Synthesis, luminescence properties, and theoretical insights of N-alkyl- or N,N-dialkyl-pyrene-1-carboxamide

We report the synthesis and photophysical properties of N-alkyl- or N,N-dialkyl-pyrene-1-carboxamide. These derivatives, as well as pyrene, exhibited blue emission. N-Alkyl-type derivatives exhibited strong fluorescence emission (Φfl = 0.61 in EtOH) in both nonpolar and polar solvents. On the other hand, N,N-dialkyl-type derivatives showed weak fluorescence emission (Φfl <0.01) due to vibrational deactivation. However, in highly viscous solvents such as glycerin, the quantum efficiencies of N-alkyl-type (Φfl = 0.91) and N,N-dialkyl-type (Φfl = 0.082) derivatives were increased. We also investigated the fluorescence mechanism of these compounds using time-dependent density-functional theory (TD-DFT). From these results, we find that highly fluorescent pyrene-1-carboxamide derivatives can be designed by introducing an appropriate functional group at the nitrogen atom of the amide. Thus, N,N-dialkyl-type pyrene-1-carboxamide has considerable potential for use in applications such as environmental response sensors and probes.

Graphical abstractN-Alkyl-pyrene-1-carboxamide derivatives exhibited bright blue emission in all solvents (for example, glycerin: Φfl = 0.91). While N,N-dialkyl-pyrene-1-carboxamide did not emit in most media studied (EtOH: Φfl <0.01), it showed relatively strong emission in viscous media (glycerin: Φfl = 0.082).Download full-size image