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Preparation method and application of photochromic chain transfer agent

A chain transfer agent and photochromic technology, applied in the direction of color-changing fluorescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of complex synthesis, difficulty in introducing spiropyran, easy leakage of spiropyran, etc., and achieve the goal of preparing Simple, conducive to large-scale industrial production, and the effect of good photochromic performance

Active Publication Date: 2016-12-07
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are usually two ways to prepare photochromic spiropyran polymers. One is to connect photochromic spiropyran units to the main chain or side chain of the polymer through copolymerization or grafting reaction. The disadvantage is that the synthesis is more complicated and the introduction of spiropyran is more difficult
The other is to blend the photochromic spiropyran with other materials to make the new material have photochromic properties. The disadvantage of this method is that the spiropyran is prone to leakage during the long-term use of the material.

Method used

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  • Preparation method and application of photochromic chain transfer agent
  • Preparation method and application of photochromic chain transfer agent
  • Preparation method and application of photochromic chain transfer agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: a kind of preparation method of photochromic chain transfer agent, concrete steps are as follows:

[0028] N-hydroxyethyl-3,3-dimethyl-6'-nitroindoline spiropyran 100mg (0.28mmol), 2-(dodecyltrithiocarbonate)-2-iso Add 112mg (0.31mmol) of butyric acid and 7mg (0.06mmol) of 4-dimethylaminopyridine into a 25ml two-neck round-bottomed flask, then add 5ml of dry dichloromethane and stir to dissolve, then stir for 0.5 Hour.

[0029] (2) Add 75 mg (0.33 mmol) of dicyclohexylcarbodiimide to 5 ml of dry dichloromethane to dissolve, then transfer to a constant pressure dropping funnel.

[0030] (3) Slowly add the solution obtained in step (2) to the solution obtained in step (1) dropwise, and react in the dark at room temperature for 24 hours after the addition is completed.

[0031] (4) Suction filter the mixed liquid after reaction to remove the generated white solid. After the resulting solution was concentrated, it was further purified by column chromatograp...

Embodiment 2

[0032] Embodiment 2: a kind of preparation method of photochromic chain transfer agent, concrete steps are as follows:

[0033] N-hydroxyethyl-3,3-dimethyl-5-chloro-6'-nitroindoline spiropyran 110mg (0.28mmol), 2-(dodecyltrithiocarbonate group) - Add 120mg (0.33mmol) of 2-isobutyric acid and 13mg (0.11mmol) of 4-dimethylaminopyridine into a 25ml two-necked round-bottomed flask, then add 5ml of dry dichloromethane and stir to dissolve. Stirred under the same conditions for 0.5 hours.

[0034] (2) Add 70mg (0.31mmol) of dicyclohexylcarbodiimide to 5ml of dry dichloromethane to dissolve, then transfer to a constant pressure dropping funnel.

[0035] (3) Slowly add the solution obtained in step (2) to the solution obtained in step (1) dropwise, and react in the dark at room temperature for 24 hours after the addition is completed.

[0036] (4) Suction filter the mixed liquid after reaction to remove the generated white solid. After the resulting solution was concentrated, it wa...

Embodiment 3

[0037] Embodiment 3: a kind of preparation method of photochromic chain transfer agent, concrete steps are as follows:

[0038]N-hydroxyethyl-3,3-dimethyl-6'-nitroindoline spiropyran 100mg (0.28mmol), 2-(tetradecyltrithiocarbonate)-2-iso Add 137mg (0.36mmol) of butyric acid and 9mg (0.08mmol) of 4-dimethylaminopyridine into a 25ml two-necked round-bottomed flask, then add 5ml of dry dichloromethane and stir to dissolve, then stir in the dark and in an ice bath 0.5 hours.

[0039] (2) Add 81 mg (0.36 mmol) of dicyclohexylcarbodiimide to 5 ml of dry dichloromethane to dissolve, then transfer to a constant pressure dropping funnel.

[0040] (3) Slowly add the solution obtained in step (2) to the solution obtained in step (1) dropwise, and react in the dark at room temperature for 24 hours after the addition is completed.

[0041] (4) Suction filter the mixed liquid after reaction to remove the generated white solid. After the resulting solution was concentrated, it was further...

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Abstract

The invention discloses a preparation method and application of a photochromic chain transfer agent. Spiropyrane compounds and trithiocarbonate chain transfer agents are subjected to esterification reaction to synthesize a novel photochromic chain transfer agent. The structure of a compound is shown in a formula I; then by using the compound shown in the formula I as the chain transfer agent, a reversible addition-fragmentation transfer (RAFT) free radical polymerization behavior of styrene is investigated, and a silicon wafer is coated with an obtained polymer with a photochromic property through a spin-coating machine, thus obtaining a polymer film with the photochromic property. According to the preparation method and the application disclosed by the invention, a photochromic group is introduced into an RAFT chain transfer agent structure, the chain transfer agent with the photochromic property is prepared, and living free radical polymerization of monomers such as styrene can be successfully realized, thereby obtaining a functional polymer with the photochromic function, controllable molecular weight and narrower molecular weight distribution. (The formula is shown in the description).

Description

technical field [0001] The invention relates to a chain transfer agent that can be used in the preparation of photoresponsive polymers, in particular to a preparation method and application of a photochromic chain transfer agent. Background technique [0002] In 1998, Rizzardo first proposed the concept of reversible addition-fragmentation chain transfer radical polymerization (RAFT) at the 37th International Polymer Congress. The RAFT polymerization method has the following advantages: (1) A wide range of applicable monomers. In addition to the common monomers methyl methacrylate and styrene, special monomers such as acrylic acid, sodium p-vinylbenzenesulfonate, hydroxyethyl methacrylate, and aminoethyl methacrylate can be polymerized smoothly, which is beneficial to Polymerization of specific functional ethylenic monomers. (2) It can be used to synthesize copolymers and homopolymers with various topological structures. (3) The polymerization reaction temperature is rela...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K9/02C08F112/08C08F2/38
CPCC07D491/107C08F112/08C09K9/02C09K2211/1029C09K2211/1088C08F2/38
Inventor 陈建钟维邦王宏张培盛洪永想吕锟余茂林
Owner HUNAN UNIV OF SCI & TECH
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