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

  • 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
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    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
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  • , 
  • Bingkai Yuan
    Bingkai Yuan
    Department of Physics and Astronomy, Shanghai Jiao Tong University, 200240 Shanghai, China
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  • , 
  • Can Li
    Can Li
    Department of Physics and Astronomy, Shanghai Jiao Tong University, 200240 Shanghai, China
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  • , 
  • 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
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    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
  • , and 
  • 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
Cite this: J. Am. Chem. Soc. 2019, 141, 7, 2843–2846
Publication Date (Web):February 7, 2019
https://doi.org/10.1021/jacs.8b10407
Copyright © 2019 American Chemical Society
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    Abstract

    Abstract Image

    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.

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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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