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BODIPY near-infrared fluorescent dye with large Stokes shift and preparation method of BODIPY near-infrared fluorescent dye

A fluorescent dye and near-infrared technology, which is applied in the fields of fluorescent dyes, fine chemicals, and organic synthesis, can solve problems such as limited applications, achieve the effects of reducing fluorescence self-quenching, wide application prospects, and increasing signal-to-noise ratio

Inactive Publication Date: 2021-10-01
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, BODIPY fluorescent dyes often have a small Stokes shift (Stokes shift is mostly <50nm), which greatly limits the application of BODIPY fluorescent dyes in biomarkers, fluorescent imaging, fluorescent probes, etc.

Method used

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  • BODIPY near-infrared fluorescent dye with large Stokes shift and preparation method of BODIPY near-infrared fluorescent dye
  • BODIPY near-infrared fluorescent dye with large Stokes shift and preparation method of BODIPY near-infrared fluorescent dye
  • BODIPY near-infrared fluorescent dye with large Stokes shift and preparation method of BODIPY near-infrared fluorescent dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1 has the preparation of large Stokes shift BODIPY class near-infrared fluorescent dye (II)

[0027] Under anhydrous conditions, a dry round bottom flask equipped with a Dean-Stark apparatus was charged with BODIPY derivative (I) (303 mg, 0.5 mmol), p-dimethylaminobenzaldehyde (745 mg, 5 mmol) and p-toluenesulfonic acid (43mg, 0.25mmol) was dissolved in 25mL of toluene and 2mL of piperidine, heated to reflux at 120°C, and reacted for 6 hours. Cool to room temperature, extract with dichloromethane, wash with water, combine the organic layers, evaporate the organic solvent under reduced pressure, and separate and purify the residue by silica gel column chromatography, the eluent is dichloromethane-petroleum ether (v:v=3: 2) to obtain a dark green solid product BODIPY-based near-infrared fluorescent dye (II) (87mg, 20%). 1 H NMR (600MHz, CDCl 3 ): δ7.68(d, J=16.2Hz, 2H), 7.51(d, J=6.0Hz, 2H), 7.46-7.41(m, 2H), 7.30(d, J=16.2Hz, 2H), 7.16 (s, 2H), 7.06-7.02 (m...

Embodiment 2

[0029] Embodiment 2 has the preparation of large Stokes shift BODIPY type near-infrared fluorescent dye (II)

[0030] Similar to Example 1, the difference is that the BODIPY derivatives (I) in this example react with p-dimethylaminobenzaldehyde in a molar ratio of 1:6; the reaction temperature is controlled at 115° C., and the reaction time is 4 hours . Yield: 15%.

Embodiment 3

[0031] Embodiment 3 has the preparation of large Stokes shift BODIPY type near-infrared fluorescent dye (II)

[0032] Similar to Example 1, the difference is that the BODIPY derivatives (I) in this example react with p-dimethylaminobenzaldehyde in a molar ratio of 1:6; the reaction temperature is controlled at 125° C., and the reaction time is 6 hours . Yield: 17%.

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PUM

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Abstract

The invention relates to a BODIPY near-infrared fluorescent dye with large Stokes shift and a preparation method thereof, wherein the BODIPY near-infrared fluorescent dye is obtained by carrying out Knoevenagel condensation reaction on a BODIPY derivative (I) and p-dimethylaminobenzaldehyde serving as raw materials under the catalytic action of p-toluenesulfonic acid and piperidine, and the chemical structural formula of the BODIPY near-infrared fluorescent dye is shown as a formula (II). The preparation method has the advantages of simple reaction steps, mild reaction conditions and good selectivity. The fluorescent dye has a high molar extinction coefficient and a large Stokes shift, the strongest electron absorption wavelength of the fluorescent dye is 703 nm, and the maximum fluorescence emission wavelength of the fluorescent dye is 813 nm. Wide application prospects are realized in the fields of biomarkers, near-infrared fluorescence imaging, photoelectric materials and the like.

Description

technical field [0001] The invention belongs to the technical fields of organic synthesis, fluorescent dyes and fine chemicals, and specifically relates to a BODIPY-type near-infrared fluorescent dye with a large Stokes shift and a preparation method thereof. Background technique [0002] The development and application of organic small molecule fluorescent dyes have received extensive attention. Classic fluorescent dyes include cyanine dyes, BODIPY dyes, rhodamine, coumarin, and fluorescein. However, the absorption and emission wavelengths of most fluorescent dyes are less than 650 nm, so these fluorescent dyes have poor tissue penetration, severe autofluorescence, and strong phototoxicity, which lead to the use of these fluorescent dyes in cell, tissue, and in vivo fluorescence imaging techniques. Applications are severely limited. Fluorescent dyes with both excitation and emission wavelengths in the near-infrared region (NIR, 650-900nm) have a relatively strong ability t...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06C09B23/14
CPCC07F5/022C09K11/06C09B23/145C09K2211/1007C09K2211/1055
Inventor 徐海军王怡李鹏飞
Owner NANJING FORESTRY UNIV