Abstract: Polycyclic aromatic hydrocarbons (PAHs) are among the most versatile materials for applications in organic light-emitting diodes (OLEDs) or photovoltaic devices (OPVs). Our goal is to improve the optoelectronic properties of the parent hydrocarbons through the incorporation of boron atoms and to overcome solubility issues by helical distortion of the molecular scaffolds. Herein, we show that an intramolecular, Ni-mediated Yamamoto C−C-coupling reaction carried out on the tetrabrominated starting material A furnishes either the doubly boron-doped dihelicene (1) or the oxadiborepin (2). The decisive factor is the choice of solvent: pyridine or THF lead to compound 1 (79 %) or 2 (81%), respectively. Both molecules are benchtop stable, soluble even in cyclohexane, and can be purified by column chromatography. They are excellent blue emitters with photoluminescence quantum efficiencies of 69% (1) and 45% (2). The dihelicene undergoes reversible reduction at a potential value of E1/2 = –1.65 V (vs. ferrocene).

Access to a doubly boron-doped dihelicene or an oxadiborepin from the same precursor

2019 Spring National Meeting

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