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
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.