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J Am Chem Soc. 2015 May 13;137(18):6097-103. doi: 10.1021/jacs.5b03017. Epub 2015 May 4.

Toward cove-edged low band gap graphene nanoribbons.

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†Max-Planck Institut für Polymerforschung, Ackermannweg 10, 55128, Mainz, Germany.
‡State Key Laboratory of Physical Chemistry of Solid Surfaces and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
§Laboratory for Chemistry of Novel Materials, University of Mons, Place du Parc 20, B-7000 Mons, Belgium.
∥Nanotech@surfaces Laboratory, Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf, Switzerland.
⊥Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland.


Graphene nanoribbons (GNRs), defined as nanometer-wide strips of graphene, have attracted increasing attention as promising candidates for next-generation semiconductors. Here, we demonstrate a bottom-up strategy toward novel low band gap GNRs (Eg = 1.70 eV) with a well-defined cove-type periphery both in solution and on a solid substrate surface with chrysene as the key monomer. Corresponding cyclized chrysene-based oligomers consisting of the dimer and tetramer are obtained via an Ullmann coupling followed by oxidative intramolecular cyclodehydrogenation in solution, and much higher GNR homologues via on-surface synthesis. These oligomers adopt nonplanar structures due to the steric repulsion between the two C-H bonds at the inner cove position. Characterizations by single crystal X-ray analysis, UV-vis absorption spectroscopy, NMR spectroscopy, and scanning tunneling microscopy (STM) are described. The interpretation is assisted by density functional theory (DFT) calculations.

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