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Perfluoroalkyl group modified solution-processable naphthalimide and preparation method thereof

A technology of perfluoroalkylamine and perfluoroalkyl, which is used in naphthalene dicarboxamide dyes/phthalimide dyes, organic chemistry, etc., can solve the problems of unsuitable solution processing and poor solubility, and achieve enhanced photothermal 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

[0004] Naphthalimides directly modified by perfluoroalkyl groups have been proved to be excellent organic semiconductor materials, and the introduction of perfluoroalkyl groups significantly enhanced the stability of the materials in field-effect transistors (Nature 2000, 404, 478-481), however, such materials Poor solubility in organic solvents, not suitable for solution processing

Method used

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  • Perfluoroalkyl group modified solution-processable naphthalimide and preparation method thereof
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  • Perfluoroalkyl group modified solution-processable naphthalimide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1 N, N'-bis(2-perfluorohexyl-1-hexylethyl)naphthalimide (8a)

[0016]

[0017] Add compound 6 (0.268g, 1mmol), compound 5a (1.342g, 3mmol), DMF (15mL) in a 25mL two-necked flask, react at 145°C for 2.5h, cool to room temperature, neutralize with 2mol / L HCl, and CH 2 Cl 2 Extracted, washed with saturated brine, dried over anhydrous magnesium sulfate, suction filtered, rotary evaporated, dichloromethane and petroleum ether column separated to obtain white solid 8a (0.411g, 36.5%). 1 HNMR (400MHz, CDCl 3 )δ H :8.72-8.80(d,4H),5.68(m,2H),3.27-3.37(m,2H),2.21-2.57(m,4H),1.90-2.01(d,2H),1.21-1.31(m, 16H),0.82-0.84(m,6H);HRMS(MALDI-TOF):Calcd for C 42 h 36 f 26 N 2 o 4 1126.2260,found:1126.2278(M - ).

Embodiment 2

[0018] Example 2 N, N'-bis(2-perfluorobutyl-1-hexylethyl)naphthalimide (8b)

[0019]

[0020] Add compound 6 (0.801g, 3mmol), compound 5b (3.125g, 9mmol), DMF (30mL) in a 100mL two-necked flask, react at 145°C for 2.5h, cool to room temperature, neutralize with 2mol / L HCl, and use CH 2 Cl 2 Extracted, washed with saturated brine, dried over anhydrous magnesium sulfate, suction filtered, rotary evaporated, dichloromethane and petroleum ether column separated to obtain white solid 8b (1.281g, 40%). 1 HNMR (400MHz, CDCl 3 )δ H :8.73-8.80(d,4H),5.68(m,2H),3.29-3.37(m,2H),2.21-2.58(m,2H),1.91-2.01(d,2H),1.21-1.34(m, 16H),0.81-0.84(m,6H);HRMS(MALDI-TOF):Calcd for C 38 h 36 f 18 N 2 o 4 926.2388, found: 926.2396 (M - ).

Embodiment 3

[0021] Example 3 N, N'-bis(2-perfluorohexyl-1-butylethyl)naphthalimide (8c)

[0022]

[0023] Add compound 6 (0.536g, 2.102mmol), compound 5c (2.515g, 8.405mmol), DMF (15mL) in a 25mL two-necked flask, react at 130°C for 2.5h, cool to room temperature, neutralize with 2mol / L HCl, use CH 2 Cl 2 Extracted, washed with saturated brine, dried over anhydrous magnesium sulfate, suction filtered, rotary evaporated, dichloromethane and petroleum ether column separated to obtain white solid 8c (1.608g, 75%). 1 HNMR (400MHz, CDCl 3 )δ H :8.73-8.80(d,4H),5.67(m,2H),3.29-3.37(m,2H),2.21-2.58(m,4H),1.91-2.01(d,2H),1.21-1.34(m, 8H),0.82-0.85(m,6H);HRMS(MALDI-TOF):Calcd for C 38 h 28 f 26 N 2 o 4 1070.1634,found:1070.1656(M - ).

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Abstract

The invention discloses perfluoroalkyl group modified solution-processable naphthalimide and a preparation method thereof, the structural formula of the naphthalimide is shown by the formula A (the formula is shown in the description), wherein the R in the formula A represents perfluoroalkyl group substituent group, which is specifically shown as the formula B, and m is selected from 1, 2, 3, 4, 5 and 6; n is selected from 1, 3, 5 and 7; X is H, Cl or Br; the preparation method of the naphthalimide comprises the steps that halogenated 1,4,5,8-Naphthalenetetracarboxylic dianhydride and the perfluoroalkyl group are taken as the starting raw materials, the mole ratio is (1:1)-(1:10), in an organic solvent, the mixture is stirred for 1-24 h under the protection of argon or nitrogen in the temperature range from the room temperature to the backflow temperature of the used solvent, the 1,4,5,8-Naphthalenetetracarboxylic dianhydride and the perfluoroalkyl group are in reaction, and the perfluoroalkyl group modified naphthalimide is generated. According to the perfluoroalkyl group modified solution-processable naphthalimide and the preparation method thereof, the alkyl group and the perfluoroalkyl group are introduced simultaneously on the matrix of the naphthalimide, the solubility of the material in the organic solvent can be enhanced remarkably, and at the same time, the light and heat stability of the naphthalimide and the device stability of the naphthalimide in the field effect transistor are enhanced.

Description

technical field [0001] The invention belongs to the fields of organic chemical industry and fine chemical industry, and in particular relates to perfluoroalkyl-modified, solution-processable naphthalimide and a preparation method thereof. Background technique [0002] Compared with the widely used inorganic semiconductors, the advantages of organic semiconductor materials are as follows: suitable for low-cost solution processing; flexible wearable devices can be prepared; there are many types and properties, which are conducive to the design and development of new materials and new devices. [0003] Perfluoroalkyl groups have a rigid rod-like structure. Fluorine atoms and perfluoroalkyl compounds have extremely high stability, oxidation resistance and hydrophobicity, and fluorine atoms can also form intermolecular hydrogen bonds with adjacent hydrogen atoms to enhance the interaction between molecules (J.Am. Chem. Soc. 1969, 91, 6235-6237). Fluorine atoms or perfluoroalkyl...

Claims

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Application Information

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IPC IPC(8): C07D471/06
CPCC09B57/08C07D471/06
Inventor 袁忠义李超蔡春生陈士肖胡昱陈义旺
Owner NANCHANG UNIV
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