We report the synthesis and properties of a variety of substituted 4,4-difluoro-4-bora-3a,4a-diaza- s-indacene (BODIPY), with potential to be developed into biological probes. The substituents at 2, 6-positions on the BODIPY were changed by the use of corresponding pyrrole building blocks. Electron-donating and withdrawing substituents were introduced on to the BODIPY core in order to study their effects on the photochemical properties. Different strategies were carried out to saponify the ester groups on the BODIPY to obtain the carboxylic acid derivatives. These carboxylic acid groups were expected to increase the water-solubility of the BODIPY as well as facilitate the bio-conjugation. However, due to incompatibility of the BODIPY core to the reaction conditions, targeted products were not obtained. In couple of cases, the meso position was functionalized by 4-formylbenzoic acid to enable the bio-conjugation of new dyes. Alternative routes to synthesize carboxylic acid derivatives of the novel BODIPYs are under investigation.
|Advisor:||Schramm, Michael P.|
|Commitee:||Nakayama, Kensaku, Narayanaswami, Vasanthy|
|School:||California State University, Long Beach|
|Department:||Chemistry and Biochemistry|
|School Location:||United States -- California|
|Source:||MAI 55/02M(E), Masters Abstracts International|
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