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Graphene Nanoribbons Derived from Zigzag Edge-Encased Poly(para-2,9-dibenzo[bc,kl]coronenylene) Polymer Chains

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    Graphene Nanoribbons Derived from Zigzag Edge-Encased Poly(para-2,9-dibenzo[bc,kl]coronenylene) Polymer Chains
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    • Doreen Beyer
      Doreen Beyer
      Center for Advancing Electronics Dresden (cfaed) and Faculty of Chemistry and Food Chemistry, Chair for Molecular Functional Materials, Dresden University of Technology, 01062 Dresden, Germany
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      Orcidhttp://orcid.org/0000-0002-7835-7857
    • Shiyong Wang
      Shiyong Wang
      Empa, Swiss Federal Laboratories for Material Science and Technology, 8600 Dübendorf, Switzerland
      Department of Physics and Astronomy, Shanghai Jiao Tong University, 200240 Shanghai, China
      More by Shiyong Wang
      Orcidhttp://orcid.org/0000-0001-6603-9926
    • Carlo A. Pignedoli
      Carlo A. Pignedoli
      Empa, Swiss Federal Laboratories for Material Science and Technology, 8600 Dübendorf, Switzerland
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      Orcidhttp://orcid.org/0000-0002-8273-6390
    • Jason Melidonie
      Jason Melidonie
      Center for Advancing Electronics Dresden (cfaed) and Faculty of Chemistry and Food Chemistry, Chair for Molecular Functional Materials, Dresden University of Technology, 01062 Dresden, Germany
      More by Jason Melidonie
    • Bingkai Yuan
      Bingkai Yuan
      Department of Physics and Astronomy, Shanghai Jiao Tong University, 200240 Shanghai, China
      More by Bingkai Yuan
    • Can Li
      Can Li
      Department of Physics and Astronomy, Shanghai Jiao Tong University, 200240 Shanghai, China
      More by Can Li
    • Jan Wilhelm
      Jan Wilhelm
      Department of Chemistry, University of Zürich, 8057 Zürich, Switzerland
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    • Pascal Ruffieux
      Pascal Ruffieux
      Empa, Swiss Federal Laboratories for Material Science and Technology, 8600 Dübendorf, Switzerland
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      Orcidhttp://orcid.org/0000-0001-5729-5354
    • Reinhard Berger*
      Reinhard Berger
      Center for Advancing Electronics Dresden (cfaed) and Faculty of Chemistry and Food Chemistry, Chair for Molecular Functional Materials, Dresden University of Technology, 01062 Dresden, Germany
      *[email protected]
      More by Reinhard Berger
      Orcidhttp://orcid.org/0000-0002-8959-7821
    • Klaus Müllen
      Klaus Müllen
      Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
      More by Klaus Müllen
      Orcidhttp://orcid.org/0000-0001-6630-8786
    • Roman Fasel*
      Roman Fasel
      Empa, Swiss Federal Laboratories for Material Science and Technology, 8600 Dübendorf, Switzerland
      Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland
      *[email protected]
      More by Roman Fasel
      Orcidhttp://orcid.org/0000-0002-1553-6487
    • Xinliang Feng*
      Xinliang Feng
      Center for Advancing Electronics Dresden (cfaed) and Faculty of Chemistry and Food Chemistry, Chair for Molecular Functional Materials, Dresden University of Technology, 01062 Dresden, Germany
      *[email protected]
      More by Xinliang Feng
      Orcidhttp://orcid.org/0000-0003-3885-2703
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2019, 141, 7, 2843–2846
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    https://doi.org/10.1021/jacs.8b10407
    Published February 7, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    In this work, we demonstrate the bottom-up on-surface synthesis of poly(para-dibenzo[bc,kl]-coronenylene) (PPDBC), a zigzag edge-encased analog of poly(para-phenylene) (PPP), and its lateral fusion into zigzag edge-extended graphene nanoribbons (zeeGNRs). Toward this end, we designed a dihalogenated di(meta-xylyl)anthracene monomer displaying strategic methyl groups at the substituted phenyl ring and investigated its applicability as precursor in the thermally induced surface-assisted polymerization and cyclodehydrogenation. The structure of the resulting zigzag edge-rich (70%) polymer PPDBC was unambiguously confirmed by scanning tunneling microscopy (STM) and non-contact atomic force microscopy (nc-AFM). Remarkably, by further thermal treatment at 450 °C two and three aligned PPDBC chains can be laterally fused into expanded zeeGNRs, with a ribbon width of nine (N = 9) up to 17 (N = 17) carbon atoms. Moreover, the resulting zeeGNRs exhibit a high ratio of zigzag (67%) vs armchair (25%) edge segments and feature electronic band gaps as low as 0.9 eV according to gaps quasiparticle calculations.

    Copyright © 2019 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.8b10407.

    • Experimental section of monomer building block 1, characterization by liquid-state NMR (1H-, 13C-, 2D-NMR) and high-resolution mass spectra (HR-MALDI-TOF, HR-ESI-MS), details of on-surface sample preparation, STM and noncontact AFM measurements as well as DFT and GW calculations (PDF)

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    Cited By

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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2019, 141, 7, 2843–2846
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.8b10407
    Published February 7, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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