Direct Photorelease of Alcohols from Boron-Alkylated BODIPY Photocages
Julie Peterson, Logan J. Fischer, Elizabeth J. Gehrmann, Pradeep Shrestha, Ding Yuan, Chamari S. Wijesooriya, Emily A. Smith, Arthur H. Winter
Abstract
BODIPY photocages allow the release of substrates using visible light irradiation. They have the drawback of requiring reasonably good leaving groups for photorelease. Photorelease of alcohols is often accomplished by attachment with carbonate linkages, which upon photorelease liberate CO2 and generate the alcohol. Here, we show that boron-alkylated BODIPY photocages are capable of directly photoreleasing both aliphatic alcohols and phenols upon irradiation via photocleavage of ether linkages. Direct photorelease of a hydroxycoumarin dye was demonstrated in living HeLa cells.
Topics & Concepts
BODIPYAlkylationChemistryEtherBoronPhotochemistryAlcoholFluorescenceOrganic chemistryCatalysisQuantum mechanicsPhysicsPhotochromic and Fluorescence ChemistryPhotoreceptor and optogenetics researchNanoplatforms for cancer theranostics