Main chain type azobenzene polymer and preparation method thereof

A technology of azobenzene and polymers, applied in the field of polymer material synthesis, can solve the problems of low stability of raw materials, harsh reaction conditions, and low conversion rate, and achieve less side reactions, mild reaction conditions, and low waste rate low effect

Active Publication Date: 2014-07-23
苏州吉尼尔机械科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are certain disadvantages in the in-situ synthesis of aromatic azo polymers nowadays. For example, some metal ions need to be introduced into the reaction system, the re...

Method used

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  • Main chain type azobenzene polymer and preparation method thereof
  • Main chain type azobenzene polymer and preparation method thereof
  • Main chain type azobenzene polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0048] Example 1. Synthesis of main chain azo polymers (PA, PB, PC)

[0049] figure 1 It is a schematic flow sheet of the present invention for preparing nitro group-containing monomers, according to the appendix figure 1 :

[0050] Synthesis of Nitro-Containing Monomer Compound A

[0051] 14.0 g of potassium carbonate and 200 mL of N, N -Dimethylformamide was stirred at 80°C for 2 hours, and 12.0 g of catechol was added to the above solution, followed by stirring for 1 hour. Then 20.0 g of 1-bromododecane was added dropwise to the above mixed solution, and a small amount of potassium iodide was added, and stirred at 80 °C for 8 hours. After that, the reaction solution was added to a 500 mL ice-salt bath beaker, Stir, let stand, and filter with suction to obtain crude product. The crude product was separated by column chromatography with an eluent of petroleum ether / ethyl acetate = 20 / 1 to obtain a pure white product. Take 8 g of the above white product, 3.2 g of 1,12-d...

Embodiment 2

[0071] Example 2. Photoinduced cis-trans isomerization of main chain azo polymers (PA, PB, PC)

[0072] The above-mentioned non-conjugated polymer PA and conjugated polymers PB and PC were dissolved in tetrahydrofuran to prepare a polymer tetrahydrofuran solution with a concentration of 0.033 mg / mL, and the solution was irradiated with ultraviolet light to study the photoinduced cis-trans isomerization of each polymer.

[0073] attached Figure 7 , attached Figure 8 , attached Figure 9 are the photo-induced cis-trans isomerization spectra of the non-conjugated polymer PA and the conjugated polymers PB and PC, respectively.

[0074] like Figure 7 As shown, the tetrahydrofuran solution (concentration of 0.033 mg / mL) of the non-conjugated polymer PA undergoes cis-trans isomerization under the irradiation of 365 nm ultraviolet light. After 35 seconds of irradiation, the azo-trans isomerization of the polymer The structure is basically in balance. Then 435 nm ultraviolet ligh...

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Abstract

The invention discloses a main chain type azobenzene polymer and a preparation method thereof. According to the preparation method, the main chain type aromatic azo polymer is prepared by adopting nitro reduction coupling reaction for the first time. The preparation method comprises the following steps: firstly synthesizing different types of monomers through a series of reactions, namely conjugate monomers and non-conjugate monomers; secondly, synthesizing a photocatalyst required by a polymerization system, namely gold nanoparticles loaded on zirconium oxide, and characterizing the photocatalyst through a series of tests; and finally carrying out nitro reduction coupling reaction of the monomers in the presence of a methylbenzene-isopropanol mixed solvent and potassium hydroxide, thus obtaining the main chain type aromatic azo polymer. The preparation method disclosed by the invention needs few polymerization reaction components, is simple, practicable, convenient in a purification process, mild in reaction conditions and has the advantages of low toxicity, high efficiency and environmental protection. The main chain type aromatic azo polymer prepared by using the method has good solubility and functionality and high optical application value.

Description

technical field [0001] The invention belongs to the field of polymer material synthesis, in particular to a conjugated and non-conjugated polymer containing azo groups in the main chain and a preparation method thereof. Background technique [0002] Aromatic azo compounds have always been favored by chemists, and have experienced hundreds of years of development history, and they are enduring. Aromatic azo compounds are widely used in traditional chemical industry as dyes, food additives, free radical reaction inducers, etc., and also show good prospects in the fields of drug release and optoelectronic chemistry. Mainly because aromatic azo compounds have the characteristics of photo-induced cis-trans isomerism and excellent photochromic properties under the action of light and heat, their research in modern high-tech fields has also attracted much attention. It has wide application potential in the fields of liquid crystal materials, photochemical molecular switches, chemi...

Claims

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Application Information

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IPC IPC(8): C08G73/00C07C245/08C07D209/88
Inventor 张伟王来兵李洁爱杨迪陈扬朱秀林屠迎锋程振平周年琛
Owner 苏州吉尼尔机械科技有限公司
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