An Unexpected "Bodipy-Like" Dipyrromethene with Ph Dependent On/Off Fluorescent Properties

Date of Award

2022

Degree Name

M.S. in Chemistry

Department

Department of Chemistry

Advisor/Chair

Shawn Swavey

Abstract

The spectroscopic properties of a fluoranthene pyrrole based, meso-mesityl substituted dipyrromethene (FlMst) were investigated.This novel compound produced visible absorption and substantial fluorescent properties. This compound is the first non-bridged dipyrromethene to produce substantial flourescence that has been recorded in literature. FlMst produced an absorption peak at 583 nm, and an emission peak at 640 nm, with a fluorescence quantum yield of 0.07. The effects of pH on optical behavior was studied through both a titration using TFA, as well as electrochemical experiments using cyclic voltammetry. The titration with TFA resulted in the loss of fluorescent, and a shift of the absorbance peak to 630 nm. Cyclic voltammetry provided supporting evidence for the effect of TFA on FlMst, offering data on molecular orbital shifts and stabilizations congruent with the titration data. This demonstrated the "On/Off switch" like behavior of FlMst in environments of varying pH. This work has a primary focus on the attributes on the FlMst dipyrromethene, but this thesis also presents a preliminary investigation of the synthesis, spectroscopy, and electrochemistry of the FlMst BODIPY.

Keywords

Chemistry, Organic Chemistry, Bodipy, Dipyrromethene, Fluorescence, pH Dependent Fluorescence, Fluorantho Mesityl

Rights Statement

Copyright © 2022, author

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