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Open click-free radical one-pot method taking copper thioxanthone carboxylate as photocatalyst and deoxidant

A technology of copper thioxanthone carboxylate and copper xanthone carboxylate, which is applied in the field of exposed "click-free radicals" to achieve the effect of saving energy and simplifying the experimental process

Active Publication Date: 2017-08-22
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, light-induced polymerization under open conditions has rarely been reported, so it becomes necessary to achieve photocontrollable polymerization under open conditions

Method used

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  • Open click-free radical one-pot method taking copper thioxanthone carboxylate as photocatalyst and deoxidant
  • Open click-free radical one-pot method taking copper thioxanthone carboxylate as photocatalyst and deoxidant
  • Open click-free radical one-pot method taking copper thioxanthone carboxylate as photocatalyst and deoxidant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Weigh 0.79mmol of propynyl methacrylate, 0.79mmol of benzyl azide, 0.24mmol of copper thioxanthone carboxylate and 0.079mmol of methyl 2-bromo-2-phenylacetate required for polymerization with an electronic balance , into a 5ml ampere tube, add 0.4mL dimethyl sulfoxide, mix evenly, and place the open ampere tube under sunlight for 18 hours to react. After the polymerization, tetrahydrofuran was added into the ammeter tube to dilute the polymer, and precipitated in methanol, filtered by suction, and dried to obtain 0.179g of solid powder.

[0040] The light control experiment steps are as follows: use an electronic balance to weigh 0.79 mol of propynyl methacrylate, 0.79 mol of benzyl azide, 0.24 mol of copper thioxanthone carboxylate and 0.079 mmol of 2-bromo-2 - Methyl phenylacetate, add in the NMR tube, add 0.4mL deuterated dimethyl sulfoxide, after mixing, the NMR spectrum at the beginning of the test. After irradiating for 30 minutes, NMR was measured, and then oxyg...

Embodiment 2

[0042]Weigh 0.79mmol of propynyl methacrylate, 0.79mmol of benzyl azide, 0.024mmol of copper thioxanthone carboxylate and 0.0079mmol of methyl 2-bromo-2-phenylacetate required for polymerization with an electronic balance , into a 5ml ampere tube, add 0.4mL dimethyl sulfoxide, mix evenly, and place the open ampere tube under sunlight for 17h. After the polymerization, tetrahydrofuran was added into the ampere tube to dilute the polymer, and precipitated in methanol, suction filtered, and dried to obtain 0.175g of solid powder.

[0043] The light control experiment steps are as follows: use an electronic balance to weigh 0.79 mol of propynyl methacrylate, 0.79 mol of benzyl azide, 0.024 mol of copper thioxanthone carboxylate and 0.0079 mmol of 2-bromo-2 - Methyl phenylacetate, add in the NMR tube, add 0.4mL deuterated dimethyl sulfoxide, after mixing, the NMR spectrum at the beginning of the test. After irradiating for 30 minutes, NMR was measured, and then oxygen was injected...

Embodiment 3

[0045] Weigh 0.79mmol of propynyl methacrylate, 0.79mmol of benzyl azide, 0.0024mmol of copper thioxanthone carboxylate and 0.00079mmol of methyl 2-bromo-2-phenylacetate required for polymerization with an electronic balance , into a 20ml ampere tube, add 0.4mL dimethyl sulfoxide, mix well, and place the open ampere tube under sunlight for 16h. After the polymerization, tetrahydrofuran was added into the ampere tube to dilute the polymer, and precipitated in methanol, suction filtered, and dried to obtain 0.172g of solid powder.

[0046] The light control experiment steps are as follows: use an electronic balance to weigh 0.79 mol of propynyl methacrylate, 0.79 mol of benzyl azide, 0.0024 mol of copper thioxanthone carboxylate and 0.00079 mmol of 2-bromo-2 - Methyl phenylacetate, add in the NMR tube, add 0.4mL deuterated dimethyl sulfoxide, after mixing, the NMR spectrum at the beginning of the test. After irradiating for 30 minutes, NMR was measured, and then oxygen was inje...

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Abstract

The invention discloses an open click-free radical one-pot method taking copper thioxanthone carboxylate as photocatalyst and deoxidant. The open click-free radical one-pot method comprises the following steps: taking the copper thioxanthone carboxylate (CU(TX)2) as the photocatalyst and the deoxidant; reducing Cu(II) in a system into Cu(I) in situ under the irradiation of sunlight; meanwhile, catalyzing ATRP (Atom Transfer Radical Polymerization) and click reaction to prepare a sequence controllable gradient copolymer. According to the method disclosed by the invention, controllable polymerization can be realized without the need of adding a ligand, so that an experiment process is greatly simplified; the sunlight is used as a light source so that energy sources are greatly saved.

Description

technical field [0001] The present invention specifically relates to an open "click-free radical" one-pot process utilizing copper thioxanthone carboxylate as a photocatalyst and oxygen scavenger. Background technique [0002] In recent years, light-induced controllable / living radical polymerization has attracted more and more attention due to its advantages of convenient operation and easy spatiotemporal control. In this field of research, there are many cutting-edge and outstanding studies utilizing photoactive compounds (photoinitiators, photosensitizers, photoreductants) to activate and deactivate controlled / living radical polymerization. The most studied controlled / living radical polymerizations are mainly concentrated on nitrogen-oxygen-stabilized radical polymerization, atom transfer radical polymerization and reversible addition-fragmentation transfer polymerization. For photoreductant catalytic systems, free radicals are formed by light-induced single-electron tran...

Claims

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Application Information

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IPC IPC(8): C08F8/48C08F38/00C08F2/48C08F4/50
CPCC08F2/48C08F4/50C08F8/48C08F2800/10C08F38/00
Inventor 张卫东薛文涛文明
Owner SUZHOU UNIV
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