Here, we focus on polycyclic aromatic derivatives of indoloindolizine where both indole and indolizine moieties are embedded in the core structure. We propose that by intensifying the aromaticity of the indolizine moiety in the molecule we can reduce the HOMO-LUMO gap, while by weakening the aromaticity of indolizine we can deliberately increase the HOMO-LUMO gap. Following the Pino-Rios and Solà's findings, we particularly focused on dearomatizing the 6-membered ring in the indolizine moiety through benzannulation of the ring to achieve highly conductive, yet, stable OFETs.