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Organic second-order nonlinear optical chromophore, synthetic method and application

A second-order nonlinear and chromophore technology, which is applied in the field of organic second-order nonlinear optical chromophores and their synthesis, can solve the problems of large intermolecular interactions, low polarization efficiency, and low solubility of polymer bases. question

Inactive Publication Date: 2017-01-04
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these chromophores are easy to aggregate in the polymer due to the large intermolecular interaction force, resulting in low solubility in the polymer base, low polarization efficiency, and small electro-optic coefficients, which cannot meet the requirements device requirements

Method used

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  • Organic second-order nonlinear optical chromophore, synthetic method and application
  • Organic second-order nonlinear optical chromophore, synthetic method and application
  • Organic second-order nonlinear optical chromophore, synthetic method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Synthesize the organic second-order nonlinear optical chromophore of D-π-A structure as shown below, it has formula (CL) structure:

[0081]

[0082] The synthetic route is as follows:

[0083]

[0084] The synthesis method is:

[0085] 1) Synthesis of compound 1 shown in the formula

[0086] Add 3.86g (0.02mol) 4-(diethylamino)-2-hydroxybenzaldehyde, 3.60g (0.03mol) 1-chlorohexane and 60mL redistilled N,N-dimethylformaldehyde into a 100mL glass three-neck flask Amide, add 4.14g (0.03mol) of dried anhydrous potassium carbonate, reflux for 12 hours under nitrogen protection, observe the reaction progress by thin layer chromatography (TLC), cool and filter to remove potassium carbonate after the raw material point almost disappears, pour into 250mL saturated In salt water, extract with ethyl acetate, dry over night with anhydrous magnesium sulfate, filter, remove ethyl acetate by rotary evaporation, and separate the residue by column chromatography (using 200-300 ...

Embodiment 2

[0105] Synthesize an organic second-order nonlinear optical chromophore with the D-π-A structure shown below, formula (HCL1):

[0106]

[0107] The synthetic route is as follows:

[0108]

[0109] The synthesis method is:

[0110] 1) Synthesis of compound 1 shown in the formula

[0111] Add 2.73g (0.01mol) 8-hydroxy-1,1,7,7-tetramethyljulonidine-9-carbaldehyde and 2.33g (0.015mol) 1,6-dichlorohexyl to a 100mL glass three-neck flask Alkanes and 40mL redistilled N,N-dimethylformamide, added 2.07g (0.015mol) of dried anhydrous potassium carbonate, refluxed for 12 hours under the protection of nitrogen, and observed the reaction progress by thin layer chromatography (TLC). After almost disappearing, it was cooled and filtered to remove potassium carbonate, poured into 250mL saturated saline, extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered, and rotary evaporated to remove ethyl acetate, and the residue was separated by column chromatography...

Embodiment 3

[0127] Synthesize an organic second-order nonlinear optical chromophore with the D-π-A structure shown below, formula (HCL2):

[0128]

[0129] The synthetic route is as follows:

[0130]

[0131] The synthesis method is:

[0132] 1) The synthesis of compound 1 shown in the formula is the same as in Example 2.

[0133] 2) Synthesis of compound 2 shown in the formula

[0134] Add 10.30g of triphenylphosphine hydrogen bromide (0.03mol), 4.98g (0.033mol) of 4-(dimethylamino)benzyl alcohol, and 200mL of chloroform dried with magnesium sulfate into a 250mL flask, and heat to reflux for 3-4 hours , spin dry. Add a small amount of chloroform to dissolve, pour into a large amount of anhydrous ether, and filter with suction to obtain a white solid with a yield of 95%.

[0135] 3) Synthesis of compound 3 shown in the formula

[0136] In a 100mL flask, add 3.92g (0.01mol) of compound 1 and 5.24g (0.011mol) of compound 2 (phosphine salt) in a molar ratio of 1:1.1 and dissolve t...

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Abstract

The invention discloses an organic second-order nonlinear optical chromophore, a synthetic method and an application. The organic second-order nonlinear optical chromophore is provided with a structure of a Formula (CL) or Formula (HCL): FORMULA, wherein G is H, para-alkoxyphenyl, thienyl, or para-dialkyl aminophenyl; R1 is alkyl, benzyl, and halogenated alkyl; R2 is methyl or trifluoromethyl; R3 is alkyl, phenyl, replaced phenyl, replaced thienyl or hydroxyalkyl. The organic second-order nonlinear optical chromophore with D-Pi-A structure has simple synthetic step and high preparation yield; besides, it has good solubility in the most organic solvent and high thermal stability; the organic second-order nonlinear optical chromophore can be widely applied to the field of optical information material.

Description

technical field [0001] The invention relates to the field of organic second-order nonlinear optical materials, in particular to an organic second-order nonlinear optical chromophore with a D-π-A structure and its synthesis method and application. Background technique [0002] With the advancement of science and technology and the rapid development of society, people have put forward higher and higher requirements for the amount of information and the speed of information dissemination. For now, the information processing, transmission and storage of up to terabits (Tb, ie 1012bits), the ultra-high-speed information flow of terabits per second (Tb / s) and the high-frequency (THz) response are very important to the current information transmission technology. posed serious challenges. With the rapid development of the information age, the requirements for communication and information materials are getting higher and higher at this stage. In the optoelectronic industry, such ...

Claims

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Application Information

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IPC IPC(8): C07D409/08C07D471/04C09K11/06C08J5/18C08L69/00C08K5/45
CPCC07D409/08C07D471/04C08J5/18C08L69/00C09K11/06C09K2211/1007C09K2211/1092C08K5/45
Inventor 薄淑晖胡超磊陈卓甄珍刘新厚
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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