LE3 .A278 2012

2012

Lukeman, Matthew

Acadia University

Bachelor of Science

Honours

Chemistry

Chemistry

A series of recently prepared meso-functionalized BODIPY dyes was studied for their possible application as fluorogenic probes for nucleophiles. The meso-formyl BODIPY dyes are non-emissive compared to their meso-acetoxy or hydroxymethyl counterparts, and thus can serve as fluorogenic off/on probes for nucleophilic attack. Preliminary kinetic studies are herein described where hemi-acetal or acetal formation is followed in real time in acetonitrile and liposomes in the presence of various alcohols and thioalcohols as substrates. It was found that electron-withdrawing groups increased the reactivity of the dyes and that the dyes were more sensitive to small nucleophiles. The photostability of the meso-acetoxymethyl BODIPY dyes was studied in the presence and absence of dissolved oxygen to provide insight on the mechanism of BODIPY photodecomposition. It was found that the dyes were more photostable in the absence of oxygen, and that the addition of cyano groups at the C2 and C6 positions drastically increased photostability. The meso-formyl dyes were further studied to explain their non-emissive behaviour and were found to be luminescent at 77 K in diethyl ether glass. In addition to the kinetic studies, the synthesis of a new series of α,β-unsaturated BODIPY aldehydes was pursued as possible sensors for Michael addition, but the reactions were unsuccessful.

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https://scholar.acadiau.ca/islandora/object/theses:900