Aldehyde group-containing visible light photosensitizer taking triphenylamine as core and synthesis and application thereof

A triphenylamine and visible light technology, applied in the preparation of organic compounds, organic chemistry, carboxylic acid nitrile preparation, etc., can solve the problems of poor solubility of dyes and the need to improve the initiation efficiency, and achieve convenient raw material sources and appropriate yield , The effect of simple synthesis method

Inactive Publication Date: 2009-12-16
CHONGQING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Under the illumination of visible light, squaraine acts as a visible light photosensitizer to sensitize the ultraviolet photoinitiator iodonium salt, and generates free radicals to initiate the polymerization of ethylenic monomers through intermolecular photoelectron transfer. However, the solubility of such dyes is not very good. Good, and its triggering efficiency needs to be improved
Traditional photoinitiators include benzophenone, trichloromethyl-s-triazine, iodonium salt, benzoin ether and its derivatives, etc. These photoinitiators have high initiation efficiency, but they can only absorb 200-300nm Ultraviolet light, almost no absorption in the visible region

Method used

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  • Aldehyde group-containing visible light photosensitizer taking triphenylamine as core and synthesis and application thereof
  • Aldehyde group-containing visible light photosensitizer taking triphenylamine as core and synthesis and application thereof
  • Aldehyde group-containing visible light photosensitizer taking triphenylamine as core and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of N-phenyl-N-(distyryl)yl-4-benzaldehyde

[0032] The synthesis proceeds in three steps:

[0033] (1) Bis-(4-formylphenyl)-aniline

[0034] Add 25ml of N,N-dimethylformamide into a 250ml three-necked flask under an ice-water bath, and slowly add 20ml of phosphorus oxychloride dropwise under the protection of argon. After the dropwise addition, 3 g of triphenylamine was added, and the reaction was refluxed at 95° C. for 4 h. After the reaction is completed, cool to room temperature, add 200ml of distilled ice water, and adjust the pH to 7-8. Pour into 200ml of dichloromethane for extraction, then extract with distilled water 3 times, and dry over anhydrous sodium sulfate. Dichloromethane was evaporated to dryness, and the product was separated by a chromatographic column, concentrated, and recrystallized (ethyl acetate:cyclohexane=1:1) to obtain a yellow solid with a yield of 43.81%, which was set aside;

[0035] (2) Synthesis of diethyl phenylphosphonate ...

Embodiment 2

[0040] Synthesis of N-phenyl-N-(4-methylstilbene)yl-4-benzaldehyde

[0041] The synthesis proceeds in three steps:

[0042] (1) Bis-(4-formylphenyl)-aniline

[0043] Synthesis is carried out by the first step of embodiment 1;

[0044] (2) Synthesis of 4-methylphenylphosphonic acid diethyl ester

[0045] Mix 0.57g of 4-methylbenzyl bromide and 3.02g of triethyl phosphite in a three-necked ground flask with a molar ratio of 1:10, add a condensing device, and react at 130°C-160°C for 6 hours. Excessive triethyl phosphite was distilled under pressure to obtain diethyl 4-methylphenylphosphonate with a yield of 80%;

[0046] (3) Synthesis of N-phenyl-N-(4-methylstilbene)-4-benzaldehyde

[0047] Add 1.50g of bis-(4-formylphenyl)-aniline and 0.62g of 4-methylphenylphosphonic acid diethyl ester (molar ratio 3:1) synthesized in step (1) into the three-necked flask, Dissolve in tetrahydrofuran solvent with a volume ratio of 100-500 times, add 0.44g sodium methoxide, react under argo...

Embodiment 3

[0049] Synthesis of N-phenyl-N-(3,4,5-trimethoxystilbene)yl-4-benzaldehyde

[0050] The synthesis proceeds in three steps:

[0051] (1) Synthesis of two-(4-formylphenyl)-aniline

[0052] Synthesis is carried out by the first step of embodiment 1;

[0053] (2) Synthesis of 3,4,5-trimethoxyphenyl phosphonic acid diethyl ester

[0054] Mix 1.02g of 3,4,5-trimethoxybenzyl bromide and 4.47g of triethyl phosphite into a three-neck flask at a molar ratio of 1:10, add a condensing device, and react 6 at 130°C-160°C Hours, the excessive triethyl phosphite was distilled under reduced pressure to obtain 3,4,5-trimethoxyphenyl phosphonic acid diethyl ester with a yield of 70%, which was set aside;

[0055] (3) Synthesis of N-phenyl-N-(3,4,5-trimethoxystilbene)-4-benzaldehyde

[0056] Add 0.60g of 3,4,5-trimethoxyphenyl phosphonic acid diethyl ester and 0.23g of basic catalyst sodium methoxide (molar ratio 1:2.5) into the three-necked flask, stir under ice-water bath for half an hour, ...

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Abstract

The invention relates to aldehyde group-containing visible light photosensitizer taking triphenylamine as a core and synthesis and application thereof. A photosensitizer plays important roles of absorbing light and performing light action. The peak value of UV-visible absorption reaches over 370 nm, the half-peak width is about 100 nm, so that the visible light photosensitizer completely meets the requirement of visible light absorption and can be used for visible light polymerization. A general formula of a chemical structure of the visible light photosensitizer is shown as above, wherein compounds in the molecular structural formula (I) represent A:R1, R2:H, R3:CH3, OCH3, OCH2CH3, OCH2CH2CH3, OCH2CH2CH2CH3, N(CH3)2, N(CH2CH3)2, N(CH2CH2CH3)2, N(CH2CH2CH2CH3)2, CN, F, NO2; B:(R1, R2:, R3:OCH3). The aldehyde group-containing visible light photosensitizer taking the triphenylamine as the core is performed chemical modification to ensure that the peak value of the UV-visible absorption moves to over 370 nm; and the aldehyde group-containing visible light photosensitizer taking the triphenylamine as the core can be used as a photosensitive initiator to form a photosensitive system used for visible light polymerization of vinyl monomers in solution with other auxiliary agents, or can be used for a photocuring material.

Description

technical field [0001] The invention belongs to the field of visible photosensitizers, in particular to a visible photosensitizer with aldehyde group-containing triphenylamine as the core and a synthetic method thereof. Background technique [0002] Efficient visible light photoinitiator system is an important field in photopolymerization research. With the advancement of laser imaging and photocuring technology, photosensitive polymer materials such as photoresists, photocurable inks, coatings and photosensitive printing plates have been developed rapidly. A key technology of these photofunctional materials is how to extend the spectral response range to long wavelengths and obtain high sensitivity. For this reason, the development of a new type of photopolymerization initiation system with high sensitivity and low energy, which is sensitive to long-wavelength visible laser light, has become a hot research topic today. One way to shift the spectral absorption of the initi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/50C07C223/06C07C221/00C07C255/58C07C253/30C08F120/14
Inventor 高放王琪刘建杨龙李红茹张胜涛
Owner CHONGQING UNIV
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