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Second-order nonlinear optical chromophore having D-pi-A structure and treating julolidine derivative as donor, and synthetic method and use thereof

A second-order nonlinear and julolidine technology, which is applied to the second-order nonlinear optical chromophore having a D-π-A structure and the synthesis and application fields of a julolidine derivative as a donor, and can Solve the problems of low solubility of polymer base, low polarization efficiency, and large interaction force, and achieve the effects of high preparation yield, reduced interaction force, and high thermal decomposition temperature

Inactive Publication Date: 2013-01-16
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 have low solubility in the polymer base due to the large intermolecular interaction force in the polymer, the polarization efficiency is not high, and the electro-optic coefficient is relatively small.

Method used

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  • Second-order nonlinear optical chromophore having D-pi-A structure and treating julolidine derivative as donor, and synthetic method and use thereof
  • Second-order nonlinear optical chromophore having D-pi-A structure and treating julolidine derivative as donor, and synthetic method and use thereof
  • Second-order nonlinear optical chromophore having D-pi-A structure and treating julolidine derivative as donor, and synthetic method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] An organic second-order nonlinear optical chromophore with a D-π-A structure was synthesized as shown below:

[0047]

[0048] The synthetic route is as follows:

[0049]

[0050] The synthesis method is:

[0051] 1) 8-bean oxygen group-1,1,7, the synthesis of 7-tetramethyljulonidine-9-formaldehyde (being 1 in the formula)

[0052] Add 2.72g (0.01mol) 8-hydroxy-1,1,7,7-tetramethyljulonidine-9-carbaldehyde, 2.05g (0.012mol) benzyl bromide, and 30mL N,N -Dimethylformamide, in N 2 Add 1.7g (0.012mol) of dried anhydrous potassium carbonate under protection, and react at 120°C for 24 hours. After the reaction is completed, cool down, remove potassium carbonate by filtration, pour the filtrate into water to obtain a dark yellow solution, add hydrochloric acid to adjust the pH to neutral nature, extracted three times with ethyl acetate, combined the organic phases, dried overnight with anhydrous magnesium sulfate, filtered, removed the ethyl acetate solvent by rotary ...

Embodiment 2

[0063] An organic second-order nonlinear optical chromophore with a D-π-A structure was synthesized as shown below:

[0064]

[0065] The synthetic route is as follows:

[0066]

[0067] The synthesis method is:

[0068] 1) The synthesis of 8-beanoxy-1,1,7,7-tetramethyljulonidine-9-carbaldehyde (1 in the formula) is the same as in Example 1.

[0069] 2) Synthesis of 2-amino-1,1,3-tricyanopropene (2 in the formula)

[0070] Add 6.6g (0.1mol) of malononitrile to KOH solution in ethanol at 0°C (2.8g / 20mL, it can be dissolved in 15 minutes), stir at room temperature for about 0.5 hours, a large amount of white precipitates are produced, and after reflux for 0.5 hours, The product is slightly pink, cooled and filtered, rinsed with cold ethanol, dissolved in 100mL of water, added dropwise with concentrated hydrochloric acid to pH=8-9, white precipitate began to precipitate, continued to dropwise added concentrated hydrochloric acid until pH=4, filtered out the precipitate ,...

Embodiment 3

[0081] An organic second-order nonlinear optical chromophore with a D-π-A structure was synthesized as shown below:

[0082]

[0083] The synthetic route is as follows:

[0084]

[0085] The synthesis steps are as follows:

[0086] 1) Synthesis of 8-tert-butyldimethylsilyloxy-1,1,7,7-tetramethyljulonidine-9-carbaldehyde (1 in the formula)

[0087] Add 2.72g (0.01mol) 8-hydroxyl-1,1,7,7-tetramethyljulonidine-9-carbaldehyde, 1.8g (0.012mol) tert-butyldimethyl Chlorosilane, 0.82g (0.012mol) imidazole and 30mL N,N-dimethylformamide, reacted at 30°C for 24 hours under sealed conditions, poured into 500ml of water, extracted three times with ethyl acetate, combined the organic phases, Dry overnight with anhydrous magnesium sulfate, filter, remove the ethyl acetate solvent by rotary evaporation, and separate by column chromatography (with 200-300 mesh silica gel as the stationary phase, and a mixture of n-hexane and acetone as the mobile phase, wherein: n-hexane and acetone ...

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Abstract

The invention relates to the organic second-order nonlinear optical material field, and especially relates to an organic second-order nonlinear optical chromophore having a D-pi-A structure, and a synthetic method and a use thereof, wherein the organic second-order nonlinear optical chromophore is prepared through treating a 1,1,7,7-tetramethyljulolidine derivative as an electron donor and tricyanodihydrofuran or tricyanopyrroline as an electron acceptor. The alkyl group on the julolidine donor N used in the synthetic method and a phenyl ring form a closed six-membered ring, and the upper surface and the lower surface of the six-membered ring are respectively connected with a methyl group, so the spatial steric hindrance structure can effectively reduce the interaction force among molecules and improve the first-order molecular hyperpolarizability (beta) of the molecules of the chromophore. The organic second-order nonlinear optical chromophore having the D-pi-A structure can be doped with an amorphous polycarbonate to prepare a polarized polymer film, and the prepared film can be used as a material in the optical signal modulation field. The structures of the organic second-order nonlinear optical chromophore are represented by formulas in the specification.

Description

technical field [0001] The invention relates to the field of organic second-order nonlinear optical materials, in particular to a kind of 1,1,7,7-tetramethyljulonidine derivatives as electron donors, tricyanodihydrofuran (TCF) Or tricyanopyrroline (TCP) is an organic second-order nonlinear optical chromophore with a D-π-A structure prepared as an electron acceptor, and a synthesis method and application of the organic second-order nonlinear optical chromophore. Background technique [0002] 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 practical second-order nonlinear optical materials are mainly inorganic materials. However, organic nonlinear optical materials have advantages that inorganic materials cannot match, such as ultra-fast response speed (sub-picosecond or even picosecond)...

Claims

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Application Information

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IPC IPC(8): C07D455/04C07F7/18G02F1/361
Inventor 刘新厚吴杰云甄珍刘家磊薄淑晖周婷婷邱玲
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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