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

Abstract

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.