Perfluoroalkyl-modified perylene imide and its preparation method

A technology of perfluoroalkyl and perylene imide, applied in the field of perfluoroalkyl modified perylene imide and its preparation, can solve the problems of poor solubility of perylene imide, unsuitable for solution processing, etc. Thermal stability, the effect of increasing solubility

Inactive Publication Date: 2017-04-26
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported perfluoroalkyl-substituted perylene imides have poor solubility and are not suitable for solution processing.

Method used

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  • Perfluoroalkyl-modified perylene imide and its preparation method
  • Perfluoroalkyl-modified perylene imide and its preparation method
  • Perfluoroalkyl-modified perylene imide and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: Preparation of N,N'-bis(2-perfluorobutyl-1-hexylethyl)peryleneimide

[0017]

[0018] 25mL two-neck flask with perylene tetracarboxylic anhydride 1 (0.72mmol, 0.281g), E 1 (2.45mmol, 0.852g), imidazole (58.76mmol, 4g), react at 145°C for 4.5h under anaerobic conditions, cool to 120°C, add appropriate amount of ethanol, reflux for 0.5h, add 12mol / L HCl to remove imidazole, use CH 2 Cl 2 Extract with saturated brine, dry with anhydrous magnesium sulfate, filter with suction, rotary steam, use CH 2 Cl 2 Using petroleum ether as the eluent, silica gel was passed through a column for separation, to obtain 0.152 g of perfluoroalkyl perylene imide 2 with a yield of 20.19%. 1 H NMR(400MHz, CDCl 3 )δ8.74(s, 2H), 8.65(s, 6H), 5.73(s, 2H), 3.36(d, 2H), 2.55(s, 2H), 2.39(s, 2H), 1.93(s, 2H) ),1.24(s,8H),0.83(s,6H); HRMS(MALDI-TOF):Calcd for C 48 H 32 F 26 N 2 O 4 ,1194.1950,found:1194.7520(M - ).

Embodiment 2

[0019] Example 2: Preparation of N,N'-bis(2-perfluorobutyl-1-hexylethyl)peryleneimide

[0020]

[0021] Add perylene tetracarboxylic anhydride 1 (0.678mmol, 0.266g), E1 (1.695mmol, 0.589g), CH3COOH (10mL) in a 25mL two-neck flask, react at 115°C for 6.5h under anaerobic conditions, and extract with CH2Cl2 and saturated brine , Dried over anhydrous magnesium sulfate, filtered with suction, rotary steamed, used CH2Cl2 and petroleum ether as eluents, separated by silica gel column to obtain perfluoroalkyl perylene imide 2a 0.256 g, yield: 35.93%. 1H NMR(400MHz,CDCl3)δ8.73(d,2H),8.64(s,6H),5.72(s,2H),3.35(s,2H),2.56(s,2H),2.35(s,2H) , 1.91 (s, 2H), 1.28 (d, 16H), 0.82 (s, 6H); HRMS (MALDI-TOF): Calcd for C48H40F18N2O4, 1050.2700, found: 1050.8290 (M-).

Embodiment 3

[0022] Example 3: Preparation of N,N'-bis(2-perfluorohexyl-1-hexylethyl)peryleneimide

[0023]

[0024] 25mL two-neck flask with perylenetetracarboxylic anhydride 1 (0.77mmol, 0.301g), E 2 (1.49mmol, 0.67g), imidazole (73.45mmol, 5g), react at 145°C under anaerobic conditions for 6.5h, cool to 120°C, add appropriate amount of ethanol, reflux for 0.5h, add 12mol / L HCl to remove imidazole, use CH 2 Cl 2 Extract with saturated brine, dry with anhydrous magnesium sulfate, filter with suction, rotary steam, use CH 2 Cl 2 Using petroleum ether as eluent, silica gel column separation, 0.278 g of perfluoroalkyl perylene imide 2b, yield: 29%. 1 H NMR(400MHz, CDCl 3 )δ8.73(s, 2H), 8.65(s, 6H), 5.73(s, 2H), 3.36(d, 2H), 2.55(s, 2H), 2.36(s, 2H), 1.94(s, 2H) ),1.24(s,16H),0.83(s,6H); HRMS(MALDI-TOF):Calcd for C 52 H 40 F 26 N 2 O 4 ,1250.2570,found:1250.8600(M - ).

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Abstract

The invention discloses a perfluoroalkyl-modified perylene imide and its preparation method. The structural general formula of the perfluoroalkyl-modified perylene imide is shown in the description, and the structural formula of R is shown in the description, wherein, X represents H, F and Br, m and n refer to the number of alkyl C atom and the number of perfluorinated alkyl C atom respectively, m is 1, 2, 3, 4, 5 or 6, and n is 1, 3, 5 or 7. In the preparation method, 3,4,9,10-perylenetetracarboxylic dianhydride and perfluoroalkylamine are used as raw materials, the molar ratio of 3,4,9,10-perylenetetracarboxylic dianhydride and perfluoroalkylamine is 1:2 to 1:6, and in a temperature range of the room temperature to the solvent reflux temperature, the raw materials are stirred for a reaction for 1-12 hours in an organic solvent under the protection of Ar or N2 to generate the perfluoroalkyl-modified perylene imide. The preparation method can significantly increase the solubility of a perylene imide type material in an organic solvent, at the same time, improve the light and heat stability of the perylene imide type material and the device stability in a field effect transistor.

Description

Technical field [0001] The invention belongs to the field of organic chemicals and fine chemicals, and relates to the perfluoroalkylation of organic semiconductor material peryleneimide and its halogenated derivatives, in particular to a perfluoroalkyl modified peryleneimide and a preparation method thereof . Background technique [0002] Compared with the widely used inorganic semiconductor materials, organic semiconductor materials have the following advantages: suitable for low-cost solution processing; can prepare wearable flexible devices; various types and properties are conducive to the design and development of new materials and new devices. [0003] The perfluoroalkyl group has a rigid rod-like structure. Fluorine atoms and perfluoroalkyl compounds have extremely high stability, oxidation resistance and hydrophobicity. Fluorine atoms can also form intermolecular hydrogen bonds with adjacent hydrogen atoms to enhance the interaction between molecules (J.Am. Chem. Soc. 196...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06
CPCC07D471/06
Inventor 袁忠义黄清方蔡春生李超胡昱陈义旺
Owner NANCHANG UNIV
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