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Fluorine-boron pyrrolizinone fluorochrome and synthesizing method thereof

A fluoroboron pyrrolizine, fluorescent dye technology, applied in the direction of azo dyes, organic dyes, luminescent materials, etc., can solve the problems of small Stokes shift, application limitations, etc., achieves few steps, high yield, wide range The effect of research and application

Active Publication Date: 2016-09-07
宜昌市蓝天彩印股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the emission group of the more common BODIPY fluorescent dyes is a six-membered ring, which is characterized by high fluorescence quantum yield and good molar extinction coefficient, and the Stokes shift of the BODIPY of the six-membered ring is small (<50nm ), leading to the limitation of its application in vivo

Method used

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  • Fluorine-boron pyrrolizinone fluorochrome and synthesizing method thereof
  • Fluorine-boron pyrrolizinone fluorochrome and synthesizing method thereof
  • Fluorine-boron pyrrolizinone fluorochrome and synthesizing method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Take 1.44g (9.00mmol) of 2,3,3-trimethylindole 1, weigh 0.86g (9.00mmol) of 2-formylpyrrole, measure 0.15L of toluene solution, take 0.24mL of organic acid, and 0.30mL of organic base The mL was mixed, heated and stirred, refluxed at 120°C for 2 hours, spin-dried and purified by filtration to obtain yellow compound 3. Take 1.20g (5mmol) of the above compound 3, take 35mL of toluene solution, 1.00mL of triethylamine, stir under electromagnetic stirring, and add 0.75mL (6.25mmol) of boron trifluoride ether solution dropwise to 120°C, condense and reflux for 0.5 Hours, TLC plate detection, the product was washed, extracted, dried, rotary evaporated, filtered and purified to obtain compound 4:

[0032]

Embodiment 2

[0034] Take 1.44g (9.00mmol) of 2,3,3-trimethylindole 1, weigh 3.44g (36.00mmol) of 2-formylpyrrole, measure 0.15L of toluene solution, take 0.24mL of organic acid, 0.30mL of organic base The mL was mixed, heated and stirred, refluxed at 120°C for 8 hours, spin-dried and purified by filtration to obtain yellow compound 3. Take 1.20g (5mmol) of the above compound 3, take 35mL of toluene solution, 1.00mL of triethylamine, stir under electromagnetic stirring, and add 0.75mL (6.25mmol) of boron trifluoride ether solution dropwise to 120°C, condense and reflux for 0.5 Hours, TLC plate detection, the product was washed, extracted, dried, rotary evaporated, filtered and purified to obtain compound 4:

[0035]

Embodiment 3

[0037] Take 1.44g (9.00mmol) of 2,3,3-trimethylindole 1, weigh 28.50g (0.30mmol) of 2-formylpyrrole, measure 0.15L of toluene solution, take 0.24mL of organic acid, 0.30mL of organic base The mL was mixed, heated and stirred, refluxed at 120°C for 8 hours, spin-dried and purified by filtration to obtain yellow compound 3. Take 1.20g (5mmol) of the above compound 3, take 35mL toluene solution, 1.00mL triethylamine, stir under electromagnetic stirring, and add 0.75mL (6.25mmol) of boron trifluoride ether solution dropwise to 120°C, condense and reflux for 0.5 Hours, TLC plate detection, the product was washed, extracted, dried, rotary evaporated, filtered and purified to obtain compound 4:

[0038]

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Abstract

The invention belongs to the technical field of the organic chemical industry, and particularly relates to a fluorine-boron pyrrolizinone fluorochrome. The chemical structural formula of the fluorochrome is shown in the description, wherein the substituent groups R1 and R2 are hydrogen or alkyl or ester or nitryl or nitrile or alkoxy or halogen or aryl or other conjugated systems, and the positions, numbers and conjugated positions of the substituent groups are flexible. A synthesizing method comprises the steps that a 2,3,3-3-methylindole derivative and 2-formyl pyrrole derivative are subjected to a condensation and complexing reaction under the action of an organic catalyst, and a novel fluorine-boron pyrrolizinone fluorescent compound is obtained. The synthesizing method has the advantages that few steps are needed, and the yield is high, and the fluorine-boron pyrrolizinone fluorochrome is beneficial to in vivo application due to the good electronic spectrum feature.

Description

technical field [0001] The invention relates to the technical field of organic chemical industry, in particular to a boron pyrrolizine fluorescent dye and a synthesis method thereof. Background technique [0002] In order to meet the ever-changing demand for fluorescent dyes in biological analysis applications, research and development of new fluorescent materials with more good fluorescence spectral properties is the key and core of the development of fluorescence analysis technology. At present, the emission group of the more common BODIPY fluorescent dyes is a six-membered ring, which is characterized by high fluorescence quantum yield and good molar extinction coefficient, and the Stokes shift of the BODIPY of the six-membered ring is small (<50nm ), which limits its application in vivo. Contents of the invention [0003] The main purpose of the present invention is to provide a kind of boron pyrrolizine fluorescent dye and its synthesis method. [0004] Technical...

Claims

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Application Information

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IPC IPC(8): C09B57/00C07F5/02C09K11/06
CPCC07F5/02C09B57/00C09K11/06C09K2211/1029C09K2211/1055
Inventor 张诺诺李玉姣晏佳莹成凯李德江
Owner 宜昌市蓝天彩印股份有限公司
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