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Azobenzene diamine chromophore with photoelectric activity and its preparing method

A technology of azophenylenediamine and chromophore, which is applied in the field of optoelectronic functional materials, can solve the problems of high price of laser light source, no contribution to polymer stability, and difficulty in accumulating chromophore, etc., and achieves excellent photochromic performance, Excellent thermal stability and high chromophore content

Inactive Publication Date: 2007-01-24
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the field of optical storage, one of the key problems in the application of polymer nonlinear optical materials is that their absorption wavelength is in the ultraviolet region, and laser light sources in the ultraviolet region are expensive and cannot be widely used
Another problem is that the thermal stability of polymer materials is not high, which is not ideal in terms of storage time and fatigue resistance.
[0003] The usual method is to use a rigid backbone to increase the glass transition temperature of the polymer. Masao et al. However, these chromophores often have only one reactive group, which does not contribute to the stability of the polymer, and it is not easy to attach the chromophore to the main chain
Studenovsky et al. (Studenovsky M, Sedlakova Z, Wang G.Macromol.Symp.2004, 212:399) designed a series of bisamino azobenzene chromophore molecules, but the maximum absorption wavelength of the chromophore molecules is only the highest Up to 373nm, still not in the visible region

Method used

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  • Azobenzene diamine chromophore with photoelectric activity and its preparing method
  • Azobenzene diamine chromophore with photoelectric activity and its preparing method
  • Azobenzene diamine chromophore with photoelectric activity and its preparing method

Examples

Experimental program
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Effect test

Embodiment 1

[0032] The raw materials used in the embodiment are as follows:

[0033] m-Phenylenediamine (analytical grade) was provided by China National Pharmaceutical (Group) Shanghai Chemical Reagent Company.

[0034] p-Nitroaniline (analytical grade) was provided by China National Pharmaceutical (Group) Shanghai Chemical Reagent Company.

[0035] Sodium nitrite (analytical grade) was provided by Shanghai Shisi Hewei Chemical Co., Ltd.

[0036] Hydrochloric acid (analytical grade) was provided by China Pharmaceutical Group Shanghai Chemical Reagent Co., Ltd.

[0037] Tetrahydrofuran (analytical grade) was provided by China National Pharmaceutical (Group) Shanghai Chemical Reagent Company.

[0038] The ratio of raw materials used is as follows:

[0039] 1 part m-phenylenediamine (moles)

[0040] 1 part of p-nitroaniline (number of moles)

[0041] 1 part of sodium nitrite (number of moles)

[0042] 5.2 parts of hydrochloric acid (the number of moles of HCl)

[0043] Synthesis of 2...

Embodiment 2

[0053] The raw materials used in the embodiment are as follows:

[0054] m-Phenylenediamine (analytical grade) was provided by China National Pharmaceutical (Group) Shanghai Chemical Reagent Company.

[0055] Aniline (analytical grade) was provided by China National Pharmaceutical (Group) Shanghai Chemical Reagent Company.

[0056] Sodium nitrite (analytical grade) was purchased from Shanghai Shisi Hewei Chemical Co., Ltd.

[0057] Hydrochloric acid (analytical pure), China Pharmaceutical Group Shanghai Chemical Reagent Co., Ltd.

[0058] The ratio of raw materials used is as follows:

[0059] 1 part m-phenylenediamine (moles)

[0060] 1 part of aniline (number of moles)

[0061] 1 part of sodium nitrite (number of moles)

[0062] 5.2 parts of hydrochloric acid (the number of moles of HCl)

[0063] Synthesis of 2,4-diaminoazobenzene:

[0064] Measure 6.0ml of concentrated hydrochloric acid and pour it into 60ml of water, add 3.6g of m-phenylenediamine to make m-phenylen...

Embodiment 3

[0067] The raw materials used in the embodiment are as follows:

[0068] m-Phenylenediamine (analytical grade) was provided by China National Pharmaceutical (Group) Shanghai Chemical Reagent Company.

[0069] p-methylaniline (analytical grade) was provided by China National Pharmaceutical (Group) Shanghai Chemical Reagent Company.

[0070] Sodium nitrite (analytical grade) was purchased from Shanghai Shisi Hewei Chemical Co., Ltd.

[0071] Hydrochloric acid (analytical pure), China Pharmaceutical Group Shanghai Chemical Reagent Co., Ltd.

[0072] The ratio of raw materials used is as follows:

[0073] 1 part m-phenylenediamine (moles)

[0074] 1 part of p-methylaniline (number of moles)

[0075] 1 part of sodium nitrite (number of moles)

[0076] 4 parts of hydrochloric acid (the number of moles of HCl)

[0077] Synthesis of 2,4-diamino-p-methylazobenzene:

[0078] Measure 6.0ml of concentrated hydrochloric acid and pour it into 60ml of water, add 3.6g of m-phenylenedia...

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Abstract

The present invention belongs to the field of photoelectronic functional material technology, and is especially one kind of optical active organic chromophore molecule of azometaphenylene diamine and its synthesis process. The present invention features that the azometaphenylene diamine compound is synthesized with metaphenylene diamine and aromatic diazo salt and through coupling reaction, has absorption wavelength in the visible light area, and possesses two reaction active primary amine groups. The azometaphenylene diamine compound may be mixed with polymer to obtain non-linear optical performance and may be reacted with diisocyanate and other active monomer to introduce polymer chain, so as to obtain polymer with high chromophore content, excellent heat stability, etc. It may be used in preparing light memory medium with high storing density and high stability.

Description

technical field [0001] The invention belongs to the technical field of photoelectric functional materials, and in particular relates to an azobenzene optically active organic chromophore molecule and a preparation method thereof. Background technique [0002] In the field of optics for more than ten years, the research of optical storage media with high storage density and high stability has attracted extensive attention. The excellent optical transparency, film-forming properties and molecular designability of polymers make them a research hotspot in both aspects, but both face some urgent problems to be solved. In the field of optical storage, one of the key problems in the application of polymer nonlinear optical materials is that their absorption wavelength is in the ultraviolet region, and laser light sources in the ultraviolet region are expensive and cannot be widely used. Another problem is that the thermal stability of polymer materials is not high, which is not id...

Claims

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Application Information

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IPC IPC(8): C09B29/085G11B7/246G11B7/2467
Inventor 浦鸿汀刘玲廖欣
Owner TONGJI UNIV
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