Typescript (photocopy). / Digitized by Kansas Correctional Industries / Department: Chemistry.

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A series of seven functionalized near-infrared aza-BODIPY dyes have been synthesized and their spectroscopic properties measured. Their fluorescence emissions could be tuned by altering the electronic substituents on the aryl-groups. A through-bond energy transfer cassette featuring two fluorescein units as donor, and an aza-BODIPY dye as acceptor, was then synthesized and its preliminary spectroscopic properties examined. This cassette exhibited absorption and fluorescence characteristics that were highly dependent on the pH and the solvent polarity. Furthermore, no energy transfer was observed upon excitation of the donor. Novel near-infrared aza-BODIPY were also synthesized via a one-pot, two step reaction. Upon demethylation and intermolecular cyclization onto the B-atom, a ~ 100 nm red¬shift of both the absorption and fluorescence emission maxima could be observed. Through-bond energy transfer cassettes based on squaraines have also been synthesized and their spectroscopic properties studied. These cassettes exhibited fast and efficient energy transfer from the donor to the acceptor. In depth experiments have also been realized to correlate the rate of energy transfer and structure on 3 different sets of through-bond energy transfer cassettes. No correlations could be made between the rate of the energy transfer and the nature of the acceptor, and the distance between the donor and acceptor. Finally, the use of DPP (diketo-pyrrolopyrolle) pigment as a potential donor for through-bond energy transfer cassettes was investigated. Three water-soluble DPPs dyes were prepared and studied. They all displayed weak fluorescence in water.

Water-soluble fluorescent probes with emission in the 600-800 nm region have significant potential in biological applications such as cell imaging. Most fluorescent probes however suffer from limited fluorescence brightness in aqueous media due to aggregation and self-quenching. Their photostability in animal models for an extended period of time is also a concern. One way of improving their photophysical properties is to encapsulate them in a protective matrix to form fluorescent nanoparticles. We have synthesized a set of six through-bond energy transfer cassettes which emit in the 600-800 nm region with Fluorescein or BODIPY as donor and benzophenoxazine dye Nile Red or cyanine dye Cy5 as acceptor. Their photophysical properties in organic and aqueous media were evaluated. Some of these cassettes were encapsulated in silica or calcium phosphate nanoparticles (20 nm in diameter) to improve their solubility and photophysical properties in aqueous media. We also synthesized some water-soluble benzophenoxazine based fluorophores and the impact of different water-soluble groups on their emission characteristics in aqueous media was studied. Selected fluorophores were used for in vitro cellular imaging studies.

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