The electron-donating capabilities of carbazoles have stimulated interest in their use as photoinduced single-electron reductants. Due to the modularity of the carbazole, a further broadening and understanding of their reactivity could be achieved by manipulating the structure. Herein, eight carbazole derivatives were synthesized, characterized, and assessed as single-electron photoreductants in the hydrodehalogenation of aryl halides and the arylation of N-methylpyrrole.