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A kind of ferrocene derivative and composition thereof that can be used as photoredox catalyst in photopolymerization

A technology of ferrocene derivatives and compositions, applied in the field of organometallic photofunctional molecule synthesis and visible light photopolymerization, which can solve the problems of irreplaceability and achieve good redox ability

Active Publication Date: 2021-01-12
安庆北化大科技园有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to these limitations, type II photoinitiators with bimolecular combinations in the ultraviolet region cannot replace type I photoinitiators.

Method used

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  • A kind of ferrocene derivative and composition thereof that can be used as photoredox catalyst in photopolymerization
  • A kind of ferrocene derivative and composition thereof that can be used as photoredox catalyst in photopolymerization
  • A kind of ferrocene derivative and composition thereof that can be used as photoredox catalyst in photopolymerization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of ferrocene derivative FcIn1:

[0036]

[0037] In 10 mL of DMF, add 0.19 g (1 mmol) 5-bromo-2-thiophene aldehyde, 0.32 g (1.5 mmol) ethynyl ferrocene, 21 mg (0.03 mmol) Pd(PPh 3 ) 2 Cl 2 , 10 mg (0.05 mmol) of cuprous iodide, 13.12 mg (0.05 mmol) of triphenylphosphine, and 1 ml of triethylamine were magnetically stirred in an oil bath at 90° C. for 9 hours under nitrogen protection. After the completion of the reaction was monitored by thin-layer chromatography, the reactant was added to water to dilute to precipitate a solid, and the stirring was continued for 1 hour. The solid was collected and purified by column chromatography to obtain a red solid. 0.31 g of the obtained red solid and 0.22 g of 1,3-indanedione were dissolved in 6 mL of a solvent with a volume ratio of toluene / methanol of 1:1, and then 0.1 mL of piperidine was added. The resulting reaction was magnetically stirred in an 80°C oil bath for 4 hours. After the completion of the reacti...

Embodiment 2

[0039] Synthesis of ferrocene derivative FcIn2:

[0040]

[0041] In 10 mL of DMF, add 0.3 g (1 mmol) 9-ethyl-6-bromo-carbazole aldehyde, 0.32 g (1.5 mmol) ethynylferrocene, 21 mg (0.03 mmol) Pd(PPh 3 ) 2 Cl 2 , 10 mg (0.05 mmol) of cuprous iodide, 13.12 mg (0.05 mmol) of triphenylphosphine, and 1 ml of triethylamine were magnetically stirred in an oil bath at 90° C. for 9 hours under nitrogen protection. After the completion of the reaction was monitored by thin-layer chromatography, the reactant was added to water to dilute to precipitate a solid, and the stirring was continued for 1 hour. The solid was collected and purified by column chromatography to obtain a red solid. 0.31 g of the obtained red solid and 0.22 g of 1,3-indanedione were dissolved in 6 mL of a solvent with a volume ratio of toluene / methanol of 1:1, and then 0.1 mL of piperidine was added. The resulting reaction was magnetically stirred in an 80°C oil bath for 4 hours. After the completion of the reac...

Embodiment 3

[0043] Synthesis of ferrocene derivative FcIn3:

[0044]

[0045] Add 0.33g (1mmol) 10-ethyl-7-bromo-3-phenothiazinaldehyde, 0.32g (1.5mmol) ethynylferrocene, 21mg (0.03mmol) Pd(PPh) to 10mL of DMF 3 ) 2 Cl 2 , 10 mg (0.05 mmol) of cuprous iodide, 13.12 mg (0.05 mmol) of triphenylphosphine, and 1 ml of triethylamine were magnetically stirred in an oil bath at 90° C. for 9 hours under nitrogen protection. After the completion of the reaction was monitored by thin-layer chromatography, the reactant was added to water to dilute to precipitate a solid, and the stirring was continued for 1 hour. The solid was collected and purified by column chromatography to obtain a red solid. 0.31 g of the obtained red solid and 0.22 g of 1,3-indanedione were dissolved in 6 mL of a solvent with a volume ratio of toluene / methanol of 1:1, and then 0.1 mL of piperidine was added. The resulting reaction was magnetically stirred in an 80°C oil bath for 4 hours. After the completion of the rea...

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Abstract

The invention discloses a ferrocene derivative which can be used as a photoredox catalyst in photopolymerization and a composition thereof. The ferrocene derivative is a molecule bridged by a carbon-carbon triple bond / double bond and a conjugate It is obtained by connecting ferrocene and 1,3-indanedione. This type of ferrocene derivative has a molecular structure of D-π-A type, and its strong intramolecular electron transfer makes it have Strong absorption, is an effective photoredox catalyst; the photoinitiation system composed of ferrocene derivatives, onium salt photoinitiators and amine compounds can effectively initiate free radical light under visible light LED light source polymerization.

Description

technical field [0001] The invention belongs to the technical field of organometallic photofunctional molecule synthesis and visible light photopolymerization, and specifically relates to a ferrocene derivative and a composition thereof which can be used as a photoredox catalyst in photopolymerization. Background technique [0002] Photopolymerization has many advantages: no organic solvent volatilization, low energy consumption, rapid and complete curing at room temperature, and high curing performance. Therefore, photopolymerization technology has developed rapidly, and it has been widely used in coatings, photoresists, 3D printing materials, electronic packaging materials, adhesives and other fields. The photopolymerization process can be initiated by a single photoinitiator molecule or by a photoinitiation system. Photoinitiators or photoinitiating systems generate free radicals, cations or anions that can initiate polymerization under light conditions to initiate polym...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F17/02C08F2/48
CPCC07F17/02C08F2/48
Inventor 王涛韩卫祥
Owner 安庆北化大科技园有限公司
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