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A facile design of azaanthracene derivatives: ACQ–AIE conversion and blue-shifted mechanofluorochromic emission
Dyes and Pigments ( IF 4.1 ) Pub Date : 2020-11-23 , DOI: 10.1016/j.dyepig.2020.108992
Mingming Huang , Hao Lu , Kun Wang , Beibei Liu , Meng Wang , Xiaoyao Qiao , Jiping Yang

Azaanthracene derivatives, e.g. phenoxazine and phenothiazine, have attracted considerable interest not only in chemistry but also in materials science for the unique electron structures and photophysical properties. However, like most organic luminogens, phenoxazine and phenothiazine both suffer from the annoying aggregation-caused quenching (ACQ) effect, which greatly limits their further application in solid state conditions. Fortunately, the discovery of aggregation-induced emission (AIE) phenomenon provides an elegant platform to solve the stubborn ACQ effect. But most of the existing AIEgens have been prepared through some complicated synthesis processes, which are commonly unpopular with environmental unfriendly, high cost, and low solubility. Therefore, it deserves great attention to explore a simple and cost effective approach to achieve the AIE modification of phenoxazine and phenothiazine. In this work, two diphenylethylene substituted azaanthracene derivatives DPE-POZ and DPE-PTZ were masterly designed and synthesized through a fairly simple one-step reaction. The introduction of multi-rotor group diphenylethylene endows the products with twisted molecular conformations, which successfully promotes the photophysical behavior conversion of ACQ-AIE. The αAIE (the ratio of PL intensity in a mixed solvent with 90 vol% fraction of water to 0 vol%)of DPE-POZ and DPE-PTZ reached 8 and 23, respectively. In addition, DPE-POZ exhibited an uncommon blue-shifted mechanofluorochromic phenomenon. The powder X-ray diffraction and single crystal X-ray diffraction characterizations revealed that the MFC properties could be attributed to the phase transition between the crystalline and amorphous states which was promoted by the loose solid molecular arrangement.



中文翻译:

氮杂蒽衍生物的简便设计:ACQ-AIE转化和蓝移的机械荧光色发射

氮杂蒽衍生物,例如吩恶嗪和吩噻嗪,不仅在化学领域而且在材料科学领域也吸引了相当大的兴趣,因为它们具有独特的电子结构和光物理性质。但是,像大多数有机发光剂一样,吩恶嗪和吩噻嗪都遭受恼人的聚集引起的猝灭(ACQ)效应,这极大地限制了它们在固态条件下的进一步应用。幸运的是,聚集诱发发射(AIE)现象的发现为解决顽固的ACQ效应提供了一个优雅的平台。但是,大多数现有的AIEgens是通过一些复杂的合成方法制备的,这些方法通常不受欢迎,而且对环境不利,成本高且溶解度低。因此,因此,探索一种简单且具有成本效益的方法来实现吩恶嗪和吩噻嗪的AIE改性非常值得关注。在这项工作中,两个二苯乙烯取代的氮杂蒽衍生物DPE-POZDPE-PTZ是通过相当简单的一步反应精心设计和合成的。多转子基团二苯乙烯的引入使产物具有扭曲的分子构象,从而成功地促进了ACQ-AIE的光物理行为转化。所述α AIE的(PL强度与水90%(体积)分数为0%(体积)的混合溶剂的比率)DPE-POZDPE-PTZ分别达到8和23。此外,DPE-POZ表现出罕见的蓝移机械荧光色现象。粉末X射线衍射和单晶X射线衍射表征表明,MFC性质可归因于松散的固体分子排列促进的结晶态和非晶态之间的相变。

更新日期:2020-11-23
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