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
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[0056] Example 1. Synthesis of Poly[9,9-di(3-sulfonatopropyl)fluorene-2,7-yleneethylene-co-alt-5,5’-(2,2’-bipyridylethylene)]
[0057] 2,7-dibromofluorene and 3-bromopropanol, 50% NaOH and the catalyst are refluxed in DMSO for 12 hours, then CH is used 2 Cl 2 Extract and spin dry the solvent to obtain a 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 crude yellow solid 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 powder. The intermediate (2) reacted with NaI in acetone solution for 24 hours and filtered. After the filtrate was spin-dried, the crude product was separated by column chromatography to obtain pale yellow cr...
Example Embodiment
[0062] Example 2. 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 the reaction was maintained for 24 hours. After the completion of the reaction, it was cooled to room temperature, the reaction solution was dropped into methanol, and the resulting precipitate was collected. After washing the precipitate with methanol, it was washed with acetone in a Soxhlet extractor for 24 hours to remove oligomers and excess catalyst. 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:
Example Embodiment
[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 are refluxed in DMSO for 12 hours, then use CH 2 Cl 2 Extract and spin dry the solvent to obtain a crude product. The crude product is recrystallized to obtain white crystals 2,7-dibromo-9,9-bis(3’-(N,N-dimethylamino)propyl)-fluorene(1’)
[0068] Intermediate (1’), compound 7 in Example 1, catalyst [Pd(PPh 3 ) 4 ], CuI is 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 completion of the reaction, it was cooled to room temperature, the reaction solution was dropped into methanol, and the resulting precipitate was collected. After washing the precipitate with methanol, the reaction was washed with acetone in a Soxhlet...
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