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Stabilizing Edge-Fluorination in Graphene Nanoribbons.

Authors
  • Panighel, Mirco
  • Quiroga, Sabela
  • Brandimarte, Pedro
  • Moreno, Cesar
  • Garcia-Lekue, Aran
  • Vilas-Varela, Manuel
  • Rey, Dulce
  • Sauthier, Guillaume
  • Ceballos, Gustavo
  • Peña, Diego
  • Mugarza, Aitor
Type
Published Article
Journal
ACS Nano
Publisher
American Chemical Society
Publication Date
Aug 17, 2020
Identifiers
DOI: 10.1021/acsnano.0c01837
PMID: 32804481
Source
Medline
Language
English
License
Unknown

Abstract

The on-surface synthesis of edge-functionalized graphene nanoribbons (GNRs) is challenged by the stability of the functional groups throughout the thermal reaction steps of the synthetic pathway. Edge-fluorination is a particularly critical case, where the interaction with the catalytic substrate and intermediate products can induce the complete cleavage of the otherwise strong C-F bonds before the formation of the GNR. Here, we demonstrate how a rational design of the precursor can stabilize the functional group, enabling the synthesis of edge-fluorinated GNRs. The survival of the functionalization is demonstrated by tracking the structural and chemical transformations occurring at each reaction step with complementary X-ray photoelectron spectroscopy and scanning tunneling microscopy measurements. In contrast to previous attempts, we find that the C-F bond survives the cyclodehydrogenation of the intermediate polymers, leaving a thermal window where GNRs withhold more than 80% of the fluorine atoms. We attribute this enhanced stability of the C-F bond to the particular structure of our precursor, which prevents the cleavage of the C-F bond by avoiding interaction with the residual hydrogen originated in the cyclodehydrogenation. This structural protection of the linking bond could be implemented in the synthesis of other sp2-functionalized GNRs.

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