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

Journal

Journal of the American Chemical Society American Chemical Society

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

Abstract

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.

Authors with CRIS profile

Maximilian Michael Ammon Professur für Experimentalphysik (Rastersondenmikroskopie) Tim Sander Professur für Experimentalphysik (Rastersondenmikroskopie) Sabine Maier Professur für Experimentalphysik (Rastersondenmikroskopie)

Additional Organisation(s)

Graduiertenkolleg 1896/2 In situ Mikroskopie mit Elektronen, Röntgenstrahlen und Rastersonden Interdisziplinäres Zentrum, Center for Nanoanalysis and Electron Microscopy (CENEM)

Related research project(s)

In-situ Characterization of Nanomaterials with Electrons, X-rays/Neutrons and Scanning Probes (GRK 1896) Oct. 1, 2013 - Sept. 30, 2022

How to cite

APA:

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://doi.org/10.1021/jacs.7b04783

MLA:

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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