| Abstract | aza-BODIPY dyes are fluorescent dyes that have numerous applications due to their photophysical properties, which can be tuned via various structural modifications of the dye's unique scaffold. These dyes are known to interact with certain peptides and proteins as well as protein aggregates. The neurotoxic Ab1-42 peptide is of particular interest due to its implications in the development and progression of Alzheimer's disease. Many approaches to synthesizing these dyes exist, but they are not facile as they require long reaction times, special reaction conditions, and extensive purifications to obtain desired aza-BODIPY dyes. This thesis highlights several initial attempts on improving the synthesis of aza-BODIPY dyes, making the reactions quicker, safer, easier to carry out, and potentially more economical to perform. Specifically, two steps leading to the formation of enones and nitrobutanone derivatives (intermediates en route to the dyes) were explored and improved by introducing the mechanomical approaches, thus allowing for a reduction in the amount of solvent or even in some cases eliminate the need for solvent all together. The introduction of tetramethylguanidine as the base allowed for the synthesis of nitrobutanone derivatives at room temperature. Further improvement included the mechanochemical synthesis of aza-BODIPY dyes by simply grinding a substituted aryl pyrrole with acetic anhydride, acetic acid, and sodium nitrite to form the aza-BODIPY precursor in moderate yields. |
