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Revisiting Acepleiadylene: Two-Step Synthesis and π-Extension toward Nonbenzenoid Nanographene

  • Pengcai Liu
    Pengcai Liu
    State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
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  • , 
  • Xing-Yu Chen
    Xing-Yu Chen
    State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
    More by Xing-Yu Chen
  • , 
  • Jiawen Cao
    Jiawen Cao
    State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
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  • , 
  • Lukas Ruppenthal
    Lukas Ruppenthal
    Department of Chemistry, Philipps University Marburg, Hans-Meerwein-Straße 4, 35032 Marburg, Germany
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  • , 
  • J. Michael Gottfried
    J. Michael Gottfried
    Department of Chemistry, Philipps University Marburg, Hans-Meerwein-Straße 4, 35032 Marburg, Germany
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    Orcidhttp://orcid.org/0000-0001-5579-2568
  • , 
  • Klaus Müllen
    Klaus Müllen
    Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
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    Orcidhttp://orcid.org/0000-0001-6630-8786
  • , and 
  • Xiao-Ye Wang*
    Xiao-Ye Wang
    State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
    *Email: [email protected]
    More by Xiao-Ye Wang
    Orcidhttp://orcid.org/0000-0003-3540-0277
Cite this: J. Am. Chem. Soc. 2021, 143, 14, 5314–5318
Publication Date (Web):March 30, 2021
https://doi.org/10.1021/jacs.1c01826
Copyright © 2021 American Chemical Society
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    Abstract

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    Acepleiadylene (APD), a nonbenzenoid nonalternant isomer of pyrene, exhibits different electronic properties from pyrene, but has been rarely studied since its first synthesis in 1956, probably due to the difficulties in synthesis and further derivatization. In this work, we revisited this long-known compound and developed a new two-step synthetic route to efficiently access APD on the gram scale. Theoretical and experimental characterizations elucidated the unique properties of APD as compared with its benzenoid isomer pyrene, particularly revealing its dipolar structure with a narrow optical gap. The functionalization of APD was demonstrated for the first time, providing doubly brominated APD as a key precursor for further π-extension. As a proof of concept, a π-extended APD and a cyclotrimer nanographene (C48H24) were constructed, opening up new avenues to nonbenzenoid nanographenes with low HOMO–LUMO gaps.

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