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Defective Nanographenes Containing Seven-Five-Seven (7–5–7)-Membered Rings

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    Defective Nanographenes Containing Seven-Five-Seven (7–5–7)-Membered Rings
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    • Yiyang Fei
      Yiyang Fei
      Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, 999077 Hong Kong, P. R. China
      More by Yiyang Fei
    • Yubin Fu
      Yubin Fu
      Centre for Advancing Electronics Dresden (CFAED), Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
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      Orcidhttp://orcid.org/0000-0002-2613-394X
    • Xueqin Bai
      Xueqin Bai
      Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, 999077 Hong Kong, P. R. China
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    • Lili Du
      Lili Du
      Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, 999077 Hong Kong, P. R. China
      More by Lili Du
    • Zichao Li
      Zichao Li
      Helmholtz-Zentrum Dresden-Rossendorf, Institute of Ion Beam Physics and Materials Research, Bautzner Landstraße 400, 01328 Dresden, Germany
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    • Hartmut Komber
      Hartmut Komber
      Leibniz-Institut für Polymerforschung Dresden e. V., Hohe Straße 6, 01069 Dresden, Germany
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      Orcidhttp://orcid.org/0000-0001-6176-6737
    • Kam-Hung Low
      Kam-Hung Low
      Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, 999077 Hong Kong, P. R. China
      More by Kam-Hung Low
      Orcidhttp://orcid.org/0000-0003-3292-8893
    • Shengqiang Zhou
      Shengqiang Zhou
      Helmholtz-Zentrum Dresden-Rossendorf, Institute of Ion Beam Physics and Materials Research, Bautzner Landstraße 400, 01328 Dresden, Germany
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      Orcidhttp://orcid.org/0000-0002-4885-799X
    • David Lee Phillips
      David Lee Phillips
      Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, 999077 Hong Kong, P. R. China
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    • Xinliang Feng
      Xinliang Feng
      Centre for Advancing Electronics Dresden (CFAED), Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
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      Orcidhttp://orcid.org/0000-0003-3885-2703
    • Junzhi Liu*
      Junzhi Liu
      Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, 999077 Hong Kong, P. R. China
      *Email: [email protected]
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      Orcidhttp://orcid.org/0000-0001-7146-0942
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2021, 143, 5, 2353–2360
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    https://doi.org/10.1021/jacs.0c12116
    Published January 27, 2021
    Copyright © 2021 American Chemical Society
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    Abstract

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    Defects have been observed in graphene and are expected to play a key role in its optical, electronic, and magnetic properties. However, because most of the studies focused on the structural characterization, the implications of topological defects on the physicochemical properties of graphene remain poorly understood. Here, we demonstrate a bottom-up synthesis of three novel nanographenes (1–3) with well-defined defects in which seven-five-seven (7–5–7)-membered rings were introduced to their sp2 carbon frameworks. From the X-ray crystallographic analysis, compound 1 adopts a nearly planar structure. Compound 2, with an additional five-membered ring compared to 1, possesses a slightly saddle-shaped geometry. Compound 3, which can be regarded as the “head-to-head” fusion of 1 with two bonds, features two saddles connected together. The resultant defective nanographenes 1–3 were well-investigated by UV–vis absorption, cyclic voltammetry, and time-resolved absorption spectra and further corroborated by density functional theory (DFT) calculations. Detailed experimental and theoretical investigations elucidate that these three nanographenes 1–3 exhibit an anti-aromatic character in their ground states and display a high stability under ambient conditions, which contrast with the reported unstable biradicaloid nanographenes that contain heptagons. Our work reported herein offers insights into the understanding of structure-related properties and enables the control of the electronic structures of expanded nanographenes with atomically precise defects.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.0c12116.

    • Synthetic procedures and characterization data for all new compounds, general experimental methods, additional NMR and HR-MS spectroscopic data and spectra, DFT calculation details, and crystallographic data (PDF)

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    CCDC 2033693 for compound 1, CCDC 2010758 for compound 2, and CCDC 2042159 for compound 3 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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    Cite this: J. Am. Chem. Soc. 2021, 143, 5, 2353–2360
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    Published January 27, 2021
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