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Benzoperylene imide derivatives, and preparation method and application thereof

A technology of benzoperyleneimide and its derivatives, which is applied in the field of benzoperyleneimide derivatives and its preparation, can solve the problems that the value of blue light radiation absorption has not been developed and applied, and the synthesis route has not been comprehensively summarized.

Inactive Publication Date: 2015-04-29
FUZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Although there have been reports on the synthesis of benzoperyleneimide at home and abroad (J. Phys. Chem. A 2012, 116, 15031509; Chem. Eur. J. 2012, 18, 13188–13194), they have not been comprehensively summarized The synthetic route of derivatives containing different substituents, more importantly, the value of this series of compounds for the absorption of blue light radiation has not been developed and applied

Method used

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  • Benzoperylene imide derivatives, and preparation method and application thereof
  • Benzoperylene imide derivatives, and preparation method and application thereof
  • Benzoperylene imide derivatives, and preparation method and application thereof

Examples

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Embodiment 1

[0032] Example 1 N,N-bis(2,6-diisopropylphenyl)-1,2,4,5,10,11-benzoperylenehexacarboxylic acid-1,2-anhydride-4,5,10,11 -Synthesis of imides

[0033] 1) Add 1g (2.55mmol) 3,4,9,10-perylenetetracarboxylic dianhydride (compound 1), 2mL (10.6mmol) 2,6-diisopropylaniline and 7g imidazole into a single-necked flask, mix well Then react at 130°C for 24 h under the protection of argon, and after cooling to room temperature, pour the reaction solution into a mixed solution of 50 mL ethanol and 60 mL 2M hydrochloric acid, filter with suction, wash the obtained solid with water twice, and then wash it with saturated NaHCO 3 The solution was washed twice, then washed with water until neutral, dried in a vacuum oven at 85°C and purified by silica gel column chromatography. 1 g of the obtained solid was added to 2 mL (10.6 mmol) of 2,6-diisopropylaniline and 7 g of Repeat the steps after imidazole to obtain 1.2 g dark red solid (compound 2), yield 66%;

[0034] 2) After preheating 20g...

Embodiment 2

[0035] Example 2 N,N-bis(2,6 diisopropylphenyl)-N-(3-trimethylsiloxypropyl)-1,2,4,5,10,11-benzoperylenehexacarboxy Synthesis of acid imides

[0036]

[0037] After compound 3 was prepared according to the method described in Example 1, 0.4 g (0.5 mmol) of compound 3 was placed in a single-necked flask filled with 1 mL (3-aminopropyl)-trimethoxysilane, and stirred under argon protection After 5 minutes, the temperature was raised to 130° C. to continue the reaction for 30 hours under the protection of argon. After cooling to room temperature, the reaction mixture was dispersed in 20 mL of petroleum ether and filtered, the solid was redispersed in petroleum ether and filtered again, and the resulting compound 4 was immediately dissolved in chloroform to avoid the formation of polymers.

Embodiment 3

[0038] Example 3 N,N-bis(2,6 diisopropylphenyl)-N-(3-isopropoxypropyl)-1,2,4,5,10,11-benzoperylene hexacarboxylic acid imide Amine Synthesis

[0039]

[0040] After compound 3 was prepared according to the method described in Example 1, 0.4 g (0.5 mmol) of compound 3 was placed in a single-necked flask containing 20 mL of propionic acid, 0.6 mL (4.3 mmol) of 3-isopropoxypropylamine was added, and It was stirred for 5 min under the protection of argon, and then the temperature was raised to 130° C. to continue the reaction under the protection of argon for 30 h. After cooling to room temperature, the reaction mixture was poured into a large amount of water, filtered with suction, and the obtained solid was washed twice with water, and then washed with saturated NaHCO 3 The solution was washed twice with water until neutral, dried in a vacuum oven at 85°C and purified by silica gel column chromatography to obtain 0.41 g of a yellow solid (compound 5), with a yield of 95%...

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Abstract

The invention discloses benzoperylene imide derivatives, and a preparation method and application thereof. The structural formula of the benzoperylene imide derivatives is disclosed in the specification. The benzoperylene imide derivatives are prepared by carrying out multiple reactions on the initial raw material 3,4,9,10-perylene tetracarboxylic acid anhydride. The benzoperylene imide derivatives have strong blue light absorptivity, the molar absorption coefficient at the maximum absorption wavelength reaches 50000 mol<-1>cm<-1> above, the benzoperylene imide derivatives have no absorption in other visible light regions within the range of 500-800nm; and the spectrum properties of the derivatives can be utilized to prepare the blue light absorbing material which is applicable to the field of daily high-energy short-wave radiation prevention, such as mobile phone screen anti-blue-light coatings, eyeglass anti-blue-light coatings, paper anti-blue-light painting and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthetic materials, and in particular relates to a benzoperyleneimide derivative with blue light absorption properties and a preparation method and application thereof. Background technique [0002] Perylene imide is one of the hot research materials in the past 20 years, and is widely used in many frontier fields such as organic semiconductor materials, organic optical materials, organic field effect transistors, and molecular switches (J. Am. Chem. Soc. 2003, 125 , 437-443; Adv. Mater. 2009, 21, 1573–1576; Angew. Chem. 2008,120,935-937; Adv.Func.Mater.,2005,15,1617-1622). The structure of perylene imide has the following characteristics: 1) a large π conjugated system with a large plane; 2) good structural stability, and can withstand high temperature and high pressure. On the basis of the perylene imide structure, adding an electron-withdrawing aromatic ring in its Bay region can greatly impr...

Claims

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Application Information

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IPC IPC(8): C07D491/16C07D471/16C07F7/18
CPCC07D471/16C07D491/16C07F7/1804C07F7/1892
Inventor 陈勇洪宇健陈守雄焦晨
Owner FUZHOU UNIVERSITY
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