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Method for preparing multiple-stimulation respond material containing thienylmaleimide by virtue of dehydration reaction process

A multi-stimuli-responsive, maleimide-based technology, applied in color-changing fluorescent materials, chemical instruments and methods, organic chemistry, etc., can solve problems such as lack of sufficient understanding of piezochromic mechanism, and achieve high quantum efficiency of solid-state fluorescence , simple synthesis steps, good thermal stability

Inactive Publication Date: 2014-01-01
FUJIAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

High-resolution fluorescence recording requires very large changes in fluorescence intensity. Due to the lack of sufficient understanding of the piezochromic mechanism at the molecular level, only a few substances have been reported to have switchable piezochromism. Color changing properties (Chung, J. Chem. Soc., 2009, 131, 8163; Luo, Adv. Mater., 2011, 23, 3261; Luo, Chem. Eur. J., 2011, 17, 10515)

Method used

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  • Method for preparing multiple-stimulation respond material containing thienylmaleimide by virtue of dehydration reaction process
  • Method for preparing multiple-stimulation respond material containing thienylmaleimide by virtue of dehydration reaction process
  • Method for preparing multiple-stimulation respond material containing thienylmaleimide by virtue of dehydration reaction process

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 1) Preparation of 3,4-dichloromaleimide:

[0037] 3.88 g of maleimide (40 mmol) was placed in a high-pressure reaction flask, 20 ml of N,N-dimethylformamide was added, followed by 6.39 ml of thionyl chloride (90 mmol), sealed. Hold the bottle mouth of the high-pressure reaction bottle, heat it to 58 ° C, and gradually a pale yellow solid is produced. After a total of 72 hours of reaction, stop heating and return to room temperature, and filter with 100 ml of water and 60 ml of dichloromethane successively to obtain 3. ,4-dichloromaleimide;

[0038] 2) Preparation of 3,4-dichloromaleic anhydride:

[0039] 0.83 g of 3,4-dichloromaleimide (5 mmol) and 100 ml of 10% NaOH aqueous solution were added to the round-bottomed flask, and the reaction was refluxed for 3 hours. L of hydrochloric acid solution, stop adding the hydrochloric acid solution dropwise after the solid is completely precipitated, stand for 1 hour, filter with suction, and dry to obtain 3,4-dichloromaleic a...

Embodiment 2

[0047] 1) Preparation of 3,4-dibromomaleimide:

[0048] Place 3.88 g of maleimide (40 mmol) in a high pressure reaction flask, add 25 ml of N,N-dimethylformamide, followed by 4.77 ml of bromine (93 mmol), seal the high pressure The bottle mouth of the reaction flask was heated to 58 °C, and a pale yellow solid was gradually produced. After a total of 48 hours of reaction, the heating was stopped and returned to room temperature, and 125 ml of water and 75 ml of dichloromethane were successively used for suction and filtration to obtain 3, 4-dibromomaleimide;

[0049] 2) Preparation of 3,4-dibromomaleic anhydride:

[0050] 1.27 g of 3,4-dibromomaleimide (5 mmol) and 150 ml of 10% NaOH aqueous solution were added to a round-bottomed flask, and the reaction was refluxed for 3 hours. After cooling, 2 mol / L of hydrochloric acid solution, stop adding the hydrochloric acid solution dropwise after the solid is completely precipitated, stand for 1 hour, filter with suction, and dry ...

Embodiment 3

[0056] 1) Preparation of 3,4-dichloromaleimide:

[0057] 3.88 g of maleimide (40 mmol) was placed in a high pressure reaction flask, 30 ml of N,N-dimethylformamide was added, followed by 7.26 ml of thionyl chloride (100 mmol), sealed. Hold the bottle mouth of the high-pressure reaction flask, heat it to 58 ° C, and gradually a pale yellow solid is produced. After a total of 72 hours of reaction, stop heating and return to room temperature, add 150 ml of water and 90 ml of dichloromethane for suction filtration to obtain 3, 4-Dichloromaleimide;

[0058] 2) Preparation of 3,4-dichloromaleic anhydride:

[0059] 0.83 g of 3,4-dichloromaleimide (5 mmol) and 200 ml of 10% NaOH aqueous solution were added to a round-bottomed flask, and the reaction was refluxed for 3 hours. L of hydrochloric acid solution, stop adding the hydrochloric acid solution dropwise after the solid is completely precipitated, stand for 1 hour, filter with suction, and dry to obtain 3,4-dichloromaleic anhydr...

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Abstract

The invention discloses a method for preparing a multiple-stimulation respond material containing thienylmaleimide by virtue of a dehydration reaction process. The method comprises the following steps: reacting maleimide with a halogenating reagent, and filtering to obtain 3,4-dihalogenmaleimide; mixing the 3,4-dihalogenmaleimide with an aqueous solution of NaOH for a reflux reaction, and then dropwise adding a hydrochloric acid solution, and then carrying out suction filtration and drying to obtain 3,4-dihalogen maleic anhydride; after reflux of the 3,4-dihalogen maleic anhydride with primary amine, an organic base and tetrahydrofuran, extracting, drying, filtering and purifying to obtain N-substituent-3,4-dihalogenmaleimide; mixing and reacting the N-substituent-3,4-dihalogenmaleimide with a palladium bis(triphenylphosphine) dichloride catalyst, N,N-dimethylformamide and 2-(tributylstannyl)thiophene, and then purifying to obtain N-substituent-3,4-bis(2'-thienyl)maleimide. The material is good in heat stability, simple in synthesis steps and high in quantum efficiency, and has the properties of piezallochromy, thermochromism, gasochromism and the like.

Description

technical field [0001] The invention relates to a method for preparing multiple stimulus response materials by dehydration reaction method, in particular to multiple stimulus response materials containing thienyl maleimide and a preparation method thereof. Background technique [0002] In recent years, organic solid fluorescent materials have attracted the interest of many researchers due to their great application potential in optoelectronic functional materials (Yang Shuaijun, Research Progress in Organic Solid Fluorescent Materials, 2013; Anthony, ChemPlusChem, 2012, 77, 518 ). With the deepening of research, it is found that some materials can only change the interaction between molecules without destroying the molecular structure, and can achieve different responses under external stimuli. Among them, stimuli-responsive fluorescence conversion materials (aerochromic, thermochromic and piezochromic materials) are of great significance for the development of information ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14C09K9/02
CPCC07D409/14C09K9/02C09K2211/1092
Inventor 凌启淡林正欢梅晓飞黄丽梅
Owner FUJIAN NORMAL UNIV
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