The Effects of Substitution by Halogen and Cyano Groups on the Decomposition of Stable 1,2-dioxetanes
Przybysz, Aaron Joseph
MetadataShow full item record
Chemiluminescent 1,2-dioxetanes substituted with cyano and bromo groups are derived from the photo-oxidation of new novel alkenes that are synthesized by the coupling reaction of substituted aromatic esters and spiro-fused ketones with or without a n-electron system in the ring or carbon-carbon double bonds in the spiro-fused ring are reported herein. The substitutions were introduced to the benzene ring via a unique diazotization of a p-amino acid in which an arenediazonium ion was created and allows the nucleophilic addition of either the cyano or bromo groups. Compounds were isolated and identified based on study by IH NMR spectroscopy and Thin Layer Chromatography. Quantum yield experiments on these molecules in tris-buffer show that increasing the electron withdrawing nature of the substituted group effects the rate of decomposition of the 1,2-dioxetanes and increases the luminescent abilities of the molecules. In addition to the procedure for the synthesis of these molecules and results from their quantum yield testing, an introduction to all types of chemiluminescent molecules and their properties are given. These two new molecules now comprise a family of newly synthesized molecules created in conjunction with Michigan Diagnostics LLC.