The slow photo-induced CO2 release of N-phthaloylglycine

Chem Sci. 2024 May 24;15(25):9719-9732. doi: 10.1039/d4sc01604a. eCollection 2024 Jun 26.

Abstract

Carboxylic acids and carboxylates may release CO2 upon oxidation. The oxidation can be conducted electrochemically as in the Kolbe synthesis or by a suitable oxidant. In N-phthaloylglycine (PG), the photo-excited phthalimide chromophore acts as an oxidant. Here, the photo-kinetics of PG dissolved in acetonitrile is traced by steady-state as well as time-resolved UV/vis and IR spectroscopy. The experiments provide clear evidence that, contrary to earlier claims, the photo-induced CO2 release is slow, i.e. it occurs on the microsecond time range. The triplet state of PG is, therefore, the photo-reactive one.