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Synthesis and Linker-Controlled Self-Assembly of Dendritic Amphiphiles with Branched Fluorinated Tails.

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Amphiphiles containing fluorinated segments tend to aggregate in the aqueous solution into structure of lower curvature than their hydrocarbon analogues due to their larger diameter. A benefit of supramolecular structures… Click to show full abstract

Amphiphiles containing fluorinated segments tend to aggregate in the aqueous solution into structure of lower curvature than their hydrocarbon analogues due to their larger diameter. A benefit of supramolecular structures incorporating fluorine moieties is their high electron density, which can be viewed in cryo-TEM with better contrast than their hydrogenated forms. A modular approach has been developed for the synthesis of a new family of nonionic branched amphiphiles consisting of oligoglycerol units (G2) as the hydrophilic part and a branched fluorinated (F27) hydrophobic part. The design of this hydrophobic moiety allows us to achieve a higher fluorine density than the previously used straight-chain perfluoroalkanes. Two different chemical approaches, amide and triazole, were used to link the hydrophilic and hydrophobic segments. In addition, the aggregation behavior was investigated by DLS and cryo-TEM. The measurements prove the formation of multivesicular (MVVs) and multilamellar (MLVs) vesicles as well as smaller unilamellar vesicles (SUVs). Further, the cell viability test proves the low cell toxicity of these nanoarchitectures for potential biomedical applications. This article is protected by copyright. All rights reserved.

Keywords: controlled self; branched fluorinated; self assembly; linker controlled; synthesis linker; assembly dendritic

Journal Title: Macromolecular bioscience
Year Published: 2022

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