Perylene diimide organic third-order nonlinear optical material, and preparation and application of perylene diimide organic third-order nonlinear optical material

A third-order nonlinear, perylene imide-based technology, applied in nonlinear optics, luminescent materials, organic chemistry, etc., to achieve the effects of easy operation, large nonlinear absorption coefficient, and high two-photon absorption characteristics

Inactive Publication Date: 2017-06-23
SHANTOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The object of the present invention is to provide a perylene imide based organic nonlinear optical material and its preparation to solve the existing problems

Method used

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  • Perylene diimide organic third-order nonlinear optical material, and preparation and application of perylene diimide organic third-order nonlinear optical material
  • Perylene diimide organic third-order nonlinear optical material, and preparation and application of perylene diimide organic third-order nonlinear optical material
  • Perylene diimide organic third-order nonlinear optical material, and preparation and application of perylene diimide organic third-order nonlinear optical material

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Experimental program
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Embodiment 1

[0034] The preparation of a peryleneimide-based organic nonlinear optical material mainly includes the following steps:

[0035] First prepare the perylene imide derivatives substituted by cyclohexane, the reaction formula is as follows:

[0036]

[0037] Then use the peryleneimide derivatives substituted by cyclohexane to react with the benzoanthrone derivatives that introduce boric acid pinacol ester at the 3rd position, and the reaction formula is as follows:

[0038]

[0039] It mainly includes the following steps: take the peryleneimide derivative (500mg, 0.76mmol) substituted by cyclohexane, introduce the benzanthrone derivative (315mg, 0.92mmol) of boric acid pinacol ester at the 3rd position and K 2 CO 3 (133mg), dissolved with toluene-ethanol mixed solution (volume ratio 3:1, 80mL). After passing nitrogen gas for 30 minutes, add 15 mg tetrakistriphenylphosphine palladium catalyst to the solvent, heat to 80° C., 1000 r / min, and react for 5 hours. Cool to room ...

Embodiment 2

[0042] A kind of preparation of perylene imide-based organic nonlinear optical material, its reaction formula is as follows:

[0043]

[0044]It mainly includes the following steps: take compound A (92mg, 0.12mmol) and dissolve it in 100ml of dichloromethane, transfer it to a quartz beaker, and place it under outdoor sunlight. The progress of the light reaction was observed by thin-layer chromatography. Due to the poor solubility of compound B, compound B after light-closing rings formed flocs, which were suspended or sank at the bottom of the beaker. The ring-closed Compound B was collected by filtration through micropores. Compound B was obtained after 24 hours as Figure 4 As shown, 3,4,9,10-perylenetetracarboximide is used as the core group, and cyclohexane and benzanthrone are used as substituent groups; two cyclohexanes are respectively connected at 3,4 ,9,10-Perylenetetracarboximide is fused to the bay position of 3,4,9,10-perylenetetracarboximide on the imide nitr...

Embodiment 3

[0047] A kind of preparation of perylene imide-based organic nonlinear optical material, the reaction formula is as follows:

[0048]

[0049] It mainly includes the following steps: taking perylene imide derivatives (0.356g, 0.5mmol) and triphenylamine derivatives (0.445g, 1.2mmol) and dissolving them in 40ml of tetrahydrofuran. Add 20ml of 2M potassium carbonate solution, treat with nitrogen for 30min, add tetrakistriphenylphosphine palladium catalyst 15mg, heat to 80°C, 1000r / min, and react for 24 hours. After cooling, it was extracted several times with dichloromethane and water, and the organic phase was removed with anhydrous sodium sulfate, separated, and dried. The crude product was separated and purified with a 200-300 mesh silica gel column, dichloromethane-n-hexane (volume ratio 1:3) mixed solvent eluent, to obtain compound C such as Figure 5 As shown, 3,4,9,10-perylenetetracarboximide is used as the core group, and cyclohexane and triphenylamine are used as su...

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Abstract

The invention relates to a perylene diimide organic third-order nonlinear optical material. 3,4,9,10-perylenetetracarboxylic diimide serves as a core group; cyclohexane and benzanthrone or triphenylamine serve as substituent groups; cyclohexane is connected with an imide nitrogen atom of the core group; and benzanthrone or triphenylamine is connected with a bay of the core group to form a whole. A preparation method comprises the steps: (1) adding a perylene diimide derivative, a benzanthrone derivative or a triphenylamine derivative with the imide nitrogen atom connected with cyclohexane, and potassium carbonate into a solvent for dissolution, (2) after supplying nitrogen for 1-30 min, adding a tetrakispalladium catalyst, heating to 80-100 DEG C at a speed of 500-1200 r/min for reaction for 3-24h , (3) carrying out extraction, knockout and dryness for many times by using dichloromethane and distilled water, and (4) separating and purifying an obtained crude product. The perylene diimide organic third-order nonlinear optical material has a large nonlinear absorption coefficient and a two-photon absorption cross-section value and is applied to a third-order nonlinear optical material aspect.

Description

technical field [0001] The invention belongs to the field of organic nonlinear optical materials, especially the field of third-order nonlinear optical materials. It designs a peryleneimide-based organic third-order nonlinear optical material and its preparation and application in the field of third-order nonlinear optics. Background technique [0002] Perylene imide is a common organic chromophore with strong and broad absorption band in the visible region, and perylene imide has high fluorescence quantum yield, large charge mobility, photothermal stability and chemical stability it is good. In addition, perylene imide has a large co-benzene ring planar structure and two imine ring structures, has high electron affinity potential energy and strong electron-accepting ability, and is often used as an electron acceptor group. When the peryleneimide group is linked with an electron-donor group, the overall nonlinear properties are greatly enhanced. Peryleneimide groups are wi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C09K11/06G02F1/361
CPCC07D471/06C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029G02F1/3612
Inventor 许良曹柳方子林郑育森鲁福身黄晓春
Owner SHANTOU UNIV
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