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Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

机译:氟化苯并噻二唑与四苯基乙烯键合的合成,表征,聚集诱导的发射,溶剂变色和机械变色

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Compounds consisting of unsubstituted, monofluoro and difluoro substituted benzothiadiazole bonded to two tetraphenylethenes were successfully prepared by palladium catalyzed Suzuki–Miyaura cross-coupling reaction of their corresponding co-monomers. All compounds exhibited aggregation-induced emission characteristics when the water fraction was higher than 60% in the THF/water mixtures. The emission maximum for the three compounds was blue-shifted when the water content reached 90% compared to that in THF solution. The intensity of emission maximum of difluorinated benzothiadiazole linked with two tetraphenylethenes was 2.5 times higher in 90% water compared to those in THF solution. Surprisingly, two liquid crystal phases with two distinct emission colors were observed only for the compound containing difluorinated benzothiadiazole bonded to two tetraphenylethene. All compounds showed remarkable solvatochromic properties in selected solvents with different polarities. The powder XRD results and mechanochromism of the compounds suggested that the solid state structures can change from one form to another by grinding, fuming or annealing processes.
机译:通过钯催化相应的共聚单体的Suzuki-Miyaura交叉偶联反应,成功制备了由未取代的,单氟和二氟取代的苯并噻二唑键合到两个四苯基乙烯上的化合物。当四氢呋喃/水混合物中的水含量高于60%时,所有化合物均表现出聚集诱导的排放特性。当水含量与THF溶液相比达到90%时,这三种化合物的最大发射量发生蓝移。在90%的水中,与两个四苯基乙烯连接的二氟苯并噻二唑的最大发射强度是THF溶液中发射强度的2.5倍。令人惊讶地,仅对于包含结合到两个四苯基乙烯上的二氟化苯并噻二唑的化合物,观察到具有两种不同发射颜色的两个液晶相。所有化合物在具有不同极性的选定溶剂中均显示出显着的溶剂变色性质。粉末XRD结果和化合物的机械变色现象表明,固态结构可以通过研磨,发烟或退火过程从一种形式改变为另一种形式。

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