Home / Nitrogen-embedded polycyclic compound with strong anti-aromaticity and stability

Nitrogen-embedded polycyclic compound with strong anti-aromaticity and stability



  PICTURE

PICTURE: Synthesis of anti-aromatic expanded azacoron via Vilsmeier type intramolecular reaction showing aromatic exchange at redox stimulus
show more

Points: Figure adapted with permission from Journal of the American Chemical Society 2019, 141. © 2019 American Chemical Society.

The synthesis and isolation of a nitrogen-embedded polycyclic compound with strong anti-aromaticity and stability was first achieved by a research team at Ehime University. This result was published on October 2, 201

9 in the Journal of the American Chemical Society .

Aromaticity is one of the most important concepts in chemistry, which has an influence on the basic properties of cyclic conjugated compounds. In general, compounds with 4n + 2 π electrons in the ring are stable because of their aromatic nature and are widely used around us: from plastics to pharmaceuticals and from dyes to organic electronics materials. On the other hand, anti-aromatic compounds with 4n π electrons in the ring lack stability, and therefore research on the synthesis and characterization of such compounds must be clarified. This report presents a fast approach to a nitrogen-embedded anti-aromatic compound with strong anti-aromaticity and stability. The new compounds were effectively synthesized in just three steps from commercially available reagents via a substitution reaction and successive intramolecular Schooll and Vilsmeier reactions. Detailed examination revealed its strong anti-aromaticity and stability even in the air.

Recently, polycyclic compounds have been studied as graphene-like molecules with a discrete structure. But compounds with aromatics and anti-aromatics have mainly been limited to annulenes and porphyrins. This report presents the first nitrogen-embedded polycyclic compound with antiaromaticity. The easy access to such compounds enables not only the disclosure of its basic properties but also its application to organic electronic materials.

###

Disclaimer: AAAS and EurekAlert! are not responsible for the accuracy of news messages sent to EurekAlert! by contributing with institutions or by using any information through the EurekAlert system.


Source link