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Organic second-order nonlinear optical chromophore having double-donor structure, and synthesis method and application thereof

A second-order nonlinear and chromophore technology, which is applied in the field of organic second-order nonlinear optical chromophore and its synthesis, can solve the problem of low polarization efficiency, failure to meet device requirements, and low electro-optic coefficient And other issues

Inactive Publication Date: 2017-09-29
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these chromophores are all single-donor chromophores, and there are almost no reports on double-donor chromophores, and most of the structures are rod-like structures. During the chemicalization process, the rod-like structure is easy to aggregate, resulting in low polarization efficiency, and the electro-optic coefficient (r33) of the microscopic first-order molecular hyperpolarizability (β) converted into a macroscopic material is low, which cannot meet the requirements of deviceization.

Method used

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  • Organic second-order nonlinear optical chromophore having double-donor structure, and synthesis method and application thereof
  • Organic second-order nonlinear optical chromophore having double-donor structure, and synthesis method and application thereof
  • Organic second-order nonlinear optical chromophore having double-donor structure, and synthesis method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0055] An organic second-order nonlinear optical chromophore with a dual-donor structure was synthesized as shown below:

[0056]

[0057] The synthetic route is as follows (formula 1):

[0058]

[0059] The synthesis method is:

[0060] S1: Synthesis of compound 2 shown in (Formula 1)

[0061] 3.25g (10mmol) tetraethyl Michler's ketone was added to redistilled THF, and then 0.95g (25mmol) NaBH 4 Add in batches, react at room temperature for 12h, after the reaction is completed, pour the reaction product into 100ml deionized water; then extract with ethyl acetate, and use anhydrous MgSO 4 The organic phase was dried, and ethyl acetate was removed by rotary evaporation to obtain 2.85 g of compound 2. The compound 2 is a white solid. This alcohol is unstable, and the next reaction should be carried out as soon as possible.

[0062] S2: Synthesis of compound 3 shown in (Formula 1):

[0063] 2.78g (8.53mmol) of compound 2 and 9ml (54mmol) of triethyl phosphate were fir...

Embodiment 2

[0079] An organic second-order nonlinear optical chromophore with a dual-donor structure was synthesized as shown below:

[0080]

[0081] The synthetic route is as follows:

[0082]

[0083] The synthesis method is:

[0084] S11: Synthesis of Compound 2 shown in (Formula 2)

[0085] N 2 Under protection, 0.48g (0.02mol) of sodium hydride (NaH) was dissolved in an appropriate amount of redistilled THF, cooled to 0 degrees in an ice-salt bath, and 3.26g (0.02mol) of cyanomethylphosphoric acid was added dropwise at this temperature ester, when the solution becomes clear, add 3.24g (0.01mol) of tetraethyl Michler's ketone, then heat to reflux for 12h, pour the reaction result into 100ml deionized water; then extract with ethyl acetate, and use anhydrous MgSO 4 The organic phase was dried, ethyl acetate was removed by rotary evaporation, and 2.25 g of compound 2 was obtained by column chromatography. The compound 2 is a yellow solid.

[0086] MS (MALDI-TOF), m / z: 347.2...

Embodiment 3

[0101] synthetic polymer film

[0102] (1) Add 0.075g of amorphous polycarbonate (APC) into 1.00mL of dibromomethane, stir for 3-5h until APC is completely dissolved, then add 0.025g of the organic second-order nonlinear optical chromophore synthesized in Example 1 (YH 3 ), to obtain the mixed solution of organic second-order nonlinear optical chromophore compound and APC, the mixed solution obtained is coated with spin coating method on the ITO glass substrate (controlling speed is 800~1200 revs / min), then at 60 °C in a vacuum oven for 24 hours to obtain a polymer film I. The thickness of the polarized polymer film is 2-4 μm.

[0103] (2) Add 0.075g of amorphous polycarbonate (APC) into 1.00mL of dibromomethane, stir for 3-5h until APC is completely dissolved, then add 0.025g of the organic second-order nonlinear optical chromophore synthesized in Example 2 (YH 4 ) to obtain a mixed solution of organic second-order nonlinear optical chromophore compound and APC, which is ...

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Abstract

The invention provides an organic second-order nonlinear optical chromophore having a double-donor structure. The organic second-order nonlinear optical chromophore having the double-donor structure has a structure as shown below in the specification, wherein R1 is methyl or trifluoromethyl; and R2 is alkyl or phenyl. After an electron donor having the double-donor structure, a conjugate pi electron bridge and an electron acceptor, which are used by the invention, are combined together, the intramolecular electron transmission capability is enhanced, and the electrooptic coefficient can be increased. Besides, the synthesized chromophore has the double-donor structure, thereby effectively reducing the intermolecular interaction force. The organic second-order nonlinear optical chromophore is doped with amorphous polycarbonate to realize synthesis of a polymer film, and the polymer film can be used as a synthetic optical signal modulation 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 double-donor structure and its synthesis method and application. Background technique [0002] With the rapid development of the information age, the requirements for communication and information materials are getting higher and higher at this stage. Nonlinear optical materials have attracted research interest in recent decades due to their great application prospects in practical fields such as optical communication, optoelectronics, and optical information processing. At present, the second-order nonlinear optical materials that have been commercialized are mainly inorganic materials, but inorganic materials have defects such as small electro-optical coefficients and long response times, which limit their wide application. It has been found that organic nonlinear optical materials have...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/06C08L69/00C08K5/45C08J5/18G02F1/361
CPCC07D409/06C08J5/18C08J2369/00C08K5/45C08L2203/16G02F1/3611G02F1/3615C08L69/00
Inventor 刘新厚杨玉慧甄珍薄淑晖邱玲
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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