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Chromophore molecule containing triptycene rigid three-dimensional structure and its synthesis method and application

A technology of three-dimensional structure and chromophore, applied in the direction of organic chemistry, etc., to achieve the effect of high yield, easy purification and few synthesis steps

Inactive Publication Date: 2016-03-09
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

In the field of polymer electro-optic materials, there are few reports on triptycene research.

Method used

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  • Chromophore molecule containing triptycene rigid three-dimensional structure and its synthesis method and application
  • Chromophore molecule containing triptycene rigid three-dimensional structure and its synthesis method and application
  • Chromophore molecule containing triptycene rigid three-dimensional structure and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] When the electron bridge B is a carbon-carbon double bond and the electron acceptor A is dimethyl tricyanofuran (TCF), the structure and synthetic route of the chromophore molecule are as follows:

[0048]

[0049] The synthesis method is:

[0050] 1. Synthesis of Compound 1

[0051] Dissolve 3.5g (0.02mol) of N-phenylmaleimide and 3.6g (0.02mol) of anthracene in 50mL of dry dichloromethane, heat and stir to reflux temperature of 60°C for 36 hours of cycloaddition reaction, and cool to room temperature, concentrated by rotary evaporation to a residual solution of about 15 mL, and filtered to remove the filtrate. The product was washed three times with petroleum ether to obtain 5.8 g of white powdery crystals with a yield of about 81%.

[0052] 2. Synthesis of Compound 2

[0053] 3.5 g of compound 1 (0.01 mol) was dissolved in 50 mL of dry dichloromethane and stirred at room temperature, and 100 mL of ether solution containing 1 g of lithium aluminum tetrahydrogen ...

Embodiment 2

[0064] When the electron bridge B is thiophene and the electron acceptor A is tricyanopyrroline (TCP), the structure and synthetic route of the chromophore molecule are as follows:

[0065]

[0066] The synthesis method is:

[0067] 1. Synthesis of Compound 1

[0068] Dissolve 3.5g (0.02mol) of N-phenylmaleimide and 3.6g (0.02mol) of anthracene in 50mL of dry dichloromethane, heat and stir to reflux temperature of 60°C for 36 hours of cycloaddition reaction, and cool to room temperature, concentrated by rotary evaporation to a residual solvent volume of about 15 mL, and filtered to remove the filtrate. The product was washed three times with petroleum ether to obtain 5.8 g of white powdery crystals with a yield of about 81%.

[0069] 2. Synthesis of compound 2

[0070] 3.5 g of compound 1 (0.01 mol) was dissolved in 50 mL of dry dichloromethane and stirred at room temperature, and 100 mL of ether solution containing 1 g of lithium aluminum tetrahydrogen (0.025 mol) was s...

Embodiment 3

[0086] Preparation of polymer electro-optic thin film materials containing chromophore ZFS used in the core material of electro-optic modulators in the field of communication:

[0087] Mix 0.02g of the chromophore ZFS prepared in Example 1 with 0.08g of amorphous polycarbonate APC, add 1.2mL of dibromomethane, and stir at 40°C for 12 hours until completely dissolved; then pass the resulting solution through a 0.22μm Filter through a tetrafluoroethylene membrane filter, spin-coat on an ITO glass substrate at a speed of 1200 rpm, and vacuum-dry the obtained polymer film at room temperature for 24 hours. The thickness of the polymer film is controlled at 3-4 μm.

[0088] The polymer film material obtains electro-optic activity by means of corona polarization (reference: Singer, K.D., M.G.Kuzyk, et al. Electro-optic phase modulation and optical second-harmonic generation in corona-poled polymer films, Applied Physics Letters, 1988, 53 (19): 1800-1802.), The polarization temperatur...

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Abstract

The invention relates to a chromophore molecule containing a triptycene rigid stereochemical structure and a synthetic method thereof, and an application of the chromophore molecule containing the triptycene rigid stereochemical structure in a polymer electrooptical material. According to the chromophore molecule and the synthetic method thereof provided by the invention, the chromophore molecule containing the triptycene rigid stereochemical structure as shown in specification can be obtained by virtue of a cycloaddition reaction of N-phenylmaleimide and anthracene and then by connecting an electron bridge part with a structure like carbon-carbon double bonds or thiophene and an electron acceptor part with a structure like tricyano furan or tricyano pyrroline. The chromophore molecule containing the triptycene rigid stereochemical structure provided by the invention is doped with a polymer (such as amorphous polycarbonate (APC)), and the mixture is subjected to polarization treatment so that a high-performance polymer electrooptical material can be obtained. The chromophore molecule containing the triptycene rigid stereochemical structure provided by the invention is easy to synthesize and separate.

Description

technical field [0001] The invention relates to a chromophore molecule containing triptycene rigid three-dimensional structure and a synthesis method thereof, as well as the application of the chromophore molecule containing triptycene rigid three-dimensional structure in polymer electro-optical materials. Background technique [0002] The nonlinear optics (NLO) performance of materials refers to the ability of materials to transfer charges relative to atoms under the photoelectric field under the action of laser light, resulting in frequency doubling effects, electro-optical effects, optical mixing, multi-photon absorption, etc. A series of optical phenomena. The electro-optic effect (EO) is a typical second-order nonlinear optical effect, which is the change of the material's own refractive index under an external electric field. Utilizing this property, it is possible to control the phase of the light wave transmitted in the material by changing the intensity of the appl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/10C07D409/14C08K5/3417C08K5/45C08L69/00C08L33/12
Inventor 甄珍张融张茂林邱玲刘新厚
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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