Chemical transformation of doubly N-confused porphodimethenes to variants of (anti)aromatic doubly N-confused porphyrinoids and σ-aromatic doubly N-confused isophlorinoids

Chemical conversion of non-aromatic trans-doubly N-confused porphodimethenes to hitherto unknown variants of doubly N-confused porphyrinoids/isophlorinoids has been unravelled by the precise interplay between the types of oxidants, the types of meso-aryl substituents and the number of heterocyclic rings in porphodimethene(s). Unique pi-reconstructions owing to sequential C-oxygenation of N-confused N-methyl pyrrole rings have led to the genesis of 18 pi aromatic doubly N-confused monooxo porphyrinoids, 16 pi antiaromatic doubly N-confused diioxo porphyrinoids and sigma-aromatic doubly N-confused tetraoxo isophlorinoids.

Automated summary

The chemical conversion of non-aromatic trans-doubly N-confused porphodimethenes to new variants of doubly N-confused porphyrinoids/isophlorinoids has been achieved by manipulating the types of oxidants, the types of meso-aryl substituents, and the number of heterocyclic rings in porphodimethene(s). This conversion leads to the formation of 18 pi aromatic doubly N-confused monooxo porphyrinoids, 16 pi antiaromatic doubly N-confused diioxo porphyrinoids, and sigma-aromatic doubly N-confused tetraoxo isophlorinoids.