Direct Photorelease of Alcohols from Boron-Alkylated BODIPY Photocages

Date
2020-03-27
Authors
Peterson, Julie
Fischer, Logan
Gehrmann, Elizabeth
Shrestha, Pradeep
Yuan, Ding
Wijesooriya, Chamari
Smith, Emily
Winter, Arthur
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Altmetrics
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Ames Laboratory
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Chemistry
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Abstract

BODIPY photocages allow release of substrates us-ing 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 gen-erate 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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This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review. To access the final edited and published work see DOI: 10.1021/acs.joc.0c00044. Posted with permission.

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