Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling
Wang XY, Richter M, He Y, Bjork J, Riss A, Rajesh R, Garnica M, Hennersdorf F, Weigand JJ, Narita A, Berger R, Feng X, Auwaerter W, Barth JV, Palma CA, Muellen K (2017)
Publication Type: Journal article
Publication year: 2017
Journal
Book Volume: 8
Article Number: 1948
Journal Issue: 1
DOI: 10.1038/s41467-017-01934-1
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.
Involved external institutions
Technische Universität Dresden
Germany (DE)
Technische Universität München (TUM)
Germany (DE)
Linköping University
Sweden (SE)
Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research
Germany (DE)
Germany (DE)
Technische Universität München (TUM)
Germany (DE)
Linköping University
Sweden (SE)
Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research
Germany (DE)
How to cite
APA:
Wang, X.-Y., Richter, M., He, Y., Bjork, J., Riss, A., Rajesh, R.,... Muellen, K. (2017). Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling. Nature Communications, 8(1). https://doi.org/10.1038/s41467-017-01934-1
MLA:
Wang, Xiao-Ye, et al. "Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling." Nature Communications 8.1 (2017).
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