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9,10-dihydroanthracene chromophore compound and its preparing process

A technology of dihydroanthracene and compound is applied in the field of chromophore compound and its preparation, which can solve the problems such as decrease in transmittance, and achieve the effects of good transmittance and large second-order nonlinear coefficient.

Inactive Publication Date: 2008-05-07
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] As a result, although the second-order nonlinear coefficient is improved, the absorption band moves to red, which reduces the transmittance of the material, that is, there is a contradiction between nonlinearity and transmittance.

Method used

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  • 9,10-dihydroanthracene chromophore compound and its preparing process
  • 9,10-dihydroanthracene chromophore compound and its preparing process
  • 9,10-dihydroanthracene chromophore compound and its preparing process

Examples

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Effect test

Embodiment 1

[0044] Example 1: Preparation of 4,5-dimethoxy-1,8-diformyl-9,10-dihydroanthracene (II) and its physical and chemical parameters.

[0045] In a 250mL four-necked bottle, add 30mL of chloroform solution containing 6-7mmol 1,1-dichloromethyl ether, pass N 2Protect, heat up to 40°C with electromagnetic stirring, and dropwise add 30 mL of chloroform solution containing 1 g (4 mmol) of compound I and 30 mL of chloroform solution containing 2.0 g of titanium tetrachloride at the same time using two dropping funnels, and continue stirring for 2 hours after the addition is complete. Cool to room temperature, pour the reaction solution into 500mL water, stir, filter, extract the liquid phase with chloroform, wash with water until neutral, separate the layers, dry with anhydrous sodium sulfate for 0.5 hours, filter, evaporate the solvent under reduced pressure, and wash with chloroform / Recrystallization from cyclohexane gave 1.34 g of compound II. Yield: 64%, melting point: 248-250°C ...

Embodiment 2

[0047] Embodiment 2: the preparation method of compound III1a, III1b and its physical and chemical parameters:

[0048] Add 0.3g (1.0mmol) of compound II into a 50mL three-neck flask filled with 10mL of absolute ethanol, pass through nitrogen protection, stir electromagnetically, and heat to reflux. Add 0.4g (2.90mmol) of compound 1A, add dropwise a 10mL absolute ethanol solution containing 5 drops of hexahydropyridine and 10 drops of acetic acid, and heat to reflux for 50 hours. Cool to room temperature, add 60 mL of chloroform, wash with water until neutral, and dry over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was separated by silica gel column chromatography (ethyl acetate:petroleum ether=1:10) to obtain a red solid, which was recrystallized from acetone / petroleum ether to obtain 0.066g / 0.034g of compound III1a / III1b, both It is a red crystal.

[0049] (III1a) productive rate: 14.4%; Melting point: 250~252 ℃; ...

Embodiment 3

[0051] Embodiment 3: the preparation method of compound III2a, III2b and its physical and chemical parameters:

[0052] In a 50mL three-necked flask, heat 0.3g (1.0mmol) of compound II in 20mL of absolute ethanol to reflux, after dissolving, add 0.64g (2mmol) of compound 2A, and after a few minutes, add dropwise 10mL containing 8 drops of hexahydro Pyridine and 16 drops of acetic acid in absolute ethanol. Heat to reflux for 60 hours. Cool to room temperature, add 75 mL of chloroform, wash with water until neutral, and dry over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was separated by column chromatography (ethyl acetate:petroleum ether=1:10 as eluent) to obtain a purple solid, which was recrystallized from acetone / petroleum ether to obtain 0.196g / 0.067g of compound III2a / III2b, all purple solids.

[0053] (III2a) Yield: 33.6%, melting point: 254-256°C. MS: m / e=599 [M + ]. 1 HNMR (300MHz, CDCl 3 ): δ(ppm)=10....

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Abstract

The present invention relates to relates to 9, 10-dihydro anthracene chromophore compound and its preparation. The preparation process includes the following steps: introducing two formyls with 1, 1-dichloromethyl ether as formylation reagent to the methoxyl para position of the material 1, 8-dimethoxyl-9, 10-dihydro anthracene under the catalysis of Lewis acid and titanium tetrachloride to obtain 4, 5-dimethoxyl-1, 8-diformyl-9, 10-dihydro anthracene; and the reflux reaction between 4, 5-dimethoxyl-1, 8-diformyl-9, 10-dihydro anthracene and isophorone -malononitrile condensate or isophorone -barbituric acid condensate in absolute alcohol as solvent in the catalysis of hexahydropyridine and acetic acid to obtain the organic compound. The compound of the present invention has high second-order non-linear coefficient and excellent transmittancy and may be used as second-order non-linear optical material, especially laser frequency doubling material.

Description

1. Technical field [0001] The invention relates to a chromophore compound and a preparation method thereof, in particular to a 9,10-dihydroanthracene chromophore compound and a preparation method thereof. 2. Background technology [0002] Ordinary light interacts with matter, and the induced electric susceptibility of its molecules is proportional to the electric field intensity of light. When sufficiently strong light, such as laser light, interacts with matter, the induced electric susceptibility of its molecules is no longer proportional to the electric field strength of the light, but has become a nonlinear function relationship: [0003] p=αE+βE 2 +γE 3 +… [0004] Similarly, the electric polarization of a macroscopic material can be expressed as follows: [0005] P=X (1) E+X (2) E. 2 +X (3) E. 3 +… [0006] P and p are the electrical polarization of macroscopic materials and microscopic molecules, X (1) and α are linear polarization coefficients, X (2) and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/58C09B1/02
Inventor 陆国元施证伟张超智李英
Owner NANJING UNIV
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