Photobases are compounds that become more basic when promoted to an excited electronic state. Previous experimental and computational studies have demonstrated that several quinoline and quinoline-derived compounds are strong photobases (pK(2)* > 14). Moreover, the strength of photobasicity was shown to depend strongly on the identity and position of the substituent group(s), with the strongest photobases having multiple electron-donating substituents on a fused benzene ring as opposed to the ring containing the photobasic nitrogen atom. These electron-donating substituents build up electron density on one side of the molecule that shifts onto the nitrogen-containing ring in the electronic transition. This shift in electron density produces an increase in negative charge on the ring nitrogen atom responsible for the photobasicity. In this paper, we expand on our previous investigation to study the effect of an additional ring nitrogen atom on photobasicity in aromatic heterocycles. In particular, we consider how the thermodynamic driving force for excited-state protonation can be tuned by changing the relative placement of the ring nitrogen atoms and varying the position and number of electron-donating substituents. In the set of 112 molecules screened, we identified 42 strong photobases with generally comparable pK(a)* but lower vertical excitation energies than the quinoline derivatives with only a single ring nitrogen atom. We additionally explored photobasicity in substituted azaindole and carboline derivatives, identifying 76 strongly photobasic compounds with pK(a)* as large as 22.6 out of the 155 compounds that we considered. Overall, this work provides new insights into the design principles necessary to develop next-generation photocatalysts that employ photobasicity.