Luminescent material having aggregation-induced emission, method of making and application thereof

A technology of aggregation-induced luminescence and luminescent materials, which is applied in the field of solid-state luminescent materials, can solve the problems that luminescent materials cannot be dyed by lipid droplets, and achieve the effects of high photostability, high biocompatibility, and high selectivity

Active Publication Date: 2015-09-02
HKUST SHENZHEN RES INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a new luminescent material with aggregation-induced luminescent properties and its preparation method and selective application in cell imaging, so as to solve the problem that the luminescent material in the prior art cannot specifically stain lipid droplets

Method used

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  • Luminescent material having aggregation-induced emission, method of making and application thereof
  • Luminescent material having aggregation-induced emission, method of making and application thereof
  • Luminescent material having aggregation-induced emission, method of making and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: Synthesis of TPE-TMAAl and TPE-TEAAl

[0068] Structural formula: also see Table 1

[0069]

[0070] (1) Synthesis of TPE-TMABr

[0071] Chinese chemical name: 4,4'-(2-(4-bromophenyl)-2-styrene-1,1-substituent)bis(N,N-dimethylaniline)

[0072] English chemical name: 4,4'-(2-(4-bromophenyl)-2-phenylethene-1,1-diyl)bis(N,N-dimethylaniline)

[0073] Synthetic method: Add 4,4'-bis(dimethylamino)benzophenone 1a (3g, 11.2mmol), 4-bromobenzophenone (3.78g, 14.5mmol) and zinc into a dry two-necked flask powder (4.18g, 64mmol), degas the above mixture while purging it with nitrogen for at least three times, then add 80mL of freshly distilled THF solvent, cool the above reaction system to -78°C in a dry ice-acetone bath, and keep it for at least 15min , adding TiCl dropwise 4 (6.11g, 32.3mmol), and then continue to reflux for 8h; after cooling to room temperature, excess zinc is filtered out, an aqueous solution of potassium carbonate is added, and extracted ...

Embodiment 2

[0086] Embodiment 2: Synthesis of TPE-TMAS and TPE-TEAS

[0087] Structural formula: also see Table 1

[0088]

[0089] (1) Synthesis of TPE-TMAS

[0090] Chinese chemical name: 3-(4-(4-(2,2-bis(4-(dimethylamino)phenyl)-1-phenylvinyl)styryl)pyridin-1-yl)propane- 1-sulfonate

[0091] English chemical name: 3-(4-(4-(2,2-bis(4-(dimethylamino)phenyl)-1-phenylvinyl)styryl)pyridinium-1-yl)propane-1-sulfonate

[0092] Synthetic method: Add TPE-TMAAl (0.5g, 1.1mmol) and 3-(4-methylpyridin-1-yl)propane-1- Sulfonate (0.265g, 1.21mmol), the mixture was degassed and purged three times with nitrogen, then 20mL of absolute ethanol and a drop of piperidine were added, and the reaction was refluxed overnight; after cooling to room temperature, the solvent, the residue was passed through a silica gel chromatography column, and ethanol / dichloromethane was used for gradient elution to obtain 0.42 g of a dark red solid product with a yield of 60%. HRMS (MALDI-TOF): C 44 h 49N 3 o 3 S ...

Embodiment 3

[0097] Embodiment 3: Synthesis of TPE-TMAOH, TPE-TMAPy and TPE-TEAOH, TPE-TEAPy

[0098] Structural formula: also see Table 1

[0099]

[0100] (1) Synthesis of TPE-TMAPy and TPE-TMAOH

[0101] TPE-TMAPy Chinese chemical name: 4,4'-(2-phenyl-2-(4-(2-(4-pyridyl)vinyl)phenyl)ethylene-1,1-substituent)bis(N ,N-Dimethylaniline)

[0102] TPE-TMAPy English chemical name: 4,4'-(2-phenyl-2-(4-(2-(4-pyridinyl)vinyl)phenyl)ethene-1,1-diyl)bis(N,N-dimethylaniline)

[0103] TPE-TMAOH Chinese chemical name: (4-(2,2-bis(4-(dimethylamino)phenyl)-1-phenylethenyl)phenyl)methanol

[0104] TPE-TMAOH English chemical name: (4-(2,2-bis(4-(dimethylamino)phenyl)-1-phenylvinyl)phenyl)methanol

[0105] Synthetic method: add TPE-TMAAl (0.5g, 1.1mmol) and sodium hydride (0.04g, 1.67mmol) prepared in step (3) of Example 5 into a reaction flask, deoxygenate by filling nitrogen, inject liquid 4-methyl Pyridine 0.142mL and DMF 20mL, stirred overnight at room temperature, slowly added water to remove ...

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Abstract

The invention discloses a luminescent material having aggregation-induced emission, a method of making and an application thereof. The luminescent material herein has properties of aggregation-induced emission/aggregation-enhanced emission with the maximum absorption wavelength red shift to a visible area so that this type of luminescent material has potential applications in the field of biology. The luminescent material allows the formation of transfer of electric charges in a molecule and exhibits strong polar dependent emission in different solvents. The luminescent material does not emit due to strong dipoalr interaction in a molecule, but emits in a weak-polar environment with a cell. The luminescent material can serve as intracellular lipid droplet and intramicroalgae lipid droplet, and has the advantages of high selectivity, high emission stability and high biological compatibility.

Description

technical field [0001] The invention relates to a series of organic luminescent materials, in particular to a solid-state luminescent material with aggregation-induced luminescence or luminescence enhancement (AIE / AEE) properties. Background technique [0002] Traditional organic light-emitting materials are always accompanied by an inevitable phenomenon: aggregation-caused quenching (ACQ). Traditional fluorescent materials usually contain large π-electron conjugated structures, which are mainly used to generate fluorescence. In the state of molecular dissolution, the solution of the fluorescent material shows strong fluorescence, but in the concentrated solution state, aggregated state or solid state, the intermolecular interaction increases and energy transfer occurs, resulting in the formation of exciplexes or excimer associations. All will consume the excited state energy, thereby greatly reducing the possibility of fluorescence emission, which is the well-known ACQ phen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D213/38C07C223/06C07C221/00C07C215/68C07C213/08G01N21/64
Inventor 唐本忠王二静洪煜柠
Owner HKUST SHENZHEN RES INST
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