Architecture and applications of novel molecular assemblies imparted by the aggregations of fluoroalkyl segments

Citation
H. Sawada et T. Kawase, Architecture and applications of novel molecular assemblies imparted by the aggregations of fluoroalkyl segments, J SYN ORG J, 57(4), 1999, pp. 291-304
Citations number
56
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
ISSN journal
00379980 → ACNP
Volume
57
Issue
4
Year of publication
1999
Pages
291 - 304
Database
ISI
SICI code
0037-9980(199904)57:4<291:AAAONM>2.0.ZU;2-8
Abstract
It was demonstrated that a series of fluoroalkylated end-capped oligomers c ontaining various functional segments such as carboxy, amide, betaine, and hydroxy groups can be prepared by the use of fluoroalkanoyl peroxides as ke y intermediates. These thus-obtained fluoroalkylated end-capped oligomers w ere soluble in water and organic solvents, and were capable of reducing the surface tension of water effectively with a clear break point resembling a CMC, which is almost the same level as that achieved by the usual low mole cular weight fluorinated surfactants. This is a unique and interesting feat ure of our fluoroalkylated end-capped oligo-surfactants. Furthermore, fluor oalkylated end-capped oligomers were suggested to form the molecular assemb lies imparted by strong aggregation of the fluoroalkylated end-groups in aq ueous solutions, and fluoroalkylated end-capped acrylic acid and sulfonic a cid oligomers were also shown to be potent and selective inhibitors of huma n immunodeficiency virus type 1 (HIV-1) in vitro. More interestingly, fluor oalkylated end-capped oligomers containing betaine or hydroxy segments coul d cause gelation, where the synergistic interactions of both the strong agg regation of the end-capped fluoroalkyl segments and the ionic or hydrogen-b onding interaction are involved in establishing a gel network in water and polar organic solvents.