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 by a concise synthetic method. Synthesis of the common precursor was optimized for two-step reactions and also for a one-pot reaction involving a 1,4-addition and successive aldol reaction from NQ. The functional compounds, such as alcohols, amines and 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%).

Key words

photolabile molecules - photoremovable groups - 1,4-naphthoquinone - 1,4-addition - aldol reaction - photorelease

Publication History

Received: 22 June 2022

Accepted after revision: 29 August 2022

Accepted Manuscript online:
29 August 2022

Article published online:
29 September 2022

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