Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling

Xiao-Ye Wang, Marcus Richter, Yuanqin He, Jonas Björk, Alexander Riss, Raju Rajesh, Manuela Garnica, Felix Hennersdorf, Jan J. Weigand, Akimitsu Narita, Reinhard Berger, Xinliang Feng, Willi Auwärter (), Johannes V. Barth (), Carlos-Andres Palma () and Klaus Müllen ()
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Xiao-Ye Wang: Max Planck Institute for Polymer Research, Ackermannweg 10
Marcus Richter: Dresden University of Technology, Mommsenstr. 4
Yuanqin He: Technical University of Munich, Lichtenbergstr. 2a
Jonas Björk: IFM, Linköping University
Alexander Riss: Technical University of Munich, James-Franck-Str. 1
Raju Rajesh: Max Planck Institute for Polymer Research, Ackermannweg 10
Manuela Garnica: Technical University of Munich, James-Franck-Str. 1
Felix Hennersdorf: Dresden University of Technology, Mommsenstr. 4
Jan J. Weigand: Dresden University of Technology, Mommsenstr. 4
Akimitsu Narita: Max Planck Institute for Polymer Research, Ackermannweg 10
Reinhard Berger: Dresden University of Technology, Mommsenstr. 4
Xinliang Feng: Dresden University of Technology, Mommsenstr. 4
Willi Auwärter: Technical University of Munich, James-Franck-Str. 1
Johannes V. Barth: Technical University of Munich, James-Franck-Str. 1
Carlos-Andres Palma: Technical University of Munich, James-Franck-Str. 1
Klaus Müllen: Max Planck Institute for Polymer Research, Ackermannweg 10

Nature Communications, 2017, vol. 8, issue 1, 1-7

Abstract: Abstract Nanographenes, namely polycyclic aromatic hydrocarbons (PAHs) with nanoscale dimensions (>1 nm), are atomically precise cutouts from graphene. They represent prime models to enhance the scope of chemical and physical properties of graphene through structural modulation and functionalization. Defined nitrogen doping in nanographenes is particularly attractive due to its potential for increasing the number of π-electrons, with the possibility of introducing localized antiaromatic ring elements. Herein we present azomethine ylide homocoupling as a strategy to afford internally nitrogen-doped, non-planar PAH in solution and planar nanographene on surfaces, with central pyrazine rings. Localized antiaromaticity of the central ring is indicated by optical absorption spectroscopy in conjunction with theoretical calculations. Our strategy opens up methods for chemically tailoring graphene and nanographenes, modified by antiaromatic dopants.

Date: 2017
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DOI: 10.1038/s41467-017-01934-1

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