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Open-Shell Nonbenzenoid Nanographenes Containing Two Pairs of Pentagonal and Heptagonal Rings

  • Junzhi Liu
    Junzhi Liu
    Center for Advancing Electronics Dresden (cfaed) & Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
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    Orcidhttp://orcid.org/0000-0001-7146-0942
  • , 
  • Shantanu Mishra
    Shantanu Mishra
    Empa, Swiss Federal Laboratories for Materials Science and Technology, Überlandstrasse 129, 8600 Dübendorf, Switzerland
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    Orcidhttp://orcid.org/0000-0002-2900-4203
  • , 
  • Carlo A. Pignedoli
    Carlo A. Pignedoli
    Empa, Swiss Federal Laboratories for Materials Science and Technology, Überlandstrasse 129, 8600 Dübendorf, Switzerland
    National Centre for Computational Design and Discovery of Novel Materials (MARVEL), 1015 Lausanne, Switzerland
    More by Carlo A. Pignedoli
    Orcidhttp://orcid.org/0000-0002-8273-6390
  • , 
  • Daniele Passerone
    Daniele Passerone
    Empa, Swiss Federal Laboratories for Materials Science and Technology, Überlandstrasse 129, 8600 Dübendorf, Switzerland
    National Centre for Computational Design and Discovery of Novel Materials (MARVEL), 1015 Lausanne, Switzerland
    More by Daniele Passerone
  • , 
  • José I. Urgel
    José I. Urgel
    Empa, Swiss Federal Laboratories for Materials Science and Technology, Überlandstrasse 129, 8600 Dübendorf, Switzerland
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    Orcidhttp://orcid.org/0000-0001-7608-2979
  • , 
  • Alberto Fabrizio
    Alberto Fabrizio
    National Centre for Computational Design and Discovery of Novel Materials (MARVEL), 1015 Lausanne, Switzerland
    Laboratory for Computational Molecular Design, École Polytechnique Fédérale de Lausanne, Avenue F.-A. Forel 2, 1015 Lausanne, Switzerland
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    Orcidhttp://orcid.org/0000-0002-4440-3149
  • , 
  • Thorsten G. Lohr
    Thorsten G. Lohr
    Center for Advancing Electronics Dresden (cfaed) & Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
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  • , 
  • Ji Ma
    Ji Ma
    Center for Advancing Electronics Dresden (cfaed) & Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
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  • , 
  • Hartmut Komber
    Hartmut Komber
    Leibniz-Institut für Polymerforschung Dresden e.V., Hohestraße 6, 01069 Dresden, Germany
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    Orcidhttp://orcid.org/0000-0001-6176-6737
  • , 
  • Martin Baumgarten
    Martin Baumgarten
    Max-Planck Institut für Polymerforschung, 55128 Mainz, Germany
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  • Clémence Corminboeuf
    Clémence Corminboeuf
    National Centre for Computational Design and Discovery of Novel Materials (MARVEL), 1015 Lausanne, Switzerland
    Laboratory for Computational Molecular Design, École Polytechnique Fédérale de Lausanne, Avenue F.-A. Forel 2, 1015 Lausanne, Switzerland
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    Orcidhttp://orcid.org/0000-0001-7993-2879
  • , 
  • Reinhard Berger
    Reinhard Berger
    Center for Advancing Electronics Dresden (cfaed) & Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
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    Orcidhttp://orcid.org/0000-0002-8959-7821
  • , 
  • Pascal Ruffieux
    Pascal Ruffieux
    Empa, Swiss Federal Laboratories for Materials Science and Technology, Überlandstrasse 129, 8600 Dübendorf, Switzerland
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    Orcidhttp://orcid.org/0000-0001-5729-5354
  • , 
  • Klaus Müllen*
    Klaus Müllen
    Max-Planck Institut für Polymerforschung, 55128 Mainz, Germany
    *[email protected]
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    Orcidhttp://orcid.org/0000-0001-6630-8786
  • , 
  • Roman Fasel*
    Roman Fasel
    Empa, Swiss Federal Laboratories for Materials Science and Technology, Überlandstrasse 129, 8600 Dübendorf, Switzerland
    Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland
    *[email protected]
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    Orcidhttp://orcid.org/0000-0002-1553-6487
  • , and 
  • Xinliang Feng*
    Xinliang Feng
    Center for Advancing Electronics Dresden (cfaed) & Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
    *[email protected]
    More by Xinliang Feng
    Orcidhttp://orcid.org/0000-0003-3885-2703
Cite this: J. Am. Chem. Soc. 2019, 141, 30, 12011–12020
Publication Date (Web):July 12, 2019
https://doi.org/10.1021/jacs.9b04718
Copyright © 2019 American Chemical Society
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    Abstract

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    Nonbenzenoid carbocyclic rings are postulated to serve as important structural elements toward tuning the chemical and electronic properties of extended polycyclic aromatic hydrocarbons (PAHs, or namely nanographenes), necessitating a rational and atomically precise synthetic approach toward their fabrication. Here, using a combined bottom-up in-solution and on-surface synthetic approach, we report the synthesis of nonbenzenoid open-shell nanographenes containing two pairs of embedded pentagonal and heptagonal rings. Extensive characterization of the resultant nanographene in solution shows a low optical gap, and an open-shell singlet ground state with a low singlet–triplet gap. Employing ultra-high-resolution scanning tunneling microscopy and spectroscopy, we conduct atomic-scale structural and electronic studies on a cyclopenta-fused derivative on a Au(111) surface. The resultant five to seven rings embedded nanographene displays an extremely narrow energy gap of 0.27 eV and exhibits a pronounced open-shell biradical character close to 1 (y0 = 0.92). Our experimental results are supported by mean-field and multiconfigurational quantum chemical calculations. Access to large nanographenes with a combination of nonbenzenoid topologies and open-shell character should have wide implications in harnessing new functionalities toward the realization of future organic electronic and spintronic devices.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.9b04718.

    • X-ray crystallographic coordinates of 15a (CIF)

    • VT-1H-NMR experiments of 4a; EPR measurements; time-dependent UV–vis–NIR spectra and CV of 4a; pristine precursor molecule (3b) on surface; STS of 5; STM lateral and voltage-pulse-induced manipulation of self-assembled tetramers of 6; loss of xylenyl groups from 3b; structural and electronic characterization of 7 on Au(111); height-dependent UHR-STM images of 8; spin-polarized DFT calculations on 4a and 8; synthetic procedures; NMR characterization; crystal structure of 15a; MALDI-TOF and ESI spectra (PDF)

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