Ferrocene derivative used as photo-oxidation reduction catalyst in photo-polymerization and composition thereof

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

Active Publication Date: 2019-01-18
安庆北化大科技园有限公司
View PDF0 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to these limitations, type II photoinitiators with bimolecular co...

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Ferrocene derivative used as photo-oxidation reduction catalyst in photo-polymerization and composition thereof
  • Ferrocene derivative used as photo-oxidation reduction catalyst in photo-polymerization and composition thereof
  • Ferrocene derivative used as photo-oxidation reduction catalyst in photo-polymerization and composition thereof

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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The present invention discloses a ferrocene derivative used as a photo-oxidation reduction catalyst in photo-polymerization and a composition thereof. The ferrocene derivative is obtained by connecting ferrocene and 1,3-indandione through a carbon-carbon triple bond/double bond and a conjugated bridged molecule; the ferrocene derivative has a D-Pi-A type molecular structure, and relatively strongintramolecular electron transfer ensures that the ferrocene derivative has strong absorption in blue-green regions, so that the ferrocene derivative is an effective photo-oxidation reduction catalyst;and a photo-initiation system formed by the ferrocene derivative, an onium salt photo-initiator and an amine compound can effectively induce free radical photo-polymerization under visible light LEDlight sources.

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products