Synthesis and Crystal Engineering of Fluorinated Rubrenes

Rubrene is known as a high-mobility organic semiconductor; here, we describe how partial fluorination enhances the oxidation stability of rubrene. Six fluorinated rubrenes are synthesized via dimerization of propargyl alcohols and via Suzuki coupling to a tetrachlorotetracene. Single crystal analysis by X-ray diffraction (XRD) revealed four molecular packing structures, including a herringbone arrangement and a 2D brick packing, which were further characterized by Hirshfeld surface analysis and fingerprint plots. Additionally, cyclic voltammetry (CV) confirmed a subsequent lowering of HOMO and LUMO energy levels with an increasing degree of fluorination.