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Silioxane precursor containing azobenzene dye and its synthesis method

A synthesis method, azobenzene technology, applied in the field of siloxane precursors and their synthesis, can solve the problems of rare design and synthesis research, difficult to achieve optical integration, easy to damage, etc., and achieve good second-order nonlinear optical properties , high yield and mild reaction conditions

Inactive Publication Date: 2008-04-16
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Inorganic crystals are the first class of nonlinear optical materials studied and used by people. Although the crystal growth technology of these materials has become increasingly mature, there are still obvious shortcomings: such as expensive, easy to damage, and only single crystals can be used. Materials work, difficult to achieve optical integration
However, the use of such dyes for the design and synthesis of siloxane precursors and related research are still rare.

Method used

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  • Silioxane precursor containing azobenzene dye and its synthesis method
  • Silioxane precursor containing azobenzene dye and its synthesis method
  • Silioxane precursor containing azobenzene dye and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] R in the general structural formula 1 is a cyano group. The synthetic route of the siloxane precursor containing azobenzene dye is as follows:

[0020]

[0021] The synthesis method is:

[0022] Add 10 mmol of 4'-(N-ethyl-N-hydroxyethyl)-amino-2-cyano-4-nitrate to a three-necked flask equipped with a reflux condenser and connected to an anhydrous and oxygen-free device at room temperature After opening the anhydrous and oxygen-free device and passing nitrogen gas for 30 minutes, add 20ml of freshly dried tetrahydrofuran and 3-5 drops of stannous octoate, stir magnetically, and then add 2.47g (10mmol) isocyanatopropane Triethoxysilane, heated to 90°C after the dropwise addition, refluxed for 72 hours, poured the reaction solution into n-hexane to produce a precipitate, filtered it with suction and dried it in vacuum to obtain a siloxane precursor containing azobenzene dye. Yield 73%, the second harmonic coefficient d after making the material 33 It is 46.1pm / V.

Embodiment 2

[0024] R in Structural Formula 1 is a nitro group. The synthetic route of the siloxane precursor containing azobenzene dye is as follows:

[0025]

[0026] The synthesis method is:

[0027] At room temperature, add 10 mmol of 4'-(N-ethyl-N-hydroxyethyl)-amino-2,4-dinitrobis to a three-necked flask equipped with a reflux condenser and connected to an anhydrous and oxygen-free device Azobenzene, after opening the anhydrous and oxygen-free device and passing nitrogen gas for 30 minutes, add 30ml of freshly dried acetone and 8-10 drops of triethylamine, stir magnetically, and then add 2.96g (12mmol) of isocyanatopropyl triethylamine Ethoxysilane, heated to 110°C after dropping, refluxed for 6 hours, poured the reaction solution into n-heptane to produce a precipitate, filtered it with suction and dried it in vacuum to obtain a siloxane precursor containing azobenzene dye. Yield 62%, the second harmonic coefficient d after making the material 33 It is 39.6pm / V.

Embodiment 3

[0029] R in Structural Formula 1 is a chlorine atom. The synthetic route of the siloxane precursor containing azobenzene dye is as follows:

[0030]

[0031] The synthesis method is:

[0032] Add 10 mmol of 4′-(N-ethyl-N-hydroxyethyl)-amino-2-chloro-4-nitro Azobenzene, after opening the anhydrous and oxygen-free device and passing nitrogen gas for 30 minutes, add 60ml of freshly dried dioxane and 5-6 drops of tin dodecyl laurate, magnetically stir, then add 4.94g (20mmol ) isocyanatopropyltriethoxysilane, heated to 140°C after the dropwise addition, and poured the reaction solution into petroleum ether to produce a precipitate after reflux for 48 hours, suction filtered and vacuum-dried to obtain silicon containing azobenzene dye Oxygen precursors. Yield 68%, the second harmonic coefficient d after making the material 33 It is 40.7pm / V.

[0033] The synthesis process of the siloxane precursor in the above examples is simple, the yield is high, and it has good second-or...

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Abstract

A siloxane precursor containing azobenzene dye and its synthesis are disclosed. In structural formula, R is nitrile, nitryl or chlorine atom. The process is carried out by addition reacting nitrogen benzide dye containing R group with carbimide propyl triethoxy-silane to obtain final product. It is cheap and simple and can be used for linked chemical bond inorganic-organic hybrid material, electro-optic modulation, optical switch and non-linear optical fields.

Description

technical field [0001] The invention relates to a kind of siloxane precursor containing azobenzene dye and its synthesis method. Background technique [0002] Since nonlinear optical materials have great application prospects in all-optical communication, optical computing, and optical information processing, the search for stable and efficient nonlinear optical materials has become a hot research field for scientists all over the world. Inorganic crystals are the first class of nonlinear optical materials studied and used by people. Although the crystal growth technology of these materials has become increasingly mature, there are still obvious shortcomings: such as expensive, easy to damage, and only single crystals can be used. material work, difficult to achieve optical integration. Therefore, since the 1970s, people began to explore organic and polymer nonlinear optical materials. This type of material has a nonlinear optical coefficient 1-2 orders of magnitude higher...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18
Inventor 钱国栋崔元靖陈鹭剑王智宇邱建荣樊先平洪樟连王民权
Owner ZHEJIANG UNIV
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