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Functional polyfluorene compound and intermediate and application thereof

A technology of polyfluorene compounds, which is applied in the application field of functionalized polyfluorene compounds in modifying carbon nanotubes, can solve the problems of difficult control of the processing process, low solubility, low efficiency, etc., and achieve correct structure determination by instruments and preparation The method is simple and the effect of high product yield

Inactive Publication Date: 2012-08-08
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

Covalent bond modification on the surface of carbon nanotubes will destroy the perfect structure of carbon nanotubes, thereby affecting various excellent properties of carbon nanotubes, and the processing process is complicated and difficult to control
In addition, the acidification, oxidation or cutting of carbon nanotubes will also affect the various properties of carbon nanotubes
The modification of carbon nanotubes through non-covalent bonds can avoid the destruction of the carbon atoms on the carbon nanotubes when covalently modifying carbon nanotubes. 2 -Defects introduced by hybridization, so that the original excellent photoelectric properties of carbon nanotubes are maintained, but this method often has disadvantages such as low solubility, poor stability, low efficiency, and high concentrations of surfactants or polymers used
All these unfavorable factors greatly limit the large-scale practical application of carbon nanotubes.

Method used

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  • Functional polyfluorene compound and intermediate and application thereof
  • Functional polyfluorene compound and intermediate and application thereof
  • Functional polyfluorene compound and intermediate and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1, preparation functionalized polyfluorene compound intermediate

[0034] 1) Put 7.3mmol of 1-pyrene boronate, 8.1mmol of 1-(6-bromohexyloxy)-4-bromobenzene and 7.5mmol of sodium bicarbonate into 40mL of tetrahydrofuran and 15mL of water, and add 0.091mmol of catalyst Pd under nitrogen protection (PPh 3 ) 4 , reflux for 18 hours. After the reaction was completed, it was cooled, extracted, washed, dried, and separated by column chromatography to obtain 1-(4-(6-bromohexyloxy)phenyl)pyrene with a yield of 84%.

[0035] 1 H NMR (400MHz, CDCl 3, ppm): δ8.23-8.16 (m, 4H), 8.09 (s, 2H), 8.04-7.97 (m, 3H), 7.56 (d, 2H), 7.10 (d, 2H), 4.08 (t, 2H ), 3.46(t, 2H), 1.96-1.87(m, 4H), 1.60-1.55(br, 4H);

[0036] 13 C NMR (100MHz, CDCl 3 , ppm): δ158.67, 137.71, 133.60, 131.76.131.20, 130.52, 128.75, 127.87, 127.49, 126.14, 125.58, 125.19, 124.89, 124.83, 114.58, 68,03, 34.03, 29.2

[0037] Anal.Calcd.for C 28 h 25 BrO: C, 73.20; H, 5.92. Found: C, 73.47; H, 5.92...

Embodiment 2

[0042] Example 2, preparation of functionalized polyfluorene compounds

[0043] Put 0.084mmol of the polyfluorene compound intermediate prepared in Example 1, 0.085mmol of 9,9-dioctyl-2,7-diboronate-fluorene, and 3.6mmol of sodium bicarbonate into 10mL of tetrahydrofuran and 4mL of water, nitrogen protection 0.84μmol catalyst Pd(PPh 3 ) 4 , reflux for 96 hours. After the reaction is completed, cool, extract, wash, dry, and settle to obtain the functionalized polyfluorene compound (abbreviated as PFPy) represented by the formula IV, with a yield of 88%.

[0044] 1 H NMR (400MHz, CDCl 3 , ppm): δ8.19-7.91 (br, 18H), 7.84-7.83 (br, 2H), 7.7l (br, 6H), 7.54-7.51 (br, 8H), 7.31-7.28 (br, 4H), 7.05-7.02(br, 4H), 6.84-6.82(br, 4H), 4.03(m, 4H), 3.94(br, 4H), 2.03(br, 4H), 1.83(br, 8H), 1.55(br, 8H), 1.08(br, 20H), 0.81-0.79(br, 10H);

[0045] 13 C NMR (100MHz, CDCl 3 ,ppm):δ158.64,158.10,151.67,141.77,138.13,137.69,135.91,133.47,131.72,131.14,130.44,129.47,128.70,128.40,127....

Embodiment 3

[0047] Example 3, preparation of carbon nanotubes modified by functionalized polyfluorene compounds

[0048] 10mg of the functionalized polyfluorene compound PFPy (M n =66000) was dissolved in 1 mL of tetrahydrofuran, and then 2 mg of starting single-armed carbon nanotubes were put into the previous solution, and the ultrasonic wave was continued for 1 hour; the dispersion was centrifuged at a speed of 3000 rpm for 10 minutes, and the supernatant black liquid was carefully collected and stored. overnight. Afterwards, the excess polymer solution was filtered off with a filter membrane with a pore size of 450 nm, and the excess polymer was washed (4×25 mL) with a large amount of tetrahydrofuran or water. After washing, the filter membrane with carbon tubes is sucked dry, and dried in a vacuum oven at 80-90°C. Finally, cut the filter membrane, carefully peel off the carbon tube from the filter membrane, and weigh it carefully. In the preparation method, the carbon nanotubes us...

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Abstract

The invention discloses a functional polyfluorene compound and an intermediate and an application thereof. The structure of the intermediate is shown in general formula I, and the structure of the functional polyfluorene compound is shown in general formula II. The invention also provides a method for preparing the above two compounds. The functional polyfluorene compound can be used for modifying carbon nano tube, and the preparing method of the functional polyfluorene compound comprises the following steps: adding carbon nano tube into the solution of the functional polyfluorene compound, carrying out ultrasound and centrifugal separation, collecting the supernatant, and obtaining the carbon nano tube modified by the functional polyfluorene compound. In the carbon nano tube, the carbon nano tube is connected with the functional polyfluorene compound via a non covalent bond. The functional polyfluorene compound and the intermediate thereof have the advantages of simple preparation method and high yield; after modification of the carbon nano tube, high stability and solubility of the originating carbon nano tube in solution can be realized while the unique structure and fine performance of the carbon tube can be maintained. The method features simple process, easy operation, and high product yield, and is applicable to large-scale practical application of the carbon nano tube.

Description

technical field [0001] The invention relates to a functionalized polyfluorene compound and its intermediate and application, in particular to the application of the functionalized polyfluorene compound in modifying carbon nanotubes. Background technique [0002] Since their discovery in 1991, carbon nanotubes have attracted widespread attention from the scientific and industrial circles for their unique structure and excellent optical, electrical and mechanical properties. However, the extremely poor solubility of carbon nanotubes in solvents limits its application. Due to the strong van der Waals force between carbon nanotubes and their large specific surface area and high surface energy, unmodified carbon nanotubes are insoluble in any organic solvent and aqueous solution. In order to expand the application field of carbon nanotubes and increase the solubility of carbon nanotubes in solvents, it is necessary to modify or functionalize them. The main modification or funct...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C25/22C07C17/26C08G61/02C01B31/02
Inventor 薄志山朱博
Owner INST OF CHEM CHINESE ACAD OF SCI
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