Journal
ACS NANO
Volume 11, Issue 6, Pages 6204-6210Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsnano.7b02316
Keywords
graphene nanoribbon; on-sulfate synthesis; dehalogenation; scanning tunneling microscopy; theoretical calculation
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Funding
- CREST JST [JPMJCR15F1]
- MEXT/JSPS KAKENHI grant [JP15K17843, JP26105004, JP26288038, JP15H00876, JP16H02286]
- MEXT
- Izumi Science and Technology Foundation
- Kansai Research Foundation for Technology Promotion (KRF)
- Kyoto Technoscience Center
- TEPCO Memorial Foundation
- Grants-in-Aid for Scientific Research [15K21719, 26105001, 26105004, 15K17843, 16H02286] Funding Source: KAKEN
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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 degrees C on Au(111) under ultrahigh-vacuum conditions. Further annealing at 400 degrees 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 synthesizing edge-fluorinated graphene nanoribbons.
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