Synthesis of novel fluoroalkylated 4-vinylpyridinium chloride oligomers as functional materials possessing surfactant and biological properties

• Published in: Journal of fluorine chemistry 1997-07, Vol.83 (2), p.125-131
• Main Authors: Sawada, Hideo, Wake, Atsuhito, Maekawa, Tomomi, Kawase, Tokuzo, Hayakawa, Yoshio, Tomita, Toshio, Baba, Masanori
• Format: Article
• Language: English
• Subjects: Anti-HIV-1 activity; Antibacterial activity; Cationic surfactants; Fluoroalkanoyl peroxides; Fluoroalkylated pyridinium oligomers; Surface tension
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/S0022-1139(97)00007-9

Perfluoropropylated and perfluoro-oxaalkylated 4-vinylpyridinium chloride oligomers were prepared by the reactions of fluoroalkanoyl peroxides with 4-vinylpyridinium chloride under very mild conditions. A series of fluoroalkylated 4-vinylpyridinium chloride co-oligomers containing carboxyl or trimethylsilyl segments were also obtained by the reactions of fluoroalkanoyl peroxides with 4-vinylpyridinium chloride and acrylic acid or trimethylvinylsilane under similar conditions. These fluoroalkylated homo- and co-oligomers containing carboxyl or trimethylsilyl segments were soluble in water and methanol. Furthermore, these oligomers were able to reduce the surface tension of water to 10–18 mN m −1 levels with a clear break point resembling a CMC (critical micelle concentration), and are applicable to new fluorinated cationic oligosurfactants. Fluoroalkylated co-oligomers were found to possess antibacterial activity against Staphylococcus aureus. In addition, fluoroalkylated co-oligomers containing carboxyl groups were potent and selective inhibitors of HIV-1 (human immunodeficiency virus type 1) in MT-4 cells. Interestingly, one of these fluoroalkylated co-oligomers containing carboxyl groups was clarified to show both antibacterial and anti-HIV-1 activities. Therefore, these oligomers are suggested to have high potential for new functional materials through their surfactant and biological properties.