Atomically precise edge chlorination of nanographenes and its application in graphene nanoribbons

Yuan-Zhi Tan, Bo Yang, Khaled Parvez, Akimitsu Narita, Silvio Osella, David Beljonne, Xinliang Feng () and Klaus Müllen ()
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Yuan-Zhi Tan: Max Planck Institute for Polymer Research, Ackermannweg 10, D-55128 Mainz, Germany
Bo Yang: Max Planck Institute for Polymer Research, Ackermannweg 10, D-55128 Mainz, Germany
Khaled Parvez: Max Planck Institute for Polymer Research, Ackermannweg 10, D-55128 Mainz, Germany
Akimitsu Narita: Max Planck Institute for Polymer Research, Ackermannweg 10, D-55128 Mainz, Germany
Silvio Osella: Laboratory for Chemistry of Novel Materials, University of Mons, Place du Parc 20, B-7000 Mons, Belgium
David Beljonne: Laboratory for Chemistry of Novel Materials, University of Mons, Place du Parc 20, B-7000 Mons, Belgium
Xinliang Feng: Max Planck Institute for Polymer Research, Ackermannweg 10, D-55128 Mainz, Germany
Klaus Müllen: Max Planck Institute for Polymer Research, Ackermannweg 10, D-55128 Mainz, Germany

Nature Communications, 2013, vol. 4, issue 1, 1-7

Abstract: Abstract Chemical functionalization is one of the most powerful and widely used strategies to control the properties of nanomaterials, particularly in the field of graphene. However, the ill-defined structure of the present functionalized graphene inhibits atomically precise structural characterization and structure-correlated property modulation. Here we present a general edge chlorination protocol for atomically precise functionalization of nanographenes at different scales from 1.2 to 3.4 nm and its application in graphene nanoribbons. The well-defined edge chlorination is unambiguously confirmed by X-ray single-crystal analysis, which also discloses the characteristic non-planar molecular shape and detailed bond lengths of chlorinated nanographenes. Chlorinated nanographenes and graphene nanoribbons manifest enhanced solution processability associated with decreases in the optical band gap and frontier molecular orbital energy levels, exemplifying the structure-correlated property modulation by precise edge chlorination.

Date: 2013
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DOI: 10.1038/ncomms3646

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