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C-H-activated Csp2-Csp3 diastereoselective gridization enables ultraviolet-emitting stereo-molecular nanohydrocarbons with mulitple H···H interactions

Author

Listed:
  • Ying Wei

    (Nanjing University of Posts & Telecommunications)

  • Chunxiao Zhong

    (Nanjing University of Posts & Telecommunications)

  • Yue Sun

    (Nanjing University of Posts & Telecommunications)

  • Shuwei Ma

    (Nanjing University of Posts & Telecommunications)

  • Mingjian Ni

    (Nanjing Tech University (NanjingTech))

  • Xiangping Wu

    (Nanjing University of Posts & Telecommunications)

  • Yongxia Yan

    (Nanjing University of Posts & Telecommunications)

  • Lei Yang

    (Nanjing University of Posts & Telecommunications)

  • Ilya A. Khodov

    (Russian Academy of Sciences)

  • Jiaoyang Ge

    (Nanjing University of Posts & Telecommunications)

  • Yang Li

    (Nanjing University of Posts & Telecommunications)

  • Dongqing Lin

    (Nanjing University of Posts & Telecommunications)

  • Yongxia Wang

    (Nanjing University of Posts & Telecommunications)

  • Qiujing Bao

    (Nanjing University of Posts & Telecommunications)

  • He Zhang

    (Nanjing University of Posts & Telecommunications)

  • Shasha Wang

    (Nanjing University of Posts & Telecommunications)

  • Juan Song

    (Nanjing University of Posts & Telecommunications)

  • Jinyi Lin

    (Nanjing Tech University (NanjingTech))

  • Linghai Xie

    (Nanjing University of Posts & Telecommunications
    Northwestern Polytechnical University
    Henan University)

  • Wei Huang

    (Nanjing University of Posts & Telecommunications
    Northwestern Polytechnical University
    Henan University)

Abstract

Gridization is an emerging molecular integration technology that enables the creation of multifunctional organic semiconductors through precise linkages. While Friedel-Crafts gridization of fluorenols is potent, direct linkage among fluorene molecules poses a challenge. Herein, we report an achiral Pd-PPh3-cataylized diastereoselective (>99:1 d.r.) gridization based on the C-H-activation of fluorene to give dimeric and trimeric windmill-type nanogrids (DWGs and TWGs). These non-conjugated stereo-nanogrids showcase intramolecular multiple H…H interactions with a low field shift to 8.51 ppm and circularly polarized luminescence with high luminescent dissymmetry factors (|gPL | = 0.012). Significantly, the nondoped organic light-emitting diodes (OLEDs) utilizing cis-trans-TWG1 emitter present an ultraviolet electroluminescent peak at ~386 nm (CIE: 0.17, 0.04) with a maximum external quantum efficiency of 4.17%, marking the highest record among nondoped ultraviolet OLEDs based on hydrocarbon compounds and the pioneering ultraviolet OLEDs based on macrocycles. These nanohydrocarbon offer potential nanoscafflolds for ultraviolet light-emitting optoelectronic applications.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-48130-6
    DOI: 10.1038/s41467-024-48130-6
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    References listed on IDEAS

    as
    1. 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.
    2. Chunguang Zhai & Xiu Yin & Shifeng Niu & Mingguang Yao & Shuhe Hu & Jiajun Dong & Yuchen Shang & Zhigang Wang & Quanjun Li & Bertil Sundqvist & Bingbing Liu, 2021. "Molecular insertion regulates the donor-acceptor interactions in cocrystals for the design of piezochromic luminescent materials," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    3. Wenjing Meng & Shun Kondo & Takuji Ito & Kazuki Komatsu & Jenny Pirillo & Yuh Hijikata & Yuichi Ikuhara & Takuzo Aida & Hiroshi Sato, 2021. "An elastic metal–organic crystal with a densely catenated backbone," Nature, Nature, vol. 598(7880), pages 298-303, October.
    4. Wei Yuan & Letian Chen & Chuting Yuan & Zidan Zhang & Xiaokai Chen & Xiaodong Zhang & Jingjing Guo & Cheng Qian & Zujin Zhao & Yanli Zhao, 2023. "Cooperative supramolecular polymerization of styrylpyrenes for color-dependent circularly polarized luminescence and photocycloaddition," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    5. Shuo Li & Kun Liu & Xue-Chen Feng & Zhao-Xian Li & Zhi-Yuan Zhang & Bin Wang & Minjie Li & Yue-Ling Bai & Lei Cui & Chunju Li, 2022. "Synthesis and macrocyclization-induced emission enhancement of benzothiadiazole-based macrocycle," Nature Communications, Nature, vol. 13(1), pages 1-7, December.
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