Strategy for Engineering High Photolysis Efficiency of Photocleavable Protecting Groups through Cation Stabilization.

ABSTRACT: Photolabile protecting groups (PPGs) enable the precise activation of molecular function with light in many research areas, such as photopharmacology, where remote spatiotemporal control over the release of a molecule is needed. The design and application of PPGs in recent years have particularly focused on the development of molecules with high molar absorptivity at long irradiation wavelengths. However, a crucial parameter, which is pivotal to the efficiency of uncaging and which has until now proven highly challenging to improve, is the photolysis quantum yield (QY). Here, we describe a novel and general approach to greatly increase the photolysis QY of heterolytic PPGs through stabilization of an intermediate chromophore cation. When applied to coumarin PPGs, our strategy resulted in s

SUBMITTER: Schulte AM 

PROVIDER: S-EPMC9284546 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature