Fluorogenic organocatalytic reactions

In this thesis, we introduce fluorescence spectroscopy as a new tool to gain insight into the interactions between the substrates and catalyst during organocatalytic reactions. The ultimate goal is to resolve the kinetics of the binding and reaction steps and obtain detailed understanding of the reaction mechanism. We use boron dipyrromethene (BODIPY) dyes as the fluorescent unit. For our purpose, it is particularly interesting to use dyes that change their fluorescence properties as a result of interaction or reaction. In chapter 2 the experimental methods are presented. This comprises the experimental tools, and details of the synthesis of the starting materials, the catalysts, and the general procedures for the preparation of the products. In chapter 3 we present the results of the Michael addition reactions of benzyl mercaptan and dimethyl malonate to BODIPYs in the presence of free and immobilized catalysts to produce succinimides and substituted β–nitro alkanes. In chapter 4 we discuss the results of the synthesis of two fluorescent chromene derivatives. We followed the formation of these compounds with fluorescence spectroscopy. In chapter 5, the results of the Biginelli synthesis of a fluorescent pyrimidone derivative of BODIPY is presented. The product has the potential to be studied in medicinal chemistry. In chapter 6, we applied total internal reflection fluorescence microscopy to study the interaction between two immobilized catalysts and starting compound, Maleimide-BODIPY. This preliminary work shows the potential of the method to get more information about the catalytic processes using single molecule detection.