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Assembled adjustment and control fluorescence enhanced aggregation-induced emission material, micro-nano sphere, preparation method and application

A technology of aggregation-induced luminescence and fluorescence enhancement, applied in the fields of luminescent materials, halogenated hydrocarbon preparation, chemical instruments and methods, etc., can solve the problems of decreased fluorescence efficiency, limited application, etc. simple craftsmanship

Active Publication Date: 2021-04-06
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of the current fluorescent materials have a problem: they have good luminescence performance in solution, but the fluorescence efficiency drops sharply in the aggregated state, that is to say, fluorescence quenching occurs.
So far, Wang and Chen et al. reported that bromine was introduced into enaminone derivatives and squaraine dyes respectively, and found that due to the heavy atom effect, the crystal or powder fluorescence quantum yield of the two materials was increased, but not more than 50%. (Adv.Optical Mater.2019,7,1801719; Chem.Eur.J.2019,25,469), low fluorescence quantum yield directly limits the application of this type of material

Method used

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  • Assembled adjustment and control fluorescence enhanced aggregation-induced emission material, micro-nano sphere, preparation method and application
  • Assembled adjustment and control fluorescence enhanced aggregation-induced emission material, micro-nano sphere, preparation method and application
  • Assembled adjustment and control fluorescence enhanced aggregation-induced emission material, micro-nano sphere, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The synthetic route of intermediate compound b:

[0048]

[0049] Synthesis of intermediate compound b

[0050] In a three-necked flask equipped with a magnetic stirrer, add 2 parts of bis(4-bromophenyl) ketone a, 5 parts of potassium acetate, 2.5 parts of bisglutaryl diboron and 0.1 part of Pd(dppf)Cl 2 Dissolve in 100 parts of 1,4-dioxane, stir at 80°C for 16-24 hours, then extract with dichloromethane, wash with saturated brine for 4 times, dry with anhydrous magnesium sulfate, filter, and distill off Solvent, the product is purified by column chromatography with petroleum ether / ethyl acetate (10:1) to obtain bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboron Heterocyclopent-2-yl)phenyl)methanone. Yield 86.5%. NMR data 1 H NMR (500MHz, CDCl 3 ): δ7.91(d, J=8.2Hz, 4H), 7.76(d, J=8.3Hz, 4H), 1.37(s, 24H) indicated that the obtained compound was the target product.

Embodiment 2

[0052] The synthetic route of intermediate compound c:

[0053]

[0054] Synthesis of intermediate compound c

[0055] Add 1 part of bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene into a three-necked flask equipped with a magnetic stirrer Base) ketone (b), 2.2 parts of m-bromoiodobenzene and 0.03 parts of tetrakis (triphenylphosphine) palladium dissolved in 60 parts of toluene, reacted at 85-100 ° C for 18-26 hours, and then used di Extracted with methyl chloride, washed with saturated brine for 4 times, dried with anhydrous magnesium sulfate, filtered, distilled off the solvent, and the product was purified by column chromatography using petroleum ether / ethyl acetate (8:1) as the eluent to obtain bis( 3'-Bromo-[1,1'-biphenyl]-4-yl)methanone. Yield: 87.2%. NMR data 1 H NMR (400Hz, CDCl 3 ):δ7.95–7.89(m,4H),7.80(t,J=1.9Hz,2H),7.72–7.67(m,4H),7.56(dddd,J=14.9,8.0,1.9,1.0Hz,4H ), 7.36(t, J=7.8Hz, 2H) indicated that the obtained compound was the target product...

Embodiment 3

[0057] The synthetic route of target compound I:

[0058]

[0059] Synthesis of target compound I

[0060] In a three-necked flask equipped with a magnetic stirrer, 3 parts of bis(3'-bromo-[1,1'-biphenyl]-4-yl)methanone obtained in Example 2, and 24 parts of zinc powder were put into 150 In a dry THF solvent, add 12 parts of titanium tetrachloride dropwise at -78°C for 30 minutes, take it out and return to room temperature naturally, react at 85-95°C for 15-24 hours after 30 minutes, and then remove The solvent was separated and purified by column to obtain 1,1,2,2-tetrakis(3'-bromo[1,1'-biphenyl]-4-yl)ethene. NMR data 1 H NMR (500Hz, CDCl 3 ): δ7.71(t,J=1.8Hz,4H),7.49(ddd,J=7.8,1.7,1.0Hz,4H),7.43(ddd,J=7.9,2.0,1.0Hz,4H),7.40– 7.33 (m, 8H), 7.26 (s, 4H), 7.17 (d, J=8.0Hz, 8H) indicated that the obtained compound was the target product.

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Abstract

The invention discloses an assembly adjustment fluorescence enhancement aggregation-induced emission material, a micro-nano sphere, a preparation method and application. The molecular formula of the luminescent material is formula I. The material disclosed by the invention is stable in structure, has aggregation-induced emission and mechanochromic properties, and is good in luminescence property, the powder state fluorescence quantum yield can reach 45.5%, and the powder fluorescence quantum yield after grinding can reach 65.6%; by adopting an aggregation method in an evaporation solvent and a poor solvent, the luminescent material can be prepared into micro-nano spheres with different sizes through self-assembly, and the fluorescence quantum yield of the nano-scale spherical assembly can reach 85.3%; the synthesis and preparation method of the aggregation-induced emission material is simple to operate, mild in reaction condition and high in yield; the aggregation-induced emission material and the assembled micro-nano spheres are insoluble in water and most of organic solvents, have high fluorescence efficiency and mechanochromic performance, and can be used in the fields of counterfeiting prevention, real-time monitoring of pressure change, biological fluorescent probes, biological imaging and the like.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to an assembly-regulated fluorescence-enhanced aggregation-induced luminescent material, micro-nano spheres, a preparation method and application thereof. Background technique [0002] Fluorescent materials have shown a very important position in the fields of organic light-emitting diodes, organic solid-state lasers, biological living cell labeling, anti-counterfeiting and fluorescent sensors. However, there is a problem with most fluorescent materials at present: their luminescence performance is very good in solution, but the fluorescence efficiency drops sharply in the aggregated state, that is to say, fluorescence quenching occurs. However, in practical applications, many of them require phosphors in a solid or thin film state, which limits the practical application of such phosphors. Aggregation-induced luminescent materials have opened up a new wa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/24C07C17/263C09K11/06C09K11/02
CPCC07C25/24C09K11/06C09K2211/1007
Inventor 苗新蕊蔡正楷李金星
Owner SOUTH CHINA UNIV OF TECH
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