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J Am Chem Soc. 2015 Feb 11;137(5):1802-8. doi: 10.1021/ja510292b. Epub 2015 Jan 27.

Molecules-oligomers-nanowires-graphene nanoribbons: a bottom-up stepwise on-surface covalent synthesis preserving long-range order.

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Dipartimento di Scienze Chimiche, Università degli Studi di Padova and Consorzio INSTM , Via Marzolo 1, 35131 Padova, Italy.


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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