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.