Synthesis and applications of bis(perfluorodecalin-1-carbonyl) peroxide

New bis(perfluorodecalin-1-carbonyl) peroxide (PFDC-PO) was prepared by the reaction of hydrogen peroxide with perfluorodecalin-1-carbonyl chloride, obtained from the chlorination of the corresponding carboxylic acid and phosphorus oxychloride in the presence of DMF. A kinetic study showed that PFDC-PO decomposes homolytically with a three-bond fission. Heptadecafluorodecahydro-1-naphthyl (F-DECALYL) end-capped oligomers were prepared by the reaction of PFDC-PO with monomers such as acrylic acid (ACA), N,N-dimethylacrylamide (DMAA), 3-methacryloxy-2-hydroxypropyltrimethylammonium chloride, and N-(1,1-dimethyl-3-oxobutyl)acrylamide (DOBAA) via a radical process. Interestingly, these F-DECALYL end-capped oligomers obtained were soluble in water and common organic solvents, although parent perfluorodecalin is insoluble in water and common organic solvents except hexane. F-DECALYL end-capped ACA oligomer was easily soluble in water and reduced the surface tension of water effectively. Additionally, F-DECALYL end-capped ACA oligomer was found to enhance dramatically luminol chemiluminescence light yield compared to the corresponding linear fluoroalkylated ACA oligomer. F-DECALYL end-capped DMAA and DOBAA oligomers were insoluble in water; however, these oligomers were soluble in common organic solvents. Especially, F-DECALYL end-capped DOBAA oligomer was found to form a monomolecular film at the air–water interface.