Facile synthesis of nitrogen-containing polycyclic aromatic hydrocarbons from perylene bisimides

Abstract

We have developed a facile procedure for the synthesis of π-extended fluorubins from perylene bisimides. Iridium-catalyzed direct borylation, the SuzukiMiyaura cross-coupling, and an acid-condensation sequence afforded π-extended fluorubins 1 in moderate yields. X-ray diffraction analysis revealed a planar structure of 1. In addition, optical analysis and DFT calculations indicated the presence of intramolecular charge-transfer interactions in 1c.