Abstract
The photohydration of o-hydroxy-α-phenylstyrene ( 7) has been studied using product studies, laser flash photolysis (LFP), and fluorescence measurements, and shown to react via excited state intramolecular proton transfer (ESIPT), to give the corresponding o-quinone methide ( 13) ( λ max = 310, 420 nm in 1 : 1 H 2O–CH 3CN). The same intermediate was also observed on LFP of o-hydroxybenzyl alcohol ( 10), a system known to give o-quinone methides efficiently, but via a different mechanism. ESIPT of 7 to give 13 is not significantly enhanced by water as the species was also observed in neat CH 3CN; addition of water (up to 1 : 1 H 2O–CH 3CN) did not increase its yield substantially. Efficient ESIPT of 7 in neat CH 3CN is corroborated by its low fluorescence emission quantum yield and subnanosecond fluorescence lifetime. These results provide new insights into ESIPT from phenol to alkene carbon, a process that has not received much attention although 7 is a close relative of o-hydroxybenzophenone ( 8), an archetypical system for the illustration of ESIPT.
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