Photochemical reaction of nitro-polycyclic aromatic hydrocarbons: effect by solvent and structure

Photochemical degradation of 1-nitropyrene, 2-nitrofluorene, 2,7-dinitrofluorene, 6-nitrochrysene, 3-nitrofluoranthene, 5-nitroacenaphthene, and 9-nitroanthracene was examined in CHCl₃, CH₂Cl₂, DMF, DMF/H₂O (80/20), CH₃CN, or CH₃CN/H₂O (80/20). The degradation mostly follows the first order kinetics; but a few follow second order kinetics or undergo self-catalysis. The photodegradation rates follow the order: CHCl₃ > CH₂Cl₂ > DMF > DMF/H₂O > CH₃CN > CH₃CN/H₂O. DMF is an exceptional solvent because three of the seven compounds undergo self-catalytic reaction. 9-Nitroanthracene, which has a perpendicular nitro group, is the fastest, while the more compact 1-nitropyrene and 3-nitrofluoranthene are the slowest degrading compounds.