Two coumarin/pyrrole-fused heterocycles were synthesized to investigate their photochemical and redox-switching properties. Photooxidation of the colorless diphenyl-substituted pyrrolocoumarin resulted in a distinct change to red and a sharp decrease in fluorescence intensity. The photooxidized product can be swiftly reverted to the original form by NaCNBH<sub>3</sub> reduction or hydrogenation