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Novel chiral aggregation-induced emission material and preparation method and application thereof

A new type of aggregation-induced luminescence technology, applied in luminescent materials, organic chemical methods, material excitation analysis, etc., can solve problems such as aggregation-induced fluorescence quenching, and achieve great application prospects and good optical properties

Active Publication Date: 2017-11-24
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the light-emitting materials used in organic light-emitting devices must be used in the state of solid thin films, so with the formation of solid thin films, aggregation fluorescence quenching will inevitably occur, which seems to be a difficult problem to solve

Method used

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  • Novel chiral aggregation-induced emission material and preparation method and application thereof
  • Novel chiral aggregation-induced emission material and preparation method and application thereof
  • Novel chiral aggregation-induced emission material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] 1. Preparation of chiral aggregation-induced luminescence materials

[0059] (1) Synthesis of Compound A: Under the protection of argon, bromotriphenylethylene (800 mg, 2.39 mmol, 1.00 eq), p-tolylboronic acid (486.7 mg, 3.58 mmol, 1.50 eq) and tetrabutyl bromide Ammonium (76.9 mg, 0.24 mmol, 0.10 eq) was placed in a 25 mL inclined two-neck round bottom flask, and toluene (10 mL) and 2 mol / L K 2 CO 3 (4mL). After stirring at 90°C for 10 minutes, tetrakis(triphenylphosphine)palladium (95.4 mg, 0.08 mmol, 0.03 eq) was added and the reaction was continued for 11 hours. After the reaction, extracted three times with ethyl acetate, anhydrous MgSO 4 dry. After filtration, the organic solvent was distilled off under reduced pressure, and the crude product was separated by silica gel column chromatography (petroleum ether) to obtain 825.7 mg of white solid A, with a yield of 99%;

[0060] The synthetic route of the step (1) is as follows:

[0061]

[0062] The compound...

Embodiment 2

[0083] 1. Preparation of chiral aggregation-induced luminescence materials

[0084] (1) Synthesis of Compound A: Under nitrogen protection, bromotriphenylethylene (500 mg, 1.49 mmol, 1.00 eq), p-tolylboronic acid (304 mg, 2.24 mmol, 1.5 eq) and tetrabutyl bromide Ammonium (48 mg, 0.15 mmol, 0.10 eq) was placed in a 25 mL inclined two-necked round bottom flask, and toluene (5.0 mL) and 2 mol / L of K 2 CO 3 (2.7 mL). After stirring at 90°C for 10 minutes, tetrakis(triphenylphosphine)palladium (59.6 mg, 0.05 mmol, 0.03 eq) was added and the reaction was continued for 15 hours. After the reaction, extracted three times with ethyl acetate, anhydrous MgSO 4 dry. After filtration, the organic solvent was evaporated under reduced pressure, and the crude product was separated by silica gel column chromatography (petroleum ether) to obtain 392 mg of white solid A with a yield of 76%;

[0085] (2) Synthesis of compound B: under nitrogen protection, compound A (173 mg, 0.5 mmol, 1.00 ...

Embodiment 3

[0089] 1. Preparation of chiral aggregation-induced luminescence materials

[0090] (1) Synthesis of Compound A: Under the protection of argon, bromotriphenylethylene (600 mg, 1.79 mmol, 1.00 eq), p-tolylboronic acid (365 mg, 2.68 mmol, 1.50 eq) and tetrabutyl bromide Ammonium (58 mg, 0.18 mmol, 0.10 eq) was placed in a 25 mL inclined two-necked round bottom flask, and toluene (5 mL) and 2 mol / L K 2 CO 3 (3 mL). After stirring at 90°C for 5 minutes, tetrakis(triphenylphosphine)palladium (72.4 mg, 0.06mmol, 0.035eq) and toluene (1 mL) were added, and the reaction was continued for 8 hours. After the reaction, extracted three times with ethyl acetate, anhydrous MgSO 4 dry. After filtration, the organic solvent was evaporated under reduced pressure, and the crude product was separated by silica gel column chromatography (petroleum ether) to obtain 620 mg of white solid A with a yield of 99%;

[0091] (2) Synthesis of compound B: under the protection of argon, compound A (600...

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Abstract

The invention discloses a novel chiral aggregation-induced emission material and a preparation method and application thereof. The structural formula of the chiral aggregation-induced emission material is as shown in formula (II). The preparation method comprises the following steps: firstly designing and synthesizing a type of novel tetraphenyl ethylene phosphate, wherein the structural formula of the novel tetraphenyl ethylene phosphate is as shown in formula (I), and enabling the tetraphenyl ethylene phosphate to react with (R)-[1,1'-binaphthyl]-2,2'-biformaldehyde so as to generate the novel aggregation-induced emission material with the chiral structure. The chiral aggregation-induced emission material has the good optical property. In a mixed system of tetrahydrofuran and water, an ultraviolet-visible absorption spectrum and a fluorescence emission spectrum of the chiral aggregation-induced emission material are changed along with the change of optical rotation. The material can be stimulated by 451 nm of blue light in the solid state, and emits 520 nm of green light. The solid-state fluorescence quantum yield is 29%. The chiral aggregation-induced emission material can be used as the chiral material applied to the fields, such as a photoelectric device and a biosensor, and has the larger application prospect.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. More specifically, it relates to a novel chiral aggregation-induced luminescent material and its preparation method and application. Background technique [0002] Chiral materials refer to materials that do not have geometric symmetry with their mirror images, and cannot use any method to make them coincide with the mirror images. It has important research significance in chemistry, biology, and material science. [0003] Due to their huge potential applications in flexible display and lighting, organic light-emitting devices such as organic light-emitting diodes (OLEDs) have been highly valued by the scientific and industrial circles in recent years, and are one of the current research and development hotspots. Organic light-emitting materials play a pivotal role in the technology of organic light-emitting devices, which directly affect the luminous efficiency and service life o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40C07C15/58C07C1/34C09K11/06G01N21/31G01N21/64
CPCC07B2200/07C07C1/34C07F9/4056C07F9/4075C09K11/06C09K2211/1007C09K2211/1011G01N21/31G01N21/64C07C15/58
Inventor 邵光何衍健余惠娟
Owner SUN YAT SEN UNIV
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