We report ruthenium(II)-catalyzed sequential C-H/N-H alkenylation cascade of phenanthroimidazole and alkenes to form novel phenanthroimidazoisoindol acrylates via dual C-H activation and aza-Michael reaction. The two nitrogen atoms of the imidazole ring act as directing groups for regioselective dual sequential ortho C-H activation. These polycyclic N-heterocycles were evaluated for their photophysical properties.