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[gh,jk,mn][6]helicene, the hitherto longest and first configurationally stable pristine bora[n]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.