On-Surface Synthesis of Porous Carbon Nanoribbons from Polymer Chains

Ammon MM, Sander T, Maier S (2017)

Publication Language: English

Publication Type: Journal article, Original article

Publication year: 2017


Book Volume: 139

Pages Range: 12976–12984

Journal Issue: 37

URI: http://pubs.acs.org/doi/abs/10.1021/jacs.7b04783

DOI: 10.1021/jacs.7b04783

Open Access Link: http://pubs.acs.org/doi/abs/10.1021/jacs.7b04783


We demonstrate the on-surface synthesis of porous carbon nanoribbons on Ag(111) via a preprogrammed isomerization of conformationally flexible polymer chains followed by dehydrogenation reactions using thermal annealing. The carbon chains are fabricated by polymerization of prochiral 1,3,5-tris(3-bromophenyl)benzene (mTBPB) directly on the surface using an Ullmann-type reaction. At room temperature, mTBPB partially self-assembles in halogen-bonded 2D networks, which transform into organometallic chains and rings after debromination. The chain and ring formation is facilitated by conformational switching from a C3h to Cs symmetry of mTBPB via rotation of m-phenylene units. The high conformational selectivity toward Cs-conformers is templated by the twofold coordination to Ag adatoms. After thermally induced covalent-linking through aryl–aryl coupling, well-ordered nanoporous chains are created. Finally, the rotation of single phenylene units in combination with dehydrogenation cross-linking reactions within the polymer chains leads to the unexpected formation of porous carbon nanoribbons. We unveil the reaction mechanism in a low-temperature scanning tunneling microscopy study and demonstrate that the rotation of m-phenylene units is a powerful design tool to promote structural control in the synthesis of cyclic covalent organic nanostructures on metal surfaces.

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Ammon, M.M., Sander, T., & Maier, S. (2017). On-Surface Synthesis of Porous Carbon Nanoribbons from Polymer Chains. Journal of the American Chemical Society, 139(37), 12976–12984. https://dx.doi.org/10.1021/jacs.7b04783


Ammon, Maximilian Michael, Tim Sander, and Sabine Maier. "On-Surface Synthesis of Porous Carbon Nanoribbons from Polymer Chains." Journal of the American Chemical Society 139.37 (2017): 12976–12984.

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