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Molecules–Oligomers–Nanowires–Graphene Nanoribbons: A Bottom-Up Stepwise On-Surface Covalent Synthesis Preserving Long-Range Order
Abstract
We report on a stepwise on-surface polymerization reaction leading to oriented graphene nanoribbons on Au(111) as the final product. Starting from the precursor 4,4″-dibromo-p-terphenyl and using the Ullmann coupling reaction followed by dehydrogenation and C-C coupling, we have developed a fine-tuned, annealing-triggered on-surface polymerization that allows us to obtain an oriented nanomesh of graphene nanoribbons via two well-defined intermediate products, namely, p-phenylene oligomers with reduced length dispersion and ordered submicrometric molecular wires of poly(p-phenylene). A fine balance involving gold catalytic activity in the Ullmann coupling, appropriate on-surface molecular mobility, and favorable topochemical conditions provided by the used precursor leads to a high degree of long-range order that characterizes each step of the synthesis and is rarely observed for surface organic frameworks obtained via Ullmann coupling.
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Citations
Cited by
Bottom-up synthesis of multifunctional nanoporous graphene
Moreno, C., Vilas-Varela, M., Kretz, B., Garcia-Lekue, A., Costache, M. V., Paradinas, M., Panighel, M., Ceballos, G., Valenzuela, S. O., Peña, D., et al. (2018) · Science · doi:10.1126/science.aar2009 · Cited by 567
On-Surface Synthesis and Characterization of 9-Atom Wide Armchair Graphene Nanoribbons
Talirz, L., Söde, H., Dumslaff, T., Wang, S., Sanchez-Valencia, J. R., Liu, J., Shinde, P., Pignedoli, C. A., Liang, L., Meunier, V., et al. (2017) · ACS Nano · doi:10.1021/acsnano.6b06405 · Cited by 320
Self-citationFrontiers of on-surface synthesis: From principles to applications
Shen, Q., Gao, H.-Y., & Fuchs, H. (2017) · Nano Today · doi:10.1016/j.nantod.2017.02.007 · Cited by 286
Face the Edges: Catalytic Active Sites of Nanomaterials
Ni, B., & Wang, X. (2015) · Advanced Science · doi:10.1002/advs.201500085 · Cited by 219
Metadata
- Authors
- Basagni, A., Sedona, F., Pignedoli, C. A., Cattelan, M., Nicolas, L., Casarin, M., & Sambi, M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2015-01-27
- Volume
- 137
- Issue
- 5
- Pages
- 1802-1808
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2334054625
- Cited by
- 271
- References
- 0
- FWCI
- 17.30
- Type
- journal article
- Language
- en
- Open access
- closed
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- The paper
- Basagni, A., Sedona, F., Pignedoli, C. A., Cattelan, M., Nicolas, L., Casarin, M., & Sambi, M. (2015). Molecules–Oligomers–Nanowires–Graphene Nanoribbons: A Bottom-Up Stepwise On-Surface Covalent Synthesis Preserving Long-Range Order. Journal of the American Chemical Society. https://doi.org/10.1021/ja510292b
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