temperature, and the reaction was carried out overnight. Pour the reaction solution into clean water, filter, wash until neutral, and dry. Recrystallized with absolute ethanol and dried to obtain white crystals with a yield of 80%. Proton NMR spectrum analysis results: 1 HNMR (CDCl3, 270MHz), 8.24 (m, 2H), 7.71 (m, 2H), 7.58 (m, 2H), nuclear magnetic resonance test shows that it is the target product.

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Abstract

The present invention relates to chiral porphyrin complex nanotweezers and a preparation method thereof and a method for separating narrow (n, m) value distribution and optically active carbon tubes from single-walled carbon nanotubes by the chiral porphyrin complex nanotweezers. It has a chemical structural formula represented by the following general formula R or general formula S: wherein, Ar is a soluble aryl group; M is a transition metal element; the general formula R is a right-handed nanotweezer molecule, and the general formula S is a left-handed nanotweezer molecule. The beneficial effects of the present invention are: the chiral porphyrin complex of the present invention can effectively separate narrow (n, m) value distribution and optically active carbon tubes from single-walled carbon nanotubes, and the separation method is relatively simple and practical, The separated carbon nanotubes have dual properties: one is optically active and can be used for chiral sensor research; the other has narrow (n, m) value distribution, which can be used to construct various organic photoelectric devices.

Description

technical field [0001] The invention relates to chiral porphyrin complex nanotweezers and a preparation method thereof, and also relates to a method for separating the chiral porphyrin complex nanotweezers from single-walled carbon nanotubes with narrow (n, m) value distribution and optically active carbon tubes . Background technique [0002] In the past two decades, the research based on single-walled carbon nanotubes (SWNTs) has been one of the most popular research topics in the world, mainly because of its excellent properties and broad application prospects. However, under the current conditions, the carbon nanotubes obtained by any preparation method are mixtures of different thicknesses and multiple (n, m) components. In addition, various impurities such as amorphous carbon, fullerene, catalyst particles and carbon nanospheres are mixed in the products obtained by many preparation methods. These impurities and multiple (n, m) components greatly limit the research a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C01B31/02
Inventor 汪锋陈启明李昱达
Owner WUHAN INSTITUTE OF TECHNOLOGY
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