<br/>Semifluorinated functionalities offer new possibilities in the design of self-assembling systems. Linear, dibranched and miktoarm amphiphiles containing hydrophilic, lipophilic and fluorophilic moieties were synthesized and characterized in an attempt to elucidate the relationship between structure and aggregate behavior in aqueous solution. For both linear and dibranched amphiphile architectures there was an exponential decrease in critical aggregation concentration (CMC) and a logarithmic increase in core microviscosity with increasing length of the fluorocarbon segment. For miktoarm amphiphiles, core microviscosity and CMC showed little variance. The linear surfactants showed enhanced kinetic stability, dissociating more slowly in the presence of human serum than did the dibranched amphiphiles or miktoarm amphiphiles. Encapsulation studies with the hydrophobic drug paclitaxel (PTX) showed that the ability to solubilize and retain PTX increased with the presence of and with the increasing size of the fluorocarbon moiety.

Structure and behavior relationships among semifluorinated linear, dibranched and miktoarm amphiphiles

249th National Meeting (2015)

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