Single charge boron fluroride complexing dipyrrole methenyl fluorochrome and application thereof

A technology of dipyrrole methine and fluorescent dye, applied in methine/polymethine-based dyes, organic dyes, luminescent materials, etc., can solve the problems that the spectrum is easily affected by environmental factors of pH, the influence of fluorescence intensity, poor stability, etc., Achieving the effect of great potential application value, good resistance to pH interference and high photostability

Active Publication Date: 2014-08-27
DALIAN UNIV OF TECH
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these dyes also have some shortcomings: such as poor stability, fluorescence intensity affected by pH, etc.
However, these fluorescent dyes have disadvantages such as poor stability, and the spectrum is easily affected by environmental factors such as pH.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Single charge boron fluroride complexing dipyrrole methenyl fluorochrome and application thereof
  • Single charge boron fluroride complexing dipyrrole methenyl fluorochrome and application thereof
  • Single charge boron fluroride complexing dipyrrole methenyl fluorochrome and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Preparation of Intermediate A

[0052]

[0053] In a 250mL single-necked round-bottom flask, add 150mL of freshly steamed DCM, and replace with nitrogen several times under reduced pressure to remove the dissolved air in the solvent; then weigh 428mg (4mmol) of pyridine-2-carbaldehyde, and make it under stirring Dissolve, then inject 0.75mL (8mmol) 2,4-dimethylpyrrole with a syringe, quickly add a few drops of trifluoroacetic acid to catalyze, the whole system is carried out under nitrogen atmosphere, and rapid magnetic stirring, overnight. The mother liquor was rotatably evaporated to remove 100mL of solvent, and then 40mL of DCM solution containing 908mg (4mmol) 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) was added dropwise under stirring within half an hour, and the color of the mother liquor changed from red to Brown to dark brown, continue to stir and gradually add 8 mL of anhydrous triethylamine dropwise. After the white smoke above the reaction solution disappe...

Embodiment 2

[0055] Preparation of Compound B

[0056]

[0057] Add A (0.65g, 2mmol) into a 100ml single-necked round bottom flask, dissolve it in 40ml of dried acetonitrile, add ethyl iodide (3.12g, 20mmol) dropwise into the reaction solution, protect it under nitrogen, and heat to reflux for 5h. The reaction solution was cooled to room temperature, the solvent was evaporated by rotary evaporation, and separated by neutral alumina column chromatography, the eluent was dichloromethane / methanol=50:1 (v / v), and finally an orange-red powder product was obtained with a yield of 58 %. 1 H NMR (400MHz,D 2 O)δ9.23(d,J=5.9Hz,1H),8.73(t,J=8.0Hz,1H),8.32(t,J=6.9Hz,2H),6.29(s,2H),4.68(q ,J=7.5Hz,2H),2.51(s,6H),1.50(t,J=7.3Hz,3H),1.35(s,6H); HR-TOF-MS C 20 h 23 BN 3 f 2 m / z 354.1945.

Embodiment 3

[0059] Synthesis of Intermediate C

[0060]

[0061] Compound A (0.65g, 2mmol) and benzaldehyde (2.2mmol) were charged into a 100mL single-necked bottle, and dried toluene (40mL), catalyst piperidine (1mL), and 4 Three molecular sieves were added to it, heated to reflux, TLC was used to monitor the reaction end point, silica gel column chromatography was used for separation and purification, the eluent was petroleum ether / ethyl acetate=5:1, and a deep red solid was obtained with a yield of 20%. 1 H NMR (400MHz, CDCl 3 )δ8.81(d,J=6.1Hz,1H),7.90(t,J=7.8Hz,1H),7.7(m,2H),7.50(m,2H),7.28-7.48(m,5H), 6.60(s,1H), 5.99(s,1H), 2.56(s,3H), 1.37(s,3H), 1.33(s,3H). TOF-LD C 25 h 22 BN 3 f 2 m / z 413.1863.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a single charge boron fluroride complexing dipyrrole methenyl fluorochrome and application thereof. The fluorochrome has a general formula I structure. In the general formula I: R1 is selected from C1-18 alkyl, R2 is selected from H, methyl, replacing or non-replacing phenyl, and replacing or non-replacing thiazolyl, R3 and R4 are respectively selected from H, methyl, replacing or non-replacing phenyl, replacing or non-replacing thiazolyl, replacing or non-replacing styryl, the replacing phenyl, the replacing thiazolyl or the replacing styryl are replaced by any following groups such as, CN, COOH, NH2, NO2, OH, SH, C1-6 alkoxy, C1-6 alkyl amino, C1-6 acylamino, halogen or C1-6 halogenated alkyl, and Y is halogen anion. The fluorochrome can be selectively located in mitochondria of a living cell, and fluorescence imaging of mitochondria in the living cell is realized.

Description

technical field [0001] The present invention relates to a new class of fluorescent dyes in the field of fine chemicals, their preparation methods and applications, in particular to a class of single-charged boron fluoride complexed dipyrromethene (BDP) fluorescent dyes, their preparation methods, and the use of the fluorescent Application of dyes in biological dyeing. Background technique [0002] As functional dyes, fluorescent dyes have been widely used in various fields of science and technology, especially in life sciences, clinical medical diagnosis, and immunoassay detection. Mitochondria are not only the main place to provide energy in the human body, but also the physiological processes involved in them are related to many diseases such as diabetes, cancer, Alzheimer's disease and so on. Therefore, research on mitochondria and their functions has attracted much attention. At present, the widely used commercial dyes for mitochondrial imaging are mainly divided into ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/04C09K11/06G01N21/64
Inventor 彭孝军张思樊江莉王静云吴彤李志勇
Owner DALIAN UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap