Preparation of multi-stimulating responsive material containing thienyl maleimide by substitution reaction method

A multi-stimulus response, maleimide technology, applied in color-changing fluorescent materials, chemical instruments and methods, organic chemistry, 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: 2013-12-25
FUJIAN NORMAL UNIV
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  • Abstract
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  • 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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  • Preparation of multi-stimulating responsive material containing thienyl maleimide by substitution reaction method
  • Preparation of multi-stimulating responsive material containing thienyl maleimide by substitution reaction method
  • Preparation of multi-stimulating responsive material containing thienyl maleimide by substitution reaction method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 1) Preparation of 3,4-dibromomaleimide:

[0035] Put 3.88 g of maleimide (40 mmol) in a high-pressure reaction bottle, add 20 ml of N,N-dimethylformamide, then add 4.77 ml of bromine (93 mmol), and seal the high pressure Heating the mouth of the reaction bottle to 58°C, a light yellow solid gradually appeared. After 48 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 - dibromomaleimide;

[0036] 2) Preparation of N-pentafluorobenzyl-3,4-dibromomaleimide:

[0037] Take 1.27 g of 3,4-dibromomaleimide (5 mmol) in a round bottom flask, add 0.69 g of potassium carbonate (5 mmol) and 20 ml of acetone, stir at room temperature for 30 minutes, the color of the solution gradually Deepen, then add 1.31 g of pentafluorobenzyl bromide (5 mmol), continue to stir at room temperature for 24 hours, stop the reaction, add a mixed solution composed of 60 ml of ethyl acetate and 60 ml ...

Embodiment 2

[0043] 1) Preparation of 3,4-dibromomaleimide:

[0044] Put 3.88 g of maleimide (40 mmol) in a high-pressure reaction flask, add 20 ml of N,N-dimethylformamide, then add 6.39 ml of thionyl chloride (90 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 72 hours of reaction, stop heating and return to room temperature. Filter with 100ml of water and 60ml of dichloromethane successively to obtain 3, 4-dibromomaleimide;

[0045] 2) Preparation of N-benzyl-3,4-dibromomaleimide:

[0046] Take 1.27 g of 3,4-dibromomaleimide (5 mmol) in a round bottom flask, add 1.04 g of potassium carbonate (7.5 mmol) and 20 ml of acetone, stir at room temperature for 30 minutes, the color of the solution gradually Deepen, then add 0.59 ml of benzyl bromide (5 mmol), continue to stir at room temperature for 24 hours, stop the reaction, add a mixture of 60 ml of ethyl acetate and 60 ml of saturated saline for extr...

Embodiment 3

[0050] 1) Preparation of 3,4-dibromomaleimide:

[0051] Put 3.88 g of maleimide (40 mmol) in a high pressure reaction flask, add 25 ml of N,N-dimethylformamide, then add 4.36 ml of bromine (85 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 125ml of water and 75ml of dichloromethane to obtain 3,4-dichloromethane Bromomaleimide;

[0052] 2) Preparation of N-methyl-3,4-dibromomaleimide:

[0053] Take 1.27 g of 3,4-dibromomaleimide (5 mmol) in a round bottom flask, add 1.31 g of potassium carbonate (10 mmol) and 25 ml of acetone, stir at room temperature for 30 minutes, the color of the solution gradually Deepen, then add 0.44 ml of iodomethane (7 mmol), continue to stir at room temperature for 24 hours, stop the reaction, add a mixture of 75 ml of ethyl acetate and 75 ml of saturated saline for extraction, and dry with magnes...

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Abstract

The invention discloses a method for preparing a multi-stimulating responsive material by a substitution reaction method. The method comprises the following steps: carrying out a reaction on maleimide, a solvent N, N-dimethylformamide and a halogenating reagent to obtain 3, 4-dihalomaleimide; carrying out a reaction on 3, 4-dihalomaleimide, potassium carbonate, acetone and a halide, and extracting, drying and purifying to obtain N-substituent-3, 4-dihalomaleimide; carrying out a reaction on N-substituent-3, 4-dihalomaleimide, a bi(triphenyl phosphine) palladium chloride catalyst, N, N-dimethylformamide and 2-tributyl stannyl thiophene, and extracting, drying, filtering and purifying to obtain the N-substituent-3, 4-bi(2'-thienyl) maleimide multi-stimulating responsive material. The multi-stimulating responsive material is good in thermal stability, simple in synthetic step and high in solid fluorescence quantum efficiency, has piezallochromic, thermochromic and gasochromic properties, and can be used for organic light emitting diodes, organic light emitting field effect transistors, organic solid lasers and fluorescence sensors.

Description

technical field [0001] The invention relates to a method for preparing multiple stimulus-responsive materials by a substitution reaction method, in particular to a multiple-stimuli-response material 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 info...

Claims

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Application Information

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