Wu Guanzhao, Liu Yangxue, Yang Zhen, Jiang Tao, Katakam Nandakumar, Rouh Hossein, Ma Liulei, Tang Yao, Ahmed Sultan, Rahman Anis U, Huang Hongen, Unruh Daniel, Li Guigen
Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.
Natl Sci Rev. 2020 Mar;7(3):588-599. doi: 10.1093/nsr/nwz203. Epub 2019 Dec 16.
The first enantioselective assembly of sandwich-shaped organo molecules has been achieved by conducting dual asymmetric Suzuki-Miyaura couplings and nine other reactions. This work also presents the first fully C-C anchored multi-layer chirality with optically pure enantiomers. As confirmed by X-ray diffraction analysis that this chiral framework is featured by a unique -symmetry in which a nearly parallel fashion consisting of three layers: top, middle and bottom aromatic rings. Unlike the documented planar or axial chirality, the present chirality shows its top and bottom layers restrict each other from free rotation, i.e., this multi-layer chirality would not exist if either top or bottom layer is removed. Nearly all multi-layered compounds showed strong luminescence of different colors under UV irradiation, and several randomly selected samples displayed aggregation-induced emission (AIE) properties. This work is believed to have broad impacts on chemical, medicinal and material sciences including optoelectronic materials in future.
通过进行双不对称铃木-宫浦偶联反应和其他九种反应,首次实现了夹心型有机分子的对映选择性组装。这项工作还展示了首个具有光学纯对映体的完全由碳-碳键连接的多层手性结构。X射线衍射分析证实,这种手性框架具有独特的对称结构,由顶层、中层和底层芳香环以近乎平行的方式组成三层结构。与已报道的平面或轴手性不同,目前的手性结构显示其顶层和底层相互限制自由旋转,即如果去除顶层或底层,这种多层手性结构将不存在。几乎所有的多层化合物在紫外光照射下都表现出不同颜色的强烈发光,并且随机选择的几个样品显示出聚集诱导发光(AIE)特性。这项工作有望在未来对化学、医学和材料科学(包括光电子材料)产生广泛影响。