Date of Award

2000

Document Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

First Advisor

Steven A. Soper

Abstract

The research presented in this dissertation entails the preparation, characterization, and analytical application of a series of novel tricarbocyanine, phthalocyanine, and napthalocyanine dyes which can be used as fluorescent probes for bioanalytical assays. The first part of this research focuses on the synthesis of a nuclear staining tricarbocyanine dye used for low-level detection of DNA restriction fragments separated via capillary electrophoresis. The second part focuses on the synthetic, purification, and applications of several tricarbocyanine, phthalocyanine, and naphthalocyanine dyes. The tricarbocyanine dyes were synthesized to contain a heavy atom-modification to enhance k isc through spin-orbit coupling and a reactive functional group to react with primary amines of various biomolecules. The heavy-atom modified tricarbocyanine dyes also possessed similar absorption and emission maxima as well as similar electrophoretic mobilities, but they have unique fluorescence lifetimes. Like the tricarbocyanine dyes, the phthalocyanine and naphthalocyanine dyes were also synthesized to contain a reactive group for facile conjugation to various biomolecules. The methodology for these dyes will be used for base-calling in DNA sequencing involving the use of a single-lane CGE separation of the near-infrared (near-IR) dye-labeled DNA fragments with the terminal bases identified via fluorescence lifetime discrimination.

ISBN

9780599853416

Pages

137

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