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Near infrared BODIPY fluorescence dye and preparation method thereof

A fluorescent dye and near-infrared technology, which is applied in the field of organic compound synthesis, can solve the problems of many synthesis steps, poor solubility, and high difficulty, and achieve the effects of good solubility, less pollution, and good reaction selectivity

Active Publication Date: 2016-04-06
南京颐维环保科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, most near-infrared BODIPY dyes have many synthesis steps, high difficulty, low yield, and poor solubility, which limit their further application in the fields of biology and environment.

Method used

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  • Near infrared BODIPY fluorescence dye and preparation method thereof
  • Near infrared BODIPY fluorescence dye and preparation method thereof
  • Near infrared BODIPY fluorescence dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Equipped with a water trap in the single-neck round bottom flask, 1,3,5,7-tetramethyl-8(2,4,6-trimethylbenzene)-BODIPY (146.4mg, 0.40mmol), 2-formyl Indene (0.862g, 1.60mmol) and p-toluenesulfonic acid (68mg) were dissolved in 25mL toluene and 2mL piperidine, the mixture was heated to reflux at 140°C, TLC was followed to detect the complete reaction of the raw materials, and the solvent was collected until evaporated to dryness. The reactant was concentrated and subjected to silica gel column chromatography, and the eluent was (petroleum ether / CH 2 Cl 2 =6:4), to obtain dark green solid A (182.0 mg, 32.33%). Esi-MS: calcdforC 102 h 106 BF 2 N 2 1407.8417, found: 1407.8459 (M+H + )( figure 1 ); 1 HNMR: (600MHz, CDCl 3 )δ8.46(d, J=4.20Hz, 2H), 8.40(d, J=7.20Hz, 4H), 7.93(d, J=16.2Hz, 2H), 7.83(d, J=8.40Hz, 2H) , 7.67(s, 1H), 7.54-7.52(m, 2H), 7.50-7.48(m, 2H), 7.46-7.42(m, 6H), 7.38-7.33(m, 4H), 7.03(s, 2H) , 6.74(s, 2H), 3.15-3.03(m, 12H), 2.40(s, 3H), 2.31-2....

Embodiment 2

[0034] Equipped with a water trap in the round bottom flask, 1,3,5,7-tetramethyl-2,6-diiodo-8(2,4,6-trimethylbenzene)-BODIPY (247.2mg, 0.40mmol) , tripolyindene formaldehyde (0.862g, 1.60mmol) and p-toluenesulfonic acid (68mg) were dissolved in 25mL toluene and 2mL piperidine, the mixture was heated to reflux at 140 ° C, TLC traced and detected that the reaction of the raw materials was complete, and the solvent was collected until evaporated to dryness. The reactant was concentrated and subjected to silica gel column chromatography, and the eluent was (petroleum ether / CH 2 Cl 2 =8:2), to obtain green solid B (196.2mg, 29.54%). Esi-MS: calcdforC 102 h 103 BF 2 I 2 N 2 1658.6272, found: 1658.6218 (M + )( Figure 5 ); 1 HNMR: (600MHz, CDCl 3 )δ8.46(d, J=8.40Hz, 2H), 8.39(t, J=8.40Hz, 6H), 7.95(d, J=16.2Hz, 2H), 7.88(d, J=7.20Hz, 2H) , 7.69(s, 2H), 7.49-7.33(m, 12H), 7.06(s, 2H), 3.14-2.99(m, 12H), 2.43(s, 3H), 2.33-2.13(m, 18H), 1.56 (s, 6H), 0.34-0.23 (m, 36H) ( F...

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Abstract

The invention relates to a near infrared BODIPY fluorescence dye and a preparation method thereof. A BODIPY derivative and 2-aldotruxene undergo a Knoevenagel condensation reaction under the catalysis action of p-toluenesulfonic acid and piperidine to synthesize the dye, and the maximal absorption wavelength and the maximal emission wavelength of the dye in an organic solvent are 650nm or above respectively. The preparation method has the advantages of simple reaction steps, mild reaction conditions and good selectivity. Like fluorescence dyes have the advantages of high molar extinction coefficient, good solubility and light stability, excellent photophysical performances, and good application prospect in cell imaging and biological marking.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a near-infrared BODIPY fluorescent dye and a preparation method thereof. Background technique [0002] Fluoroboron dipyrrole dye (BODIPY) is a new type of fluorescent dye that has emerged in recent years, and it is a complex formed by dipyrromethene and boron trifluoride. The dye molecule has high photothermal stability, which can avoid the rapid degradation of the dye structure caused by the irradiation of the excitation light, the rise of temperature or the change of the detection environment of the dye itself during the fluorescence analysis process, ensuring the stability of the spectral analysis signal sex. In addition, BODIPY fluorescent dyes have high molar absorptivity, high fluorescence quantum yield, fluorescence signal is insensitive to solvent polarity and pH, narrow fluorescence spectrum peak, long fluorescence lifetime, moderate redox...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09B23/12C07F5/02
Inventor 徐海军袁雪梅孙丹徐莉黄超伯姚建峰
Owner 南京颐维环保科技有限公司
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