Rapid access to functionalized nanographenes through a palladium-catalyzed multi-annulation sequence†

Abstract

Nanographenes and polycyclic aromatic hydrocarbons exhibit many intriguing physical properties and have potential applications across a range of scientific fields, including electronics, catalysis, and biomedicine. To accelerate the development of such applications, efficient and reliable methods for accessing functionalized analogs are required. Herein, we report the efficient synthesis of functionalized small nanographenes from readily available iodobiaryl and diarylacetylene derivatives via a one-pot, multi-annulation sequence catalyzed by a single palladium catalyst. This method enables the preparation of small nanographenes bearing various polar functional groups, such as hydroxy, amino, and pyridinic nitrogen atoms, which are otherwise difficult to incorporate. These functional groups provide valuable sites for further derivatization, allowing the modulation of small nanographenes' solubility, optoelectronic properties, and photochromic and vapochromic behaviors. Our new method thus provides a platform for facile access to novel carbon-based materials.