Experimental and Theoretical Investigations of Surface-Assisted Graphene Nanoribbon Synthesis Featuring Carbon-Fluorine Bond Cleavage

ACS Nano
Hironobu HayashiHiroko Yamada

Abstract

Edge-fluorinated graphene nanoribbons are predicted to exhibit attractive structural and electronic properties, which, however, still need to be demonstrated experimentally. Hence, to provide further experimental insights, an anthracene trimer comprising a partially fluorinated central unit is explored as a precursor molecule, with scanning tunneling microscopy and X-ray photoelectron spectroscopy analyses, indicating the formation of partially edge-fluorinated polyanthrylenes via on-surface reactions after annealing at 350 °C on Au(111) under ultrahigh-vacuum conditions. Further annealing at 400 °C leads to the cyclodehydrogenation of partially edge-fluorinated polyanthrylenes to form graphene nanoribbons, resulting in carbon-fluorine bond cleavage despite its high dissociation energy. Extensive theoretical calculations reveal a defluorination-based reaction mechanism, showing that a critical intermediate structure, obtained as a result of H atom migration to the terminal carbon of a fluorinated anthracene unit in polyanthrylene, plays a crucial role in significantly lowering the activation energy of carbon-fluorine bond dissociation. These results suggest the importance of transient structures in intermediate states for synth...Continue Reading

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Citations

Apr 6, 2018·Physical Chemistry Chemical Physics : PCCP·Jing LiuKai Wu
Mar 8, 2018·Advanced Materials·Qiang SunWei Xu
Jun 27, 2018·Nature Communications·Daniel M Packwood, Taro Hitosugi
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Sep 9, 2020·Journal of the American Chemical Society·Yolanda L LiYves Rubin
Oct 20, 2021·Angewandte Chemie·Jesús Castro-EstebanDiego Peña

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