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Formation of Nitrogen-Doped Positively Curved Molecules by π-Extension

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2024, 26, 18, 3901-3905
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    Formation of Nitrogen-Doped Positively Curved Molecules by π-Extension
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    • Zhen Xia
      Zhen Xia
      Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, P. R. China
      More by Zhen Xia
    • Weifan Wang
      Weifan Wang
      Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, P. R. China
      More by Weifan Wang
    • Gang Zhang*
      Gang Zhang
      Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, P. R. China
      *E-mail: [email protected]
      More by Gang Zhang
      Orcidhttps://orcid.org/0000-0002-4674-7252
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    Organic Letters

    Cite this: Org. Lett. 2024, 26, 18, 3901–3905
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    https://doi.org/10.1021/acs.orglett.4c01087
    Published April 26, 2024
    Copyright © 2024 American Chemical Society
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    Abstract

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    Two nitrogen-doped positively curved aromatic molecules bearing doubly fused pentagonal rings were synthesized and characterized. Crystallographic analysis confirms the formation of a bowl-shaped structure, which is induced by the fusion of adjacent pentagons to the rigid aromatic planes. Both compounds demonstrate good photoluminescence. These electron-rich bowl-shaped molecules can associate with C60 to form complexes in 2:1 ratio in toluene with different association constants depending on the molecular dimension of the hosts.

    Copyright © 2024 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.4c01087.

    • Experimental details, NMR spectra, X-ray crystal data of compounds 4 and 5, photophysical and electrochemical measurements, 1H NMR titration, and DFT calculations (PDF)

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    CCDC 2340039–2340040 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Cited By

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    This article is cited by 4 publications.

    1. Xu-Lang Chen, Si-Qian Yu, Zi-You Zheng, Zhao-Yi Cheng, An-Na Chen, Jia-Qi Liang, Xin Sun, Chunyang Zheng, Xiaohuan Huang, Han-Yuan Gong. Adaptive nitrogen-containing buckybowl: a versatile receptor for curved and planar aromatic molecules. Chemical Science 2025, 16 (17) , 7537-7543. https://doi.org/10.1039/D5SC00988J
    2. Zikang Ma, Lin Wan, Yude Ji, Weifan Wang, Gang Zhang. π‐Extended Nitrogen‐Doped Molecular Bowls Comprising Adjacent Pentagons. Chemistry – A European Journal 2025, 2 https://doi.org/10.1002/chem.202500924
    3. Xu-Lang Chen, Si-Qian Yu, Jia-Qi Liang, Xiaohuan Huang, Han-Yuan Gong. Nitrogen-containing polycyclic aromatic hydrocarbons (PAHs) with bowl-shaped structures: synthesis, architecture, and applications. Organic Chemistry Frontiers 2025, 12 (4) , 1340-1354. https://doi.org/10.1039/D4QO01934B
    4. Tian Liu, Weifan Wang, Gang Zhang. A nitrogen-doped bowl-shaped molecule containing a central heptagonal ring. Organic Chemistry Frontiers 2024, 11 (19) , 5408-5414. https://doi.org/10.1039/D4QO01278J
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    Organic Letters

    Cite this: Org. Lett. 2024, 26, 18, 3901–3905
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.4c01087
    Published April 26, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

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