In 2021, Musolino and co-workers published a comprehensive structure-function survey of the trifluoromethyl aryl diazirine motif, varying the electronics on the aromatic ring. As shown in Fig. , the absorbances associated with the diazirine group shifted to longer wavelengths when electron-donating groups were appended to the para-position of the aryl ring, while electron-withdrawing groups had the opposite effect. Superficially, this result might seem puzzling: if the central carbon of the diazirine motif is sp hybridized (as is implied by the typical structural representation of a diazirine, with four sigma bonds attached to the central carbon atom), then why should functionality present at the para-position of the aromatic ring affect the electronics of the diazirine so dramatically?