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Azo compound with nonlinear optical properties and its synthesis method

An azo compound and nonlinear optics technology, applied in the field of new azo compounds and their synthesis, can solve the problems of less research on azo compound materials, small molecular weight of azo compounds, inhibition of nonlinear characteristics, etc. The effect of single product, easy operation and control

Active Publication Date: 2019-10-08
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although many studies on azo materials have been reported and even industrialized, there are still few studies on azo compound materials with nonlinear properties.
The molecular weight of azo compounds is small, and the conjugated system is not large, which seriously inhibits its nonlinear characteristics

Method used

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  • Azo compound with nonlinear optical properties and its synthesis method
  • Azo compound with nonlinear optical properties and its synthesis method
  • Azo compound with nonlinear optical properties and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Synthesis of 5-(1-(2'-amino-5'-sodium sulfonate phenyl)diazenyl)-1-naphthalenesulfonate sodium azo compound

[0037] At room temperature, weigh sodium nitrite (0.6900g, 0.01mol), 5-amino-1-naphthalenesulfonic acid (2.2325g, 0.01mol) and anhydrous sodium carbonate (1.6958g, 0.016mol) and dissolve in 100ml distilled water , and stir to make it evenly mixed to form a mixed liquid A.

[0038] Dilute concentrated hydrochloric acid (1.75ml, 0.02mol) into 1mol / L dilute hydrochloric acid. Under ice-water bath conditions, the mixed solution A was added dropwise in dilute hydrochloric acid, and solution B was formed after ten minutes of reaction; under ice-water bath conditions, p-aminobenzenesulfonic acid (1.7319g, 0.01mol), sodium hydroxide (0.8 g, 0.02mol) was dissolved in 40ml of distilled water to form solution C.

[0039]Under the condition of ice-water bath, solution B was added dropwise to solution C, and the reaction was continued for 3-5 hours;

[0040] Af...

Embodiment 2

[0042] Example 2: Synthesis of 5-(1-(2'-amino-5'-sodium formate phenyl)diazenyl)-1-naphthalenesulfonic acid sodium azo compound

[0043] At room temperature, take sodium nitrite (0.6900g, 0.01mol) and dissolve it in 10ml of distilled water to prepare an aqueous solution of sodium nitrite for subsequent use;

[0044] Dissolve 5-amino-1-naphthalenesulfonic acid (2.2325g, 0.01mol) and anhydrous sodium carbonate (1.6958g, 0.016mol) in 100ml of distilled water, then add sodium nitrite solution, stir for ten minutes to make it evenly mixed to form Mixture A;

[0045] Dilute concentrated hydrochloric acid (1.75ml, 0.02mol) into 1mol / L dilute hydrochloric acid. Under the condition of ice-water bath, add the mixed solution A dropwise into dilute hydrochloric acid, and form solution B after 10 minutes of reaction;

[0046] Under ice-water bath conditions, p-aminobenzoic acid (1.3714 g, 0.01 mol) and sodium hydroxide (0.8 g, 0.02 mol) were dissolved in 50 ml of distilled water to form ...

Embodiment 3

[0049] Example 3: Synthesis of 5-(4'-hydroxyphenyl)diazenyl)-1-naphthalenesulfonate sodium azo compound

[0050] At room temperature, take sodium nitrite (0.6900g, 0.01mol) and dissolve it in 10ml of distilled water to prepare an aqueous solution of sodium nitrite for subsequent use;

[0051] Dissolve 5-amino-1-naphthalenesulfonic acid (2.2325g, 0.01mol) and anhydrous sodium carbonate (1.0600g, 0.01mol) in 80ml of distilled water, then add sodium nitrite solution, stir for 10 minutes, and mix well Form a mixture A;

[0052] Dilute concentrated hydrochloric acid (1.75ml, 0.02mol) into 1mol / L dilute hydrochloric acid. Under the condition of ice-water bath, add the mixed solution A dropwise into dilute hydrochloric acid, and form solution B after 10 minutes of reaction;

[0053] Under ice-water bath conditions, phenol (0.9411 g, 0.01 mol), sodium hydroxide (0.8 g, 0.02 mol) and 20 ml of acetone were dissolved in 30 ml of distilled water to form solution C. At this temperature,...

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Abstract

The invention relates to an azo group-containing organic compound with a non-linear optical property and a synthetic method thereof. A single substituent-containing aromatic compound and 5-amino-1-naphthalenesulfonic acid serve as main raw materials to synthesize an azo naphthalenesulfonic acid compound under the condition of ice-water bath through azo coupling reaction. The synthetic method of the azo compound is simple, convenient, controllable and high in yield, and the product has an excellent non-linear optical property and potential application prospects in fields such as optical devices, anti-fatigue devices and optical limiting devices.

Description

technical field [0001] The invention relates to a class of azo compounds, in particular to a novel azo compound with nonlinear optical properties and a synthesis method thereof. The invention belongs to the field of optical smart material technology and related devices. Background technique [0002] Since the development of nonlinear optical materials, many nonlinear optical materials such as organic, inorganic, polymer, and organometallic have emerged as the times require. Among them, organic materials, as the leading force, have developed rapidly in the nonlinear field. Compared with other nonlinear materials, organic materials have the advantages of strong controllability, easy structure regulation, strong activatability, and strong compatibility with other macromolecules. Therefore, organic nonlinear materials are widely used as nonlinear dominant materials. various fields. Among them, azo compounds, as a branch of organic nonlinear materials, have also received extens...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/47C07C303/32
Inventor 周立明李聪高丽君崔静孙全文李留洋方少明
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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