Direct Photorelease of Alcohols from Boron-Alkylated BODIPY Photocages | Zendy

Julie Peterson | Zendy; Logan J. Fischer | Zendy; Elizabeth J. Gehrmann | Zendy; Pradeep Shrestha | Zendy; Ding Yuan | Zendy; Chamari S. Wijesooriya | Zendy; Emily A. Smith | Zendy; Arthur H. Winter | Zendy

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Direct Photorelease of Alcohols from Boron-Alkylated BODIPY Photocages

Author(s) -

Julie Peterson,

Logan J. Fischer,

Elizabeth J. Gehrmann,

Pradeep Shrestha,

Ding Yuan,

Chamari S. Wijesooriya,

Emily A. Smith,

Arthur H. Winter

Publication year - 2020

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.0c00044

Subject(s) - bodipy , alkylation , chemistry , ether , boron , photochemistry , alcohol , fluorescence , organic chemistry , catalysis , physics , quantum mechanics

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 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.

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