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Preparation method of phenanthroline bridged dicorrole derivatives

A derivative, the technology of o-phenanthroline, is applied in the field of preparation of o-phenanthroline bridged bicarbrole derivatives, can solve problems such as no reports on synthesis research, achieve simple synthesis route, good reaction selectivity, The effect of the simple separation method

Inactive Publication Date: 2021-03-09
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Bridging corrole derivatives at both ends of o-phenanthroline makes it not only have the excellent properties of corrole, but also retain the coordination performance of o-phenanthroline. It is worthy of more in-depth and effective research in terms of synthesis and application research. research work, and no synthetic studies on this aspect have been reported

Method used

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  • Preparation method of phenanthroline bridged dicorrole derivatives
  • Preparation method of phenanthroline bridged dicorrole derivatives
  • Preparation method of phenanthroline bridged dicorrole derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0023] The 5-p-boronate phenyl corrole derivative (III) (0.3mmol) and 2,9-bis(p-bromostyryl)-1,10-phenanthroline (III) (0.12mmol) were added to the reaction and dissolved in tetrahydrofuran (15mL), then weighed anhydrous cesium carbonate (1.2mmol) into the reactor and added water and methanol (2mL / 2mL) in proportion, and added tetrakis (three Phenylphosphine)palladium (0.024mmol), heated to reflux and reacted for 12h, after the reaction was completed, the organic phase was extracted with dichloromethane and washed with saturated aqueous ammonium chloride solution, the organic layer was dried over anhydrous sodium sulfate, and the solvent was spin-dried under reduced pressure, The o-phenanthroline bridged biscorrole derivative (I) was obtained by separation and purification through silica gel column chromatography with dichloromethane-petroleum ether as the eluent, with a yield of 35%. 1 H NMR (CDCl 3 , 600MHz, ppm) δ9.08-9.07(d, J=1.8Hz, 4H), 8.76(s, 4H), 8.70(s, 4H), 8.56(s,...

Embodiment 2

[0025] The 5-p-boronate phenyl corrole derivative (III) (0.3mmol) and 2,9-bis(p-bromostyryl)-1,10-phenanthroline (III) (0.12mmol) were added to the reaction and dissolved in tetrahydrofuran (15mL), then weighed anhydrous cesium carbonate (1.2mmol) into the reactor and added water and methanol (2mL / 2mL) in proportion, and added tetrakis (three Phenylphosphine)palladium (0.024mmol), heated to reflux and reacted for 15h, after the reaction was completed, the organic phase was extracted with dichloromethane and washed with saturated aqueous ammonium chloride solution, the organic layer was dried over anhydrous sodium sulfate, and the solvent was spin-dried under reduced pressure, The o-phenanthroline bridged biscorrole derivative (I) was obtained by separation and purification through silica gel column chromatography with dichloromethane-petroleum ether as the eluent, with a yield of 31%.

Embodiment 3

[0027] Add 5-p-boronate phenyl corrole derivative (0.12mmol) (II) and 2,9-bis(p-bromostyryl)-1,10-phenanthroline (0.06mmol) (II) to the reaction and dissolved in tetrahydrofuran (8mL), then weighed anhydrous sodium carbonate (1.08mmol) into the reactor and added water and methanol (1mL / 1mL) in proportion, and added tetrakis (three Phenylphosphine)palladium (0.012mmol), heated to reflux and reacted for 12h, after the reaction was completed, the organic phase was extracted with dichloromethane and washed with saturated aqueous ammonium chloride solution, the organic layer was dried over anhydrous sodium sulfate, and the solvent was spin-dried under reduced pressure, The o-phenanthroline bridged biscorrole derivative (I) was obtained by separation and purification through silica gel column chromatography with dichloromethane-petroleum ether as the eluent, with a yield of 15%.

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Abstract

The invention discloses a phenanthroline bridged bis-corrole derivative and a preparation method thereof, the chemical structure of the phenanthroline bridged bis-corrole derivative is shown as (I), and the phenanthroline bridged bis-corrole derivative is obtained by performing Suzuki coupling reaction on a 5 p-borate phenyl corrole derivative and 2, 9-bis(p-bromostyryl)-1, 10-phenanthroline underthe catalytic action of tetra(triphenylphosphine palladium. The compound is simple in preparation method, mild in reaction condition, simple and convenient to operate and excellent in optical performance, and can be applied to the aspects of anti-tumor activity, fluorescent probes, photodynamic therapy and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of o-phenanthroline bridged biscorrole derivatives. Background technique [0002] Corrole is a macrocyclic compound composed of four pyrrole conjugated links. The N and C in the molecule are all sp2 hybridized, and the remaining p orbital is occupied by a single electron or a lone pair of electrons, forming a macrocyclic compound with 18 electrons. Pi bond. Compared with porphyrin, corrole molecule has one less carbon atom and smaller inner cavity, which can stabilize high-valent metal ions, and has lower oxidation potential than porphyrin, higher fluorescence quantum yield, and larger Stokes Stein shift and stronger red light absorption, it is an important class of multifunctional compounds. Especially in recent years, researches on the use of corrole compounds as cancer detection reagents and photosensitizers for photodynamic therapy (PDT) have at...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00
CPCC07D519/00
Inventor 徐海军蒋浩王怡宋宇婷付博
Owner NANJING FORESTRY UNIV