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Polymer containing azobenzene circlet on side chain and preparation method thereof

A technology for azobenzene and polymers, applied in the field of preparation of polymers containing azobenzene small rings in the side chain, to achieve the effects of controllable molecular weight, clear structure and narrow molecular weight distribution

Active Publication Date: 2013-08-14
ZHEJIANG KELI NEW MATERIAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, polymers with cyclic azobenzene ringlets "hanging" on polymer side chains have not been reported

Method used

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  • Polymer containing azobenzene circlet on side chain and preparation method thereof
  • Polymer containing azobenzene circlet on side chain and preparation method thereof
  • Polymer containing azobenzene circlet on side chain and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0030] refer to figure 1Shown, a kind of side chain contains the polymkeric substance of azobenzene small ring and preparation method, comprises the following steps:

[0031] Step 1) Take compound The compound is obtained by etherification with 1,6-dibromohexane and azidation with sodium azide , (3) through the coupling reaction with the diazonium salt of m-aminophenylacetylene to obtain the compound , (4) Cyclic azo compounds were obtained by the intramolecular Click reaction of the azide / alkynyl CuAAC method , (5) Etherification with bromoundecyl alcohol and esterification with methacryloyl chloride to obtain methyl methacrylate (MMA) monomer containing azobenzene small ring cyclic- AZOMMA, its structural formula is:

[0032] ;

[0033] Step 2) Living radical polymerization of monomers by reversible addition-fragmentation transfer (RAFT); the polymerization system includes monomers, RAFT reagents, and free radical initiators; wherein, in molar ratio, [monomer] ...

Embodiment 1

[0039] 1. If figure 1 As shown, the synthesis of the monomer mainly has the following steps:

[0040] Step 1) Add 2.0g 2,2 to a 500mL three-neck flask ， -Dihydroxybiphenyl, 2.97g K 2 CO 3 , 300mL of acetone, 70 o C oil bath was heated to reflux. Add 2.8 g of 1,6-dibromohexane in acetone solution dropwise into the reaction system. React for half an hour after dropping. The reaction solution was suction filtered, the filtrate was rotary evaporated to remove the solvent, and the crude product was purified by column chromatography to obtain compound (2).

[0041] Step 2) Add 4.0g compound (2), 1.13g NaN to a 50mL round bottom flask 3 , and after 30mL DMF at 50 o C oil bath was reacted for 24 hours. After the reaction was completed, the reaction solution was poured into ethyl acetate, washed with water three times, and the organic phase was collected, and the solvent was removed by rotary evaporation to obtain compound (3).

[0042] Step 3) Add 4.25g m-aminophenylace...

Embodiment 2

[0049] Embodiment two: compound (4), (5) and homopolymer P cycle -UV-Vis absorption spectrum of AZOMMA

[0050] Weigh compound (4) and compound (5) 0.554mg, homopolymer P cycle -AZOMMA 0.225mg was prepared into 10mL tetrahydrofuran solution for use, and the concentration of azophenyl groups in the solution was 5×10 -5 mol / L. The above solutions were respectively dropped on the quartz glass plate to dry naturally to form a thin film for use. The above solution and film were tested for UV-Vis absorption, such as image 3 . It was found that relative to the solution state, the maximum absorption peak of compound (5) had a red shift of 5nm in the thin film, but this phenomenon was not observed for compound (4) and homopolymer.

[0051] The above solution of compound (4) was irradiated with 365nm ultraviolet light for different time to measure the change of its ultraviolet-visible absorption, such as Figure 4 . Due to the existence of the azobenzene structure, the trans-c...

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Abstract

The invention discloses a polymer containing an azobenzene circlet on a side chain and a preparation method thereof. The preparation method comprises the following steps: synthesizing an intermediate compound (4) containing alpha-azido-omega-alkynyl through diazo coupling reaction and azotizing reaction, and then carrying out CuAAC intramolecular cyclization and the like to obtain a monomer containing the azobenzene circlet; and polymerizing the monomer by utilizing an RAFT (Reversible Addition-Fragmentation Chain Transfer Polymerization) method to obtain a functional polymer which contains the azobenzene circlet on the side chain and is definite in structure. Due to adoption of the technical scheme, the polymer is controllable in molecular weight, narrow in molecular weight distribution and definite in structure; cycle tension generated by a cycle structure in the structure of the synthesized polymer which contains the azobenzene circlet on the side chain has special influences on photo-isomerization property, grating property and the like of the polymer and can improve the photo-isomerization property, grating property and the like of the polymer.

Description

technical field [0001] The invention belongs to the field of high-molecular polymers, and in particular relates to a preparation method of polymers containing azobenzene small rings in side chains. Background technique [0002] Based on the fact that cyclic polymers have no end groups, compared with linear polymers, cyclic polymers exhibit many improved or unique physical properties, such as smaller fluid size, lower intrinsic viscosity, larger refractive index and more high glass transition temperature, etc. Designing and synthesizing cyclic polymers and studying their properties have attracted attention in recent years. In 2006, Grayson et al first combined ATRP with Cu + A combination of catalyzed "Click" reactions provides almost quantitative access to cyclic polystyrene via azide / alkynyl head-to-tail annulation (cf: Boyd A. Laurent and Scott M. Grayson. J. AM. CHEM. SOC. 2006 , 128, 4238-4239), since CuAAC "Click" ring closure has become a widely used method for prep...

Claims

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Application Information

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IPC IPC(8): C08F120/36C08F2/38
Inventor 周年琛李江玉朱秀林潘向强张正彪
Owner ZHEJIANG KELI NEW MATERIAL TECH CO LTD
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