Synthesis and Properties of Diindeno[1,2,3-cd:1′,2′,3′-mn]pyrene and Two of Its Aza-Analogs

The incorporation of heteroatoms into polycyclic aromatic hydrocarbons (PAHs) has been recognized as valuable tool to alter their inherent optical and electrochemical properties and are thought as promising next-generation semiconductor materials. We herein report the synthesis of diindenopyrene, a fragment of C(70 )and two of its nitrogen-doped aza-analogs. The developed synthetic procedure is based on Bronsted-acid-mediated cycloisomerization followed by Pd-catalyzed C-H-activation as key-steps. The impact of N-doping on the optical and electrochemical properties has been studied and the experimental results are supported by DFT calculations.

Automated summary

The incorporation of heteroatoms into polycyclic aromatic hydrocarbons (PAHs) is a valuable tool to alter their optical and electrochemical properties and is considered a promising next-generation semiconductor material. In this study, the synthesis of diindenopyrene, a fragment of C(70), and two of its nitrogen-doped analogs is reported. The developed synthetic procedure involves Bronsted-acid-mediated cycloisomerization followed by Pd-catalyzed C-H activation. The impact of N-doping on the optical and electrochemical properties is studied and supported by DFT calculations.