Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A near-infrared high quantum yield dye and its preparation and application

A high-quantum, near-infrared technology, used in benzoxanthene dyes, luminescent materials, analytical materials, etc., can solve the problems of difficult fluorescence quantum yield and long emission

Active Publication Date: 2019-03-12
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is very difficult to obtain structures with longer emission and high fluorescence quantum yield.

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
  • A near-infrared high quantum yield dye and its preparation and application
  • A near-infrared high quantum yield dye and its preparation and application
  • A near-infrared high quantum yield dye and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103]

[0104] 0.193 g (0.001 mol) of compound II-1 and 0.161 g (0.001 mol) of compound III-1 were added to 5 ml of concentrated sulfuric acid, and then heated and stirred at 100° C. for 2 h. After cooling, the reaction solution was slowly poured into 200 ml of ice water, then 1 ml of perchloric acid (70%) was added dropwise under stirring, and a large amount of distilled water was added, and solids were precipitated after standing, filtered, and vacuum-dried , purified by column chromatography to obtain 0.343g of compound I-1, with a yield of 82%. ESIMS: Theoretical calculation m / z: 319.18, actual test m / z: 319.20. lambda abs. max / nm=615nm,λ em max / nm=638nm,Ф f = 0.80.

[0105] 0.418g (0.001mol) of compound I-1, 0.202g (0.001mol) of di-tert-butyl dicarbonate and 0.101g (0.001mol) of triethylamine were added to 10 ml of anhydrous dichloromethane respectively, After stirring for 24 hours at room temperature, the solvent was removed under vacuum, dried and purified ...

Embodiment 2

[0108]

[0109] Compound III-11 was prepared from commercial compound III-1 and ethyl iodide according to literature (Org. Lett., 2011, 13, 6488-6491), with a yield of 50%.

[0110] 0.217 g (0.001 mol) of compound II-2 and 0.189 g (0.001 mol) of compound III-2 were added to 5 ml of concentrated sulfuric acid, and then heated and stirred at 100° C. for 2 h. After cooling, the reaction solution was slowly poured into 200 ml of ice water, then 1 ml of perchloric acid (70%) was added dropwise under stirring, and a large amount of distilled water was added, and solids were precipitated after standing, filtered, and vacuum-dried , purified by column chromatography to obtain 0.399 g of compound I-4, with a yield of 85%. ESIMS: Theoretical calculation m / z: 371.21, actual test m / z: 371.24. lambda abs. max / nm=635nm,λ em max / nm=658nm,Ф f = 0.73.

[0111] Dissolve 0.470 g (0.001 mmol) of compound I-4 in 5 ml of anhydrous THF, and add dropwise to 3 ml of CH containing 1 mmol un...

Embodiment 3

[0113]

[0114]Compound II-3 was prepared from 7-hydroxy-1-methyl-1,2,3,4-tetrahydroquinoline according to the literature (J.Am.Chem.Soc., 2007,129,9986-9998), the yield 76%. Compound III-3 was prepared from commercial compound III-1 and methyl iodide according to literature (Org. Lett., 2011, 13, 6488-6491), with a yield of 42%.

[0115] 0.191 g (0.001 mol) of compound II-3 and 0.189 g (0.001 mol) of compound III-3 were added to 5 ml of concentrated sulfuric acid, and then heated and stirred at 100° C. for 2 h. After cooling, the reaction solution was slowly poured into 200 ml of ice water, then 1 ml of perchloric acid (70%) was added dropwise under stirring, and a large amount of distilled water was added, and solids were precipitated after standing, filtered, and vacuum-dried , purified by column chromatography to obtain 0.391 g of compound I-6, with a yield of 88%. ESIMS: Theoretical calculation m / z: 345.20, actual test m / z: 345.26. lambda abs. max / nm=633nm,λ em ...

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 novel near-infrared high-quantum-yield dye which has the following structural formula I shown as the original specification, wherein R1, R2, R6 and R7 are hydrogen, a low-level alkyl, an ether group and a substituted alkyl or acyl that are independent respectively; R3, R4, R5, R8, R9 and R10 are hydrogen, a low-level alkyl or halogen that are independent respectively; R11 is hydrogen, methyl, a cyano group or trifluoromethyl; X<theta> is a negative ion. The invention discloses a preparation method of the dye. The dye has good biocompatibility, low toxicity, longer fluorescence-emission and high fluorescence quantum yield, the autofluorescence of a background is avoided, a fluorescence image with high signal-to-noise ratio can be obtained, and the dye is used for fluorescence labeling for nucleolar RNA in a biological system and plays an important pole in a study process of physiology related to the nucleolar RNA.

Description

technical field [0001] The invention relates to a near-infrared nucleolus RNA dye, and provides a novel near-infrared dye with high quantum yield, preparation and application. Background technique [0002] Owing to its high spatiotemporal resolution and fast and non-invasive operation, small molecule fluorescent dye-based fluorescence imaging has become a powerful tool for visual observation of biological phenomena (such as biomolecular detection, labeling, cancer diagnosis and treatment, etc.) in living systems. . RNA is a particularly important biomolecule in living systems, and RNA in the nucleus is located in the nucleolus, where they play crucial roles in gene coding, transcription, and expression. Many physiological processes in biochemical processes, including cell proliferation and differentiation, are closely related to the function of RNA. Therefore, real-time imaging of RNA is of great significance in biochemical research. Many fluorescent imaging techniques (R...

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): C07D311/78C07D311/00C09B57/14C09K11/06G01N21/64
CPCC07D311/78C09B57/14C09K11/06C09K2211/1029C09K2211/1059C09K2211/1092G01N21/6486
Inventor 汪鹏飞牛广乐刘卫敏张洪艳
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com