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Simonov KA, Generalov AV, Vinogradov AS, et al. Synthesis of armchair graphene nanoribbons from the 10,10'-dibromo-9,9'-bianthracene molecules on Ag(111): the role of organometallic intermediates. Sci Rep. 2018;8(1):3506doi: 10.1038/s41598-018-21704-3.
Simonov, K. A., Generalov, A. V., Vinogradov, A. S., Svirskiy, G. I., Cafolla, A. A., McGuinness, C., Taketsugu, T., Lyalin, A., Mårtensson, N., & Preobrajenski, A. B. (2018). Synthesis of armchair graphene nanoribbons from the 10,10'-dibromo-9,9'-bianthracene molecules on Ag(111): the role of organometallic intermediates. Scientific reports, 8(1), 3506. https://doi.org/10.1038/s41598-018-21704-3
Simonov, K A, et al. "Synthesis of armchair graphene nanoribbons from the 10,10'-dibromo-9,9'-bianthracene molecules on Ag(111): the role of organometallic intermediates." Scientific reports vol. 8,1 (2018): 3506. doi: https://doi.org/10.1038/s41598-018-21704-3
Simonov KA, Generalov AV, Vinogradov AS, Svirskiy GI, Cafolla AA, McGuinness C, Taketsugu T, Lyalin A, Mårtensson N, Preobrajenski AB. Synthesis of armchair graphene nanoribbons from the 10,10'-dibromo-9,9'-bianthracene molecules on Ag(111): the role of organometallic intermediates. Sci Rep. 2018 Feb 22;8(1):3506. doi: 10.1038/s41598-018-21704-3. PMID: 29472611; PMCID: PMC5823938.
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Sci Rep. 2018 Feb 22;8(1):3506. doi: 10.1038/s41598-018-21704-3.

Synthesis of armchair graphene nanoribbons from the 10,10'-dibromo-9,9'-bianthracene molecules on Ag(111): the role of organometallic intermediates.

Scientific reports

K A Simonov, A V Generalov, A S Vinogradov, G I Svirskiy, A A Cafolla, C McGuinness, T Taketsugu, A Lyalin, N Mårtensson, A B Preobrajenski

Affiliations

  1. Department of Physics and Astronomy, Uppsala University, Box 516, 75120, Uppsala, Sweden. [email protected].
  2. MAX IV Laboratory, Lund University, Box 118, 22100, Lund, Sweden. [email protected].
  3. V.A. Fock Institute of Physics, St. Petersburg State University, 198504, St. Petersburg, Russia. [email protected].
  4. MAX IV Laboratory, Lund University, Box 118, 22100, Lund, Sweden.
  5. V.A. Fock Institute of Physics, St. Petersburg State University, 198504, St. Petersburg, Russia.
  6. School of Physical Sciences, Dublin City University, Dublin, D09, Ireland.
  7. School of Physics, Trinity College Dublin, College Green, Dublin, D02, Ireland.
  8. Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, 060-0810, Japan.
  9. Global Research Center for Environment and Energy Based on Nanomaterials Science (GREEN), National Institute for Materials Science (NIMS), Tsukuba, 305-0044, Japan.
  10. Department of Physics and Astronomy, Uppsala University, Box 516, 75120, Uppsala, Sweden.
  11. MAX IV Laboratory, Lund University, Box 118, 22100, Lund, Sweden. [email protected].

PMID: 29472611 PMCID: PMC5823938 DOI: 10.1038/s41598-018-21704-3

Abstract

We investigate the bottom-up growth of N = 7 armchair graphene nanoribbons (7-AGNRs) from the 10,10'-dibromo-9,9'-bianthracene (DBBA) molecules on Ag(111) with the focus on the role of the organometallic (OM) intermediates. It is demonstrated that DBBA molecules on Ag(111) are partially debrominated at room temperature and lose all bromine atoms at elevated temperatures. Similar to DBBA on Cu(111), debrominated molecules form OM chains on Ag(111). Nevertheless, in contrast with the Cu(111) substrate, formation of polyanthracene chains from OM intermediates via an Ullmann-type reaction is feasible on Ag(111). Cleavage of C-Ag bonds occurs before the thermal threshold for the surface-catalyzed activation of C-H bonds on Ag(111) is reached, while on Cu(111) activation of C-H bonds occurs in parallel with the cleavage of the stronger C-Cu bonds. Consequently, while OM intermediates obstruct the Ullmann reaction between DBBA molecules on the Cu(111) substrate, they are required for the formation of polyanthracene chains on Ag(111). If the Ullmann-type reaction on Ag(111) is inhibited, heating of the OM chains produces nanographenes instead. Heating of the polyanthracene chains produces 7-AGNRs, while heating of nanographenes causes the formation of the disordered structures with the possible admixture of short GNRs.

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