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Second-order non-linear optical polymer containing azo and thiophene ring, and its synthesizing method and use

A second-order nonlinear, polymer technology, applied in the field of nonlinear optical materials, can solve problems such as stability degradation

Inactive Publication Date: 2009-06-24
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these materials all use C=C bonds as conjugated π-electron bridges, and the carbon-carbon double bond system has the problem of singlet oxygen, which reduces its stability.

Method used

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  • Second-order non-linear optical polymer containing azo and thiophene ring, and its synthesizing method and use
  • Second-order non-linear optical polymer containing azo and thiophene ring, and its synthesizing method and use
  • Second-order non-linear optical polymer containing azo and thiophene ring, and its synthesizing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Synthesis of 3,4-dibutyl-5-amino-2-thiophenecarbaldehyde tin tetrachloride complex

[0055] 45 g (0.2 mol) of SnCl 2 2H 2 O was dissolved in 60ml of concentrated hydrochloric acid, when the system temperature dropped to 5°C, 17.8 grams (0.066mol) of 3,4-dibutyl-5-nitro-2-thiophenecarbaldehyde was added at one time, and stirred at 40°C for 1 hour to obtain Off-white solid suspension.

Embodiment 2

[0057] Synthesis of 3,4-dibutyl-5-amino-2-thiophenecarbaldehyde

[0058] The off-white solid suspension obtained in Example 1 was adjusted to alkaline with 40wt% NaOH aqueous solution, then extracted with ether, and the ether layer was washed with MgSO 4 After drying and evaporation, the obtained crude product can be directly used in the next reaction.

Embodiment 3

[0060] Synthesis of 2-[4-(N,N-dihydroxyethylamino)azophenyl]3,4-dibutyl-5-thiophenecarbaldehyde

[0061] The 3,4-dibutyl-5-amino-2-thiophenecarbaldehyde tin tetrachloride complex off-white solution obtained in Example 1; or the 3,4-dibutyl-5-amino obtained in Example 2 The hydrochloric acid solution of -2-thiophenecarbaldehyde was cooled to 2°C; 0.067 moles of NaNO 2 Dissolve in 15ml of water, and slowly add dropwise to the above gray-white solution or the hydrochloric acid solution of 3,4-dibutyl-5-amino-2-thiophenecarbaldehyde at below 5°C, and continue to stir for 1 hour to obtain a diazonium salt solution .

[0062] Dissolve 0.080mol of N, N-dihydroxyethylaniline in 10ml of 36% HOAC, cool to 3°C in an ice-salt bath, slowly add the above diazonium salt solution dropwise to the HOAC of N,N-dihydroxyethylaniline In the solution, the reaction temperature is controlled below 5°C, the pH value of the system is adjusted between 3 and 6 with NaOH, and the stirring is continued f...

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Abstract

The invention relates to the field of nonlinear optical materials, in particular to a class of second-order nonlinear optical polymers containing azo and thiophene rings with the Optical polymers prepare cross-linked polyurethane-based polymers or polarized polymer films. The novel high-performance second-order nonlinear optical polymer containing azo and thiophene rings of the invention greatly improves photochemical stability because N=N bonds are used to replace C=C bonds. This type of material contains two or more -OH, which can be further reacted to prepare crosslinked polymer films or polarized polymer films, which have higher thermal stability and light stability than non-crosslinked polymers. Sexuality and orientation stability. Furthermore, since such azo compounds or their azo intermediates are blue to red compounds, they are also useful as pigments, dyes, paints, and the like.

Description

technical field [0001] The invention relates to the field of nonlinear optical materials, in particular to a new type of high-performance second-order nonlinear optical polymer containing azo and thiophene rings and its synthesis method, as well as a second-order nonlinear optical polymer containing azo and thiophene rings Preparation of cross-linked polyurethane polymer or polarized polymer film. Background technique [0002] Second-order nonlinear optical materials are mainly used in electro-optic modulation, frequency conversion and optical switching (modulation), etc. They have a wide range of applications in the fields of optical communication and optical signal processing (optical computing). At present, the practical second-order nonlinear optical materials are mainly inorganic materials. Compared with inorganic materials, organic materials have the advantages of large nonlinear optical coefficient, fast response speed, high optical damage threshold, molecular design...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/36C07D409/06C08L75/04G02B1/04
Inventor 沈玉全邱玲祖凤华张涛郭昆朋
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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