FUNCTIONALIZATION OF BODIPY-DYE SCAFFOLD USING CLICK-CHEMISTRY REACTIONS

• Main Author: Polenz, Bradley P.
• Other Authors: Sergei V Dzyuba
• Format: Others
• Language: en
• Published: Texas Christian University 2011
• Subjects: College of Science and Engineering
• Online Access: http://etd.tcu.edu/etdfiles/available/etd-05042011-125626/

The design, synthesis and uses of small fluorescent molecules are among most active areas of modern research especially with 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes. The spectroscopic properties of the BODIPY dyes can be altered by structural modification of the dye. One of the leading synthetic tools with many numerous applications is the copper-promoted alkyne-azide cycloaddition, commonly known as `click-chemistry'. Knowing the modification of BODIPY dyes, the use of a single alkyne-containing BODIPY scaffold might be an interesting tool to create several structurally and functionally-diverse fluorescent dyes using `click chemistry'-type of reactions (Chapter 1). Earlier cycloaddition studies in the group found a small amount of 5-I-triazole-BODIPY as a side product. It was found that low concentrations of the alkyne and the use of DMAP led to the formation of 5-I-triazoles as the only cycloaddition products. This methodology was applied for the synthesis of the 5-iodo-triazole-containing BODIPY dyes (Chapter 2). Modification of a BODIPY scaffold via isoxazole tether was demonstrated for the first time. It was discovered that ZnBr2 is a viable general catalyst for the formation of the isoxazole moiety. Some of the isoxazole-click BODIPY dyes were tested for their ability to recognize distinct conformations of the soluble amyloid oligomers (Chapter 3). Using photochemistry to facilitate the tio-yne reaction it appeared that by simply switching solvents, it was possible to completely switch between cis and trans isomers of the BODIPY dyes (Chapter 4).