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

Near-infrared light excited fluorescent dye as well as preparation method and application thereof

A technology for exciting fluorescence and near-infrared light, which is applied in the direction of luminescent materials, azo dyes, organic dyes, etc., can solve the problems of complex synthesis steps and poor photostability of parent molecules, and achieve enhanced fluorescence of organic molecules, low toxicity, and high quantum Yield effect

Pending Publication Date: 2018-06-08
SUZHOU BAIYUAN GENT CO LTD
View PDF0 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Therefore, the technical problem to be solved in the present invention is to overcome the poor photostability of the near-infrared light-excited fluorescent dyes in the prior art, the complex synthesis steps of the parent molecule, and various defects in the field of biological recognition.

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
  • Near-infrared light excited fluorescent dye as well as preparation method and application thereof
  • Near-infrared light excited fluorescent dye as well as preparation method and application thereof
  • Near-infrared light excited fluorescent dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The preparation method of the near-infrared light-excited fluorescent dye (II) provided in this embodiment:

[0036] Has formula (II) structure:

[0037]

[0038] Its preparation method is as follows:

[0039]

[0040] (1) Preparation of intermediate 1-II

[0041] Add 0.06mol of anhydrous aluminum chloride and 20ml of dichloromethane into a 100ml eggplant-shaped bottle, place in an ice-salt bath, stir, cool down to 0°C, add 4-bromo-2,3-bis(chloromethyl)- 1H-pyrrole 0.01mol, continue to cool down to -10°C, start dropping 0.03mol of chloroacetyl chloride, control the temperature -4°C, and react for 12 hours; slowly pour the reaction solution into saturated sodium bicarbonate solution, add deionized water 25ml, adjusted to pH 8.0 with sodium carbonate, extracted three times with chloroform, collected the organic phase, dried with anhydrous magnesium sulfate for 3 hours, filtered with suction, and evaporated the organic solvent to obtain intermediate 1-II.

[0042]...

Embodiment 2

[0054] The preparation method of the near-infrared light-excited fluorescent dye (III) provided in this embodiment:

[0055] Has the structure of formula (III):

[0056]

[0057] Its preparation method is as follows:

[0058]

[0059] (1) Preparation of intermediate 1-III

[0060] Add 0.4mol of anhydrous aluminum chloride and 150ml of dichloromethane into a 500ml eggplant-shaped bottle, place in an ice-salt bath, stir, cool down to -3°C, add 4-bromo-2,3-bis(chloromethyl) -1H-pyrrole 0.05mol, continue to cool down to -8°C, start to drop 0.2mol of chloroacetyl chloride, control the temperature -3°C, and react for 11 hours; slowly pour the reaction solution into saturated sodium bicarbonate solution, add deionized 100ml of water, adjusted to pH 8.0 with sodium carbonate, extracted three times with chloroform, collected the organic phase, dried with anhydrous magnesium sulfate for 3 hours, filtered with suction, and distilled off the organic solvent to obtain intermediate ...

Embodiment 3

[0073] The preparation method of the near-infrared light-excited fluorescent dye (IV) provided in this embodiment:

[0074] Has formula (IV) structure:

[0075]

[0076] Its preparation method is as follows:

[0077]

[0078] (1) Preparation of intermediate 1-IV

[0079] Add 0.28mol of anhydrous aluminum chloride and 100ml of dichloromethane into a 500ml eggplant-shaped bottle, place in an ice-salt bath, stir, cool down to -2°C, add 4-bromo-2,3-bis(chloromethyl) -1H-pyrrole 0.04mol, continue to cool down to -7°C, start to drop 0.14mol of chloroacetyl chloride, control the temperature at 0°C, and react for 10 hours; slowly pour the reaction solution into saturated sodium bicarbonate solution, add deionized water 100ml, adjusted to pH 7.0 with sodium carbonate, extracted three times with chloroform, collected the organic phase, dried with anhydrous magnesium sulfate for 3 hours, filtered with suction, and evaporated the organic solvent to obtain intermediate 1-IV.

[00...

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 relates to the field of photo-functional materials, in particular to a near-infrared light excited fluorescent dye. The near-infrared light excited fluorescent dye has a structure shownas the formula (I) in the description. The emission wavelength of the near-infrared light excited fluorescent dye is 700-1200 nm, own fluorescence of biomolecules is weaker in the range, so that background interference can be avoided, and higher sensitivity is obtained; the dye is in covalent bonding with biomacromolecules, is stable in structure, good in photostability and high in sensitivity, can be used in different application fields such as cell imaging, fluorescence probes, laser dyes, fluorescence sensors and the like, and shows good practicability. According to a preparation method, raw material cost is low, no pollution is produced, the process is simple, and yield is high; the prepared fluorescent dye is novel in structure, good in performance and suitable for being widely applied in the fields of biology, environment and the like.

Description

technical field [0001] The invention relates to the field of optical functional materials, in particular to a near-infrared light-excited fluorescent dye and a preparation method and application thereof. Background technique [0002] The wide application of fluorescence detection technology in DNA hybridization test, immune detection, gene recombination detection, etc. has greatly promoted the development of near-infrared light-excited fluorescent dyes. In the past few years alone, there have been a large number of literature and patents on this type of functional dye research. and applications are reported. The emission wavelength of fluorescent dyes excited by near-infrared light is 700-1200nm. In this range, the autofluorescence of biomolecules is weak, which can avoid background interference and obtain higher analytical sensitivity, and at the same time reduce damage to living organisms. Near-infrared light-excited fluorescent dyes can be widely used as safe and non-inv...

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
IPC IPC(8): C09K11/06C09B57/00G01N21/64
CPCC09B57/00C09K11/06G01N21/64C09K2211/1007C09K2211/1022C09K2211/1029C09K2211/107C09K2211/1092G01N21/6486
Inventor 车团结徐进章赵芳
Owner SUZHOU BAIYUAN GENT CO LTD
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