Date of Award

5-31-2017

Document Type

Campus Access Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Jonathan Rochford

Second Advisor

Michelle Foster

Third Advisor

Neil Reilly

Abstract

Photoacoustic (PA) imaging has recently caught the attention of researchers due to its capability of generating high contrast images in deep tissue at a lower cost when compared with traditional diagnostic imaging. However, the field of PA imaging is lacking a sufficient library of molecular contrast agents that absorb within the biological transparency window (700-1300 nm). Chapter 1 of this dissertation presents a literature survey encompassing the current state-of-the-art in molecular photoacoustic contrast agents for application in biomedical imaging. Chapter 2 pertains to the design, synthesis and characterization of electron-rich dimethylaminophenyl and dimethylaminothiophene functionalized curcuminoid molecules, for application as PA contrast agents, whose absorbance is red-shifted toward the biological transparency window. A systematic approach was taken with respect to the design of a library of curcuminoid dyes whereby the terminal groups attached to the curcuminoid core were varied in an incremental fashion, i.e. a series of aryl and dimethylamino-aryl terminal groups were chosen based upon the phenyl, naptha and thiophene ring systems. The photophysical and electrochemical properties of each dye are presented using a combination of techniques including UV-Vis electronic absorption spectroscopy, steady-state and time-resolved fluorescence emission spectroscopy, and cyclic voltammetry. The electronic properties of these curcuminoid dyes are further probed by computational analysis using density functional theory methods. The absorbance characteristic and photoacoustic properties did not surpass previous curcuminoid compounds, the data collected provides vital structural and photo-physical information in improving the availability of efficient curcuminoid contrast agents for PA imaging.

Comments

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Available for download on Sunday, June 30, 2019

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