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Fluorene based water soluble conjugated polymer and process for preparing same

A compound and group technology, applied in biological testing, material testing products, organic chemistry, etc., can solve the problems of poor polymer stability, low detection sensitivity, weak luminescence intensity, etc., and achieve excellent luminescence performance, thermal stability, etc. The effect of good performance and excellent luminous properties

Inactive Publication Date: 2005-03-16
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the research, there are many problems to be solved urgently, such as poor stability of polymers, weak luminescence intensity, low detection sensitivity, poor detection selectivity, and the development of more detection systems, etc.

Method used

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  • Fluorene based water soluble conjugated polymer and process for preparing same
  • Fluorene based water soluble conjugated polymer and process for preparing same
  • Fluorene based water soluble conjugated polymer and process for preparing same

Examples

Experimental program
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Effect test

Embodiment 1

[0056] Embodiment 1, the synthesis of Poly[9,9-di(3-sulfonatopropyl)fluorene-2,7-yleneethylene-co-alt-5,5'-(2,2'-bipyridylene)]

[0057] 2, 7-dibromofluorene and 3-bromopropanol, 50% NaOH and the catalyst were refluxed in DMSO for 12 hours, and CH 2 Cl 2 Extract and spin dry the solvent to obtain crude product. The crude product was separated by column chromatography to obtain 2,7-dibromo-9,9-di(3-hydroxyl-propyl)-fluorene (1) as a yellow powder solid. The intermediate (1) was reacted with MsCl in a mixed solution of THF and triethylamine for 3 hours and filtered, and the filtrate was spin-dried to obtain a yellow solid crude product. The crude product was separated by column chromatography to obtain 2,7-dibromo-9,9-di(3-methane-sulfonatopropyl)-fluorene (2) as a yellow powdery solid. Intermediate (2) was reacted with NaI in acetone solution for 24 hours and filtered, and the crude product was separated by column chromatography to obtain light yellow crystal 2,7-dibromo-9,9...

Embodiment 2

[0062] Embodiment 2, the synthesis of Poly[(9,9-di(3-sulfonatopropylfluorene-col-alt-(1,4-benzo-18-crown-6)]

[0063] Add compound 4, 1, 4-bromo-benzo-18-crown-6 and catalyst [Pd(PPh 3 ) 4 ], CuI. The reaction system was heated to 70°C and maintained for 24 hours. After the reaction was completed, it was cooled to room temperature, the reaction solution was dropped into methanol, and the resulting precipitate was collected. After the precipitate was washed with methanol, the reaction was washed with acetone in a Soxhlet extractor for 24 hours to remove oligomers and excess catalyst, and after vacuum drying, a bright yellow solid was obtained

[0064] Poly[(9,9-di(3-sulfonatopropylfluorene-col-alt-(1,4-benzo-18-crown-6))].

[0065] 2. Cationic water-soluble polymer:

Embodiment 3

[0066] Example 3, Poly[(9,9-bis(3'-((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene)-co-alt-5,5'-( Synthesis of 2,2'-bipyridylethylene)]Dibromide

[0067] 2,7-dibromofluorene and 3-dimethylaminopropylchloride hydrochloride, 50% NaOH and the catalyst were refluxed in DMSO for 12 hours, and then the 2 Cl 2 Extract and spin dry the solvent to obtain crude product. The crude product was recrystallized to obtain white crystals of 2,7-dibromo-9,9-bis(3'-(N,N-dimethylamino)propyl)-fluorene(1')

[0068] With intermediate (1 '), compound 7 in embodiment 1, catalyst [Pd(PPh 3 ) 4 ], CuI mixed and dissolved in toluene. Under the protection of inert gas, the reaction system was heated to 70° C., and the reaction was maintained for 72 hours. After the reaction was completed, it was cooled to room temperature, the reaction solution was dropped into methanol, and the resulting precipitate was collected. After the precipitate was washed with methanol, the reaction was washed with ...

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Abstract

The invention relates to a fluorene based water soluble conjugated polymer, process for preparing same and use in chemical / biological detection, wherein fluorenes compounds containing substituent groups are used as raw material for synthesizing water-soluble conjugated polymer with fluorenes as the conjugated chain primary structure through a series of organic reactions including metallic catalyse, the synthesized polymeric compound has fine light-emitting performance, and has good fluorescent quenching effect to certain specific groups or compounds.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, and in particular relates to a fluorene-based ionic water-soluble conjugated polymer, a preparation method thereof, and an application in chemical / biological detection. technical background [0002] As an excellent electroluminescent material, organic conjugated polymers have been widely used in flexible flat panel displays, polymer batteries, light-emitting batteries, and light-emitting diodes. In recent years, scientists have discovered that the existence of certain trace substances can greatly change the photoelectric properties of conjugated polymers. This change in photoelectric properties makes conjugated polymers a good prospect as a high-sensitivity sensor material. [0003] Conjugated polymers were initially used in chemical / biological detection, mainly by introducing cyclodextrin or cyclic crown ethers into the side chains of conjugated polymers to detect metal ions. S...

Claims

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Application Information

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IPC IPC(8): C07C43/235C07D323/00C07D401/04G01N33/48
Inventor 黄维范曲立陈轶黄艳琴
Owner FUDAN UNIV
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