Abstract
Proton-transfer reactions provide the fundamental basis for acid-base chemistry in protic solvents. Literally hundreds of examples of excited-state proton- transfer reactions are known[1]. Picosecond, time-resolved measurements on spectrally distinct acid-base pairs yield direct kinetic information and provide insight into the effect of molecular structure on excited-state proton-transfer dynamics[2,3]. One particularly interesting and seemingly paradoxical system is 1-naphthol. From a Fllrster cycle calculation, 1-naphthol is predicted to have an excited state pK similar to 2-naphthol[4], for which steady-state emission from both the neutral (acidic) and anionic (basic) excited-state species is clearly observed. In contrast, the neutral form of excited 1-naphthol shows “very weak” fluorescence which is “extremely difficult” to measure[5]. Detailed studies of the mechanism and kinetics of excited-state proton transfer in 1-naphthol are needed to elucidate how the differences in molecular structure between these molecules affect excited-state proton-transfer processes.
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