Bipyridine triphenylamine aldehyde fluorescent material with aggregation-induced emission effect as well as preparation method and application of bipyridine triphenylamine aldehyde fluorescent material
A dipyridine triphenylamine aldehyde, aggregation-induced luminescence technology, applied in luminescent materials, material analysis by optical means, analysis of materials, etc., can solve the problems of fluorescence quenching, reducing the application value of fluorescent probes and biological imaging, etc. Improved imaging resolution, good aggregate-state luminescence performance, and simple synthesis
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Embodiment 1
[0036] Embodiment 1: the synthesis of intermediate TPA1
[0037]
[0038] Add phosphorus oxychloride (3.6ml) dropwise to N,N-dimethylformamide (30ml) under ice-bath conditions, stir for 15 minutes and move to room temperature to continue stirring for 1 hour to obtain a reddish-brown solution; Triphenylamine (24.5 mmol, 6 g) was added to the solution, heated to 80° C. under nitrogen protection, and the reaction was continued for 6 hours. After completion of the reaction, cool to room temperature, use 1mol / L sodium hydroxide solution to adjust the pH of the reaction solution to between 7-8, obtain a large amount of precipitate, obtain light green solid TPA1 (22.9mmol, 6.25g) by suction filtration, use 62.5ml ethanol The crude product was recrystallized to obtain relatively pure white crystal TPA1.
[0039] The H NMR spectrum of triphenylamine monoaldehyde TPA1 is as follows: figure 1 Shown: 1H NMR (400MHz, DMSO-d6) ppm 6.89 (d, J = 8.53Hz, 2H) 7.17-7.28 (m, 6H) 7.43 (t, J =...
Embodiment 2
[0040] Embodiment 2: the synthesis of intermediate DITPA
[0041]
[0042] Triphenylamine monoaldehyde (11.0mmol, 3g) was mixed with potassium iodide (11mmol, 1.8g) and 36% acetic acid (45ml), stirred at 80°C for 1 hour, then potassium iodate (14.9mmol, 3.18g) was added, and the solution It immediately turned purple, continued heating and stirring for 4 hours, cooled to room temperature and filtered with suction to obtain green solid DITPA (8.1 mmol, 4.25 g), yield: 73.6%.
[0043] The H NMR spectrum of diiodotriphenylamine monoaldehyde DITPA is as follows: figure 2 Shown: 1H NMR (400MHz, DMSO-d6) ppm6.96 (d, J = 8.53Hz, 4H) 7.01 (d, J = 8.53Hz, 2H) 7.73 (d, J = 8.28Hz, 4H) 7.77 (d , J=8.53Hz, 2H) 9.82(s, 1H).
Embodiment 3
[0044] Embodiment 3: the synthesis of compound DPTPA
[0045]
[0046] Dissolve diiodotriphenylamine aldehyde (525mg, 1.0mmol) and pyridine-4-boronic acid (247mg, 2.0mmol) in 8ml of freshly distilled tetrahydrofuran, then weigh the catalyst tetrakistriphenylphosphine palladium (0.01mmol, 11.5mg) and add In the reaction tube, under the protection of nitrogen, inject 0.8ml potassium carbonate aqueous solution (1.5mol / L), heat to 66°C under magnetic stirring, keep the reaction system in a slightly boiling state, react for 6 hours, the solution changes from yellow to reddish brown, cool After reaching room temperature, spin dry THF, add water to dissolve the precipitated salt, and filter with suction. The resulting filter cake is recrystallized with 20ml of ethanol to obtain DPTPA (0.85mmol, 365 mg) as orange-yellow crystals, yield: 85%.
[0047] The H NMR spectrum of dipyridine triphenylamine aldehyde DPTPA is as follows: image 3 Shown: 1H NMR (400MHz, DMSO-d6) ppm 7.14 (d, ...
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