BODIPY photocages allow 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 CO 2 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.
Selective deprotection of functional
groups using different wavelengths
of light is attractive for materials synthesis as well as for achieving
independent photocontrol over substrates in biological systems. Here,
we show that mixtures of recently developed visible light-absorbing
BODIPY-derived photoremovable protecting groups (PRPGs) and a coumarin-derived
PRPG can undergo wavelength-selective activation, giving independent
optical control over a mixture of photocaged substrates using biologically
benign long-wavelength light.
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