Pyrene reacts with potassium thiocyanate and organic isothiocyanates in the presence of
trifluoromethanesulfonic acid to afford primary and secondary pyrene-1-carbothioamides in high yields.
These compounds were efficiently oxidatively desulfurized with Oxone® to the corresponding
carboxamides. The amides display solid-state fluorescence with quantum efficiencies up to 62%,
originating from monomers, aggregates (such as preformed dimers), and/or excimers, depending on the
substituent at the nitrogen atom. Single crystal X-ray diffraction characterization of one highly emissive
compound supports this assumption.