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A kind of water-soluble porphyrin conjugated polymer and its preparation method and application

A conjugated polymer, water-soluble technology, applied in the field of water-soluble porphyrin-conjugated polymers and its preparation, luminescent biosensors, can solve the problem of scarcity of water-soluble porphyrin-conjugated polymers

Inactive Publication Date: 2016-03-09
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of the soluble porphyrin conjugated polymers are only soluble in organic solvents, and the types of water-soluble porphyrin conjugated polymers are rare, and there is no literature or patent report on the water-soluble porphyrin conjugated polymers of this patent and its preparation method

Method used

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  • A kind of water-soluble porphyrin conjugated polymer and its preparation method and application
  • A kind of water-soluble porphyrin conjugated polymer and its preparation method and application
  • A kind of water-soluble porphyrin conjugated polymer and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Preparation of 5,15-di-p-bromophenyl-10,20-di-p-n-hexylphenyl zinc porphyrin monomer (Porphyrinmonomer)

[0035] (1) Preparation of p-bromophenyl dipyrromethane was prepared according to the method disclosed in literature DengLJ, GuZJ, CaoZC, ShenP, LiXL, ZhangLJ, TanST.Mater.Sci.Eng.B2012,177:1641-1648.

[0036] Dissolve 10mmol of p-n-hexylbenzaldehyde and 10mmol of p-bromophenyldipyrromethane in 500mL of dichloromethane, flow argon for 10 minutes, add 10mmol of trifluoroacetic acid, stir at room temperature for 30 minutes, and then add 0.1mmol of p-tetrachlorobenzene quinone, stirred at room temperature for 1 hour, then neutralized by adding 20 mmol triethylamine, removed the solvent by rotary evaporation, then added 60 mL of methanol solution containing 12 mmol zinc acetate, heated to reflux, reacted for 2 hours, and obtained 5,15-di-p-bromo Phenyl-10,20-di-p-n-hexylphenyl zinc porphyrin monomer (23%).

[0037] Such as figure 1 As shown, in DMF solution,...

Embodiment 2

[0038] Embodiment 2: Preparation of water-soluble porphyrin conjugated polymer P1

[0039] (1) Dissolve 0.1mmol 5,15-di-p-bromophenyl-10,20-di-p-n-hexylphenyl zinc porphyrin in 20mL tetrahydrofuran, add 10.0mmol 9,9'-di-n-hexyl-2,7-diboron Acetate fluorene and 9.9mmol 1,4-dibromo-2,5-bis(N,N-diethylamino)alkoxybenzene, argon for 15 minutes, add 0.8mmol tetrakistriphenylphosphorous palladium catalyst and 5mL of 0.1mol / L potassium carbonate aqueous solution, continued to flow argon for 20 minutes, heated and refluxed for 24 hours under the protection of argon, added methanol for precipitation, filtered to obtain the precipitate, and used methanol, n-hexane, and The precipitate was washed with chloroform, the chloroform phase was collected, precipitated with methanol, filtered with suction, and dried to obtain neutral polymer N1 (56%).

[0040] (2) Dissolve 100 mg of N1 in 20 mL of THF, add 0.5 mL of iodomethane, stir at room temperature for 24 hours, filter the precipitate, was...

Embodiment 3

[0042] Embodiment 3: Preparation of water-soluble porphyrin conjugated polymer P2

[0043] (1) Dissolve 0.5mmol 5,15-di-p-bromophenyl-10,20-di-p-hexylphenyl zinc porphyrin in 20mL tetrahydrofuran, add 10.0mmol 9,9'-di-n-hexyl-2,7-diboron Acetate fluorene and 9.5mmol 1,4-dibromo-2,5-bis(N,N-diethylamino)alkoxybenzene, argon flowed for 15 minutes, and 0.8mmol tetrakistriphenylphosphorous palladium catalyst and 5mL of 0.1mol / L potassium carbonate aqueous solution, continued to flow argon for 20 minutes, heated to reflux under the protection of argon for 28 hours, added methanol for precipitation, filtered to obtain the precipitate, and used methanol, n-hexane, and The precipitate was washed with chloroform, the chloroform phase was collected, precipitated with methanol, filtered with suction, and dried to obtain neutral polymer N2 (51%).

[0044] (2) Dissolve 100 mg of N2 in 20 mL of THF, add 0.5 mL of iodomethane, stir at room temperature for 24 hours, filter the precipitate, w...

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Abstract

The invention discloses a water-soluble porphyrin conjugated polymer and a preparation method thereof. The preparation method comprises the following steps: carrying out reaction on p-bromobenzaldehyde and pyrrole to obtain p-bromophenyl dipyrrylmethanes, further carrying out reaction on the p-bromophenyl dipyrrylmethanes and benzaldehyde or a derivative thereof and metal coordination to obtain 5,15-bi-p-bromophenyl-10,20-diaryl metalloporphyrin, carrying out reaction on the metalloporphyrin compound, 1,4-dibromo-2,5-bi(N, N-diethyl amido) alkoxyl benzene and aromatic diborate ester with the catalysis of a palladium catalyst by virtue of Suzuki to obtain a neutral porphyrin conjugated polymer, and ionizing a side chain of the neutral porphyrin conjugated polymer by virtue of methyl iodide to obtain the water-soluble porphyrin conjugated polymer. The water-soluble porphyrin conjugated polymer prepared by the invention can be dissolved in a mixed solvent of a water / organic solvent with the water volume percentage of 98-70, has excellent luminescence property and water solubility and can be used as an organic luminous organism sensor.

Description

technical field [0001] The invention belongs to the field of polymer material synthesis, and relates to a water-soluble porphyrin conjugated polymer and a preparation method thereof. The product is mainly used for a luminescent biosensor. Background technique [0002] Conjugated polymers have a strong light-harvesting ability and can be used to amplify fluorescent sensing signals. They have a wide range of applications in medical diagnosis, gene detection, and environmental monitoring, providing a new sensing mode for the development of biosensors. Among them, water-soluble conjugated polymers combine the photoelectric properties of traditional conjugated polymers with the water-solubility characteristics of polyelectrolytes, showing some unique properties, and have attracted much attention in recent years. [(1)ZhuCL,LiuLB,YangQ,LvFT,WangS.Chem.Rev.2012,112,4687.(2)HoHA,NajariA,LeclercM.Acc.Chem.Res.2008,41,168.[3]AhnDJ,KimJM. Acc.Chem.Res.2008,41,805.[4]FengXL,LiuLB,WangS,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C09K11/06
Inventor 汪凌云李会会曹德榕
Owner SOUTH CHINA UNIV OF TECH