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A coumarin type organic third-order nonlinear optical material and preparation and application thereof

A third-order nonlinear and optical material technology, applied in the field of organic third-order nonlinear optical materials, to achieve low cost, great application value, and high two-photon absorption characteristics

Active Publication Date: 2019-05-21
SHANTOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, coumarin is rarely used in third-order nonlinear optical materials

Method used

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  • A coumarin type organic third-order nonlinear optical material and preparation and application thereof
  • A coumarin type organic third-order nonlinear optical material and preparation and application thereof
  • A coumarin type organic third-order nonlinear optical material and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] A kind of preparation of coumarin type organic nonlinear optical material A mainly comprises the following steps:

[0031] (1) Prepare the coumarin derivatives after bromination at the 6-position first:

[0032]

[0033] First react coumarin and liquid bromine in dichloromethane solution at room temperature for 48 hours, wash with a large amount of saturated sodium carbonate solution, extract with dichloromethane, remove excess solvent by rotary evaporator, use methanol recrystallization, filter and dry to obtain yellow Solid powder, the crude product was separated and purified on a 200-300 mesh silica gel column using dichloromethane-n-hexane (volume ratio 2:5) as the eluent to obtain a coumarin derivative after bromination at the 6-position.

[0034]

[0035] (2) Then prepare the coumarin derivatives substituted by p-position N,N-dimethylbenzene:

[0036] It mainly includes the following steps: take the coumarin derivative (500mg, 2.2mmol) after the bromination...

Embodiment 2

[0039] A kind of preparation of coumarin type organic nonlinear optical material B mainly comprises the following steps:

[0040] (1) According to the method of Example 1, the brominated coumarin derivative at the 6-position was prepared.

[0041] (2) Prepare the coumarin derivatives substituted by triphenylamine:

[0042]

[0043] It mainly includes the following steps: take the brominated coumarin derivative (500mg, 2.2mmol) at the 6th position, introduce the derivative of boric acid pinacol ester (927mg, 2.5mmol) at the 4th position of triphenylamine and K 2 CO 3 (133mg), dissolved with toluene ethanol mixed solution (3:1, 80ml). After passing nitrogen gas for 30 minutes, add 15 mg tetrakistriphenylphosphine palladium catalyst to the solvent, heat to 80°C, 1000r / min, and react for 8 hours. After the reaction, cool to room temperature, wash with a large amount of water, extract with dichloromethane, remove excess solvent with a rotary evaporator, add 100 mL of dichloro...

Embodiment 3

[0046] A kind of preparation of coumarin-based organic nonlinear optical material C, its reaction formula is as follows, mainly comprises the following steps:

[0047]

[0048] (1) According to the method of Example 1, the brominated coumarin derivative at the 6-position was prepared.

[0049] (2) Prepare the coumarin derivatives substituted by carbazole phenyl:

[0050] It mainly includes the following steps: taking the brominated coumarin derivative (500mg, 2.2mmol) at the 6th position, introducing the derivative of boric acid pinacol ester (922mg, 2.5mmol) at the 4th position on the carbazole phenyl group and K 2 CO 3 (133mg), dissolved with toluene ethanol mixed solution (3:1, 80ml). After passing nitrogen gas for 30 minutes, add 15 mg tetrakistriphenylphosphine palladium catalyst to the solvent, heat to 80°C, 1000r / min, and react for 8 hours. After the reaction, cool to room temperature, wash with a large amount of water, extract with dichloromethane, remove excess so...

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Abstract

The invention relates to a coumarin type organic third-order nonlinear optical material. An arylamine derivative is connected to the 6 site of a core group that is coumarin, and includes N,N-dimethylbenzene, triphenylamine and carbazole phenyl. Preparation mainly includes dissolving a coumarin derivative the 6 site of which is substituted with bromine, the arylamine derivative of bis(pinacolato)diboron and potassium carbonate into a solvent; feeding nitrogen for 30 min; adding a tetrakis(triphenylphosphine) palladium catalyst; heating the mixture to 80-100 DEGC, and reacting the mixture for 6-24 h, with the stirring speed being 1000-1200 r / min; performing multiple times of extraction with dichloromethane and distilled water and performing liquid separation and drying; and subjecting an obtained crude product to separation and purification. The arylamine derivative is introduced to the 6 site of the coumarin to form a large D-pi-A configuration, so that the nonlinear absorption coefficient and the two-photon absorption cross section value of coumarin molecules can be improved, and the disclosed material can be used as a third-order nonlinear optical material. The method is simple and easy to operate, raw materials are easily available and cheap, and the disclosed material has high application value.

Description

technical field [0001] The invention belongs to the field of organic third-order nonlinear optical materials, in particular to a coumarin-type organic third-order nonlinear optical material and its preparation and application in the third-order nonlinear optical field. Background technique [0002] Coumarin compounds are a class of substances with their own aromatic odor. These compounds have a benzopyrone structure and are widely distributed in plants in nature. They are a class of natural products with important functions. Due to the particularity of the coumarin ring structure, it can be structurally modified at many positions. According to the electron-withdrawing or electron-donating properties of the introduced modification group, the entire coumarin compound molecule can form a new electronic conjugated structure. In addition, there is a large conjugated system formed by C=C and C=O double bonds in the coumarin molecule itself, and the lactone structure in the coumari...

Claims

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Application Information

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IPC IPC(8): C07D311/18C07D405/10G02F1/361
Inventor 许良郑育森龙雪婷张文英鲁福身
Owner SHANTOU UNIV