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Method for preparing multiple-stimulation respond material containing thienylmaleimide by virtue of two-step process

A multi-stimulus response, maleimide technology, applied in luminescent materials, color-changing fluorescent materials, chemical instruments and methods, etc., can solve the problem of lack of sufficient understanding of the piezochromic mechanism, and achieve high solid-state fluorescence quantum efficiency. , the synthesis steps are simple, and the thermal stability is good.

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 two-step process
  • Method for preparing multiple-stimulation respond material containing thienylmaleimide by virtue of two-step process
  • Method for preparing multiple-stimulation respond material containing thienylmaleimide by virtue of two-step process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1) Preparation of 3,4-dibromomaleimide:

[0030] Put 3.88 g of maleimide (40 mmol) in a high pressure reaction flask, add 20 ml of N,N-dimethylformamide, then add 4.62 ml of bromine (90 mmol), seal the high pressure Heating the mouth of the reaction bottle to 58°C, gradually a light yellow solid was produced. After 48 hours of reaction, stop heating and return to room temperature, add 100 ml of water and 60 ml of dichloromethane for suction filtration, and obtain 3, 4-dibromomaleimide;

[0031] 2) Preparation of 3,4-bis(2'-thienyl)maleimide:

[0032] Put 0.51 g of 3,4-dibromomaleimide (2 mmol) and 7.02 mg of bistriphenylphosphine palladium dichloride catalyst (0.01 mmol) into a 25 ml two-necked flask, vacuumize, Infuse nitrogen gas, repeat pumping and irrigation three times, inject 1.27 ml of 2-tributylstannylthiophene (4 mmol) and 10 ml of N,N-dimethylformamide with a syringe, raise the temperature to 100°C, and react for 12 hours , stop heating and drop back to room ...

Embodiment 2

[0037] 1) Preparation of 3,4-dichloromaleimide:

[0038] Put 3.88 g of maleimide (40 mmol) in a high-pressure reaction flask, add 25 ml of N,N-dimethylformamide, then add 5.81 ml of thionyl chloride (80 mmol), seal Close the mouth of the high-pressure reaction bottle and heat it to 58°C. Gradually, a light yellow solid is produced. After 54 hours of reaction, stop heating and return to room temperature. Add 125ml of water and 75ml of dichloromethane successively for suction and filtration to obtain 3 , 4-dichloromaleimide;

[0039] 2) Preparation of 3,4-bis(2'-thienyl)maleimide:

[0040] Put 0.33 g of 3,4-dichloromaleimide (2 mmol) and 35.10 mg of bistriphenylphosphine palladium dichloride catalyst (0.05 mmol) into a 25 ml two-necked flask, vacuumize, Infuse nitrogen, repeat pumping and irrigation three times, inject 2.54 ml of 2-tributylstannylthiophene (8 mmol) and 10 ml of anhydrous N,N-dimethylformamide with a syringe, raise the temperature to 100°C, and react At 12 hou...

Embodiment 3

[0042] 1) Preparation of 3,4-dibromomaleimide:

[0043] Put 3.88 g of maleimide (40 mmol) in a high pressure reaction bottle, add 30 ml of N,N-dimethylformamide, then add 5.13 ml of bromine (100 mmol), seal the high pressure Heating the mouth of the reaction bottle to 58°C, gradually a light yellow solid was produced. After 72 hours of reaction, stop heating and return to room temperature, add 150 ml of water and 90 ml of dichloromethane for suction and filtration to obtain 3, 4-dibromomaleimide;

[0044] 2) Preparation of 3,4-bis(2'-thienyl)maleimide:

[0045] Put 0.51 g of 3,4-dibromomaleimide (2 mmol) and 3.51 mg of bistriphenylphosphine palladium dichloride catalyst (0.005 mmol) into a 25 ml two-necked flask, vacuumize, Infuse with nitrogen, repeat pumping and irrigation three times, inject 3.81 ml of 2-tributylstannylthiophene (12 mmol) and 10 ml of N,N-dimethylformamide with a syringe, raise the temperature to 100°C, and react for 12 hours , stop heating and return to...

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Abstract

The invention relates to a method for preparing a multiple-stimulation respond material by virtue of a two-step process. The method comprises the following steps: putting maleimide into a reaction bottle, adding N,N-dimethylformamide and a halogenating reagent, heating until the temperature reaches 58 DEG C for reacting for 48-72 hours, and adding water and dichloromethane sequentially for suction filtration to obtain 3,4-dihalogenmaleimide; putting 3,4-dihalogenmaleimide and a palladium bis(triphenylphosphine) dichloride catalyst into a flask, vacuumizing, then filling the flask with nitrogen, injecting anhydrous N,N-dimethylformamide and 2-(tributylstannyl)thiophene, increasing the temperature to 100 DEG C for reacting for 12 hours, cooling, then adding the mixed solution of dichloromethane and saturated potassium fluoride aqueous solution, then extracting, drying, filtering and purifying through column chromatography to obtain 3,4-bis(2'-thienyl)maleimide. The material prepared by the method provided by the invention has the advantages of good heat stability, simple synthesis steps, high solid-state fluorescent quantum efficiency and the like, and also has the properties of piezallochromy, thermochromism, solvent induced chromism and the like.

Description

technical field [0001] The invention relates to a two-step method for preparing multiple stimulus response materials, in particular to multiple stimulus response materials containing thienylmaleimide 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 photoelectric functional materials (Shuaijun Yang, Research Progress in Organic Solid Fluorescent Materials, 2013; Anthony, ChemPlusChem, 2012, 77, 518 ). With the deepening of people's research, it is found that some materials can only change the interaction between molecules without destroying the molecular structure, and can achieve different responses to external stimuli. Among them, stimuli-responsive fluorescent conversion materials (aerochromic, thermochromic and piezochromic materials) are of great significance for the development of information storage, optical re...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09K9/02C07D409/14
Inventor 凌启淡林正欢梅晓飞
Owner FUJIAN NORMAL UNIV
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