Preparation method of multi-responsiveazobenzene functionalized polymer

A multi-response, azobenzene technology, applied in the field of organic chemistry, can solve the problems of photoresponsive group shedding, polymer molecular structure and performance without light reversible changes, etc., achieving low reaction temperature and simple synthesis method Effect

Inactive Publication Date: 2016-03-30
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] At present, polymers with triple stimuli responses to temperature, pH and light have been reported, but such polymers undergo photocleavage reactions under light conditions, and the photoresponsive groups are detached from the polymer chain, which makes the molecular structure and properties of the polymer itself No reversible change with light
With the continuous in-depth research on stimuli-responsive polymer systems, simple multiple stimuli-responsive polymers can no longer meet the needs of scientists, and there is an urgent need to design and synthesize polymers that respond to multiple stimuli and make reversible changes to external stimuli. Material

Method used

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  • Preparation method of multi-responsiveazobenzene functionalized polymer
  • Preparation method of multi-responsiveazobenzene functionalized polymer
  • Preparation method of multi-responsiveazobenzene functionalized polymer

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Embodiment 1

[0025] Preparation of polydimethylaminoethyl (meth)acrylate: add 8 ml of anhydrous tetrahydrofuran to a 10 ml dry schlenk bottle, and add complexing agents to the schlenk bottle in sequence under nitrogen protection 0.144 g of 1,1,4,7,10,10-hexamethyltriethylenetetramine (HMTETA), 8.334 g of monomer dimethylaminoethyl methacrylate (DMAEMA), after 15 minutes, add 0.076 g of catalyst Cuprous bromide (CuBr), then stop filling the nitrogen gas, and stopper the bottle mouth with a rubber stopper. After three cycles of liquid nitrogen freezing-suction-thawing, after the air in the bottle is exhausted, the schlenk bottle is slowly heated to 40 degrees Celsius, and after the temperature is stable, the initiator α-bromoisobutyrate ethyl Ester (EBIB) 0.065 ml, reacted at 40 degrees Celsius for 24 hours. After the reaction is over, quench the schlenk bottle with liquid nitrogen to terminate the reaction, and add a large amount of CH 2 Cl 2 Dilute the product, then use a neutral alumin...

Embodiment 2

[0027] Preparation of m-trifluorotoluene azophenol: 3.22 g of m-trifluorotoluidine, 6 ml of concentrated HCl (38%) and 12 ml of deionized water were added to a 250 ml three-neck flask. Add 1.394 g NaNO to a 100 ml flask 2 and 7 ml of deionized water, stirred to dissolve. Under the condition of 0-5 degrees Celsius, slowly drop the sodium nitrite solution into the m-trifluorotoluidine / hydrochloric acid solution and stir for 2 hours. After the addition is completed, stir for another 2 hours to make the reaction complete. When the starch potassium iodide test paper turns blue, filter the product, and cool the filtrate (yellow) to obtain a diazonium salt solution.

[0028] Add 1.88 grams of phenol, 1.2 grams of NaOH and 10 milliliters of deionized water into a 250-ml beaker, and dissolve 10 milliliters of 1.88 grams of NaOH at 0-5 2 CO 3Add the aqueous solution dropwise into the phenol / sodium hydroxide solution. After stirring completely, add the above-mentioned diazonium salt d...

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Abstract

The invention discloses a preparation method of a multi-responsive azobenzene functionalized polymer. The preparation method comprises the following steps: synthesizing a polymer of poly-dimethylaminoethyl (meth)acrylate by virtue of atom transfer radical polymerization reaction of a polymer monomer of dimethylaminoethyl methacrylate; synthesizing azobenzene small-molecule m-trifluoromethylazophenol with phenolic hydroxyl by virtue of diazo reaction by taking m-trifluorotoluidine and phenol as raw materials; then performing nucleophilic substitution with dibromobutane to generate azobenzene small-molecule 3-trifluoromethyl-4-brombutylazobenzene containing active bromine at one end; and performing quaterisation at 35 DEG C to graft azo groups to poly-dimethylaminoethyl (meth)acrylate to finally obtain azobenzene functionalized poly-dimethylaminoethyl methacrylate. The synthetic method disclosed by the invention is simple and feasible, the reaction temperature is lower than the conventional reaction temperature, and the synthesized polymer not only has temperature responsive property and pH responsive property but also has light responsive property, so that the polymer is a novel polymer with temperature, pH and light responsive properties.

Description

technical field [0001] The invention belongs to the field of organic chemistry and provides a method for synthesizing an azobenzene functionalized polymer with multiple responses. Background technique [0002] Stimulus-responsive polymer materials refer to the ability to sense various external conditions such as light, heat, electric field, magnetic field, pH, ionic strength, various chemical substances, etc., and respond quickly to make their own molecular structure reversible or irreversible. A class of polymer materials that cause changes in physical and chemical properties. In recent years, stimuli-responsive polymers have attracted extensive attention due to their potential applications in drug delivery, biosensing, chemical separation, cell culture, enzyme immobilization, and bioelectrocatalysis. [0003] In recent years, with the continuous in-depth research of stimuli-responsive polymers, the stimuli response has developed from a single stimulus to a double (multipl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F120/34C08F8/44
CPCC08F8/44C08F2810/10C08F120/34
Inventor 王国杰袁婷婷
Owner UNIV OF SCI & TECH BEIJING
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