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A kind of hexadendritic azosiloxane dye and its synthetic method

A technology of azo siloxane and synthesis method, applied in azo dyes, organic dyes, chemical instruments and methods, etc., can solve the problems of low thermal stability, difficult device application, etc., achieve good solubility, reduce static electricity, etc. Effects of interaction, enhanced loading concentration and polarization efficiency

Inactive Publication Date: 2011-12-28
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, organic materials often have low thermal stability and are difficult to be applied in practical devices.

Method used

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  • A kind of hexadendritic azosiloxane dye and its synthetic method
  • A kind of hexadendritic azosiloxane dye and its synthetic method
  • A kind of hexadendritic azosiloxane dye and its synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] R 1 for nitro, R 2 Be the synthetic method of the hexabranch azosiloxane dye of hydrogen, its step is as follows:

[0023] (1) Dissolve 1 mole of 1,1,1-tris(4-hydroxyphenyl)ethane in 600 mL of ethanol solution, add dropwise to an aqueous solution containing 2 moles of sodium hydroxide, reflux and stir for half an hour. Then 3 moles of 3-chloropropyl-1,2-diol were added, and the reflux reaction was continued for 4 hours. Cool after the reaction, pour the solvent into water, extract with ethyl acetate, and distill off the solvent under reduced pressure to obtain a dendritic nucleus containing propylene glycol. Its synthetic reaction formula is:

[0024]

[0025] NMR: 1 H NMR (500 MHz, DMSO- d 6 ): δ = 2.03 (s, 3H, C H 3 ), 3.43 (d, 6H, OC H 2 ), 3.80 (m, 6H, O H ), 3.95 (m, 3H, C H ), 4.67(d, 3H, C H 2 OH), 4.95 (d, 3H, C H 2 OH), 6.82 (d, 6H, Ar H ), 6.91 (d, 6H, Ar H ).

[0026] 13 C NMR (125 MHz, DMSO- d 6 ): δ = 157.167, 141.785, 129.695, 114....

Embodiment 2

[0044] R 1 for nitro, R 2 Be the synthetic method of the six branched azosiloxane dyes of chlorine, its step is as follows:

[0045] (1) Dissolve 1 mole of 1,1,1-tris(4-hydroxyphenyl)ethane in 600 mL of ethanol solution, add dropwise to an aqueous solution containing 5 moles of potassium hydroxide, reflux and stir for half an hour. Then 4 moles of 3-chloropropyl-1,2-diol were added, and the reflux reaction was continued for 4 hours. Cooling after the reaction is over, the solvent is poured into water, extracted with ethyl acetate, and the solvent is distilled off under reduced pressure to obtain a dendritic nucleus containing propylene glycol; its synthetic reaction formula is:

[0046]

[0047] NMR: 1 H NMR (500 MHz, DMSO- d 6 ): δ = 2.03 (s, 3H, C H 3 ), 3.43 (d, 6H, OC H 2 ), 3.80 (m, 6H, O H ), 3.95 (m, 3H, C H ), 4.67(d, 3H, C H 2 OH), 4.95 (d, 3H, C H 2 OH), 6.82 (d, 6H, Ar H ), 6.91 (d, 6H, Ar H ).

[0048] 13 C NMR (125 MHz, DMSO- d 6 ): δ = 157...

Embodiment 3

[0064] R 1 for hydrogen, R 2 Be the synthetic method of the six branched azosiloxane dyes of nitro, its step is as follows:

[0065] (1) Dissolve 1 mole of 1,1,1-tris(4-hydroxyphenyl)ethane in 600 mL of ethanol solution, add dropwise to an aqueous solution containing 5 moles of sodium hydroxide, reflux and stir for half an hour. Then 5 moles of 3-chloropropyl-1,2-diol were added, and the reflux reaction was continued for 4 hours. Cool after the reaction, pour the solvent into water, extract with ethyl acetate, and distill off the solvent under reduced pressure to obtain a dendritic nucleus containing propylene glycol. Its synthetic reaction formula is:

[0066] NMR: 1 H NMR (500 MHz, DMSO- d 6 ): δ = 2.03 (s, 3H, C H 3 ), 3.43 (d, 6H, OC H 2 ), 3.80 (m, 6H, O H ), 3.95 (m, 3H, C H ), 4.67(d, 3H, C H 2 OH), 4.95 (d, 3H, C H 2 OH), 6.82 (d, 6H, Ar H ), 6.91 (d, 6H, Ar H ).

[0067] 13 C NMR (125 MHz, DMSO- d 6 ): δ = 157.167, 141.785, 129.695, 114.142,...

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Abstract

The hexadendritic azosiloxane dye disclosed by the present invention has a general structural formula such as formula 1, wherein when R1 is nitro, R2 is hydrogen or chlorine; when R1 is hydrogen, R2 is nitro. The synthesis method is as follows: 1,1,1-tris(4-hydroxyphenyl)ethane and 3-chloropropyl-1,2-diol are synthesized by Williamson ether to prepare a dendritic nucleus containing propylene glycol, and then combined with 4-[(2-N-Ethylanilino)ethoxy]-4-oxobutanoic acid was subjected to esterification reaction, and then diazo-coupling reaction with phenol derivatives was carried out to obtain six branched bifurcations with hydroxyl groups Nitrogen chromophore, the chromophore is added with isocyanate propyltriethoxysilane to obtain hexadendritic azosiloxane dye. The synthesis method has the advantages of simple process, mild conditions, readily available raw materials and high yield. The six-branched azosiloxane dye has good solubility and film-forming processability, large nonlinear optical performance and high thermal stability. Formula 1

Description

technical field [0001] The invention relates to a six-branched azosiloxane dye and a synthesis method thereof. Background technique [0002] Nonlinear optics plays an important role in the development of optoelectronics and photonics technology. Using different nonlinear optical effects such as frequency mixing, sum frequency, difference frequency, and electro-optic, many optical information such as optical modulation, optical switching, optical storage, and optical limiting can be prepared. Processing components. Therefore, the development of new nonlinear optical materials is of great significance to economic construction and national defense security. [0003] Common nonlinear optical materials mainly include inorganic crystals, organic crystals, and polymer materials. Inorganic crystals are the first class of second-order nonlinear optical materials studied and used by people, such as lithium niobate, gallium arsenide and other inorganic crystals. The development of th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B33/18C07F7/18
CPCC09B69/106C07F7/1804C09B69/008C09B69/103
Inventor 钱国栋林文鑫崔元靖高俊阔郁建灿王智宇樊先平王民权
Owner ZHEJIANG UNIV
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