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Second-order non-linear optical chromophore containing trianilino group and its synthesis process

A second-order nonlinear, triphenylamine-based technology, applied in the field of D-π-A type second-order nonlinear optical chromophore and its synthesis, can solve the problems of long response time, easy damage, limited application, etc., and achieve high heat The effect of decomposition temperature

Inactive Publication Date: 2007-01-03
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Such materials have good comprehensive physical and chemical properties, such as easy growth of large-sized single crystals, high chemical stability, good optical uniformity, and phase matching, etc., but the polarization of inorganic materials is caused by lattice distortion, and the response time Long, and the nonlinear coefficient is not high enough, easy to dehydrate, deliquescence, easy to damage when interacting with laser, etc., which limits its practical application

Method used

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  • Second-order non-linear optical chromophore containing trianilino group and its synthesis process
  • Second-order non-linear optical chromophore containing trianilino group and its synthesis process
  • Second-order non-linear optical chromophore containing trianilino group and its synthesis process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Example 1: Synthesis of (4-((4-(4-nitrostyryl)phenyl)anilino)phenyl)methanol.

[0058] 1) 17.5ml of phosphorus oxychloride and 13.8g of N,N-dimethylformamide were mixed and stirred in an ice-water bath for 30 minutes, and then 10g of triphenylamine was added. Under the protection of nitrogen, the temperature was raised to 85° C., and the reaction was carried out for 12 hours. After the reaction solution was cooled to room temperature, it was poured into ice-water mixture and stirred vigorously. After the ice cubes melted, 10% NaOH solution was added drop by drop to adjust the pH value to neutral, and placed until a large amount of precipitation occurred. It was extracted with dichloromethane, and the extract was dried with magnesium sulfate and then rotary evaporated to obtain a black-green oily viscous liquid. Peroxide a short column after dissolving in toluene. Concentrate the toluene solution and leave it overnight, filter the solid precipitate and recrystallize t...

Embodiment 2

[0061] Example 2: Synthesis of 3-(4-((4-hydroxymethylphenyl)anilino)phenyl)-2-(4-nitrophenyl)acrylonitrile.

[0062] 1) Prepare 4-((4-hydroxymethylphenyl)phenylamino)benzaldehyde with steps 1) and 2) of Example 1.

[0063] 2) 2.5g of 4-((4-hydroxymethylphenyl)phenylamino)benzaldehyde and 1.7g of p-nitrophenylacetonitrile were mixed and dissolved in 20ml of pyridine, and several drops of piperidine were added for catalysis. The reaction solution was heated to 120°C, reacted for 6 hours under the protection of nitrogen, cooled, poured into the ice-water mixture, extracted with 50ml of dichloromethane after the ice was dissolved, and the extract was repeatedly washed with water and dried. The crude product was subjected to column chromatography with dichloromethane as eluent, and then recrystallized in ethanol to obtain pure chromophore 3-(4-((4-hydroxymethylphenyl)anilino)phenyl)-2- (4-nitrophenyl)acrylonitrile. Yield: 53%. 1 H NMR (500MHz, CDCl 3 , δppm): δ1.69 (s, 2H, -Ph-...

Embodiment 3

[0064] Example 3: 2-(3-(4-((4-hydroxymethylphenyl)anilino)styryl)-5,5-dimethylcyclohexen-2-enylidene)malononitrile Synthesis.

[0065] 1) Prepare 4-((4-hydroxymethylphenyl)phenylamino)benzaldehyde with steps 1) and 2) of Example 1.

[0066] 2) Take 16.5ml of 3,5,5-trimethylcyclohexene-2-enone, dissolve 6.6g of malononitrile in 55ml of N,N-dimethylformamide, add 1.8ml of piperidine , 0.4ml of acetic acid and 0.2g of acetic anhydride as catalysis, stirred at room temperature for 2 hours, heated to 120°C under nitrogen protection, and reacted for 12 hours. After cooling to room temperature, the reaction mixture was poured into 500ml of deionized water, and the crude product was collected by suction filtration and washed with brine, treated with boiling water, and separated by column chromatography (ethyl acetate / petroleum ether=1:12) to obtain light brown solid 2-(3,5,5-trimethylcyclohexene-2-enylidene ) malononitrile. Yield: 56%. 1 H NMR (500MHz, CDCl 3 , δppm): δ1.04(s, 6H...

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Abstract

The second-order non-linear optical cromophore containing trianilino group has the structural expression as shown. The second-order non-linear optical cromophore containing trianilino group is prepared in a mild process with compound triphenylamine as main material and through formylation, aldehyde group reduction and final heated reaction with acceptor molecule containing active methylene group. It has high thermal decomposition temperature, may be bonded with polymer or inorganic 3D network, and may have changeable polarizability and absorption peak.

Description

technical field [0001] The invention relates to a D-π-A type second-order nonlinear optical chromophore containing a triphenylamine group and a synthesis method thereof. Background technique [0002] When a high-energy laser propagates in a medium, the strong light first induces a nonlinear response in the medium, and then the medium changes the light field nonlinearly when it produces a reaction, so that the phase, frequency, amplitude or other transmission of the outgoing light This phenomenon belongs to the phenomenon of nonlinear optics (NLO). Nonlinear optics is the science of studying the interaction that modulates light, which reflects the basic law of the interaction between the medium and the intense laser beam. Nonlinear optical phenomena are of great significance both in theory and in applications. Therefore, the development of various nonlinear optical materials has become a frontier research field across the century, and plays an important role in information p...

Claims

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Application Information

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IPC IPC(8): C07C255/42C07D307/56C07D253/00
Inventor 钱国栋陈鹭剑崔元靖高俊阔金学峰王智宇邱建荣樊先平洪樟连王民权
Owner ZHEJIANG UNIV
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