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Organic second-order nonlinear optical chromophore with D-pi-A structure and its synthesis method and use

A technology of second-order nonlinearity and synthesis method, which is applied in the field of organic second-order nonlinearity and can solve the problems of low solubility, large intermolecular interaction force, and small electro-optic coefficient.

Active Publication Date: 2015-04-29
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, due to the large intermolecular interaction force in the polymer, these chromophores have low solubility in the polymer base and are easy to aggregate, resulting in low polarization efficiency and small electro-optic coefficients, which cannot be well Meet the requirements of deviceization

Method used

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  • Organic second-order nonlinear optical chromophore with D-pi-A structure and its synthesis method and use
  • Organic second-order nonlinear optical chromophore with D-pi-A structure and its synthesis method and use
  • Organic second-order nonlinear optical chromophore with D-pi-A structure and its synthesis method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0126] An organic second-order nonlinear optical chromophore with a D-π-A structure was synthesized as shown below:

[0127]

[0128] The synthetic route is as follows:

[0129]

[0130] 1) Synthesis of compound 1 represented by 1 in the formula

[0131] Add 2.72g (0.01mol) 8-hydroxyl-1,1,7,7-tetramethyljulonidine-9-carbaldehyde, 2.05g (0.015mol) 6-chloro-1-hexyl to a 50mL glass three-neck flask Alcohol and 30mL redistilled N,N-dimethylformamide, in N 2 Add 1.7g (0.012mol) of dried anhydrous potassium carbonate under protection, react overnight at 120°C, cool down after the reaction, remove potassium carbonate by filtration, pour the filtrate into water to obtain a dark blue solution, and extract it three times with ethyl acetate , combine the organic phases, dry the combined organic phases with anhydrous magnesium sulfate overnight, filter, and remove ethyl acetate by rotary evaporation, and the residue is separated by column chromatography (using 200-300 mesh silica ...

Embodiment 2

[0154] An organic second-order nonlinear optical chromophore with a D-π-A structure was synthesized as shown below:

[0155]

[0156] The synthetic route is as follows:

[0157]

[0158] Compound 1 represented by 1 in the formula, compound 2 represented by 2 in the formula, compound 3 represented by 3 in the formula, compound 4 represented by 4 in the formula and compound 5 represented by 5 in the formula Synthesis and embodiment 1 same.

[0159] 1) Synthesis of compound 6 shown in the formula

[0160] Dissolve 5.4g (75mmol) ethyl vinyl ether in 25ml redistilled tetrahydrofuran under N 2 Cool to -85°C under protection, add 38.5ml (1.3M, 50mmol) tert-butyllithium n-hexane solution dropwise; After keeping at -15°C for 30-60 minutes, cool down to -80°C, add dropwise 5ml of THF solution in which 2.8g (25mmol) trifluoroacetophenone was dissolved at this temperature, and keep at this temperature for 40 minutes after the dropwise addition , then allowed to heat up naturally...

Embodiment 3

[0169] An organic second-order nonlinear optical chromophore with a D-π-A structure was synthesized as shown below:

[0170]

[0171] The synthetic route is as follows:

[0172]

[0173] 1) Synthesis of compound 3 shown in the formula

[0174] Dissolve 1 equivalent of compound 1 and 1.5 equivalents of compound 2 in an appropriate amount of redistilled DMF, and add 1.2 equivalents of K 2 CO 3 (dried in a muffle furnace for more than 4 hours), at N 2 Stir the reaction overnight at 110°C under protection; 2 Cool to room temperature under protection, pour it into deionized water and stir, the mixture is extracted with ethyl acetate, the organic phases are combined, washed with saturated NaCl, anhydrous MgSO 4 The combined organic phases were dried overnight, filtered, and ethyl acetate was removed by rotary evaporation, purified by column chromatography (the volume ratio of petroleum ether: acetone was 400:50), and a yellow solid was obtained after drying with a yield of...

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Abstract

The invention relates to the field of organic second-order nonlinear optical materials and especially relates to an organic second-order nonlinear optical chromophore which has a D-pi-A structure and utilizes julolidine or its derivative as an electron donor, a thiophene ring or a cyclic polyene structure as a conjugate electron bridge and tricyano-dihydro furan or trifluoro-substituted tricyano-dihydro furan as an electron acceptor, and its synthesis method and use. Through combination of the used electron donor, conjugate pi electron bridge and electron acceptor, the organic second-order nonlinear optical chromophore can improve an intramolecular electron transfer capability and improve intermolecular steric hindrance. The organic second-order nonlinear optical chromophore can effectively improve a chromophore molecule first-order hyperpolarization rate (beta) and can effectively reduce intermolecular interaction. The organic second-order nonlinear optical chromophore adopted with amorphous polycarbonate can be used for preparation of a polarized polymer film. The polarized polymer film can be used as a material in the optical signal modulation field. The organic second-order nonlinear optical chromophore has a structure shown in the following description.

Description

technical field [0001] The invention relates to the field of organic second-order nonlinear optical materials, in particular to an electron donor using julonidine or its derivatives, a thiophene ring or a cyclopolyene structure as a conjugated electron bridge, and tricyanodihydrofuran (TCF) or trifluoro-substituted tricyanodihydrofuran (CF 3 -TCF) is an electron acceptor organic second-order nonlinear optical chromophore with D-π-A structure and its synthesis method and application. Background technique [0002] With the development of the information age, the requirements for communication and information materials are getting higher and higher at this stage. Due to problems such as low transmission efficiency and poor heat dissipation, microelectronic integrated circuits have been gradually replaced by optoelectronic technologies that integrate optics, electronics, and materials science. Optoelectronics technology can use electro-optic and photoelectric conversion, and a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18C07D471/10C08L69/00C08K5/5419C08K5/45G02F1/37G02F1/355
Inventor 甄珍张艾蕊薄淑晖张茂林吴杰云刘新厚邱玲
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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