Both photo-and electrochemical transformations represent excellent opportunities for the development of environmentally friendly methodologies which, if combined, would result in improved methodologies. Thus, we present here a family of naphthalene diimide photocatalysts comparing a "pure" photochemical and an electro-photochemical transformation; by means of a CÀ H substitution in (hetero)aromatic systems with CÀ C bond formation. We identify a system that has the potential to be applied in both approaches with minor changes in the reaction conditions and recognize the excitation of radical anion of naphthalene diimides as the key event. Both approaches produce similar yields and reaction rates, although a consecutive photoinduced electron transfer (conPET) process shows in principle a simpler setup and more tolerance to a poor catalyst solubility, the electro-PET process improves selectivity and gives more room for optimization. The more accessible "pure" photochemical approach could be used as an initial assessment for photocatalytic transformation and electrophotocatalytic transformation.

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We describe the effect of water addition in the catalyst performance for a C−H functionalization of benzene. Improved yields and selectivity were achieved in a consecutive photoredox catalysis in contrast to the reaction without water. Mechanistic analysis demonstrated this is due to a better catalyst stability and faster kinetic rather than a change in the different steps of the mechanism. The addition of water constitutes a convenient approach to improve catalyst performance, and it was also observed with other catalysts.

We present a computational approach for predicting key properties of organic radical anions, including excited-state lifetimes and redox potentials. The approach shows good agreement with experimental data and has potential...