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    Facile Access to Polymeric Vesicular Nanostructures: Remarkable ω-End group Effects in Cholesterol and Pyrene Functional (Co)Polymers

    Access Status
    Fulltext not available
    Authors
    Xu, J.
    Tao, L.
    Boyer, C.
    Lowe, Andrew
    Davis, T.
    Date
    2011
    Type
    Journal Article
    
    Metadata
    Show full item record
    Citation
    Xu, J. and Tao, L. and Boyer, C. and Lowe, A. and Davis, T. 2011. Facile Access to Polymeric Vesicular Nanostructures: Remarkable ω-End group Effects in Cholesterol and Pyrene Functional (Co)Polymers. Macromolecules. 44 (2): pp. 299-312.
    Source Title
    Macromolecules
    DOI
    10.1021/ma102386j
    ISSN
    0024-9297
    School
    Nanochemistry Research Institute
    URI
    http://hdl.handle.net/20.500.11937/42743
    Collection
    • Curtin Research Publications
    Abstract

    Hydrophilic homopolymers of N,N-dimethylacrylamide (DMA) and N-(2-hydroxypropyl) methacrylamide (HPMA), as well as select examples of statistical copolymers with N-acryloxysuccinimide (NAS) were prepared with well-defined molecular characteristics employing a series of new RAFT chain transfer agents containing 1−4 hydrophobic functional groups in the R fragment based on pyrene, cholesterol, or octadecane, resulting in hydrophilic homopolymers containing between only 6−23 wt % hydrophobic end groups. PolyDMA (PDMA) and polyHPMA (PHPMA) homopolymers, of varying molar masses, with either bis pyrenyl or cholesteryl end groups self-assembled in aqueous media forming spherical vesicles with sizes in the range of several hundred nm up to ca. one micrometer. Lower molar mass PDMA−NAS copolymers with two cholesteryl end-groups at the ω-termini assemble to give clear tubular vesicles, whereas such copolymers of a higher molar mass preferentially form spherical polymersomes. The presence of two spatially close rigid rings at the ω-terminus is shown to be crucial in vesicle formation since a PDMA homopolymer with two octadecyl ω-end-groups self-assembles to yield polymeric micelles with an average hydrodynamic diameter of ~20 nm as determined by dynamic light scattering.The presence of a C16 alkyl spacer in the R fragment in a novel dithioester CTA with two pyrenyl functional groups and its use in the polymerization of a PDMA homopolymer yields spherical polymersomes in water, in a similar manner to those formed using a CTA without a spacer, except there is no direct FE-SEM evidence of open-mouth species perhaps indicating that the added flexibility associated with the spacer groups helps facilitate full vesicle closure. The synthesis of a biodegradable bis-pyrenyl dithioester, containing disulfide bridges, facilitates the preparation of PDMA-based polymersomes capable of dithiothreitol-induced pyrene release as evidenced by fluorescence emission spectroscopy. The same biodegradable polymersomes are also shown to be able to sequester the hydrophilic model drug Rhodamine B whose controlled release is demonstrated to be dependent on the presence, or absence, of dithiothreitol as determined by UV−vis spectroscopy.

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