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Updated: Jan 23, 2026
From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Synthesis and Crystal Engineering of Fluorinated Rubrenes
Fritz Henke1, Adrian Kishonti2,3, Steffen L Woltering2,3
1Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany.
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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.
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