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Tripod-shaped tetraaminepyrene and preparation method thereof, electrode modified by tripod-shaped tetraaminepyrene film and preparation method thereof

The technology of tripod-shaped tetraamine pyrene and tetraamine pyrene is applied in the field of electrode surface modification materials, which can solve the problems of poor stability, low surface adsorption efficiency, difficult synthesis of bridged molecular system, etc., and achieves high stability, low price of raw materials, Simple and efficient synthesis method

Active Publication Date: 2019-05-14
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] In view of the above analysis, the present invention aims to provide a tripod-shaped tetraaminepyrene and its preparation method, a tripod-shaped tetraaminepyrene thin-film modified electrode and a preparation method to solve the difficulty in synthesizing the bridging molecular system used in the interface modification method in the prior art. , poor stability and low surface adsorption efficiency

Method used

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  • Tripod-shaped tetraaminepyrene and preparation method thereof, electrode modified by tripod-shaped tetraaminepyrene film and preparation method thereof
  • Tripod-shaped tetraaminepyrene and preparation method thereof, electrode modified by tripod-shaped tetraaminepyrene film and preparation method thereof
  • Tripod-shaped tetraaminepyrene and preparation method thereof, electrode modified by tripod-shaped tetraaminepyrene film and preparation method thereof

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preparation example Construction

[0049] Specifically, the preparation method of the above-mentioned tripod-shaped tetraamine pyrene comprises the following steps:

[0050] Step a: dissolving 1,3,6,8-tetrabromopyrene and diarylamine derivatives in an organic solvent to obtain a mixture of 1,3,6,8-tetrabromopyrene and diarylamine derivatives, wherein, 1 , the molar ratio of 3,6,8-tetrabromopyrene to diarylamine derivatives is 1:(4-10);

[0051] Step b: Add alkali and nitrogen to the mixture of 1,3,6,8-tetrabromopyrene and diarylamine derivatives to remove oxygen, and obtain 1,3,6,8-tetrabromopyrene and diarylamine after deoxygenation A mixture of arylamine derivatives, wherein the molar ratio of 1,3,6,8-tetrabromopyrene to base is 1:(4-10);

[0052] Step c: Add the palladium catalyst to the deoxygenated mixture of 1,3,6,8-tetrabromopyrene and diarylamine derivatives, and under nitrogen protection, 1,3,6,8-tetrabromopyrene and diarylamine The derivatives are refluxed at 90°C-140°C for 6h-48h, and the reaction ...

Embodiment 1

[0075] This embodiment provides a method for preparing tripod-like tetraaminepyrene having a structure shown in formula II, comprising the following steps:

[0076] Di(4-bromophenyl)amine (654mg, 2mmol), pyridine-4-boronic acid (1.23g, 10mmol), tetrakis(triphenylphosphine)palladium (231mg, 0.2mmol) and potassium carbonate (3.26g, 23.6 mmol) was dissolved in 20 mL of toluene, and heated to reflux for 24 hours under nitrogen protection. After the reaction, the system was cooled to room temperature, the solvent was removed under reduced pressure, and column chromatography separation and purification (eluent: petroleum ether / ethyl acetate 1 / 1, v / v) obtained diarylamine derivatives, producing The rate is 86%.

[0077] Dissolve 1,3,6,8-tetrabromopyrene (100mg, 0.20mmol) and diarylamine derivatives (484mg, 1.5mmol) in 10mL DMF to obtain 1,3,6,8-tetrabromopyrene and diarylamine Amine derivative mixture, wherein, the molar ratio of 1,3,6,8-tetrabromopyrene to diarylamine derivative i...

Embodiment 2

[0082] This embodiment provides a method for preparing tripod-like tetraaminepyrene having a structure shown in formula III, comprising the following steps:

[0083] Dissolve p-fluorobenzonitrile (1 g, 8.3 mmol), p-aminobenzonitrile (300 mg, 2.5 mmol), potassium tert-butoxide (28 mg, 0.25 mmol) in 20 mL DMSO, and stir for 24 hours under nitrogen protection. The reaction mixture was then poured into water and a precipitate formed. Filter, wash with water, and dry in vacuo to obtain a diarylamine derivative with a yield of 79%.

[0084] 1,3,6,8-Tetrabromopyrene (100mg, 0.2mmol) and diarylamine derivatives (263mg, 1.2mmol) were dissolved in 10mL DMF to obtain 1,3,6,8-tetrabromopyrene and diaryl Amine derivative mixture, wherein, the molar ratio of 1,3,6,8-tetrabromopyrene to diarylamine derivative is 1:6; Potassium phosphate (230mg, 1.1mmol) and nitrogen are added to 1,3,6 , 8-tetrabromopyrene and diarylamine derivative mixture are deoxygenated to obtain the deoxygenated 1,3,6,...

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Abstract

The invention relates to a quadripod-shaped tetramine pyrene, a preparation method thereof, a quadripod-shaped tetramine pyrene thin film modified electrode and a preparation method, belongs to the technical field of electrode surface modified materials, and solves the problem that a bridging molecule system adopted by an interface modification method in the prior art is difficult in synthesis, low in stability and low in surface adsorption efficiency. The quadripod-shaped tetramine pyrene is of the following structure, and is prepared through a coupling reaction of 1,3,6,8-tetrabromo pyrene and a diarylamine derivative under the catalysis of a palladium catalyst. The quadripod-shaped tetramine pyrene provided by the invention can be used for electrode modification.

Description

technical field [0001] The invention relates to an electrode surface modification material, in particular to a tripod-shaped tetraamine pyrene and a preparation method thereof, an electrode modified with a tripod-shaped tetraamine pyrene film and a preparation method. Background technique [0002] The adsorption and assembly of metal or semiconductor interfaces has important research applications in the fields of molecular electronics, light-emitting diodes, solar cells, sensors, and protective coatings. For example, In the review article of Nature Chemistry (2012, 4, 443-455), the research status of molecular systems containing gold-sulfur bonds in the nanoscale field was described, and the gold surface interface functionalized with gold-sulfur bonds was introduced in the sensing , molecular recognition, molecular catalysis and other fields of property research. [0003] The traditional interface modification method is mainly through the bridging of mercapto, siloxy, car...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/38C07C255/58C07C253/30C07C229/60C07C227/18
CPCC07B2200/07C07C227/18C07C229/60C07C253/30C07C255/58C07D213/38
Inventor 钟羽武唐健洪邵将洋
Owner INST OF CHEM CHINESE ACAD OF SCI
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