Date of Award

2002

Degree Name

Chemistry

College

College of Science

Type of Degree

M.S.

Document Type

Thesis

First Advisor

Robert J. Morgan

Second Advisor

Michael L. Norton

Third Advisor

Lawrence R. Schmitz

Abstract

(PICs, Figure 1) are a new class of fluorescent dyes which are prepared by an exceedingly flexible methodology. Using computational chemical methods, the excitation and emission maxima of these dyes were simulated. This was best accomplished through geometry optimization (MM+) followed by calculating the electronic spectrum with ZINDO/S. This protocol has been found to be effective and has the potential to greatly streamline the design of new longer wavelength dyes. Several new longer wavelength dyes have now been identified as synthetic targets.

The presence of amino groups on a known fluorescent ring system is well established to markedly affect the optical properties of the dye. Methodology had been developed toward the amination of different position on the 2-(2-pyridyl)-carboxyl-quinoline ring system, leading to the testing of 3 new amino substituted fluorescent dyes, including 4-amino-2-(2-pyridyl)-quinoline. This is also the precursor to 4-isothiocyanato-2-(2-pyridyl)-quinoline, which is a potentially useful cellular tag for proteins.

The behavior of green fluorescent PICs in live smooth muscle cells was probed using confocal microscopy. Several dyes were proven to be effective in staining the mitochondria. A novel red (488/675nm) nuclear envelope stain was identified and investigated.

Subject(s)

Basic dyes.

Chemistry, Organic.

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