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Article
Direct Photorelease of Alcohols from Boron-Alkylated BODIPY Photocages
The Journal of Organic Chemistry
  • Julie A. Peterson, Iowa State University
  • Logan J. Fischer, Iowa State University
  • Elizabeth J. Gehrmann, Iowa State University
  • Pradeep Shrestha, Iowa State University
  • Ding Yuan, Iowa State University
  • Chamari S. Wijesooriya, Iowa State University and Ames Laboratory
  • Emily A. Smith, Iowa State University and Ames Laboratory
  • Arthur H. Winter, Iowa State University
Document Type
Article
Disciplines
Publication Version
Submitted Manuscript
Publication Date
3-27-2020
DOI
10.1021/acs.joc.0c00044
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.

Comments

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.

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
Julie A. Peterson, Logan J. Fischer, Elizabeth J. Gehrmann, Pradeep Shrestha, et al.. "Direct Photorelease of Alcohols from Boron-Alkylated BODIPY Photocages" The Journal of Organic Chemistry (2020)
Available at: http://works.bepress.com/arthur_winter/34/