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Polysiloxane with sulphonyl indole chromophore side group, its preparation and application

A technology of polysiloxane and sulfone-based azoindole, which is applied in instruments, optical components, optics, etc., can solve the problems of no indole chromophore and no polymer, and achieve convenient purification and mild reaction conditions , the effect of rich content

Inactive Publication Date: 2005-11-23
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far there is no report on the indole chromophore with the sulfone group as the acceptor, and there is no report on the polymer with the sulfone indole chromophore group

Method used

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  • Polysiloxane with sulphonyl indole chromophore side group, its preparation and application
  • Polysiloxane with sulphonyl indole chromophore side group, its preparation and application
  • Polysiloxane with sulphonyl indole chromophore side group, its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] R is an indolyl substituted propylene group, when x is 0.25, the synthetic route is as follows:

[0018]

[0019] The synthesis method is:

[0020] Dissolve p-ethylsulfonyl aniline (2.79g, 0.015mol) in 9.90g 40% fluoroboric acid (about 0.045mol), cool to 0-5°C in an ice bath, slowly add sodium nitrite (1.04g, 1.04g, 0.015 mol) dissolved in 4 mL of water, and the reaction temperature is controlled below 5°C. After half an hour of reaction, the filter cake was quickly filtered with suction. The filter cake was washed several times with cold absolute ethanol and anhydrous ether. After draining, 4.05g of light yellow powder was obtained, which was p-ethylsulfonyl aniline diazofluoroborate. The yield 95%, put in the refrigerator for later use.

[0021] In a Schlenk tube equipped with a stirring magnet, add hydrogen-containing silicone oil, N-allyl indole, a little dichlorodicyclopentadiene platinum catalyst, anhydrous toluene, and at 60°C under argon protection The reaction wa...

Embodiment 2

[0024]

[0025] R is an indolyl-substituted propylene group, when x is 0.21, the synthetic route is as follows:

[0026] The synthesis method is as follows: Weigh the above 250 mg polysiloxane polymer 1, put it into a 30ml test tube, add N-methylpyrrolidone (make the solution mass percentage concentration 8-15%), stir at room temperature until the polymer is complete Dissolve in an ice bath. After the temperature of the solution drops to 0℃, add 66 mg of p-ethylsulfonyl aniline diazofluoroborate, react for 8 hours under ice bath conditions, and then add 0.2 g of anhydrous K 2 CO 3 Keep the ice bath conditions, continue to stir for 1 hour, filter, wash the reaction tube with tetrahydrofuran, collect the filtrate, extract the tetrahydrofuran under reduced pressure, add 20ml methanol to obtain a red precipitate, filter, collect the red solid, wash with methanol several times, vacuum After drying, the desired second-order nonlinear optical polysiloxane (poly(indolyl) (sulfone azoind...

Embodiment 3

[0028] R is indolyl substituted propylene and carbazolyl substituted propylene, when x is 0.17, the synthetic route is as follows:

[0029]

[0030] The synthesis method is: in a Schlenk tube equipped with a stirring magnet, add hydrogen-containing silicone oil, N-allyl indole, a little dichlorodicyclopentadiene platinum catalyst, anhydrous toluene, and under argon protection conditions The reaction was stirred at 60°C for 48 hours, cooled to room temperature, then N-allylcarbazole was added, and the reaction was continued to stir at 60°C for 60 hours under argon protection, and a large amount of solvent was evaporated under reduced pressure. Then add appropriate amount of methanol, put it in the refrigerator and freeze for two hours, pour out the supernatant, dissolve the precipitate in a small amount of chloroform, and then re-precipitate with methanol, so several times, a light white solid polysiloxane 4, 40℃ Vacuum drying. Wherein, the molar ratio of the hydrogen-containing ...

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Abstract

The invention relates to polysiloxanes linked with sulfonyl azoindole chromophore having a structural formula disclosed in the specification, where x=0.05-0.60, n=30-100, R is selected from various hydrocarbyl, aromatic radicals and other heterogeneous ring compound functional group. These macromolecular compounds are obtained through the reaction between polysiloxane macromolecules with indolyl linked to lateral chains and ethyl sulphone phenylamine diazonium fluoroborate. These macromolecules possesses rather high second order non-linear optical performance and good combination properties.

Description

Technical field [0001] The invention relates to a second-order nonlinear optical polysiloxane polymer material with side groups of a sulfone azoindole chromophore and a preparation method and application thereof. Background technique [0002] With the advent of lasers in the 1960s, people began to observe and study nonlinear optical phenomena in materials. At present, this nonlinear optical material has become one of the important material foundations of laser technology, and plays an indispensable role in laser frequency doubling, frequency mixing, parametric amplification and oscillation, integrated optics, and optical communications. Compared with traditional inorganic nonlinear optical materials, organic polymer materials have attracted the research interest and research enthusiasm of many scientists due to their good solubility, structural tunability and high nonlinear optical properties. The practical application of second-order nonlinear optical materials requires the mate...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G77/392C08G77/52G02B1/04
Inventor 李振黄成花建丽秦金贵
Owner WUHAN UNIV
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