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Thienyl phosphorescent iridium complex as well as preparation method and application thereof

A technology of thiophene-based phosphorescence and iridium complexes, applied in the field of material science, can solve the problems of light instability and easy decomposition, and achieve the effects of good stability and simple preparation method.

Inactive Publication Date: 2014-06-25
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these photosensitizers are unstable to light and are easily decomposed under light conditions. A new generation of photosensitizers, especially near-infrared photosensitizers, has yet to be developed.

Method used

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  • Thienyl phosphorescent iridium complex as well as preparation method and application thereof
  • Thienyl phosphorescent iridium complex as well as preparation method and application thereof
  • Thienyl phosphorescent iridium complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of iridium complex 3,8-(2-thiophene)-phenanthroline iridium-2-phenylpyridine complex: Weigh 1 mmol of 3,8-dibromophenanthroline iridium-2-phenylpyridine complex And 2.4mmol of 2-thiophene pinacol borate; Add the tetrakis (triphenylphosphine) palladium that molar number is 5%; Add the sodium carbonate aqueous solution 20mL that concentration is 2M wherein; Add the DMF of 40mL, temperature 70 ℃, Stir for 36 hours; after the reaction, cool the reaction solution to room temperature, pour it into water, and stir for 30 minutes; use dichloromethane to extract the water phase several times, combine the organic phase, and dry the organic phase with anhydrous magnesium sulfate; filter the above solution , the filtrate was removed, and the solvent was removed in vacuo. The crude product was obtained, and the pure product was obtained by thin-layer column chromatography.

[0028] The H NMR spectrum of the complex is characterized by figure 1 shown.

[0029] Its abso...

Embodiment 2

[0031] Preparation of iridium complex 3,8-(2-thiophene)-o-phenanthroline iridium-2-phenylquinoline complex: Weigh 3,8-dibromophenanthroline iridium-2-phenylpyridine complex 1mmol and 2.4mmol of 2-thiophene pinacol borate; add tetrakis(triphenylphosphine) palladium with 5% molarity; add 20mL of aqueous sodium carbonate solution with a concentration of 2M; add 40mL of DMF at a temperature of 70°C , stirred for 36 hours; after the reaction, the reaction solution was cooled to room temperature, poured into water, and stirred for 30 min; with dichloromethane, extracted the water phase several times, combined the organic phase, and dried the organic phase with anhydrous magnesium sulfate; filtered the above solution, the filtrate was removed, and the solvent was removed in vacuo. The crude product was obtained, and the pure product was obtained by thin-layer column chromatography.

[0032] The H NMR spectrum of the complex is characterized by figure 2 shown.

[0033] Its absorpt...

Embodiment 3

[0034] Example 3: Singlet oxygen generation experiment

[0035] The singlet oxygen generation experiment was carried out in a mixed solution of ethanol: water = 4:1 volume ratio, and the singlet oxygen produced by the complex under near-infrared light and 1,3-diphenylisobenzofuran (DPBF) were investigated. Reaction, the production of singlet oxygen is indicated by consumption of 1,3-diphenylisobenzofuran, and the change of ultraviolet absorption at 410nm indicates the ability of singlet oxygen generation. The results are as follows Figure 7 and Figure 8 shown.

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Abstract

The invention discloses a thienyl phosphorescent iridium complex. A preparation method for the thienyl phosphorescent iridium complex comprises the following steps: weighing 3,8-dibromoiridium phenanthroline-2-phenylpyridine complex (or 3,8-dibromoiridium phenanthroline-2-phenylquinoline complex) and 2-thiophene pinacol borate at a molar ratio of 1:(0.1-12), and adding tetra(triphenyl phosphine) palladium with the molar percentage of 1-20%; adding sodium carbonate aqueous solution with a proper concentration of 2 M, adding an appropriate amount of DMF (dimethyl formamide), and stirring at a temperature of 25-75 DEG C for 1-75 hours; after the reaction is finished, cooling the reaction solution to a room temperature, pouring the reaction solution in water, and stirring for 1-30 minutes; extracting a water phase by use of dichloromethane, combining an organic phase, and drying the organic phase by use of anhydrous magnesium sulphate; filtering the solution, removing the filtrate, and removing a solvent in vacuum to obtain a crude product. The iridium complex obtained by the preparation method disclosed by the invention is used for generating singlet oxygen from a steady-state near-infrared light, good in stability, and expected to be applied in the aspect of near-infrared photodynamic therapy.

Description

technical field [0001] The invention belongs to the field of material science, in particular to a class of thienyl phosphorescent iridium complexes 3,8-(2-thiophene)-o-phenanthroline iridium-2-phenylpyridine and 3,8-(2-thiophene)-o- Phenanthroline iridium-2-phenylquinoline and its preparation method and application. Background technique [0002] The photosensitizer absorbed by the tissue is excited by the laser irradiation of a specific wavelength, and the photosensitizer in the excited state transfers energy to the surrounding oxygen to generate highly active singlet oxygen, which oxidizes the adjacent biomacromolecules Reaction, produce cytotoxicity and cause cell damage and even death, so as to achieve the effect of photodynamic therapy. Therefore, the generation of singlet oxygen is the basis of the treatment of photodynamic therapy. [0003] Photodynamic therapy, as a therapy with a solid scientific basis, is as effective as surgery, chemotherapy or radiotherapy for s...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F15/00A61K41/00A61P35/00
Inventor 周治国薛峰峰石敏卢阳杨红杨仕平
Owner SHANGHAI NORMAL UNIVERSITY
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