Nitrobenzyl-based PPGs are often considered the most commonly used PPGs. These PPGs are traditionally identified as Norrish Type II reaction as their mechanism was first described by Norrish in 1935. Norrish elucidated that an incident photon (200 nm –10 s. Following resonance of the π-electrons, a five-membered ring is formed before the PPG is cleaved yielding 2-nitrosobenzaldehyde and a carboxylic acid.
Overall, nitrobenzyl-based PPGs are highly general. The list of functional groups that can be protected include, but are not limited to, phosphates, carboxylates, carbonates, carbamates, thiolates, phenolates and alkoxides. Additionally, while the rate varies with a number of variables, including choice of solvent and pH, the photodeprotection has been exhibited in both solution and in the solid-state. Under optimal conditions, the photorelease can proceed with >95% yield. Nevertheless, the photoproducts of this PPG are known to undergo imine formation when irradiated at wavelengths above 300 nm. This side product often competes for incident radiation, which may lead to decreased chemical and quantum yields.