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On-surface synthesis of anthracene-fused zigzag graphene nanoribbons from 2,7-dibromo-9,9'-bianthryl reveals unexpected ring rearrangements

Xiushang Xu1, Amogh Kinikar2*, Marco Di Giovannantonio3,2, Carlo Antonio Pignedoli2, Pascal Ruffieux2, Klaus Müllen4, Roman Fasel5,2, Akimitsu Narita1

1 Okinawa Institute of Science and Technology Graduate University, Kunigamigun 904-0495 (Japan)

2 Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf (Switzerland)

3 Istituto di Struttura della Materia (ISM)-Consiglio Nazionale delle Ricerche (CNR), 00133 Roma (Italy)

4 Max Planck Institute for Polymer Research, 55128 Mainz (Germany)

5 Department of Chemistry, Biochemistry and Pharmaceutical Sciences, University of Bern, 3012 Bern (Switzerland)

* Corresponding authors emails: amogh.kinikar@empa.ch
DOI10.24435/materialscloud:fq-nq [version v1]

Publication date: Feb 08, 2024

How to cite this record

Xiushang Xu, Amogh Kinikar, Marco Di Giovannantonio, Carlo Antonio Pignedoli, Pascal Ruffieux, Klaus Müllen, Roman Fasel, Akimitsu Narita, On-surface synthesis of anthracene-fused zigzag graphene nanoribbons from 2,7-dibromo-9,9'-bianthryl reveals unexpected ring rearrangements, Materials Cloud Archive 2024.23 (2024), https://doi.org/10.24435/materialscloud:fq-nq


On-surface synthesis has emerged as a powerful strategy to fabricate unprecedented forms of atomically precise graphene nanoribbons (GNRs). However, the on-surface synthesis of zigzag GNRs (ZGNR) has met with only limited success. In the paper where the data are discussed, we report the synthesis and on-surface reactions of 2,7-dibromo-9,9'-bianthryl as the precursor towards π-extended ZGNRs. Characterization by scanning tunneling microscopy and high-resolution noncontact atomic force microscopy clearly demonstrated the formation of anthracene-fused ZGNRs. Unique skeletal rearrangements were also observed, which could be explained by intramolecular Diels-Alder cycloaddition. Theoretical calculations of the electronic properties of the anthracene-fused ZGNRs revealed spin-polarized edge-states and a narrow bandgap of 0.20 eV.

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External references

Journal reference (Paper in which the method is described)
Precision Chemistry (2024) doi:10.1021/prechem.3c00116


MARVEL on surface synthesis graphene nanoribbons

Version history:

2024.23 (version v1) [This version] Feb 08, 2024 DOI10.24435/materialscloud:fq-nq