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On-surface synthesis of non-benzenoid polycyclic aromatics

19 October 2021
On-surface synthesis of non-benzenoid polycyclic aromatics

Dana Nachtigallová from IOCB Prague and CATRIN (Olomouc) in collaboration with the laboratory of Pavel Jelínek from the Institute of Physics, Martin Kotora of Faculty of Science, Charles University, and Libor Veis of J. Heyrovsky Institute of Physical Chemistry published a joint experimental and theoretical study on aromatic systems containing non-benzenoid rings.

These molecules represent a widely studied class of compounds due to their environmental implication, but they are usually poorly available using traditional methods of organic synthesis in solution.

The present study renders a new route for the synthesis of nonalternant polycyclic aromatic hydrocarbons containing up to four kinds of non-benzoid rings. The scientists applied on-surface chemistry, where the synthesis is driven by internal stress imposed by the surface itself to the molecule. The theoretical calculations proved the surprising aromaticity of these nonalternant systems.

On-surface synthesis of non-benzenoid molecules including four–eight-membered rings.

The original paper

  • Mallada, B.; de la Torre, B.; Mendieta-Moreno, J. I.; Nachtigallová, D.; Matěj, A.; Matoušek, M.; Mutombo, P.; Brabec, J.; Veis, L.; Cadart, T.; Kotora, M.; Jelínek, P. On-Surface Strain-Driven Synthesis of Nonalternant Non-Benzenoid Aromatic Compounds Containing Four- to Eight-Membered Rings, J. Am. Chem. Soc. 2021, 143, 36, 14694-14702. https://pubs.acs.org/doi/10.1021/jacs.1c06168

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