Direct Photorelease of Alcohols from Boron-Alkylated BODIPY Photocages

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2020-03-27
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Peterson, Julie
Fischer, Logan
Gehrmann, Elizabeth
Shrestha, Pradeep
Yuan, Ding
Wijesooriya, Chamari
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Smith, Emily
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Winter, Arthur
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Ames National Laboratory

Ames National Laboratory is a government-owned, contractor-operated national laboratory of the U.S. Department of Energy (DOE), operated by and located on the campus of Iowa State University in Ames, Iowa.

For more than 70 years, the Ames National Laboratory has successfully partnered with Iowa State University, and is unique among the 17 DOE laboratories in that it is physically located on the campus of a major research university. Many of the scientists and administrators at the Laboratory also hold faculty positions at the University and the Laboratory has access to both undergraduate and graduate student talent.

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Chemistry

The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).

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The Department of Chemistry was founded in 1880.

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1880-present

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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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Wed Jan 01 00:00:00 UTC 2020
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