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- l-carbonyl chloride, obtained from the chlorination of the corresponding carboxylic acid and pho sphorus oxychloride in the presence of DMF. A kinetic study showed that PFD C-PO decomposes homolytically with a three-bond fission. Heptadecafluorodec ahydro-1-naphthyl (F-DECALYL) end-capped oligomers were prepared by the rea ction of PFDC-PO with monomers such as acrylic acid (ACA), N.N-dimethylacry lamide (DMAA), 3-methacryloxy-2-hydroxypropyltrimethylammonium chloride, an d N-(1,1 -dimethyl-3-oxobutyl)acrylamide (DOBAA) via a radical process. Int erestingly, these F-DECALYL end-capped oligomers obtained were soluble in w ater and common organic solvents. although parent perfluorodecalin is insol uble in water and common organic solvents except hexane. F-DECALYL end-capp ed 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 compare d to the corresponding linear fluoroalkylated ACA oligomer. F-DECALYL end-c apped DMAA and DOBAA oligomers were insoluble in water: however. these olig omers were soluble in common organic solvents. Especially, F-DECALYL end-ca pped DOBAA oligomer was found to form a monomolecular film at the air-water interface. (C) 2001 Elsevier Science Ltd. All rights reserved.