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

Research output: Contribution to journalArticlepeer-review

57 Scopus citations

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.

Original languageEnglish
Pages (from-to)588-599
Number of pages12
JournalNational Science Review
Volume7
Issue number3
DOIs
StatePublished - Mar 1 2020

Keywords

  • C-symmetry
  • aggregation-induced emission (AIE)
  • architecture chirality
  • multi-layer 3D chirality
  • multi-layered organic framework (M-LOF)
  • organo sandwich chirality

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