1,4-Naphthoquinone Derivative as Efficient Photolabile Molecule: Concise Synthesis and Photorelease of Various Functional Compounds

Abstract

We report on a series of 1,4-naphthoquinone (NQ)-based photolabile molecules, including various functional compounds to be released under light irradiation. They were efficiently prepared from a common precursor for a photoremovable masking group by attaching different functional compounds such as alcohols, amines, and acids with the concise synthetic method. Synthesis of the common precursor was optimized for two-step reactions and also for one-pot reaction involving a 1,4-addition and successive aldol reaction from NQ. The functional compounds, such as alcohols, amines, carboxylic, phosphoric, and sulfonic acids, were masked with the NQ-based precursor and were successfully released by irradiation with UV light (λ = 360 nm) in high yields (> 90%).