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Tripolyindenyl conjugated tri-BODIPY near-infrared fluorescent dye and preparation method thereof

A fluorescent dye, polyindenyl technology, applied in azo dyes, organic dyes, luminescent materials, etc., can solve the problems of many synthesis steps, poor solubility, limited application, etc., and achieves good solubility, simple and easy preparation method, The effect of good photostability

Active Publication Date: 2020-09-29
NANJING FORESTRY UNIV
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  • Summary
  • 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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  • Tripolyindenyl conjugated tri-BODIPY near-infrared fluorescent dye and preparation method thereof
  • Tripolyindenyl conjugated tri-BODIPY near-infrared fluorescent dye and preparation method thereof
  • Tripolyindenyl conjugated tri-BODIPY near-infrared fluorescent dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] In a round bottom flask equipped with a Dean-Stark apparatus, 1,5,7-tetramethyl-3-(4-N-N-dimethyl)-vinylbenzene-8-(2,4,6-trimethylbenzene) -BODIPY (237mg, 0.477mmol), 2,7,12-triformyltripolyindene (94mg, 0.159mmol) and freshly dried p-toluenesulfonic acid (79mg) were dissolved in 25mL toluene and 1mL piperidine, and the mixture was heated to reflux for 24 hours, cooled to room temperature, diluted with dichloromethane, washed with water, the organic layer was dried over anhydrous sodium sulfate, the organic solvent was evaporated under reduced pressure, the residue was separated and purified by silica gel column chromatography, and the eluent was (100% CH 2 Cl 2 ) to obtain compound 1 (32 mg, 10%) as a black-green solid. 1 HNMR: (400MHz, CDCl 3 )δ8.46(d, 3H), 7.90(d, 3H), 7.79(d, 3H), 7.67(s, 4H), 7.64-7.53(m, 8H), 7.39(d, 3H), 7.28(d , 3H), 6.99(s, 6H), 6.69(t, 12H), 3.11(m, 6H), 3.04-2.90(m, 18H), 2.38(s, 9H), 2.32(dd, 6H), 2.17( s, 18H), 1.49 (d, 18H), 0.32 (t, 1...

Embodiment 2

[0030] In a round bottom flask equipped with a Dean-Stark apparatus, 1,5,7-tetramethyl-3-(4-N,N-dianilinostyryl)-8-(2,4,6-trimethylbenzene )-BODIPY (415 mg, 0.63 mmol), 2,7,12-triformyltripolyindene (128 mg, 0.21 mmol) and freshly dried p-toluenesulfonic acid (100 mg) were dissolved in 25 mL of toluene and 1 mL of piperidine, and the mixture was heated to reflux 28 hours, cooled to room temperature, diluted with dichloromethane, washed with water, the organic layer was dried over anhydrous sodium sulfate, the organic solvent was evaporated under reduced pressure, the residue was separated and purified by silica gel column chromatography, and the eluent was (100% CH 2 Cl 2 ) to obtain black-green solid compound 2 (45 mg, 9%). 1 H NMR: (600MHz, CDCl 3 )δ8.43(d, J=8.4Hz, 3H), 7.86(d, J=16.2Hz, 3H), 7.80(d, J=7.8Hz, 3H), 7.72(d, J=16.2Hz, 3H) , 7.62(s, 3H), 7.56(d, J=8.4Hz, 1H), 7.54(d, J=8.4Hz, 6H), 7.43(d, J=16.2Hz, 3H), 7.39-7.37(m, 2H), 7.30(d, J=7.8Hz, 9H), 7.26(d, J=16.2...

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Abstract

The invention relates to a tripolyindenyl conjugated tri-BODIPY near-infrared fluorescent dye and a preparation method thereof. The tripolyindenyl conjugated tri-BODIPY near-infrared fluorescent dye is synthesized by carrying out Knoevenagel condensation reaction on a BODIPY derivative and tripolyindenyl containing 2, 7, 12-triformyl under the catalytic action of p-toluenesulfonic acid and piperidine. The preparation method has the advantages of simple reaction steps, mild reaction conditions and good selectivity. The fluorescent dye has the advantages of high molar extinction coefficient, favorable solubility, favorable light stability and other excellent photophysical properties. The red shift of the strongest electron absorption spectrum of the dye reaches 650 nm or above, the maximum fluorescence emission wavelength reaches 700 nm or above, and the dye is a near-infrared organic fluorescent dye with a very good application prospect and can be applied to the fields of biomarkers, fluorescent probes, photovoltaic materials and the like.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, functional fluorescent dyes and fine chemicals, and in particular relates to a tri-indenyl conjugated tri-BODIPY near-infrared fluorescent dye and a preparation method thereof. Background technique [0002] Boron-dipyrromethene (BODIPY) dyes, as near-infrared organic fluorescent dyes, are favored by the scientific community for their superior photophysical properties and easy-to-modify chemical structures. They have high molar extinction coefficient and fluorescence quantum yield; have strong absorption in the visible light region; are not easily affected by solvent polarity; have good photothermal stability, and can be free from changes in the detection environment such as excitation irradiation and temperature rise Effect on fluorescence analysis. Therefore, BODIPY compounds have great application value in the fields of photodynamic therapy, ion recognition, pH fluorescent p...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06C09B57/00
CPCC07F5/022C09K11/06C09B57/00C09K2211/1014C09K2211/1011C09K2211/1055
Inventor 徐海军李鹏飞宋宇婷王怡赵越
Owner NANJING FORESTRY UNIV
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