Enantioselective assembly of multi-layer 3D chirality

Guanzhao Wu; Yangxue Liu; Zhen Yang; Tao Jiang; Nandakumar Katakam; Hossein Rouh; Liulei Ma; Yao Tang; Sultan Ahmed; Anis U Rahman; Hongen Huang; Daniel Unruh; Guigen Li

doi:10.1093/nsr/nwz203

Enantioselective assembly of multi-layer 3D chirality

Natl Sci Rev. 2020 Mar;7(3):588-599. doi: 10.1093/nsr/nwz203. Epub 2019 Dec 16.

Authors

Guanzhao Wu^{1

2}, Yangxue Liu², Zhen Yang¹, Tao Jiang³, Nandakumar Katakam², Hossein Rouh², Liulei Ma², Yao Tang², Sultan Ahmed², Anis U Rahman¹, Hongen Huang¹, Daniel Unruh², Guigen Li^{1

2}

Affiliations

¹ Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.
² Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.
³ School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China.

Abstract

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 3D chirality with optically pure enantiomers. As confirmed by X-ray diffraction analysis that this chiral framework is featured by a unique C₂ -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 3D 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.

Keywords: C2-symmetry; aggregation-induced emission (AIE); architecture chirality; multi-layer 3D chirality; multi-layered organic framework (M-LOF); organo sandwich chirality.