A monodisperse cyclic azobenzene-tetraethylene glycol copolymer and its preparation method and use

A technology of cyclic azobenzene and monodispersity, which is applied in the field of polymer materials and can solve the problems of few reports

Active Publication Date: 2017-07-07
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the difficulty of precisely synthesizing cyclic polymers with definite molecular weights, there are still few related reports.

Method used

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  • A monodisperse cyclic azobenzene-tetraethylene glycol copolymer and its preparation method and use
  • A monodisperse cyclic azobenzene-tetraethylene glycol copolymer and its preparation method and use
  • A monodisperse cyclic azobenzene-tetraethylene glycol copolymer and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Example 1: Preparation of the first generation bromine-containing intermediate and chain extender.

[0076] 1. Preparation of tetraethylene glycol intermediate (Br-TEG-OH).

[0077] Take 3.88 g (20 mmol) of tetraethylene glycol, 1.4 mL (20 mmol) of triethylamine and 10 mL of dry dichloromethane and place them in a 50 mL three-necked flask equipped with a stirring device, cool in an ice-salt bath and control the temperature to 0~5℃. Dissolve 3 mL (20 mmol) of 6-bromohexanoyl chloride in 5 mL of dry dichloromethane, and add it dropwise into a three-necked flask with a constant pressure dropping funnel, controlling the solution temperature at 0-5 °C. After the dropwise addition was completed, the reaction was carried out at room temperature for 2.5 h. After the reaction was completed, it was suction filtered, and the filtrate was washed with dilute hydrochloric acid, 1M NaOH and saturated NaCl aqueous solution to pH=7. The obtained organic phase was dried over anhydrous...

Embodiment 2

[0094] Embodiment 2: Preparation of the 2nd to 6th generation bromine-containing intermediates.

[0095] 1. The second generation of bromine-containing intermediates (α-alkynyl-(Azo-TEG) 2 -ω-bromo).

[0096] Add 1.82 g (2.5 mmol) of the first-generation bromine-containing intermediate (α-alkynyl-(Azo-TEG) 1 -ω-bromine) and 20 mL of dry dichloromethane, after argon for 30 min, add 35.8 mg (0.25 mmol) CuBr and 0.06 mL (0.25 mmol) PMDETA, slowly add 1.82 g (3 mmol) dropwise under the protection of argon ) chain extender (TMS-alkynyl-Azo-TEG-azide), react at room temperature for 1 h after the dropwise addition, and obtain the second-generation bromine-containing intermediate protected by TMS; then add 0.4 mL (0.8 mmol ) TBAF, stirred at room temperature for 1 h, then poured into ethyl acetate, extracted three times with deionized water, dried the organic layer with anhydrous magnesium sulfate overnight, filtered with suction, rotary evaporated, and purified by column chromatogr...

Embodiment 3

[0106] Embodiment three: the preparation of linear copolymer intermediate and cyclic copolymer.

[0107] 1. The first generation of linear copolymer intermediates ( l -(Azo 2 -TEG 1 )) and cyclic copolymers ( c -(Azo 2 -TEG 1 )) preparation.

[0108] (a) l -(Azo 2 -TEG 1 ) preparation: take 0.548 g (1 mmol) α-alkynyl-(Azo-TEG) 1 -ω-bromine, 0.552g (1 mmol) K 2 CO 3 , 0.017 g (0.1 mmol) KI and 40 mL DMF were placed in a 100 mL round bottom flask equipped with a stirring device. 0.444 g (2 mmol) of 3-alkynyl-4’-hydroxyazobenzene (HAAzo) was dissolved in 15 mL of DMF, slowly added dropwise to the reaction system, and reacted at 80 °C for 4 h. The reaction solution was naturally cooled to room temperature, then poured into ethyl acetate, extracted three times with deionized water, dried the organic layer with anhydrous magnesium sulfate overnight, filtered with suction, rotary evaporated, and purified by column chromatography to obtain l -(Azo 2 -TEG 1 ) (yield 0.82...

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Abstract

The invention discloses a monodispersity annular azobenzene and tetraglycol copolymer and a preparation method and application thereof. The monodispersity annular azobenzene and tetraglycol copolymer has the structural formula shown as follows (please see the formula in the specification), wherein n is 1, 2, 3, 4, 5 or 6. The preparation method includes the steps of preparing a chain extender, preparing various generations of bromine-containing intermediates, preparing a linear copolymer intermediate, preparing an annular copolymer and the like. Compared with a multi-dispersity copolymer obtained through a traditional method, monodispersity annular azobenzene has outstanding optical properties and machining performance. In addition, the copolymer has amphipathy, a photosensitive nanometer material can be obtained through polymer self-assembling and is used for the field of biological detection and medicine control release, and wide and important potential application value is achieved.

Description

technical field [0001] The invention belongs to the field of macromolecular materials, and in particular relates to a monodisperse cyclic azobenzene-tetraethylene glycol copolymer with photoresponsive properties and amphiphilicity, its preparation method, and its use in the preparation of optical materials and biological materials the use of. Background technique [0002] The precision synthesis of monodisperse polymers with defined chain lengths and chemical structures not only allows accurate knowledge of the relationship between molecular structure and its properties, but also enables the prediction and optimization of material properties. At present, there are mainly two methods for synthesizing monodisperse polymers: stepwise growth method and exponential growth method. The stepwise growth method was initially used to synthesize polypeptides, and then used to synthesize oligomers with precisely controlled chain length and structure; while the exponential growth method ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/06
CPCC08G65/48
Inventor 周年琛蒋习徐效飞潘向强张伟张正彪朱秀林
Owner SUZHOU UNIV
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