p-Extended benzo[1,2:4,5]di[7]annulene bis(dicarboximide)s - a new class of non-alternant polycyclic aromatic dicarboximides

Aromatic dicarboximides are a class of molecules represented by the well-known rylene bis(dicarboximide)s, in particular perylene or naphthalene bis(dicarboximide)s, which show pronounced optoelectronic properties and are applied as color pigments, fluorescent dyes and organic semiconductors. Herein we extend the family of aromatic bis(dicarboximide)s and report the synthesis of the first series of non-alternant aromatic dicarboximides by twofold Pd-catalyzed [5 + 2] annulation. Characterization by UV/vis spectroscopy and cyclic voltammetry (CV) measurements give insight into the optoelectronic characteristics of the hitherto unexplored substance class of heptagon-containing imides. Theoretical studies by nucleus independent chemical shift (NICS) XY-scans and anisotropy of the induced current density (ACID) plots demonstrate the influence of both the non-alternant carbon framework and the imide moieties on aromaticity of the synthesized bisimides. A series of non-alternant aromatic dicarboximides was synthesized by manipulating the perylene bisimide framework through the introduction of heptagonal rings, which strongly alter their optoelectronic properties.

Automated summary

In this study, a series of non-alternant aromatic dicarboximides were synthesized by manipulating the perylene bisimide framework through the introduction of heptagonal rings. Characterization and theoretical studies provided insights into the optoelectronic properties and aromaticity of these newly synthesized compounds.