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Near-infrared truxene-based conjugate dual-BODIPY fluorescent dye and preparation method thereof

A technology of trisindenyl and fluorescent dyes, which is applied in the direction of azo dyes, organic dyes, and luminescent materials, and can solve the problems of many synthesis steps, poor solubility, and limited applications, and achieve good solubility and simple and easy preparation methods , the effect of high molar absorptivity

Active Publication Date: 2017-07-07
南京颐维环保科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, most near-infrared fluoroboron-dipyrrole dyes have many steps to synthesize, are difficult, and have poor solubility, which limits their further application in the fields of biology, environment, and medicine.

Method used

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  • Near-infrared truxene-based conjugate dual-BODIPY fluorescent dye and preparation method thereof
  • Near-infrared truxene-based conjugate dual-BODIPY fluorescent dye and preparation method thereof
  • Near-infrared truxene-based conjugate dual-BODIPY fluorescent dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Equipped with a water trap in the round bottom flask, 1,5,7-tetramethyl-3-vinylthiophene-8-(2,4,6-trimethylbenzene)-BODIPY (120mg, 0.26mmol), 2, 6-dialdehyde-based triacinene (80mg, 0.13mmol) and p-toluenesulfonic acid (50mg) were dissolved in 25mL toluene and 2mL piperidine, the mixture was heated to reflux, and TLC was tracked to detect that the reaction of the raw materials was complete. The solvent was collected until it was evaporated to dryness, washed with water, Extract with dichloromethane, combine the organic layers, remove the organic solvent under reduced pressure, and the residue is separated and purified by silica gel column chromatography, and the eluent is (petroleum ether / CH 2 Cl 2 =1:1), to obtain compound a (17.4 mg, 28.9%) as a black-green solid. 1 H NMR: (600MHz, CDCl 3 )δ8.50-8.39(m, 3H), 7.86(d, J=24.30Hz, 2H), 7.79(d, J=12.24Hz, 2H), 7.62-7.58(m, 4H), 7.50-7.48(d , 1H), 7.44-7.34(m, 8H), 7.27(d, J=5.76Hz, 2H), 7.07(t, J=9.60Hz, 2H), 6.98(s, 4H...

Embodiment 2

[0031] Equipped with a water trap in the round bottom flask, 1,5,7-tetramethyl-3-vinylbenzene (4-methoxy)-8-(2,4,6-trimethylbenzene)-BODIPY (150mg , 0.31mmol), 2,6-dialdehyde-based tripolyindene (92mg, 0.15mmol) and p-toluenesulfonic acid (50mg) were dissolved in 25mL toluene and 2mL piperidine, the mixture was heated to reflux, TLC tracking detection raw material reaction was complete, collected The solvent was evaporated to dryness, washed with water, extracted with dichloromethane, the organic layers were combined, and the organic solvent was removed under reduced pressure. The residue was separated and purified by silica gel column chromatography, and the eluent was (petroleum ether / CH 2 Cl 2 =1:1) to obtain compound b (22.8 mg, 15.2%) as a black-purple solid. 1 HNMR: (600MHz, CDCl 3 ( d, 6H), 7.50(d, J=6.6Hz, 1H), 7.45-7.39(m, 4H), 7.26(d, J=15.6Hz, 2H), 6.99-6.95(m, 8H), 6.70(s , 2H), 6.64(s, 2H), 3.83(s, 6H), 3.11-3.01(m, 6H), 2.37(s, 6H), 2.31-2.19(m, 6H), 2.16(s, ...

Embodiment 3

[0033] A water separator is equipped in the round bottom flask, and 1,5,7-tetramethyl-3-vinylbenzene (4-(1-piperidine))-8-(2,4,6-trimethylbenzene)- BODIPY (155mg, 0.28mmol), 2,6-dialdehyde tripolyindene (83mg, 0.14mmol) and p-toluenesulfonic acid (50mg) were dissolved in 25mL toluene and 2mL piperidine, the mixture was heated to reflux, and the reaction of raw materials was tracked and detected by TLC Completely, collect the solvent until it is evaporated to dryness, wash with water, extract with dichloromethane, combine the organic layers, remove the organic solvent under reduced pressure, and the residue is separated and purified by silica gel column chromatography, and the eluent is (petroleum ether / CH 2 Cl 2 =1:1), a black solid compound c (45.0 mg, 28.0%) was obtained. 1 H NMR: (600MHz, CDCl 3)δ8.47-8.41(m, 3H), 7.80(d, J=18.00Hz, 2H), 7.81-7.77(m, 2H), 7.66(t, J=24.00Hz, 4H), 7.59-7.57(m , 4H), 7.50(d, J=6.00Hz, 1H), 7.46-7.39(m, 4H), 7.27(d, J=18.00Hz, 2H), 6.99(s, 4...

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Abstract

The invention relates to a near-infrared truxene-based conjugate dual-BODIPY fluorescent dye and a preparation method thereof. The fluorescent dye is synthesized by virtue of Knoevenagel condensation reaction of a BODIPY derivative and dialdehyde-containing truxene under the catalysis of p-toluenesulfonic acid and piperidine. The preparation method has the beneficial effects of simple reaction steps, mild reaction conditions and relatively good selectivity. The fluorescent dye has excellent physical properties of relatively high molar extinction coefficients, good solubility and light stability and the like, the highest electronic absorption spectrum red shift reaches above 650nm, the fluorescence emission wavelength reaches 680nm, and the fluorescent dye has very high application prospects. The fluorescent dye has good potential application prospects in the fields of cell imaging, bio-labeling or photoelectric materials and the like.

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 near-infrared trisindenyl conjugated bis-BODIPY fluorescent dye and a preparation method thereof. Background technique [0002] Fluoroboron dipyrrole dye (BODIPY) is a compound formed by the complexation of dipyrromethene and boron trifluoride. BODIPY fluorescent dyes have the advantages of high molar absorptivity, high fluorescence quantum yield, insensitive fluorescence signal to solvent polarity and pH, narrow fluorescence spectrum peak, long fluorescence lifetime, moderate redox potential, negligible triplet state, etc. ; Moreover, the BODIPY fluorescent molecular core is relatively stable and has certain chemical activity, the structure is easy to modify, and the absorption and emission wavelengths can be adjusted to the near-infrared region. Based on the above advantages, BODIPY fluorescent dy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06C09B57/00
CPCC07F5/022C09B57/00C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1096
Inventor 徐海军杨剑陶家宇康熙元朱晓蕾
Owner 南京颐维环保科技有限公司
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