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Perfluoro alkyl substituted perylene bis diimines and derivative and preparation method thereof

A perylene bis-diimide and perfluoroalkyl technology, which is applied in the fields of organic and fine chemicals, can solve the problems that the solubility of perylene bis-diimide or bisbenzimidazole perylene cannot be significantly increased, and achieve increased stability, Ease of operation and improved solubility

Inactive Publication Date: 2008-03-12
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing modifications to the perylene parent cannot significantly increase the solubility of perylene bis-diimide or bisbenzimidazole perylene in organic solvents, and the introduction of cyano groups utilizes highly toxic CN-containing - raw material

Method used

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  • Perfluoro alkyl substituted perylene bis diimines and derivative and preparation method thereof
  • Perfluoro alkyl substituted perylene bis diimines and derivative and preparation method thereof
  • Perfluoro alkyl substituted perylene bis diimines and derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1 Preparation of 1-perfluorooctyl N, N'-diisooctyl perylene bis-diimide

[0019]

[0020] In a 5mL flask, add 49mg of 1-bromo-N,N'-diisooctylperylenebisdiimide (0.071mmol), 65mg of copper powder (1.0mmol), 1mL of N-methylpyrrolidone, 120μL (0.40mmol) of iodoperylene Fluorooctane, under the protection of Ar, kept the system at 100°C, reacted for 13h, and passed through a silica gel column to obtain 41 mg of 1-perfluorooctyl N,N'-diisooctylperylene bis-diimide, melting point 178°C, yield 50 %, MS: 1032; 1 H-NMR (400M, CDCl 3 ): δ=0.85-1.98(m, 30H), 4.19(m, 4H, CH 2 ), 8.34 (d, 1H, perylene ring), 8.64 (m, 3H, perylene ring), 8.75 (d, 1H, perylene ring), 8.80 (d, 1H, perylene ring), 8.93 (s, 1H, perylene ring ); 13 C-NMR (400M, CDCl 3 ):δ=10.79,14.26,23.25,24.23,28.88,30.95,38.18,44.55,122.68,123.00,123.91,124.20,124.67,126.70,128.36,129.48,130.27,131.21,132.04,132.26,132.67,133.10,135.19, 137.71, 163.03, 163.52, 163.58, 163.82; 19 F-NMR (400M, CDCl 3 ):...

Embodiment 2

[0021] Example 2 Preparation of 1,7-diperfluorooctyl N, N'-dioctylperylenebisdiimide

[0022]

[0023] Add 83mg (0.11mmol) 1,7-dibromo-N,N'-dioctylperylene bis-diimide, 66mg (1.0mmol) copper powder, 1mL N-methylpyrrolidone, 150μL (0.56mmol) iodine to a 5mL flask Substituted perfluorooctane, under the protection of Ar, kept the system at 80°C, reacted for 12h, and passed through a silica gel column to obtain 41mg of 1,7-diperfluorooctyl N,N'-dioctylperylene bis-diimide, melting point 105°C , yield 25.9%, MS: 1450.

Embodiment 3

[0024] Example 3 Preparation of 1-perfluorohexyl N, N'-dicyclohexyl perylene bis-diimide

[0025]

[0026] Add 64mg 1-bromo-N,N'-dicyclohexylperylenebisdiimide (0.10mmol), 64mg copper powder (1.0mmol), 1mL N-methylpyrrolidone, 180μL (0.40mmol) Fluorohexane, under the protection of Ar, keep the system at 100°C, react for 24h, and pass through a silica gel column to obtain 45 mg of 1-perfluorohexyl N,N'-diisooctylperylene bis-diimide, melting point 164°C, yield 52% .

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Abstract

The present invention provides a perfluoroalkyl substituted 3, 4, 9, 10-perylene double diimine, the derivative perfluoroalkyl substituted dibenzimidazoles perylene and the preparation methods. In the method, the bromine substituted 3, 4, 9, 10-perylene double diimine or bromide substituted dibenzimidazole perylene and the perfluorine iodine substituted alkyl are used as the raw materials; the copper powder or copper-tin alloy powder is used as the catalyst; the reaction is done for 1 to 72 hours in the organic solvent at the temperature between 40 and 160 DEG C; the Br on the garland of raw material is replaced by the perfluoroalkyl to produce the perfluoroalkyl substituted 3, 4, 9, 10-perylene double diimine or the perfluoroalkyl substituted double benzimidazoles perylene of the good solubility, thermal stability and stability.

Description

technical field [0001] The invention belongs to the technical field of organic chemical industry and fine chemical industry, and relates to the perfluoroalkylation of perylene matrix in 3,4,9,10-perylene bisdiimide and bisbenzimidazole perylene. Background technique [0002] The concept of organic semiconductor was first proposed in 1954, and now it has become one of the hotspots of people's research. The reason why organic semiconductors are valued is that compared with traditional inorganic semiconductors, it has the following advantages: [0003] 1 There are many kinds of organic molecules, and the chemical structure is easy to change, which is beneficial to the design of materials and devices. [0004] 2. Organic semiconductors are easy to form large-area films, and it is easy to achieve large-scale growth. [0005] 3. Organic polymers can conduct electricity and emit light, which is convenient for photoelectric integration. [0006] 4. Low cost. [0007] 5. There ar...

Claims

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Application Information

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IPC IPC(8): C07D498/22C07D471/06
Inventor 肖义袁忠义
Owner DALIAN UNIV OF TECH
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