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Fluorescent dye with large Stokes shift and preparation method thereof

A fluorescent dye and displacement technology, which is applied in the field of preparation of the fluorescent dye, can solve the problems of fluorescence self-quenching and lower imaging resolution, and achieve good strong acid resistance

Active Publication Date: 2021-08-27
NORTHWEST UNIV(CN)
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  • Description
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  • Application Information

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Problems solved by technology

If the Stokes shift of the organic dye itself is relatively small, it is easy to cause fluorescence self-quenching in the biological imaging process, thereby reducing the imaging resolution.

Method used

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  • Fluorescent dye with large Stokes shift and preparation method thereof
  • Fluorescent dye with large Stokes shift and preparation method thereof
  • Fluorescent dye with large Stokes shift and preparation method thereof

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Embodiment

[0051] The present invention has a method of preparation of a fluorescent dye having a large Stokes displacement, in particular, according to the following steps, reactive Image 6 Indicated;

[0052] Step 1, with isoevanagel condensation reaction by Knoevenagel in the Knoevenagel condensation reaction. The intermediate Tem is synthesized.

[0053]

[0054] Specifically: 0.2 g of acetic anhydride, 0.4 ml of glacial acetic acid and 1.8 ml piperidine were added to 250 ml of tri-necked flask, and then 16.5 ml (110 mmol) of isophorone, 6.6 g (110 mmol) Nitrile and dissolved in 55 mL N, N-dimethylformamide, stirred at 120 ° C for 6 h. Cooled to room temperature after the reaction was completed. The reaction mixed solution was injected into ice water, precipitated brown solid, dried and purified using column chromatography, and the eluent as petroleum ether: dichloromethane = 1: 1 (V: V) to obtain a yellow solid;

[0055] Step 2, with 4-bromo-1,8 naphthalide and N- (2-aminoethyl) morphol...

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Abstract

The invention discloses a fluorescent dye with large Stokes shift and a preparation method thereof. The preparation method comprises the steps that firstly, isophorone and malononitrile serve as raw materials, and an intermediate TEM is synthesized through a Knoevenagel condensation reaction; then, 4-bromo-1, 8-naphthalic anhydride and N-(2-aminoethyl) morpholine are used as raw materials, and an intermediate BMD is synthesized; then BMD and 4-piperazine-1-benzaldehyde are used as raw materials, and an intermediate NAA is synthesized; finally, the fluorescent dye is synthesized by taking TEM and NAA as raw materials. In the dye, naphthalimide is used as an FRET energy donor, and a dicyanoisophorone derivative is used as an energy receptor, so that the increase of Stokes shift is realized. By testing fluorescence emission spectrums in various organic solvents, the Stokes shift is within 173-234 nm, and obvious fluorescence signal emission is realized.

Description

Technical field [0001] The present invention belongs to the preparation of fluorescent dye, and more particularly to a fluorescent dye having large Stokes displacement, further involves the preparation method of the fluorescent dye. Background technique [0002] Traditional organic fluorescent dyes, such as Bodipy, fluorescein and Rodam, etc., although they have been widely used in high-tech fields such as luminescent materials, fluorescent probes, fluorescent markers. However, since these organic fluorescent dyes have the disadvantage of photophysody and optical properties in the practical application, they limit their wide application. [0003] Stokes Shift is one of the important parameters for evaluating the physical properties of fluorescent dyes. If the stokes of the organic dye itself is relatively small, it is easy to cause fluorescence from the quenching phenomenon during the biomara, thereby reducing the imaging resolution. Therefore, it is important to design and synth...

Claims

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Application Information

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IPC IPC(8): C07D221/14C09K11/06G01N21/64C09B23/14
CPCC07D221/14C09K11/06G01N21/643C09B23/143C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1044Y02E10/542
Inventor 李剑利凤旭凯刘萍厍梦尧廖静文
Owner NORTHWEST UNIV(CN)
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