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Photobases are compounds that become strong bases after electronic excitation. Recent experimental studies have highlighted the photobasicity of the 5-R quinoline compounds, demonstrating a strong substituent dependence to the pKa*. In this paper, we describe our systematic study of how the thermodynamic driving force for photobasicity is tuned through substituents in four families of nitrogen-containing heterocyclic aromatics. We show that substituent position and identity both significantly impact the pKa*. We demonstrate that