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Facile strategy for obtaining luminescent polymorphs based on the chirality of a boron-fused azomethine complex
Chemical Communications ( IF 4.9 ) Pub Date : 2020-11-20 , DOI: 10.1039/d0cc06383e
Shunsuke Ohtani 1, 2, 3 , Yusuke Takeda 1, 2, 3 , Masayuki Gon 1, 2, 3 , Kazuo Tanaka 1, 2, 3 , Yoshiki Chujo 1, 2, 3
Affiliation  

A chloro-substituted boron-fused azomethine complex (BAmCl) having a stereogenic boron center was synthesized for obtaining a luminescent chiral crystal. We succeeded in isolating the (R)- and (S)-enantiomers of BAmCl and preparing the homochiral polymorphic crystal, while we obtained the racemic crystal with rac-BAmCl. Single crystal X-ray diffraction analyses suggest that a variety of intermolecular interaction patterns and intrinsic flexibility of the molecular framework should play a significant role in stabilizing the homochiral crystal. We found the difference in molecular arrangements between the racemic and the homochiral crystals, and we observed distinctly different emission colors. In particular, we observed heat-initiated homogeneous racemization without the need for a solvent or catalyst in the molten state of the homochiral crystal (R)-BAmCl. Our results mean that chiral resolution of a flexible fused-skeleton having a stereogenic boron center can be a platform for creating luminescent polymorphic materials.

中文翻译:

基于硼稠合的偶氮甲碱络合物的手性获得发光多晶型物的简便策略

合成具有立体生成的硼中心的氯取代的硼稠合的偶氮甲碱络合物(BAmCl),以获得发光手性晶体。我们成功分离了BAmCl的(R)和(S)对映异构体并制备了同手性多晶型晶体,同时获得了具有外消旋-BAmCl。单晶X射线衍射分析表明,各种分子间相互作用模式和分子框架的固有柔性在稳定同手性晶体中应发挥重要作用。我们发现外消旋和同手性晶体之间的分子排列存在差异,并且观察到明显不同的发光颜色。尤其是,我们观察到热引发的均相消旋作用,而无需在均手性晶体(R)-BAmCl的熔融状态下使用溶剂或催化剂。我们的结果意味着具有立体生成的硼中心的柔性熔融骨架的手性拆分可以成为产生发光多晶型材料的平台。
更新日期:2020-11-21
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