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Stereoselective gridization and polygridization with centrosymmetric molecular packing

Author

Listed:
  • Dongqing Lin

    (Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications)

  • Ying Wei

    (Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications)

  • Aizhong Peng

    (Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications)

  • He Zhang

    (Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications)

  • Chunxiao Zhong

    (Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications)

  • Dan Lu

    (Jilin University)

  • Hao Zhang

    (Jilin University)

  • Xiangping Zheng

    (Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications)

  • Lei Yang

    (Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications)

  • Quanyou Feng

    (Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications)

  • Linghai Xie

    (Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications
    Northwestern Polytechnical University (NPU))

  • Wei Huang

    (Institute of Advanced Materials (IAM), Nanjing University of Posts and Telecommunications
    Northwestern Polytechnical University (NPU))

Abstract

The gridarenes, with well-defined edges and vertices, represent versatile nanoscale building blocks for the installation of frameworks and architectures but suffer from difficulty in stereoselective control during their synthesis. Here we report a diastereoselective gridization of superelectrophilic diazafluorene-containing substrates (AmBn) with crescent shapes into Drawing Hands grids (DHGs). The meso-selectivity reaches 75.6% diastereomeric excess (de) during the gridization of A1B1-type substrates and maintains ~80% de during the polygridization of A2B2-type monomers. Such stereocontrol originates from the centrosymmetric molecular packing of two charge-delocalized superelectrophiles with synergistically π–π stacking attractions and coulombic repulsions. As meso-stereoregular structures show 20∼30 nm in length, the rigid ring/chain-alternating polygrids have a Mark–Houwink exponent of 1.651 and a molecular weight (M) dependence of the hydrodynamic radius Rh ∼ M1.13. Via the simulation of chain collapse, meso-configured polygridarenes still adopt rod-like conformations that facilitate the high rigidity of organic nanopolymers, distinguished from toroid backbones of rac-type polygrids.

Suggested Citation

  • Dongqing Lin & Ying Wei & Aizhong Peng & He Zhang & Chunxiao Zhong & Dan Lu & Hao Zhang & Xiangping Zheng & Lei Yang & Quanyou Feng & Linghai Xie & Wei Huang, 2020. "Stereoselective gridization and polygridization with centrosymmetric molecular packing," Nature Communications, Nature, vol. 11(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-15401-x
    DOI: 10.1038/s41467-020-15401-x
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    Cited by:

    1. Ying Wei & Chunxiao Zhong & Yue Sun & Shuwei Ma & Mingjian Ni & Xiangping Wu & Yongxia Yan & Lei Yang & Ilya A. Khodov & Jiaoyang Ge & Yang Li & Dongqing Lin & Yongxia Wang & Qiujing Bao & He Zhang & , 2024. "C-H-activated Csp2-Csp3 diastereoselective gridization enables ultraviolet-emitting stereo-molecular nanohydrocarbons with mulitple H···H interactions," Nature Communications, Nature, vol. 15(1), pages 1-11, December.

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