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Title: Fluorine-programmed nanozipping to tailored nanographenes on rutile TiO 2 surfaces

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.
Authors:
ORCiD logo [1] ; ORCiD logo [2] ; ORCiD logo [3] ; ORCiD logo [2] ; ORCiD logo [4] ; ORCiD logo [2] ; ORCiD logo [2] ; ORCiD logo [3]
  1. Jagiellonian University, Łojasiewicza (Poland); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
  2. Jagiellonian University, Łojasiewicza (Poland)
  3. Friedrich Alexander University Erlangen-Nuremberg, Erlangen (Germany)
  4. Espeem S.A.R.L., Esch-sur-Alzette (Luxembourg)
Publication Date:
Grant/Contract Number:
AC05-00OR22725
Type:
Accepted Manuscript
Journal Name:
Science
Additional Journal Information:
Journal Volume: 363; Journal Issue: 6422; Journal ID: ISSN 0036-8075
Publisher:
AAAS
Research Org:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org:
USDOE Office of Science (SC)
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE
OSTI Identifier:
1489571

Kolmer, Marek A., Zuzak, Rafal, Steiner, Ann Kristin, Zajac, Lukasz, Engelund, Mads, Godlewski, Szymon, Szymonski, Marek, and Amsharov, Konstantin. Fluorine-programmed nanozipping to tailored nanographenes on rutile TiO2 surfaces. United States: N. p., Web. doi:10.1126/science.aav4954.
Kolmer, Marek A., Zuzak, Rafal, Steiner, Ann Kristin, Zajac, Lukasz, Engelund, Mads, Godlewski, Szymon, Szymonski, Marek, & Amsharov, Konstantin. Fluorine-programmed nanozipping to tailored nanographenes on rutile TiO2 surfaces. United States. doi:10.1126/science.aav4954.
Kolmer, Marek A., Zuzak, Rafal, Steiner, Ann Kristin, Zajac, Lukasz, Engelund, Mads, Godlewski, Szymon, Szymonski, Marek, and Amsharov, Konstantin. 2019. "Fluorine-programmed nanozipping to tailored nanographenes on rutile TiO2 surfaces". United States. doi:10.1126/science.aav4954.
@article{osti_1489571,
title = {Fluorine-programmed nanozipping to tailored nanographenes on rutile TiO2 surfaces},
author = {Kolmer, Marek A. and Zuzak, Rafal and Steiner, Ann Kristin and Zajac, Lukasz and Engelund, Mads and Godlewski, Szymon and Szymonski, Marek and Amsharov, Konstantin},
abstractNote = {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.},
doi = {10.1126/science.aav4954},
journal = {Science},
number = 6422,
volume = 363,
place = {United States},
year = {2019},
month = {1}
}

Works referenced in this record:

Generalized Gradient Approximation Made Simple
journal, October 1996
  • Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias
  • Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868
  • DOI: 10.1103/PhysRevLett.77.3865