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Pyrenyl-containing radical initiator, and synthesis method and use thereof

A synthesis method and initiator technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as inapplicability of initiators

Inactive Publication Date: 2014-07-16
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It solves the problem that conventional commercial initiators are not suitable for the synthesis of specific group-terminated polymers, thus providing a new method for obtaining pyrenyl-containing polymers (each polymer chain is terminated by about 1 pyrene group) The selection scheme, and then laid the foundation for the preparation of graphene by the dispersion aid assisted liquid phase exfoliation method

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  • Pyrenyl-containing radical initiator, and synthesis method and use thereof
  • Pyrenyl-containing radical initiator, and synthesis method and use thereof
  • Pyrenyl-containing radical initiator, and synthesis method and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0042] Take a 150ml three-neck flask, mix 40ml of dichloromethane, 50.1mg (0.18mmol) of 4,4'-azo(4-cyanovaleric acid) (as shown in general formula B1), 92.9mg (0.40mmol) of pyrene Methanol (as shown in the general formula C1, where x=1), 8.6mg (0.07mmol) DMAP, 64.9mg (0.48mmol) HOBT were added to it successively, and a homogeneous solution was prepared under magnetic stirring. Then, under the conditions of ice-water bath and nitrogen protection, EDC.HCl / dichloromethane solution (86.3 mg (0.45 mmol) EDC.HCl dissolved in 10 ml of dichloromethane) was slowly added dropwise. After the dropwise addition was completed for 30 minutes, the ice-water bath was removed, and the temperature of the reaction system was raised to 30° C. for 24 hours of reaction. The reaction solution was filtered, and the filtrate was diluted to 100ml with dichloromethane. The solution was subjected to 3 times of 1M HCl (3×50ml), 3 times of saturated NaHCO 3 solution (3×50ml), three times of distilled wate...

Embodiment 2

[0045] The pyrene group-containing small molecule compound pyrenemethanol in Example 1 was replaced with pyrenebutanol (as shown by the general formula C1, where x=4), and the dosage was 104.3mg (0.38mmol); the dosage of dichloromethane was adjusted to 45ml, The amount of DMAP was adjusted to 19.5mg (0.16mmol), the amount of EDC.HCl was adjusted to 80.5mg (0.42mmol) without HOBT, the reaction temperature was adjusted to 25°C, and the reaction time was extended to 26 hours; other operating conditions were the same as in Example 1 . Obtain light yellow solid compound, productive rate is greater than 86%, and molecular structural formula is:

Embodiment 3

[0047] Take a 150ml three-neck flask, mix 70ml of dichloromethane, 50.3mg (0.18mmol) of 4,4'-azo (4-cyanovaleric acid), 97.1mg (0.42mmol) of pyrenemethylamine (as represented by the general formula C2) Shown, where x=1), 106.4mg (0.49mmol) Sulfo-NHS was added to it successively, and a homogeneous solution was prepared under magnetic stirring. Then, under the conditions of ice-water bath and nitrogen protection, EDC.HCl / dichloromethane solution (89.7mg (0.47mmol) EDC.HCl dissolved in 10ml of dichloromethane) was slowly added dropwise. After the dropwise addition was completed for 1 hour, the ice-water bath was removed, the temperature of the reaction system was raised to 35° C., and the reaction was carried out for 18 hours. The reaction solution was filtered, and the filtrate was diluted to 100ml with dichloromethane. The solution was subjected to 3 times of 1M HCl (3×50ml), 3 times of saturated NaHCO 3 solution (3×50ml), three times of distilled water (3×50ml), and the orga...

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Abstract

The invention discloses a pyrenyl-containing radical initiator, and a synthesis method and use thereof. The initiator is a pyrenyl-containing azo compound with a symmetric structure, and can generate two primary radicals containing pyrenyl with the same molecular structures after thermal decomposition. A common commodity azo initiator and a pyrenyl-containing small molecule compound are taken as raw materials, and synthesis is carried out by adopting esterification reaction or amidation reaction. The pyrenyl-containing radical initiator disclosed by the invention can be used as a thermal initiator for alkene compound polymerization reaction to synthesize the pyrenyl-containing high-molecular compound, the pyrene group is located at the tail end of a macromolecular chain, and a single macromolecular chain contains 0.9-1.2 pyrene groups averagely; the synthesized pyrenyl-containing high-molecular compound can serve as a dispersing aid to be applied to a dispersing aid-assisted liquid-phase stripping method, so as to prepare graphene from natural graphite.

Description

technical field [0001] The invention relates to the field of functional chemical initiators, and more specifically relates to the innovation of a pyrenyl-containing azo free radical initiator and its synthesis method and application. Background technique [0002] Because of its unique structure, excellent performance and broad application prospects, graphene has caused a worldwide research boom since it came out in 2004, and the low-cost macro-preparation of high-quality graphene is the basis for all research and applications. The preparation of graphene from natural graphite is currently the most effective way to obtain graphene materials. The main preparation methods include micromechanical exfoliation, graphite oxide reduction and liquid phase exfoliation. Among them, the micromechanical exfoliation method can produce high-quality graphene, but the yield is low, and it is only suitable for basic research. Although the graphite oxide reduction method can realize the low-c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F4/04C08F120/14C08F112/08C08F126/06C08F299/02C01B31/04C07C255/61C07C253/30C01B32/19
Inventor 崔健闫业海陈钊辛兰霞赵帅
Owner QINGDAO UNIV OF SCI & TECH