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Aggregation-induced emission compound as well as preparation method and application thereof

An aggregation-induced luminescence and compound technology, which is applied in the field of aggregation-induced luminescence compounds and their preparation, can solve problems such as the reduction of fluorescence quantum yield, and achieve the effects of easy long-term storage, improved synthesis efficiency, and stable fluorescence quantum yield.

Inactive Publication Date: 2016-06-15
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to molecular aggregation of such molecules in the solid state, the fluorescence quantum yield is lower than that in the liquid state.

Method used

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  • Aggregation-induced emission compound as well as preparation method and application thereof
  • Aggregation-induced emission compound as well as preparation method and application thereof
  • Aggregation-induced emission compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0038] The preparation method of the aggregation-induced luminescence compound comprises the following steps:

[0039] (1) 1eq of the compound of formula VII or 0.5eq of the compound of formula VIII 2eq~3eq or 0.5eq~0.15eq of Pd(PPh 3 ) 4 And 0.5eq~0.15eq of phase transfer catalyst, mixed in a solvent with a pH value of 9~12, fully reacted under an inert gas atmosphere at 70°C~100°C, to obtain a compound of formula V or compound of formula VI Wherein, the phase transfer catalyst is tetrabutylammonium bisulfate, tetrabutylammonium bromide or benzyltriethylammonium chloride; the solvent is that the mass ratio of organic solvent to water is 2:1~4:1 A mixed solvent, the organic solvent is toluene, tetrahydrofuran or dioxane.

[0040] (2) 1eq of a compound of formula V or 0.5eq of a compound of formula VI, 4eq to 6eq of carbon tetrabromide and 8eq to 12eq of triphenylphosphine are fully reacted in an organic solvent at 80°C to 150°C to obtain formula III compound or compo...

Embodiment 1

[0044] a kind of like figure 1 The synthetic route diagram of the dendrimer with fluorene as the central core shown comprises the following steps:

[0045] Synthesis of a central core with a bromine functional group: 3.604g (20mmol) of fluorenone, 13.270g (40mmol) of carbon tetrabromide and 17.530g (80mmol) of triphenylphosphine were placed in 100mL of anhydrous dichloromethane, stirred and refluxed 24h. The crude product was separated by a column to obtain 4.7 g of yellow solids, and a central core with a bromine functional group was obtained, and the chemical structural formula was

[0046] (1) Synthesis of the first generation of dendrimers (I-A2)

[0047] 0.68g (2mmol) 9-dibromoethylene-fluorene, 1.53g (5mmol) borate of fluorenone, 0.23g (0.2mmol) tetrakis (triphenylphosphine) palladium, 68mg (0.2mmol) tetrabutylsulfuric acid Ammonium hydrogen and 0.83 g (6 mmol) of potassium carbonate were placed in a mixed solution of 40 mL of toluene and 20 mL of distilled water, h...

Embodiment 2

[0052] Repeat Example 1 with the same steps as described, the difference is that the p-methoxyphenylboronic acid in the step (3) is replaced with the borate of fluorenone to obtain the product I-A2A4, the chemical structural formula is

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Abstract

The invention discloses an aggregation-induced emission compound. The aggregation-induced emission compound has a chemical structural formula shown in the general formula I or II. The invention further discloses a preparation method of the compound. The aggregation-induced emission compound and the preparation method have the advantages that the synthesis is simple and the product is simple to purify and the like; synthesized conjugate dendritic macromolecules have an aggregation-induced emission property and higher heat stability and have certain application prospect in organic electroluminescence devices and fluorescence sensing.

Description

technical field [0001] The invention belongs to the technical field of preparation of polymer materials, and more specifically relates to an aggregation-induced luminescent compound and its preparation method and application. Background technique [0002] Aggregation-induced emission (aggregation-induced emission, AIE) was first reported in 2001 by Professor Tang's research group. Tang's research group found that silole derivatives hardly emit light in solution, but the light emission is greatly enhanced after forming a solid. Compounds with AIE properties have fundamentally overcome the problem of aggregation caused quenching (ACQ), which has aroused extensive research interest. So far, AIE systems covering the entire visible wavelength range from blue to red light have been developed, and will Fluorescent molecules with this characteristic are used in the detection of chemical and biological molecules (such as glucose, DNA, etc.), biological imaging, organic electrolumine...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00C09K11/06C07C22/04C07C49/675H01L51/50
CPCC07C22/04C07C49/675C08G83/003C09K11/06C09K2211/1416H10K50/11C09B11/04C09B57/00
Inventor 朱明强陈泽强
Owner HUAZHONG UNIV OF SCI & TECH
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