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January 24, 2026The Journal of Organic Chemistry2 citations

Synthesis and Crystal Engineering of Fluorinated Rubrenes

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FHFritz HenkeAKAdrian KishontiSWSteffen L. Woltering

Key Points

  • The aim is to explore how partial fluorination affects the oxidation stability and electronic properties of rubrene.
  • Synthesize six fluorinated rubrenes using dimerization of propargyl alcohols and Suzuki coupling.
  • Perform single crystal analysis using X-ray diffraction to identify molecular packing structures.
  • Conduct Hirshfeld surface analysis and fingerprint plots for characterization.
  • Use cyclic voltammetry to measure HOMO and LUMO energy levels in relation to fluorination degree.
  • Four distinct molecular packing structures were identified, including herringbone and 2D brick packing.
  • Cyclic voltammetry showed a decrease in both HOMO and LUMO energy levels with increased fluorination.
  • Partial fluorination significantly enhanced the oxidation stability of rubrene.

Abstract

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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Cite This Study

Henke et al. (2026) studied this question.

synapsesocial.com/papers/6974602bbb9d90c67120a0fdhttps://doi.org/10.1021/acs.joc.5c02355
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