Synthesis and Photophysical Properties of a 13,13′-Bibenzo[b]perylenyl Derivative as a π‑Extended 1,1′-Binaphthyl Analog

A 13,13′-bibenzo­[b]­perylenyl derivativean axially chiral π-extended compound in which two perylene subunits fused to 1,1′-binaphthyl scaffoldhas been synthesized from 1,8-dibromo­phenanthrene using an anionic cyclodehydrogenation reaction in the presence of potassium metal as the key step. The pair of enantiomers can be separated by chiral high-performance liquid chromatography (HPLC), which showed a strong circular dichroism (CD) (Δε = 330 M–1 cm–1 at 449 nm, |gCD| = 5.8 × 10–3 at 453 nm), high fluorescence quantum yield (Φf = 64%), and strong circular polarized luminescence (CPL) (|gCPL| = 5 × 10–3 at 454 nm) in solution phase.