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Synthesis method of dipyrromethene N, O-boron difluoride derivative

A dipyrromethene and boron difluoride technology, which is applied in the field of synthesis of dipyrromethene N,O-boron difluoride derivatives, can solve the problems of complex preparation process, many reaction steps, and complex process , to achieve the effect of simple preparation, simple steps, and simple reaction operation

Inactive Publication Date: 2016-06-22
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

[0003] The synthesis of dipyrrole methylene boron dyes (BODIPY) is generally prepared by using pyrrole as a raw material and reacting with acid chloride or acid anhydride in two steps, but the yield is low; it can also use pyrrole and aldehyde as raw materials through condensation-oxidation- Complexation is prepared in three steps, and due to the limitation of the oxidation step, the total yield is also low; the asymmetric BODIPY is prepared by reacting pyrrolone and another molecule of pyrrole, but the preparation of pyrrolone is a bottleneck restricting the method (Burgess , K.etal.Chem.Rev.2007,107,4891-4932.)
In addition, HBO (Ziessel, R. etal. Org. Lett. 2012, 14, 230-233.) dyes were also synthesized, using o-hydroxyaniline and o-hydroxybenzaldehyde to prepare benzoxazole, and then combined with BF 3 ·OEt 2 Complexation, but there are many reaction steps and the process is complicated
In 2013, Pandey et al. reported a dipyrromethene N, O-boron difluoride dye, but the preparation process was complicated and the yield was very low (Pandey, D.S.etal.DaltonTrans.2013, 42, 1696-1707.)

Method used

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  • Synthesis method of dipyrromethene N, O-boron difluoride derivative
  • Synthesis method of dipyrromethene N, O-boron difluoride derivative
  • Synthesis method of dipyrromethene N, O-boron difluoride derivative

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Experimental program
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Effect test

Embodiment 1

[0027]

[0028] To a 10 mL Schlenk reaction flask, add 2a (126.2 mg, 0.5 mmol), 5 mL of acetonitrile, N-H pyrrole 3a (67.1 mg, 1.0 mmol) and BF 3 ·OEt 2 (141.9 mg, 1.0 mmol). The reaction was stirred at 30 °C for 14 h. TLC showed that after the reaction was over, add 5mL saturated NaHCO 3 Aqueous solution was used to quench the reaction, the reaction solution was transferred to a separatory funnel, water (30 mL) was added, extracted with dichloromethane (3×10 mL), and the organic phases were combined. Dry over anhydrous magnesium sulfate and filter. The volatile components were removed, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C / ethyl acetate, v / v=3:1) to obtain the target product 1a (100.8mg, yield 65% ).

Embodiment 2

[0030] The reaction steps and operations are the same as in Example 1, except that the solvent is dichloromethane. The reaction was stopped, and the target product 1a (46.5 mg, yield 30%) was obtained after post-processing. It shows that dichloromethane with low polarity is not as effective as acetonitrile with high polarity as a solvent.

Embodiment 3

[0032] The reaction steps and operations are the same as in Example 1, except that the reaction solvent is nitromethane. The reaction was stopped, and the target product 1a (96.1 mg, yield 62%) was obtained after post-processing. It shows that the effects of nitromethane and acetonitrile are roughly the same.

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Abstract

The invention discloses a synthesis method of a dipyrromethene N, O-boron difluoride derivative. The method takes ketene dithioacetals, a pyrrole compound and boron trifluoride ethyl ether as reaction raw materials to carry out one-step reaction to obtain a dipyrromethene N, O-boron difluoride derivative. Compared with reported synthesis methods of dipyrromethene boron difluoride analogues, the method provided by the invention has the advantages of easily available raw materials, simple operation, and mild synthesis reaction conditions, etc.

Description

technical field [0001] The invention relates to a synthesis method of dipyrromethene N, O-boron difluoride derivatives. Easy to prepare dithioketene, pyrrole compound and BF 3 ·OEt 2 Preparation of dipyrromethene N,O-boron difluoride derivatives as starting materials. Compared with the existing synthetic method, the present invention has the characteristics of readily available raw materials, simple and convenient operation, mild synthetic reaction conditions and high yield. Background technique [0002] Pyrrole N,N- or N,O-boron difluoride complexes are an important class of organic light-emitting materials, which have the advantages of good photostability, near-infrared excitation, high molar absorptivity, and high fluorescence quantum yield, and are widely used In the fields of organic photosensitizers, laser dyes and chemical sensors (Ziessel, R. et al. Angew. Chem., Int. Ed. 2008, 47, 1184-1201; Chang, Y. et al. , 2168-2176.). Common pyrrole boron difluoride comple...

Claims

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Application Information

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IPC IPC(8): C07F5/02
Inventor 余正坤杨小格
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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