Photoacids, compounds that undergo excited state proton transfer (ESPT), can be used to control pH spatially and temporally in various chemical and biological processes, such as acid-catalyzed polymerization. We propose to use Schiff base chemistry to investigate the effect of structural changes on the ESPT mechanism and energetics. Here we examine the photochemistry of structural isomers, 8-phenylimino-2-naphthol and 8-phenylimino-1-naphthol, to study intermolecular versus intramolecular ESPT mechanisms, respectively. These Schiff bases introduce additional excited state pathways, including photoisomerization and excited state energy transfer. We use steady-state and time-resolved absorption and emission spectroscopy to probe the different photochemical pathways of these targets along with control 1-naphthalaniline. The competing excited state pathways among the different candidates will be discussed.

Investigating excited state pathways of 8-phenyliminonaphthol isomers

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