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Amphiphilic fluorescent molecule switch and preparation method and application thereof

A fluorescent molecule and amphiphilic technology, applied in the field of fluorescent probes, can solve the problems of loss of structural image information, failure of self-assembly of fluorescent dyes or fluorescent molecular switches, etc., and achieve the effects of reducing cost, increasing self-assembly performance, and simple optical path.

Active Publication Date: 2017-06-13
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the above defects or improvement needs of the prior art, the present invention provides an amphiphilic fluorescent molecular switch, its preparation method and application, the purpose of which is to synthesize an amphiphilic fluorescent molecular switch Imidazole-fluorophores self-assemble into micro-nano structures and perform super-resolution fluorescence imaging, thereby solving the problem that the prior art fluorescent dyes or fluorescent molecular switches cannot self-assemble. In theory, it is possible to label polymers for fluorescence imaging Technical issues with loss of structural image information due to inhomogeneous fluorochrome labeling

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  • Amphiphilic fluorescent molecule switch and preparation method and application thereof
  • Amphiphilic fluorescent molecule switch and preparation method and application thereof
  • Amphiphilic fluorescent molecule switch and preparation method and application thereof

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preparation example Construction

[0048] The present invention provides the preparation method of amphiphilic fluorescent molecular switch tetrakis (tetraethylene glycol monomethyl ether)-hexaaryl biimidazole-boron fluoride dipyrrole, such as image 3 shown, including the following steps:

[0049] (1) Compound A, pinacol borate and potassium acetate are mixed evenly according to the molar ratio of 1:1.5:5.4, and the catalyst dose of PdCl is added 2 , dispersed in dry dioxane, heated to 90°C for 24 hours under the protection of nitrogen, and separated after the completion of the reaction to obtain a white solid B;

[0050] (2) Under the protection of nitrogen, dissolve tetrabromobenzaldehyde and 2,4-dimethylpyrrole in tetrahydrofuran according to the molar ratio of 1:2.1. When it is completely dissolved, slowly drop trifluoroacetic acid and stir overnight at room temperature , then add the tetrahydrofuran solution of dichlorodicyanobenzoquinone to the reaction solution that was stirred overnight, after reactin...

Embodiment 1

[0069] An amphiphilic fluorescent molecular switch, which is four (tetraethylene glycol monomethyl ether) - hexaaryl biimidazole - boron fluoride dipyrrole, has such as figure 1 The structure shown, wherein R is four (tetraethylene glycol monomethyl ether), its preparation method, as image 3 shown, including the following steps:

[0070] (1) In a 250mL round bottom flask, compound A (3.35g, 7.153mmol), pinacol diborate (2.72g, 10.73mmol), potassium acetate (2.81g, 38.61mmol) and catalyst Pd (dppf ) Cl 2 (0.26g, 0.36mmol) was dispersed in 100mL of dry dioxane, heated to 90°C for 24h under nitrogen protection. When the reaction is complete, cool to room temperature, carefully pour the reaction solution into saturated saline, extract with dichloromethane, then wash with deionized water, dry with anhydrous sodium sulfate, filter with suction, add appropriate amount of silica gel powder and spin dry under reduced pressure , the obtained powder was purified by silica gel chromat...

Embodiment 2

[0078] The amphiphilic fluorescent molecular switch tetrakis(tetraethylene glycol monomethyl ether)-hexaarylbiimidazole-boron fluoride dipyrrole self-assembled by the present invention, and super-resolution means are used to study the morphology of the assembled structure, including the following step:

[0079] (1) Dissolve tetrakis(tetraethylene glycol monomethyl ether)-hexaarylbiimidazole-boron fluoride dipyrrole in different concentrations of ethanol to prepare a mother solution with a concentration of 1ug / ml~50ug / ml, and add to the Add high-purity water dropwise to the mother liquor and mix evenly to obtain a mixed liquor. The mixed liquor is subjected to rotary evaporation on a rotary evaporator, and by controlling the volatilization speed of the liquid, self-made amphiphilic fluorescent molecular switches with different shapes are obtained. Observation sample mother solution for assembling micro-nanostructures.

[0080] (2) Let the sample mother liquid obtained in step ...

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Abstract

The invention discloses an amphiphilic fluorescent molecule switch. The amphiphilic fluorescent molecule switch is characterized in that the amphiphilic fluorescent molecule switch is hydrophilic group-hexaarylbiimidazole-fluorophore, wherein the hexaarylbiimidazole is a photochromic unit and is used for controlling the light emitting and quenching of the fluorophore; the fluorophore is used for emitting fluorescence; the fluorophore is connected with the hexaarylbiimidazole through a non-conjugated alkyl chain; the hydrophilic group is used for increasing the hydrophilcity and self-assembly property of the amphiphilic fluorescent molecule switch. The amphiphilic fluorescent molecule switch has the advantages that by synthesizing tetra(methyl tetraglycol)-hexaarylbiimidazole-boron fluoride dipyrrole for the self-assembly function and the imaging of a super-resolution imaging system, the higher resolution is realized, and the finer structure is observed; the sample preparation process is simple, the instrument requirement is lower, and the dynamic assembly process of the self-assembly body may be observed.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and more specifically relates to a fluorescent molecular switch controlled by a single wavelength, its preparation method and application. Background technique [0002] Photochromic materials refer to a class of materials that can reversibly change their optical properties and undergo color changes after being excited by light sources of different wavelengths. Such materials have attracted extensive research interest due to their wide potential applications in pressure sensing, permanent electricity, molecular electronics, fluorescent sensing, erasable storage, and optical lenses. In the past two years, based on photochromic materials, the design and synthesis of fluorescent molecular switches and super-resolution imaging technology for nanomaterials have been reported. In this technique, light is used to modulate the fluorescent switching behavior of probes. As a very convenient mea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K9/02C09K11/06G01N21/64
CPCC07F5/022C09K9/02C09K11/06C09K2211/1096G01N21/6428
Inventor 朱明强龚文亮华琼新
Owner HUAZHONG UNIV OF SCI & TECH
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