Date of Award

2020

Degree Type

Thesis

Degree Name

Master of Science in Chemistry

Department

Chemistry

First Advisor

Mindy Levine

Abstract

The sensitive, selective, and practical detection of aliphatic alcohols is a continuing technical challenge with significant impact in public health work and environmental remediation efforts. Reported in the first manuscript is the use of a β-cyclodextrin derivative to promote proximity-induced interactions between aliphatic alcohol analytes and a brightly colored organic dye, which result in highly analyte-specific color changes that enabled accurate alcohol identification. Linear discriminant analysis of the color changes enabled resulting in 100% differentiation of the colorimetric signals obtained from methanol, ethanol, and isopropanol in combination with BODIPY and Rhodamine dyes. The resulting solution-state detection system has significant broad-based applicability because it uses only easily available materials to achieve such detection, with moderate limits of detection obtained. Future research with this sensor system will focus on decreasing limits of detection as well as on optimizing the system for quantitative detection applications.

Reported in Chapter 2 of this thesis are our efforts towards the development of similar cyclodextrin-based systems for the detection of anabolic steroids that are of interest in illegal doping scandals. These systems, in close analogy to other systems developed in our group, rely on the fact that combining the target analytes with a high quantum yield fluorophore results in a measurable, analyte-specific change in the fluorophore emission signal. Promising results were seen in our solution-state detection of anabolic steroids via the use of β-cyclodextrin derivatives as supramolecular scaffolds and Rhodamine 6G as the signal transducing element. Using linear discriminant analysis, arrays were generated, illustrating the differentiation and classification of the analytes with high selectivity in the system. Limits of detection falling below the micromolar range show a high sensitivity of the system. Current efforts are focused on improving the reproducibility of these experiments to enable a high functioning detection system as well as efforts toward moving to a solid-state detection system.

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