Abstract
Chiral organic fluorophores have significant promise in the development of efficient emitters of circularly polarized light. Herein we describe a helically chiral boron dipyrromethene (BODIPY) with a hitherto unreported N,N,O,C-boron-chelation motif, synthesised by means of a one-pot boron metathesis, nucleophilic aromatic substitution (SNAr), Suzuki coupling, boron chelation, cascade reaction. Resolution of the racemic BODIPY (by preparative HPLC on a chiral stationary phase) allowed examination of the chiroptical properties of the resulting enantiomers (lambda(max)(abs)=593nm, lambda(max)(em)=622nm, epsilon=30000m(-1)cm(-1), phi(F)=0.49, vertical bar g(lum vertical bar)=3.7x10(-3) (hexane)). This is the first example of circularly polarised emission from a non-C-2-symmetric helically chiral N,N,O,C-BODIPY and as such provides a valuable benchmark for future developments in this compound series.