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Synthesis and preparation method of tripolyindenyl coumarin-corrole-porphyrin quaternary system star-shaped compound

A technology of triindenyl-based triindenyl derivatives, which is applied in the field of preparation of star compounds based on triindenyl quaternary system, can solve the problems of complex reaction, many synthesis steps, and low yield, and achieve the goal of reaction The effect of good selectivity, simple synthetic route and simple separation method

Active Publication Date: 2021-02-02
南京博裕环境科技有限公司
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  • Summary
  • 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 novel star compounds that are easy to synthesize with good energy / electron transfer processes. the meaning of

Method used

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  • Synthesis and preparation method of tripolyindenyl coumarin-corrole-porphyrin quaternary system star-shaped compound
  • Synthesis and preparation method of tripolyindenyl coumarin-corrole-porphyrin quaternary system star-shaped compound
  • Synthesis and preparation method of tripolyindenyl coumarin-corrole-porphyrin quaternary system star-shaped compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 2,7-bisbromo-12-coumarinyltriindene derivative (II) (681.8mg, 0.75mmol), meso-phenylboronic ester corrole derivative (III) (582.4mg, 0.7mmol ), anhydrous potassium carbonate (1.04g, 7.5mmol) were dissolved in 30mL of tetrahydrofuran, and 3mL of water and 3mL of methanol were added thereto, and tetrakis(triphenylphosphine)palladium (58mg, 0.05mmol) was rapidly added thereto under argon protection , 65 ° C reaction 10h. After the reaction was completed, the solvent was spin-dried, dissolved in dichloromethane, washed with saturated brine, the organic layer was dried over anhydrous sodium sulfate, evaporated under reduced pressure to dry the solvent, and dichloromethane-petroleum ether (v:v=1:1) The eluent was separated and purified by silica gel column chromatography to obtain the tripolyindenylcoumarin-corrole intermediate (IV) with a yield of 38%. 1 H NMR (CDCl 3 , 600MHz, ppm) δ9.14(d, J=3.6Hz, 2H), 8.87-8.80(m, 2H), 8.77-8.72(m, 2H), 8.59(s, 2H), 8.53-8.41(m, 1H), ...

Embodiment 2

[0026] Dissolve tripolyindenylcoumarin-corrole intermediate (IV), meso-phenyl borate zinc porphyrin derivative (V) (279mg, 0.3mmol), anhydrous potassium carbonate (345mg, 2.5mmol) In 20mL of tetrahydrofuran, 2mL of water and 2mL of methanol were added thereto, tetrakis(triphenylphosphine)palladium (12mg, 0.01mmol) was quickly added thereto under the protection of argon, and reacted at 65°C for 10h. After the reaction was completed, the solvent was spin-dried, extracted with dichloromethane, washed with saturated brine, the organic layer was dried over anhydrous sodium sulfate, evaporated under reduced pressure to dry the solvent, and dichloromethane-petroleum ether (v:v=1:1) The eluent was separated and purified by silica gel column chromatography to obtain 113 mg of star compound (I) of ternary indenylcoumarin-corrole-porphyrin quaternary system, with a yield of 20%. 1 H NMR (CDCl 3 , 600MHz, ppm) δ9.15(s, 1H), 9.02(d, J=2.4Hz, 2H), 8.92-8.78(m, 5H), 8.76(m, 4H), 8.62(d, J=1...

Embodiment 3

[0028]2,7-bisbromo-12-coumarinyltriindene derivative (II) (681.8mg, 0.75mmol), meso-phenyl borate corrole derivative (III) (582.4mg, 0.7mmol ), anhydrous potassium carbonate (1.04g, 7.5mmol) were dissolved in 30mL of tetrahydrofuran, and 3mL of water and 3mL of methanol were added thereto, and tetrakis(triphenylphosphine) palladium (35mg, 0.03mmol) was rapidly added thereto under argon protection , Reaction at 75°C for 8h. After the reaction was completed, the solvent was spin-dried, dissolved in dichloromethane, washed with saturated brine, the organic layer was dried over anhydrous sodium sulfate, evaporated under reduced pressure to dry the solvent, and dichloromethane-petroleum ether (v:v=1:1) The eluent was separated and purified by silica gel column chromatography to obtain the tripolyindenylcoumarin-corrole intermediate (IV) with a yield of 31%.

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Abstract

The invention discloses a synthesis and preparation method of a tripolyindenyl coumarin-corrole-porphyrin quaternary system star-shaped compound as shown in a formula (I) which is described in the specification. The preparation method comprises the following steps: carrying out two-step Suzuki coupling reaction by using 2, 7-dibromo-12-coumarin-based tripolyindenyl with a borate corrole derivativeand a borate zinc porphyrin derivative in sequence to obtain the tripolyindenyl coumarin-corrole-porphyrin quaternary system star-shaped compound shown in the formula (I). The star-shaped compound issimple in synthesis method, mild in reaction condition and relatively simple and convenient to separate and purify. Different groups in the synthesized star-shaped molecules can be subjected to intermolecular high-efficiency energy transfer after being excited by light, and can be applied to the fields of optical molecular absorption antennas, organic solar cells, artificial simulated biologicalphotosynthesis and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of a star compound based on a three-indenyl quaternary system. Background technique [0002] Light-induced energy / electron transfer plays an important role in photochemical reactions, solar energy utilization, and photosynthetic mechanisms. The application of molecular models based on light-induced energy / electron transfer mechanisms in optical molecular devices, solar cells, and artificial photosynthesis has become a very active research field at home and abroad. Dye molecules with electron / energy donating and acceptor properties have shown broad application prospects in organic optoelectronic functional materials. In molecular models of different structural types, the unique three-dimensional star-like structure of star-shaped compounds is beneficial to regulate the photoelectric properties and morphological characteristics of molecules, and multip...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00
CPCC07D519/00
Inventor 徐海军王怡蔡方建李鹏飞付博
Owner 南京博裕环境科技有限公司
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