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

Double-BODIPY near-infrared fluorescent dye with AIE effect and preparation method of double-BODIPY near-infrared fluorescent dye

A fluorescent dye and near-infrared technology, applied in the direction of organic dyes, luminescent materials, styrene-based dyes, etc., can solve the problems of low yield, small quantity, and many synthesis steps, and achieve high molar extinction coefficient, large Stor Kex shift, the effect of broad application prospects

Active Publication Date: 2021-10-01
NANJING FORESTRY UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, AIE-effect near-infrared fluorescent dye molecules still have the problems of many synthesis steps, low yield, and small quantity.

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
  • Double-BODIPY near-infrared fluorescent dye with AIE effect and preparation method of double-BODIPY near-infrared fluorescent dye
  • Double-BODIPY near-infrared fluorescent dye with AIE effect and preparation method of double-BODIPY near-infrared fluorescent dye
  • Double-BODIPY near-infrared fluorescent dye with AIE effect and preparation method of double-BODIPY near-infrared fluorescent dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The preparation of embodiment 1 compound (II)

[0024] Under anhydrous conditions, terephthalaldehyde (80mg, 0.6mmol) and BODIPY derivative (I) (672mg, 1.4mmol) were dissolved in a mixed solution of methanol and dichloromethane (v / v, 16mL / 8mL), A methanol solution of sodium methoxide (1M, 6 mL) was added dropwise thereto, and after the dropwise addition was completed, the reaction was carried out at room temperature for 6 hours. Add water to quench the reaction, extract with dichloromethane, dry the organic layer over anhydrous sodium sulfate, evaporate the solvent under reduced pressure, and separate and purify by silica gel column chromatography, the eluent is dichloromethane-petroleum ether (v:v=9 : 1), to obtain compound (II) (244mg, 38%). 1 H NMR (400MHz, CDCl 3 ): δ7.91(s, 4H), 7.38-7.39(d, J=3.6Hz, 2H), 7.28(s, 2H), 6.97(s, 4H), 6.83-6.84(d, J=3.6Hz, 2H), 6.04(s, 2H), 2.64(s, 6H), 2.60(s, 6H), 2.34(s, 6H), 2.13(s, 12H), 1.44(s, 6H), 1.41(s, 6H ).

Embodiment 2

[0025] Embodiment 2 has the preparation of the double BODIPY class near-infrared fluorescent dye (III) of AIE effect

[0026] Compound (II) (214mg, 0.2mmol), 4-(diphenylamino)benzaldehyde (328mg, 1.2mmol) and freshly dried p-toluenesulfonic acid (17mg, 0.1mmol) were added to 100mL of A two-neck reaction flask equipped with a Dean-Stark device, then add 10mL toluene and 0.2mL piperidine, stir and heat to reflux for 5 hours; after the reaction is completed, cool to room temperature, extract with dichloromethane, wash with water, dry, and evaporate the solvent under reduced pressure Separation and purification by silica gel column chromatography, the eluent is dichloromethane-petroleum ether (v:v=2:3), to obtain double BODIPY near-infrared fluorescent dye (III) with AIE effect (200mg, 48%). 1 H NMR (600MHz, CDCl 3): δ7.91(s, 4H), 7.55-7.63(m, 4H), 7.47-7.48(d, J=8.4Hz, 4H), 7.42(d, J=3.6Hz, 2H), 7.27-7.30( t, J=7.8Hz, 12H), 7.26(s, 4H), 7.23-7.24(d, J=7.8Hz, 8H), 7.13-7.14(d, J...

Embodiment 3

[0027] Embodiment 3 has the double BODIPY class near-infrared fluorescent dye (III) solution ultraviolet-visible absorption spectrum of AIE effect

[0028] Dissolve the double BODIPY type near-infrared fluorescent dye (III) with AIE effect in dichloromethane, and configure the concentration to be 1×10 -5 mol / L dichloromethane solution, and measure its UV-Vis absorption spectrum. figure 1 The ultraviolet-visible absorption spectrum of the fluorescent dye (III) solution prepared for Example 2 of the present invention.

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 a double-BODIPY near-infrared fluorescent dye with an AIE effect and a preparation method of the double-BODIPY near-infrared fluorescent dye. The two-step Knoevenagel condensation reaction are carried out on a BODIPY derivative (I), terephthalaldehyde and 4-(diphenylamino) benzaldehyde in sequence to obtain a compound (III); by introducing a strong donor / acceptor group with an AIE effect, the traditional BODIPY fluorescent dye is converted into an AIE molecule from an ACQ molecule, and shows a good aggregation-induced emission effect in a near-infrared region. In addition, the fluorescent dye has a large Stokes shift (70nm), and has a wide application prospect in the fields of luminescent materials, biological fluorescence imaging, chemical sensors, photodynamic therapy and the like as a novel near-infrared AIE fluorescent dye. The preparation method is mild in reaction condition, relatively good in selectivity and relatively simple and convenient in separation and purification.

Description

technical field [0001] The invention belongs to the technical fields of organic compound synthesis, functional fluorescent dyes and fine chemicals, and specifically relates to a double BODIPY near-infrared fluorescent dye with AIE effect and a preparation method thereof. Background technique [0002] Due to the π-conjugated system of traditional fluorescent molecules, the spatial structure is not three-dimensional enough. In the aggregated state, the molecules collide with each other and cause energy loss. At this time, fluorescence quenching (ACQ) caused by aggregation occurs. This phenomenon greatly restricts the application range of fluorescent materials. In 2001, Academician Tang Benzhong's research group reported an organic fluorescent molecule with the phenomenon of "aggregation-induced emission (AIE)". Contrary to ACQ molecules, AIE molecules are restricted in molecular motion in the aggregated state, which can inhibit the non-radiative transition process and promote...

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 Applications(China)
IPC IPC(8): C07F5/02C09B23/14C09K11/06
CPCC07F5/022C09K11/06C09B23/145C09K2211/1055C09K2211/1007C09K2211/1014C09K2211/1092
Inventor 徐海军王怡李鹏飞宗轩莱
Owner NANJING FORESTRY UNIV
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