Degree Type

Thesis

Date of Award

2020

Degree Name

Doctor of Philosophy

Department

Chemistry

Major

Organic Chemistry

First Advisor

Arthur H Winter

Abstract

The research herein describes design of BODIPY derived photoremovable protecting groups. Chapter 1 describes the design and synthesis of red-shifted BODIPY photoremovable protecting groups. The initial boron-fluorinated BODIPY derivatives have low quantum yields of photorelease. Boron-methylation of these red-shifted BODIPY photoremovable protecting groups effectively increases quantum yields of release. The boron methyl bond is thermally stable; however, upon irradiation it is cleaved and replaced with solvent, resulting in a chromophore with a higher quantum yield of fluorescence. Chapter 2 describes the application of this photoproduct for single molecule localization microscopy. Chapter 3 discusses the ability for the boron-methylated BODIPY derivatives to release alcohols directly from the meso position without use of a carbonate linkage. Chapter 4 describes selective photorelease of red and green BODIPY photoremovable protecting groups along with a UV-absorbing coumarin photoremovable protecting group.

DOI

https://doi.org/10.31274/etd-20200624-72

Copyright Owner

Julie Ann Peterson

Language

en

File Format

application/pdf

File Size

242 pages

Available for download on Wednesday, June 16, 2021

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