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Preparation method for tripolymerized indenyl BODIPY-fullerene starlike compound

A technology of trisindenyl and fullerene, which is applied in the field of organic synthesis, can solve the problems of complex reaction, many synthesis steps, and low yield, and achieve the effects of high-efficiency energy/electron transfer and strong light absorption capacity

Active Publication Date: 2018-12-14
NANJING FORESTRY UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, star compounds with a donor-acceptor structure still have shortcomings such as many synthetic steps, complex reactions, and low yields. Therefore, it is important to design and synthesize new easily synthesized star compounds with efficient energy / electron transfer processes. the meaning of

Method used

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  • Preparation method for tripolymerized indenyl BODIPY-fullerene starlike compound
  • Preparation method for tripolymerized indenyl BODIPY-fullerene starlike compound
  • Preparation method for tripolymerized indenyl BODIPY-fullerene starlike compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Under argon protection conditions, meso-phenylboronic acid ester BODIPY derivative (III) (1.20mmol, 540.2mg), 7,12-dibromotriindaldehyde derivative (II) (0.60mmol, 417.9mg) and anhydrous sodium carbonate (21.60mmol, 2.28g) were added to the reaction flask, tetrahydrofuran (70mL), methanol and water (v / v, 3.0mL / 3.0mL) were added, and tetrakis(triphenylphosphine) palladium ( 0.12mmol, 138.6mg), heated to 70°C and refluxed for 24h. After the reaction, cooled to room temperature, added saturated ammonium chloride solution, extracted the crude product with dichloromethane, combined the organic layers and dried over anhydrous sodium sulfate. Recover the solvent by distillation under reduced pressure, and use dichloromethane-petroleum ether (volume ratio 1:2) as the eluent to obtain 84.4 mg of tripolyindenyl BODIPY intermediate (IV) through silica gel chromatography column separation, yield: 12%. UV-vis (CH 2 Cl 2 ), λ max / nm[λ×10 -5 (L·mol -1 cm -1 )]: 330 (0.13579), ...

Embodiment 2

[0031] Under argon protection conditions, meso-phenylboronic acid ester BODIPY derivative (III) (1.20mmol, 540.2mg), 7,12-dibromotriindaldehyde derivative (II) (0.60mmol, 417.9mg) and anhydrous sodium carbonate (21.60mmol, 2.28g) were added to the reaction flask, tetrahydrofuran (70mL), methanol and water (v / v, 2.0mL / 2.0mL) were added, and tetrakis(triphenylphosphine) palladium ( 0.06mmol, 69.3mg), heated to 70°C and refluxed for 24h. After the reaction, cooled to room temperature, added saturated ammonium chloride solution, extracted the crude product with dichloromethane, combined the organic layers and dried over anhydrous sodium sulfate. Recover the solvent by distillation under reduced pressure, and use dichloromethane-petroleum ether (volume ratio 1:2) as the eluent to separate through silica gel chromatography to obtain the tripolyindenyl BODIPY intermediate (IV), with a yield of 10 %.

[0032] Under the protection of argon, tripolyindenyl BODIPY intermediate (IV) (0.0...

Embodiment 3

[0034] Under argon protection conditions, meso-phenylboronic ester BODIPY derivative (III) (1.38mmol, 621.0mg), 7,12-dibromotriindaldehyde derivative (II) (0.60mmol, 417.9mg) and anhydrous potassium carbonate (21.60mmol, 2.98g) were added to the reaction flask, tetrahydrofuran (60mL), methanol and water (v / v, 2.5mL / 2.5mL) were added, and tetrakis(triphenylphosphine) palladium ( 0.08mmol, 92.4mg), heated to 70°C and refluxed for 24h. After the reaction, cooled to room temperature, added saturated ammonium chloride solution, extracted the crude product with dichloromethane, combined the organic layers and dried over anhydrous sodium sulfate. Recover the solvent by distillation under reduced pressure, and use dichloromethane-petroleum ether (volume ratio 1:2) as the eluent to separate through silica gel chromatography to obtain the tripolyindenyl BODIPY intermediate (IV), with a yield of 15 %.

[0035] Under the protection of argon, tripolyindenyl BODIPY intermediate (IV) (0.020...

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Abstract

The invention provides a tripolymerized indenyl BODIPY-fullerene starlike compound shown in a formula (I). The compound is prepared by the following steps: carrying out Suzuki coupled reaction betweena 7,12-dibromo tripolymerized indenyl aldehyde derivative shown in a formula (II) and a meso-phenyl borate BODIPY derivative shown in a formula (III) to generate a tripolymerized indenyl BODIPY intermediate shown in a formula (IV); carrying out a dipolar cycloaddition reation between the tripolymerized indenyl BODIPY intermediate and fullerene shown in a formula (V) to generate the tripolymerizedindenyl BODIPY-fullerene starlike compound shown in the formula (I). The preparation method of the tripolymerized indenyl BODIPY-fullerene starlike compound is simple, mild in reaction condition andsimple to separate. The synthesized starlike compound has a high light absorbing capability, different groups in molecules interact, and efficient intramolecular energy transfer is carried out subjected to optical excitation, so that the compound can be applied to the fields of solar batteries, molecular absorption antennas, photosynthesis simulation and the like. The formulae are shown in the description.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of a three-indenyl BODIPY-fullerene star compound. Background technique [0002] Dye molecules with electron / energy donating and acceptor properties have shown broad application prospects in optical molecular devices, solar cells, and artificial photosynthesis. In the molecular models of different structural types, the star compound has a unique three-dimensional star-shaped structure, which is not only conducive to the regulation of the photoelectric properties and morphological characteristics of the molecule, but also to the enhancement of its solubility; in addition, multiple outwardly extending arms It is also conducive to improving the efficiency of charge transfer and energy transfer, so star compounds have attracted more and more attention. However, star compounds with a donor-acceptor structure still have shortcomings such as many synthetic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06
CPCC07F5/022C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1096
Inventor 徐海军蔡方建袁雪梅王石发蔡正春
Owner NANJING FORESTRY UNIV
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