Fluorine-programmed nanozipping to tailored nanographenes on rutile TiO2 surfaces

Kolmer, Marek A.; Zuzak, Rafal; Steiner, Ann Kristin; Zajac, Lukasz; Engelund, Mads; Godlewski, Szymon; Szymonski, Marek; Amsharov, Konstantin

doi:10.1126/science.aav4954

Title: Fluorine-programmed nanozipping to tailored nanographenes on rutile TiO₂ surfaces

Journal Article · 03 January 2019 · Science

DOI: https://doi.org/10.1126/science.aav4954 · OSTI ID:1489571

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Jagiellonian University, Łojasiewicza (Poland); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Jagiellonian University, Łojasiewicza (Poland)
Friedrich Alexander University Erlangen-Nuremberg, Erlangen (Germany)
Espeem S.A.R.L., Esch-sur-Alzette (Luxembourg)

The rational synthesis of nanographenes and carbon nanoribbons directly on nonmetallic surfaces has been an elusive goal for a long time. In this paper, we report that activation of the carbon (C)–fluorine (F) bond is a reliable and versatile tool enabling intramolecular aryl-aryl coupling directly on metal oxide surfaces. A challenging multistep transformation enabled by C–F bond activation led to a dominolike coupling that yielded tailored nanographenes directly on the rutile titania surface. Because of efficient regioselective zipping, we obtained the target nanographenes from flexible precursors. Fluorine positions in the precursor structure unambiguously dictated the running of the “zipping program,” resulting in the rolling up of oligophenylene chains. Finally, the high efficiency of the hydrogen fluoride zipping makes our approach attractive for the rational synthesis of nanographenes and nanoribbons directly on insulating and semiconducting surfaces.

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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1489571

Journal Information:: Science, Journal Name: Science Journal Issue: 6422 Vol. 363; ISSN 0036-8075

Publisher:: AAASCopyright Statement

Country of Publication:: United States

Language:: English

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