A highly fluorescent bora[6]helicene exhibiting circularly polarized light emission

Abstract

Heteroatom-doped helicenes have attracted great research interest due to their inherent chirality enabling fascinating new applications. Herein we present our successful synthesis of 19c-boratribenzo[<i>gh</i>,<i>jk</i>,<i>mn</i>][6]helicene, the hitherto longest and first configurationally stable pristine bora[<i>n</i>]helicene. It displays intense orange fluorescence and circularly polarized light (CPL) emission with a high quantum yield of up to 84%. X-ray single crystal analysis reveals a highly twisted, helical shape and intriguing intermolecular stacking. Complexation with a size-complemental aza[4]helicene yielded an unprecedented hetero-chiral π-π-stacked helicene dimer.