Flexible organic tribo-luminescent material based on benzothiophene oxide and preparation and use methods thereof
A benzothiophene and triboluminescence technology, which is applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the difficulty in monitoring the damage of stress sensing materials, and restrict the flexible development and practical application of organic triboluminescence materials. Difficult to prepare film and other problems, to achieve the effect of improving order, easy purification and simple process
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Embodiment 1
[0051] (1) Synthesis of intermediate [3,3'-diiododibenzothiophene sulfone]
[0052]
[0053] Dissolve dibenzothiophene sulfone (5.00g, 23.12mmol) in 50mL acetic acid, add 5mL H 2 O and 5mLH 2 SO 4 , iodine (7.04 g, 27.75 mmol) and periodic acid (6.32 g, 27.75 mmol) were added with stirring. Raise the temperature to solvent reflux, stir and reflux for 16 hours, then cool the reaction solution, pour the reaction solution into water, filter with suction, and evaporate the filtrate to dryness with a rotary evaporator. Purification was carried out by silica gel column chromatography, and the eluent was a mixed solution of dichloromethane and n-hexane with a volume ratio of 1:1. 7.30 g of pure product was obtained with a yield of 67.5%.
[0054] (2) Synthesis of intermediate [3-diphenylamino-3'-iododibenzothiophene sulfone]
[0055]
[0056] Under nitrogen atmosphere, add diphenylamine (0.40g, 2.36mmol) into a 250mL dry three-necked flask, then add 3,3'-diiododibenzothiop...
Embodiment 2
[0061] (1) Synthesis of intermediate [3-carbazolyl-3'-iododibenzothiophene sulfone]
[0062]
[0063] With reference to step (2) in Example 1, carbazole was used instead of diphenylamine to synthesize 3-carbazolyl-3'-iododibenzothiophene sulfone. (yield is 55.2%)
[0064] (2) Synthesis of the target product [3-carbazolyl-3'-diphenylphosphinyl dibenzothiophene sulfone] (M2)
[0065]
[0066] With reference to step (3) in Example 1, use 3-carbazolyl-3'-iododibenzothiophene sulfone to replace 3-diphenylamino-3'-iododibenzothiophene sulfone to synthesize 3-carbazolyl- 3'-Diphenylphosphinyldibenzothiophene sulfone. (The yield is 60.8%)
[0067] To sum up, the material synthesized in the present invention has amorphous triboluminescent properties, is extremely sensitive to external stimulus and cracks of the substrate material, and is accompanied by an easily detectable fluorescent signal. The material synthesis method is simple, the luminescence quantum efficiency is high...
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