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Aggregation-induced luminescent material and preparation method thereof

An aggregation-induced luminescence, halophenyl technology, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve problems such as limiting arylmaleimide derivatives, and achieve low cost and good thermal stability. , the effect of high efficiency

Active Publication Date: 2014-11-12
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The concentration quenching effect and the aggregation-induced fluorescence quenching effect largely limit the further application of arylmaleimide derivatives in the field of optoelectronics

Method used

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  • Aggregation-induced luminescent material and preparation method thereof
  • Aggregation-induced luminescent material and preparation method thereof
  • Aggregation-induced luminescent material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 1) Preparation of two (4-bromophenyl) fumaronitriles:

[0037] Add 0.98g of p-bromophenylacetonitrile (5mmol) into a 50ml double-necked flask, pump nitrogen three times, add 0.51g of iodine (2mmol) under nitrogen protection, then inject 20ml of anhydrous diethyl ether, stir at -78°C, Slowly add 5ml of pre-prepared methanol solution of sodium methoxide (2mol / L) dropwise. After the dropwise addition, use an ice-water bath to control the reaction temperature of the system. At this time, the color of the solution becomes darker, and a large amount of light yellow solid precipitates out. Continue to react for 3 hours , and then add 3% hydrochloric acid aqueous solution to neutralize, stop the reaction, filter with suction, wash with ice methanol / water mixed solution (v / v=1:2), and dry in vacuo to obtain bis(4-bromophenyl)trans-butyl Dicarbonitrile;

[0038] 2) Preparation of 3,4-bis(4'-bromophenyl)maleimide

[0039] Add 0.78g of bis(4-bromophenyl)fumaronitrile (2mmol) into...

Embodiment 2

[0047] 1) Preparation of two (4-chlorophenyl) fumaronitriles:

[0048] Add 0.76g of p-chlorophenylacetonitrile (5mmol) in a 50ml double-necked flask, pump nitrogen three times, add 0.76g of iodine (3mmol) under nitrogen protection, then inject 20ml of anhydrous tetrahydrofuran, stir at -78°C, Slowly add 7ml of pre-prepared methanol solution of sodium methoxide (2mol / L). After the addition is complete, use an ice-water bath to control the reaction temperature of the system. At this time, the color of the solution becomes darker, and a large amount of light yellow solid precipitates. Continue to react for 4 hours , and then add 4% hydrochloric acid aqueous solution to neutralize, stop the reaction, filter with suction, wash with ice methanol / water mixed solution (v / v=1:2), and dry in vacuo to obtain bis(4-chlorophenyl)trans-butyl Dicarbonitrile;

[0049] 2) Preparation of 3,4-bis(4'-chlorophenyl)maleimide

[0050] Add 0.60 g of bis(4-chlorophenyl) fumaronitrile (2 mmol) into a...

Embodiment 3

[0056] 1) Preparation of two (4-iodophenyl) fumaronitriles:

[0057] Add 1.22g of p-iodophenylacetonitrile (5mmol) into a 50ml double-necked bottle, pump nitrogen three times, add 1.02g of iodine (4mmol) under nitrogen protection, and then inject 20ml of anhydrous 1,4-dioxane , stirred at -78°C, and slowly added 9ml of methanol solution (2mol / L) of sodium methoxide prepared in advance dropwise. Solid precipitated, continued to react for 3 hours, then added 5% hydrochloric acid aqueous solution to neutralize, stopped the reaction, filtered with suction, washed with ice methanol / water mixed solution (v / v=1:2), and dried in vacuum to obtain di(4 - iodophenyl) fumaronitrile;

[0058] 2) Preparation of 3,4-bis(4'-iodophenyl)maleimide

[0059] Add 0.96g of bis(4-iodophenyl)fumaronitrile (2mmol) into a 50ml round bottom flask, pump nitrogen three times, add 10ml of anhydrous tetrahydrofuran, the reactant is partially dissolved, and then add 5ml of the pre-prepared Methanol solutio...

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Abstract

The invention discloses an aggregation-induced luminescent material and a preparation method thereof. The preparation method comprises the following steps: 1) adding iodine, an organic solvent and a sodium methoxide methanol solution into halobenzyl cyanide, and reacting for 3-4 hours to obtain a product 1; 2) adding an organic solvent and a sodium methoxide methanol solution into the product 1, and reacting for 2 hours to obtain a product 2; 3) proportionally adding potassium carbonate, acetone and halide into the product 2, and reacting for 5 hours to obtain a product 3; and 4) proportionally mixing the product 3, carbazole, inorganic alkali, CuI, 1,4-dioxane and cyclohexyl diamine, reacting for 12 hours, and purifying to obtain the target product N-substituted-3,4-di(4'-carbazolylphenyl)maleimide. The aggregation-induced luminescent material has the advantages of high heat stability, low cost, high solid fluorescence quantum efficiency, favorable biocompatibility and the like, and has wide application prospects in the fields of optical sensors, biomarkers, photoelectric devices and the like.

Description

technical field [0001] The invention relates to an aggregation-induced luminescent material and a preparation method thereof, in particular to an aggregation-induced luminescent material containing 4-carbazole phenylmaleimide and a preparation method thereof. Background technique [0002] Most organic light-emitting materials have strong fluorescence in the solution state, but the fluorescence is weakened or even quenched in the aggregated state ( Phys.Chem., 1954, 1, 275), which largely limits the application of these materials, so it is of far-reaching significance to design and synthesize compounds with enhanced fluorescence in the aggregated state. In 2001, Tang Benzhong et al. (Tang, J. Mater. Chem., 2001, 11, 2974) found that silole derivatives hardly emit light in the dilute solution state, but emit strong fluorescence in the aggregated state. They named this abnormal phenomenon Aggregation Induced Emission (AIE), which has attracted great attention from the scienti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14C09K11/06
Inventor 林正欢凌启淡梅晓飞黄丽梅
Owner FUJIAN NORMAL UNIV