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Coumarin-based bridged silane and preparation method thereof

A coumarin-based, bisilane technology is applied in chemical instruments and methods, compounds of Group 4/14 elements of the periodic table, organic chemistry, etc. The effect of mild, good light response properties

Active Publication Date: 2019-12-06
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there is no report on the bridged silane material obtained by grafting coumarin into the organic bridged silane monomer

Method used

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  • Coumarin-based bridged silane and preparation method thereof
  • Coumarin-based bridged silane and preparation method thereof
  • Coumarin-based bridged silane and preparation method thereof

Examples

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Effect test

Embodiment 1

[0061] A preparation method of coumarin-based bridged silane, comprising steps as follows:

[0062] (1) Dissolve 7-N,N-diethylamino-4-methylcoumarin (4.63g, 20mmol) in 120mL 1,4-dioxane, add selenium dioxide ( 3.33 g, 30 mmol). The reaction mixture was heated to 90°C under vigorous stirring and reacted for 48h. After the reaction, the reaction system was filtered and rotary evaporated to obtain the intermediate product 1, which was dissolved in 130mL of methanol, and sodium borohydride (1.52g, 40mmol) was added in five batches under the condition of 0-4°C ice-water bath . Then the reaction system was raised to room temperature and stirred at room temperature for 8 h. Carefully add 40mL of 1mol / L HCl solution to the reaction system for hydrolysis, and extract the obtained red solution three times with 20mL of anhydrous dichloromethane, combine the organic phases, and use 30mL deionized water and 30mL saturated sodium bicarbonate solution for the organic phases in sequence a...

Embodiment 2

[0070] A preparation method of coumarin-based bridged silane, comprising steps as follows:

[0071] (1) Dissolve 7-N,N-diethylamino-4-methylcoumarin (4.63g, 20mmol) in 120mL 1,4-dioxane, add selenium dioxide ( 3.33 g, 30 mmol). The reaction mixture was heated to 85°C under vigorous stirring and reacted for 36h. After the reaction, the reaction system was filtered and rotary evaporated to obtain the intermediate product 1, which was dissolved in 130mL of methanol, and sodium borohydride (1.90g, 50mmol) was added in five batches under the condition of 0-4°C ice-water bath . Afterwards, the reaction system was raised to room temperature, and the reaction was stirred at room temperature for 4 h. Carefully add 30mL of 1mol / L HCl solution to the reaction system for hydrolysis, and extract the obtained red solution three times with 20mL of anhydrous dichloromethane, combine the organic phases, and use 30mL of deionized water and 30mL of saturated sodium bicarbonate solution in tur...

Embodiment 3

[0077] A preparation method of coumarin-based bridged silane, comprising steps as follows:

[0078] (1) Dissolve 7-N,N-diethylamino-4-methylcoumarin (4.63g, 20mmol) in 120mL 1,4-dioxane, add selenium dioxide ( 2.22g, 20mmol). The reaction mixture was heated to 80°C under vigorous stirring and reacted for 24h. After the reaction was completed, the reaction system was filtered and rotary evaporated to obtain an intermediate product 1, which was dissolved in 130 mL of methanol, and sodium borohydride (1.14 g, 30 mmol) was added in three batches under the condition of an ice-water bath at 0-4°C . Afterwards, the reaction system was raised to room temperature, and the reaction was stirred at room temperature for 4 h. Carefully add 40mL of 1mol / L HCl solution to the reaction system for hydrolysis, and extract the obtained red solution three times with 20mL of anhydrous dichloromethane, combine the organic phases, and use 30mL deionized water and 30mL saturated sodium bicarbonate ...

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Abstract

The invention relates to a coumarin-based bridged silane and a preparation method thereof. The coumarin-based bridged silane has a structure shown in formula I. 7-N,N-diethylamino-4-methyl coumarin isused as raw material, oxidized and reduced to obtain 7-N,N-diethylamino-4-hydroxymethyl coumarin, the 7-N,N-diethylamino-4-hydroxymethyl coumarin is acylated with chloroacetyl chloride to obtain 7-N,N-diethylamino-4-ethyl chloroacetate coumarin, last the coumarin-based bridged silane is obtained by substitution reaction between 7-N,N-diethylamino-4-ethyl chloroacetate coumarin and amine-containing bridged silane. The coumarin-based bridged silane obtained by the invention has good light response performance, can be used for designing and preparing light response performance materials, and hasimportant application value. The preparation method of the invention has the advantages of simple synthesis process, mild reaction conditions and strong operability.

Description

technical field [0001] The invention relates to a coumarin-based bridging silane and a preparation method thereof, belonging to the field of preparation of functional organic silicon compounds. Background technique [0002] Bridged silane is an organosilicon compound in which two silane groups are connected by an organic bridging group, and its structural formula can be expressed as X 3 Si–R–SiX 3 (In the formula, X is a group such as hydrogen, chlorine, alkyl, alkoxy, acyloxy, etc., and R is an organic bridging group). The organic bridging group has a wide range of adjustability. By designing the chemical composition and structure of the organic bridging group, the physical and chemical properties of the bridging silane can be effectively adjusted. Therefore, bridging silanes with different functions or functions can be obtained. Silanes and their corresponding polymeric materials. [0003] Photoresponsive materials, as a kind of smart materials, have been widely used in...

Claims

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Application Information

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IPC IPC(8): C07F7/18
CPCC07F7/1804C07F7/1892
Inventor 朱庆增张鑫
Owner SHANDONG UNIV
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