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Synthesis method of commercial BODIPY

A synthesis method and compound technology, applied in the field of fluorescent dye synthesis, can solve the problems of long synthesis steps, low synthesis yield, serious environmental pollution, etc., and achieve the effect of reducing synthesis cost and high-efficiency synthesis method

Active Publication Date: 2019-01-18
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis steps of the BODIPY compound disclosed in the existing literature are relatively long, the consumption of raw materials is large, the synthesis yield is low, and factors such as serious environmental pollution make it very expensive in price

Method used

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  • Synthesis method of commercial BODIPY
  • Synthesis method of commercial BODIPY
  • Synthesis method of commercial BODIPY

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] 1. Dissolve 1.03g (5.3mmol) of compound 1 in 60mL of acetonitrile, add 0.91g (21.2mmol) of lithium chloride, use an electrosynthesizer, constant current mode, 3mA current and stir at room temperature for 8h. After the reaction was finished, the reaction solution was transferred to a round bottom flask and concentrated under reduced pressure, and then purified by column chromatography to obtain 0.92g of yellow solid compound 2 with a yield of 66%. The structural characterization data were: 1 H NMR (600MHz, CHCl 3 -d) δ: 7.13(s, 1H), 7.07(d, J=4.2Hz, 2H), 6.42(d, J=4.4Hz, 2H); 13 C NMR (151MHz, CDCl 3 )δ: 145.7, 134.1, 131.4, 127.9, 119.1.

[0031] 2. Dissolve 200mg (0.76mmol) of compound 2 in 5mL of toluene, add 1mL of 2.5mol / L (2.5mmol) sodium carbonate aqueous solution, 43mg (0.04mmol) tetrakistriphenylphosphopalladium, 145mg (1.14mmol) thiophene-2 - Boric acid 3-1, heat the reaction solution to reflux for 5 hours under the protection of nitrogen, after ...

Embodiment 2

[0036]

[0037]1. Compound 2 was synthesized according to the method in Step 1 of Example 1.

[0038] 2. Compound 5-1 was synthesized according to the method in Step 2 of Example 1.

[0039] Dissolve 130mg (0.42mmol) of compound 5-1 in 5mL of toluene, add 0.3mL 2.5mol / L (0.75mmol) sodium carbonate aqueous solution, 24.3mg (0.03mmol) tetrakistriphenylphosphopalladium, 148.7mg (0.63mmol) (E)-(4-(2-methoxy-2-oxyethoxy)styryl)boronic acid 4-2, under the protection of nitrogen, the reaction solution was heated to reflux for 5h, after the reaction was completed, use a separatory funnel After extraction, the organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain 143 mg of reddish-brown solid compound 5-3 with a yield of 73%. The structural characterization data are: 1 H NMR (600MHz, CHCl 3 -d) δ: 8.20(dd, J=3.8, 1.1Hz, 1H), 7.64-7.56(m, 3H), 7.47(dd, J=5.1, 1.1Hz, 1H), 7.32(d, J=16.3Hz ,1H),7.2...

Embodiment 3

[0043]

[0044] 1. Dissolve 1.2g (4.3mmol) of compound 1' in 60mL of acetonitrile, add 273mg (6.4mmol) of lithium chloride, use an electrosynthesizer, constant current mode, 2mA current and stir at room temperature for 10h. After the reaction was finished, the reaction solution was transferred to a round bottom flask and concentrated under reduced pressure, then purified by column chromatography to obtain 1.17g of tan solid compound 2' with a yield of 86%, and the structural characterization data were: 1 H NMR (600MHz, CHCl 3 -d) δ: 7.11(s, 1H), 7.06(d, J=4.3Hz, 1H), 6.97(d, J=4.2Hz, 1H), 6.43(d, J=4.3Hz, 1H), 6.35( d, J=4.2Hz, 1H), 3.69(s, 3H), 3.34(t, J=7.5Hz, 2H), 2.79(t, J=7.5Hz, 2H); 13 C NMR (151MHz, CDCl 3 ): δ172.5, 164.0, 142.1, 135.7, 133.2, 132.4, 129.3, 127.8, 120.3, 117.5, 51.8, 32.8, 24.3.

[0045] 2. Dissolve 300mg (0.96mmol) of compound 2' in 5mL of toluene, add 2mL of 2.5mol / L (5mmol) sodium carbonate aqueous solution, 55.5mg (0.05mmol) tetrakistriphenyl...

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Abstract

The invention discloses a synthesis method of commercial BODIPY. According to the synthesis method, two types of chloro-BODIPY, which are generated by electrochemical halogenation reaction, are used as basic raw materials and synthesis of various commercial BODIPY is finished through Suzuki coupling reaction, ester hydrolysis reaction and acylation and esterification reaction; a whole synthesis route is green and environmentally friendly and is economical and efficient; the two types of chloro-BODIPY, which are prepared through an electrochemical method, have stable properties and are easy tostore and operate; gram-level preparation can be realized and the synthesis cost of the commercial BODIPY is greatly reduced; domestication of the commercial BODIPY is realized.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fluorescent dyes, in particular to a synthesis method of commercialized BODIPY. Background technique [0002] Since Treibs and Kreuzer synthesized BODIPY fluorescent dye compound for the first time in 1968, after half a century of development, BODIPY fluorescent dye, as a newer dye compound, has received extensive attention, and has also become one of the most commonly used fluorescent dye compounds. . Compared with other dye compounds, BODIPY dyes have the following advantages: (1) The main structure is generally not directly connected to amino groups, hydroxyl groups, etc., so it is not sensitive to pH; (2) The fluorescence quantum yield is high, and some can even Close to the level of 0.1; (3) Compared with fluorescein and cyanine dyes, BODIPY dyes have better photostability; (4) due to the narrow half-peak of its fluorescence spectrum, it has high sensitivity in fluorescent identificatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/06
CPCC25B3/27
Inventor 杨俊李建龙张畅李飞
Owner SHAANXI NORMAL UNIV
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