Nitrogen-embedded polycyclic chemical compounds with strong antiaromaticity and stability were synthesized and isolated for the first time utilizing pyrrole as a vital unit. An expedited approach towards stable antiaromatic polycyclic compounds permits not only the revealing of its fundamental properties but also its application to natural digital materials.
The synthesis and isolation of a nitrogen-embedded polycyclic compound with strong antiaromaticity and stability were achieved for the first time by a study group at Ehime University. This outcome was published on October 2, 2019, in the Journal of the American Chemical Society.
Aromaticity is among the essential concepts in chemistry, which influences the fundamental properties of cyclic conjugated compounds. In general, compounds with 4n+2 π electrons in the ring are steadily resulting from their aromatic nature, and are broadly used around us: from plastics to pharmaceuticals, and from dyes to natural electronics materials. Alternatively, antiaromatic chemical compounds with 4n π electrons in the ring lack stability, and thus research on the synthesis and characterization of such compounds remains to be explained.
In this report, an expedited strategy toward a nitrogen-embedded antiaromatic compound with robust antiaromaticity and stability is offered. The brand new compounds have been efficiently synthesized in just three moves from commercially available reagents through a substitution reaction and progressive intramolecular Schooll and Vilsmeier-type reactions. The detailed investigation unveiled its robust antiaromaticity and stability even in the air.