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
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.
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