Corannulene-based acenes

Abstract

Synthesis of diacenes still represents a considerable challenge due to their poor stability and low solubility. In this work, we have designed and synthesized two novel corannulene-based pentacenes, CORA-monPA and CORA-bisPA. X-ray crystallographic analysis revealed their unique geometry and slip-stack columnar structure. Furthermore, the absorption and emission spectra in combination with DFT calculations were used to investigate the photophysical properties and (anti)aromaticity of CORA-monPA and CORA-bisPA. Importantly, the X-ray crystallographic analysis and ¹H NMR investigations revealed that CORA-monPA underwent the Diels–Alder reaction with C₆₀ to form the fullerene adduct CORA-monPA-C₆₀, which is packed as two comma-shaped swirl-like structures in the solid phase.