Aryl diazirine reagents are ubiquitous in the chemical biology field, and yet in the vast majority of cases, the aromatic rings incorporated into the diazirine motif have been limited to simple monsubstituted benzenes. While the analogous azide reagents (as well as some representative diazoalkanes) have been extended to include better chromophores, permitting longer wavelength activation, no such investigations have been made for trifluoromethyl aryl diazirines, perhaps because of a perception that the saturated central carbon atom would not permit effective conjugation to an extended pi system.