We are developing new photoremovable protecting groups that are based on trans o-phenolvinylketone derivatives, and can be used to photorelease alcohols in applications. When irradiated, trans-1 , forms it singlet excited state.  To undergo photoenolization the singlet excited state of 1  intersystem crosses to its triplet excited state, which forms 1,4-biradical and gives enols. The biradical has a lifetime of several nanoseconds and decays to form cis-1 . We are performing product studies, laser flash photolysis and theoretical calculation to identify the intermediates formed upon exposing 1  to light and how to control the competition between the photoenolization and trans-cis isomerization.

Trans phenolvinylhydroxy derivatives as novel photoremovable protecting groups to understand the mechanism and rate of photorelease via trans-cis isomerism

244th National Meeting (2012)

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