Double Click for Chirality: Chiral Dibenzo‐cycloocta‐bis‐triazoles via Strain‐Promoted Alkyne‐Azide Cycloaddition

Abstract The synthetically convenient strain promoted double azide cycloaddition of the Sondheimer‐Wong diyne produces resolvable chiral dibenzo‐cycloocta‐bis‐triazoles whose stereogenicity, to date, has gone unrecognised. Enantiomers were separable by chiral HPLC and showed no racemization at 100 °C. This unique method to produce chiral substrates was exploited for the synthesis and resolution of a chiral fluorescent BF 2 ‐azadipyrromethene, with absorption and emission spanning the important spectral range of 600 to 700 nm. The fluorophore properties were studied utilising X‐ray structural analysis, electronic circular dichroism spectra and DFT calculations.