The design, synthesis and application of rubicene based polycyclic aromatic hydrocarbons (PAHs)

Abstract

Rubicene, a key nanofragment of C₇₀, is attracting great attention owing to its unique molecular structure and physicochemical properties. As an indeno-annelated polycyclic aromatic hydrocarbon (indeno-PAH), rubicene itself has a planar p-orbital surface that could provide increased intermolecular electronic coupling, affording interesting optoelectronic properties. Interestingly, most of the substituted and aryl annulated rubicene PAHs possess twisted structures, which may demonstrate different optoelectronic properties. To date, many efforts have been made in the synthesis of rubicene PAHs, which demonstrate potential applications in organic field effect transistors (OFETs), organic solar cells (OSCs), sensors, lithium batteries, etc. However, the functionalization of rubicene remains a long-standing challenge from the synthetic perspective. In this mini-review, we summarized the major synthetic routes to construct rubicene PAHs, their physicochemical properties, and various applications. In the end, we propose a future direction on the development of rubicene PAHs.