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Benzo five-membered ring-benzyne sulfonium salt derivative as well as preparation method and application thereof

A five-membered ring and sulfonium salt technology, which is applied in the field of new material organic chemicals, can solve problems affecting the photoinitiation effect, achieve wide applicability, broaden the scope of application, and have good matching effects

Pending Publication Date: 2022-07-05
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the sulfonium salt with a stilbene structure is also disadvantageous. The double bond in the stilbene structure will be isomerized under light conditions, competing with the S-C bond cleavage of the sulfonium salt, making the photoinitiator The absorbed energy cannot be completely used for molecular excitation and breaks the S-C bond, which affects its photoinitiation effect
Therefore, the molecule can be designed as a photoinitiator with a triple bond structural unit to avoid the photoisomerization reaction of the molecule. In addition, it has been reported that there are fewer sulfonium salt molecules with a triple bond structural unit. , Benzo five-membered ring-phenylynylsulfonium salt derivatives with high initiating performance is a technical difficulty for us

Method used

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  • Benzo five-membered ring-benzyne sulfonium salt derivative as well as preparation method and application thereof
  • Benzo five-membered ring-benzyne sulfonium salt derivative as well as preparation method and application thereof
  • Benzo five-membered ring-benzyne sulfonium salt derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1: Synthesize target sulfonium salt molecule (I)-1-PF according to the following route 6 -

[0051]

[0052] (a) Boric acid, water, room temperature, 3h; potassium iodide, anhydrous potassium carbonate, iodine, water, tetrahydrofuran, 50℃, 12h;

[0053] (b) bis(triphenylphosphine)palladium(II) chloride, potassium carbonate, N,N-diformamide, 130°C, 48h;

[0054] (c) methyl trifluoromethanesulfonate, dichloromethane, dark, room temperature, 24h; potassium hexafluorophosphate, room temperature.

[0055] 1. Synthesis of (I)-1a

[0056] 2-Aminophenol (21.8g, 0.20mol), boric acid (3.09g, 0.05mol) and solvent distilled water (100mL) were added to a 250mL three-necked flask containing a magnetic rotor, and then propyne was slowly added dropwise through a constant pressure dropping funnel Aldehyde (10.8 g, 0.2 mol) was added to the reaction system, and after the addition was completed, the mixture was stirred at room temperature for 3 h, and the reaction proces...

Embodiment 2

[0065] Embodiment 2: Synthesize target sulfonium salt molecule (I)-2-PF according to the following route 6 -

[0066]

[0067] (a) Boric acid, water, room temperature, 3h; potassium iodide, anhydrous potassium carbonate, iodine, water, tetrahydrofuran, 50℃, 12h;

[0068] (b) bis(triphenylphosphine)palladium(II) chloride, potassium carbonate, N,N-diformamide, 130°C, 48h;

[0069] (c) methyl trifluoromethanesulfonate, dichloromethane, dark, room temperature, 24h; potassium hexafluorophosphate, room temperature.

[0070] 1. Synthesis of (I)-2a

[0071] 2-aminothiophenol (25.0g, 0.20mol), boric acid (3.09g, 0.05mol) and solvent distilled water (100mL) were added to a 250mL three-necked flask containing a magnetic rotor, and then slowly added dropwise through a constant pressure dropping funnel Propargyl aldehyde (10.8 g, 0.2 mol) was added to the reaction system, and after the addition was completed, the mixture was stirred at room temperature for 3 h, and the reaction proc...

Embodiment 3

[0080] Embodiment 3: Synthesize target sulfonium salt molecule (I)-7-PF according to the following route 6 -

[0081]

[0082] (a) Boric acid, water, room temperature, 3h; potassium iodide, anhydrous potassium carbonate, iodine, water, tetrahydrofuran, 50℃, 12h;

[0083] (b) Copper powder, potassium carbonate, 18-crown-6, o-dichlorobenzene, 200℃, 48h;

[0084] (c) bis(triphenylphosphine)palladium(II) chloride, potassium carbonate, N,N-diformamide, 130°C, 48h;

[0085] (d) methyl trifluoromethanesulfonate, dichloromethane, dark, room temperature, 24h; potassium hexafluorophosphate, room temperature.

[0086] 1. Synthesis of (I)-7a

[0087] Add o-phenylenediamine (21.6g, 0.20mol), boric acid (3.09g, 0.05mol) and solvent distilled water (100mL) to a 250mL three-necked flask containing a magnetic rotor, then slowly add propargyl aldehyde dropwise through a constant pressure dropping funnel (10.8 g, 0.2 mol) was added to the reaction system, and after the addition was compl...

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Abstract

The invention relates to a benzo five-membered ring-benzyne sulfonium salt derivative as well as a preparation method and application thereof. The specific molecular structure of the benzo five-membered ring-benzyne sulfonium salt derivative is as shown in the following formula (I). Molecules and benzyne groups form a large conjugated structure through five-membered hybridization of benzo, the synthesis route is simple, and the prepared sulfonium salt has good light absorption and photo-acid production efficiency in a near ultraviolet-visible light region. The invention relates to the field of photoinitiators, in particular to application of the photoinitiators serving as radiation curing photoinitiators in the fields of ultraviolet-visible light emitting LED photocuring and photoresists, and application of the photoinitiators in various occasions such as radiation curing formula products, particularly UV-Vis-LED photocuring coatings and the like.

Description

【Technical field】 [0001] The present invention relates to the technical field of organic chemicals of new materials, in particular to a class of benzofive-membered ring-benynyl sulfonium salt derivatives, its chemical process preparation technology, its use as a radiation curing photoinitiator, and its use in radiation curing Curing formula products, especially in UV-Vis-LED light-curing coatings, and many other applications. 【Background technique】 [0002] Light-curing technology is a green and environmentally friendly technology, which is widely used in coatings, inks, electronic communications, photoresists, dental materials, and 3D printing. Since visible light curing technology and visible light LED light source have the advantages of stable light source, environmental protection and safety, it is of great significance to develop new visible light initiators. As one of the important components of the visible light curing system, the visible light initiator has a great ...

Claims

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Application Information

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IPC IPC(8): C07D263/56C07D277/64C07D235/06C08F2/50
CPCC07D263/56C07D277/64C07D235/06C08F2/50
Inventor 金明廖文
Owner TONGJI UNIV
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