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Amphiphilic molecules with aggregation-induced emission effects, preparing method thereof and uses of the amphiphilic molecules

A technology of aggregation-induced luminescence and amphiphilic molecules, which can be used in luminescent materials, material excitation analysis, chemical instruments and methods, etc. The effect of stable luminous efficiency

Inactive Publication Date: 2016-02-24
SUZHOU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above ideas all need to use other materials to wrap the fluorescent probe, which is complicated and difficult to implement.

Method used

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  • Amphiphilic molecules with aggregation-induced emission effects, preparing method thereof and uses of the amphiphilic molecules
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  • Amphiphilic molecules with aggregation-induced emission effects, preparing method thereof and uses of the amphiphilic molecules

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Synthesis of TPE-11.

[0036] (1) Under the protection of argon, 400mg (0.82mmol) of 1-bromo-4-(2-(4-bromophenyl)-1,2-diphenylvinyl)benzene, 622mg (1.64mmol) 4 -11-bromoundecyl ethynylbenzoate, 100mg (0.08mmol) tetrakis(triphenylphosphine) palladium, 20mg (0.08mmol) cuprous iodide were added to a 100mL three-necked flask containing 50mL of tetrahydrofuran, Add 5mL (36.07mmol) of triethylamine under stirring conditions, heat to 70°C and reflux for 10 hours. After the reaction is completed, tetrahydrofuran is distilled off under reduced pressure. The residue is extracted with a water / dichloromethane system and the organic phase is separated. Dry over anhydrous sodium sulfate for more than 0.5 hours, distill under reduced pressure to remove dichloromethane and obtain a crude product. Purify by silica gel column chromatography with ethyl acetate: petroleum ether=1:10 (v / v) to obtain a yellow solid The yield is 8%;

[0037]

[0038] (2) Add the intermediate obtained ...

Embodiment 2

[0043] Example 2: Synthesis of TPE-11.

[0044] (1) Under the protection of nitrogen, mix 200mg (0.41mmol) of 1-bromo-4-(2-(4-bromophenyl)-1,2-diphenylvinyl)benzene, 311mg (0.82mmol) of 4- Ethynyl benzoic acid 11-bromoundecyl ester, 38mg (0.04mmol) bis(triphenylphosphine) palladium dichloride, 10mg (0.04mmol) cuprous iodide were added to a 100mL three-necked flask containing 40mL tetrahydrofuran Add 3mL (21.64mmol) of triethylamine under stirring conditions, heat to 85°C and reflux for 20 hours. After the reaction is completed, tetrahydrofuran is distilled off under reduced pressure. The residue is extracted with a water / dichloromethane system to separate the organic Phase, dried with anhydrous sodium sulfate for more than 0.5 hours, distilled under reduced pressure to remove dichloromethane to obtain a crude product, and purified by silica gel column chromatography using ethyl acetate: petroleum ether = 1:10 (v / v) eluent Yellow solid intermediate, the yield is 6%;

[0045]

[00...

Embodiment 3

[0047] Example 3: Determination of the fluorescence properties of TPE-11.

[0048] Dissolve 2mg TPE-11 in 2mL deionized water to prepare a TPE-11 aqueous solution mother liquor with a concentration of 1mg / mL, dilute to a concentration of 25 and 15μg / mL, and excite at 360nm wavelength to obtain the fluorescence emission spectrum of TPE-11. Such as figure 2 Shown.

[0049] From figure 2 It can be seen that the synthesized amphiphilic molecule TPE-11 has a strong fluorescence emission peak around 500nm, indicating that the molecule can emit green fluorescence in an aqueous solution. In addition, the fluorescence intensity of high concentration (25μg / mL) TPE-11 is higher than that of low concentration (15μg / mL) TPE-11, indicating that TPE-11 has a typical aggregation-induced luminescence effect.

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Abstract

The invention discloses amphiphilic molecules with aggregation-induced emission effects, a preparing method thereof and uses of the amphiphilic molecules. The general structure of the amphiphilic molecules is shown as a formula I (with n being any integer from 9 to 13). The amphiphilic molecules are prepared by a two-step reaction process, wherein the process includes 1) modifying tetraphenyl ethylene with long alkyl chains by a coupling reaction and 2) refluxing the product of the former reaction in pyridine to obtain the amphiphilic molecules. The amphiphilic molecules are extremely low in critical aggregation concentration, high in aggregate fluorescence quantum efficiency, low in working concentration and good in biocompatibility. When the amphiphilic molecules are used as chromophores and applied to cell imaging, both contrast and distinguishability are high. The amphiphilic molecules have a wide application prospect when being used as fluorescence probes.

Description

Technical field [0001] The invention belongs to the technical field of cell imaging, and relates to an amphiphilic molecule with aggregation-induced luminescence effect, a preparation method thereof, and use as a fluorescent probe in cell imaging. Background technique [0002] With the development of life sciences, in order to obtain intuitive information about molecular biological functions, people are devoted to researching various imaging technologies. Fluorescence imaging (FI) has gradually become the focus of attention because of its non-destructive, good selectivity, and high sensitivity. Therefore, the research on fluorescent dyes with excellent performance has become an important research direction, and the main ones currently used for live cell imaging are organic dyes. [0003] The fluorescent chromophores in traditional organic dyes are mainly rigid planar molecules with large conjugated systems. They have strong fluorescence in dilute solutions, but they have weak fluo...

Claims

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Application Information

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IPC IPC(8): C07D213/30C09K11/06G01N21/64
CPCC07D213/30C09K11/06C09K2211/1029G01N21/6428
Inventor 宋波周士新夏怡君
Owner SUZHOU UNIV
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