期刊
JOURNAL OF FLUORINE CHEMISTRY
卷 121, 期 2, 页码 111-130出版社
ELSEVIER SCIENCE SA
DOI: 10.1016/S0022-1139(03)00040-X
关键词
end-capped fluoroalkyl; oligomer; molecular aggregate; self-assembly; surface activity; anti-HIV-1 activity; antibacterial activity
A variety of fluoroalkyl end-capped oligomers were prepared under mild conditions by the use of fluoroalkanoyl peroxide as a key intermediate. These oligomers can form the self-assembled molecular aggregates with the aggregations of end-capped fluoroalkyl groups in aqueous and organic media. Fluorinated self-assembled molecular aggregates containing carboxyl and sulfo groups were suggested to interact with positively charged HIV-1 to exhibit a potent anti-HIV-1 activity in vitro. In contrast, fluoroalkyl end-capped oligomers containing cationic segments exhibited not only the unique surface active properties imparted by fluorine as well as the usual low-molecular fluorinated surfactants. but also high surface antibacterial activity. Fluoroalkyl end-capped oligomers containing betaine-type segments were found to cause a gelation where the strong aggregation of the end-capped fluoroalkyl groups is involved in establishing the physical gel network in water and polar organic solvents under non-crosslinked conditions. Similarly, fluoroalkyl end-capped oligomers containing hydroxyl groups could cause a gelation, where the aggregation of fluoroalkyl groups and hydrogen-bonding interaction is involved in establishing a physical gel network in water and polar organic solvents under non-crosslinked conditions. Fluoroalkanoyl peroxide is also a convenient tool for the preparation of new fluoroalkyl end-capped oligomers containing recognition moieties such as diacetone segments. These fluorinated oligomers containing recognition moieties could form the self-assembled molecular aggregates to recognize selectively the hydrophilic amino and N,N-dimethylamino compounds as guest molecules. (C) 2003 Elsevier Science B.V. All rights reserved.
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