Abstract

The design and characterization of molecules that undergo excited-state intra- and intermolecular proton transfer reactions are of interest because of the unique energy and directional characters that determine the behavior of many systems with a wide range of applications. This chapter focuses on two systems that exhibit excited state proton-transfer reaction: 2-(2′-hydroxyphenyl)benzoselenazole (HBSE) and 3-hydrxyflavone (3HF) (Scheme). HBSE is a derivative of 2-(2”-hydroxyphenyl)benzothiazole that, upon electronic excitation, rapidly undergoes an intramolecular H-atom transfer reaction to give keto tautomer (K). The results for HBSE in solution are discussed using fs detection of its emission. The experiments show that the fast nonradiative processes are related to in-plane and out-of-plane motions in the initially formed K phototautomer. For 3HF in solution, the different observed dynamics of inter and intramolecular proton transfer reaction are affected by H-bonding interactions with the solvent molecule.

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