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Large-Stokes-displacement near-infrared BODIPY (boron-dipyrromethene) dye and preparation and application thereof

A near-infrared and dye technology, applied to organic dyes, azo dyes, analytical materials, etc., can solve the problems of difficult synthesis and limited application, and achieve the effects of reduced detection sensitivity, reduced fluorescence self-quenching, and reduced photodamage

Inactive Publication Date: 2017-08-11
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the synthesis of such dyes is difficult, which largely limits their application.

Method used

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  • Large-Stokes-displacement near-infrared BODIPY (boron-dipyrromethene) dye and preparation and application thereof
  • Large-Stokes-displacement near-infrared BODIPY (boron-dipyrromethene) dye and preparation and application thereof
  • Large-Stokes-displacement near-infrared BODIPY (boron-dipyrromethene) dye and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The synthesis of embodiment 1 compound NIR-BOD (X=S, O)

[0040] N 2 Under gas protection, HO-B-CHO (130mg, 0.3mmol; R 1 , R 2 , R 4 =CH 3 , R 3 =CH 3 CH 2 ), o-aminothiophenol (75.1mg, 0.6mmol) and sodium metabisulfite (57.7mg, 0.304mmol) were refluxed for 2 hours, cooled, spin-dried the solvent, and purified by column chromatography to obtain a reddish-brown solid with a yield of 52.8%. When X=0, it is consistent with the method in Example 1. (HO-B-CHO is self-made in this laboratory, the self-made method refers to the patent number: ZL 201310636785.7, and o-aminothiophenol and sodium metabisulfite are purchased)

Embodiment 2

[0041] The synthesis of embodiment 2 compound NIR-BOD (X=N)

[0042] N 2 Under gas protection, HO-B-CHO (200mg, 0.46mmol; R 1 , R 2 , R 4 =CH 3 , R 3 =CH 3 CH 2 ), o-phenylenediamine (99.5mg, 0.92mmol) was refluxed for 2 hours, cooled, spin-dried to dry the solvent, and purified by column chromatography to obtain a dark brown solid with a yield of 43.2%.

Embodiment 3

[0043] The synthesis of embodiment 3 compound BOD-thiol (X=S)

[0044] Dissolve compound NIR-BOD (50mg, 0.093mmol, R 1 , R 2 , R 4 =CH 3 , R 3 =CH 3 CH 2 ), and triethylamine (25.8 μL, 0.19 mmol) was added thereto, and then 2,4-dinitrobenzenesulfonyl chloride (50.7 mg, 0.19 mmol) was added under ice bath, then the ice bath was removed, and the reaction was carried out at room temperature for 1 h . After the reaction was completed, the solvent was distilled off and separated and purified by column chromatography to obtain a red solid with a yield of 39.0%. (X=O, the method in the preparation method example 3 of N is consistent)

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Abstract

The invention discloses large-Stokes-displacement near-infrared BODIPY (boron-dipyrromethene) dye NIR-BOD and synthesis and application thereof. The dye NIR-BOD herein is prepared via cycling reaction of formyl BODYIPY. Through ESIPIT (excited state intramolecular proton transfer) mechanism and hydrogen-bond interaction between protons on intramolecular hydroxyl and nitrogen atoms on adjourning heterocyclic rings, the dye can emit large-Stokes-displacement (>200 nanometers) near-infrared fluorescence.

Description

technical field [0001] The invention belongs to the field of fine chemical industry and relates to a near-infrared BODIPY dye that can be used to construct a large Stokes shift, in particular to a near-infrared BODIPY dye NIR-BOD with a large Stokes shift and its synthesis and application. Background technique [0002] Boron-dipyrromethene (BODIPY for short) fluorescent dyes are a new type of fluorescent molecular dyes with excellent performance. They have relatively stable molar extinction coefficient and fluorescence quantum yield. spectral properties. In addition, these dyes exhibit good tolerance to both solvent polarity and pH. Dye molecules generally have a certain conjugation plane, and under certain conditions, their fluorescence emission can be regulated by gaining and losing electrons. This kind of dye can be applied to fluorescent labeling, biological detection, etc. through appropriate modification. Dyes with near-infrared fluorescence emission can greatly redu...

Claims

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Application Information

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IPC IPC(8): C09B57/00C09K11/06G01N21/64
CPCC09B57/00C09K11/06C09K2211/1029C09K2211/1033C09K2211/1037G01N21/643
Inventor 赵春常费强
Owner EAST CHINA UNIV OF SCI & TECH
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