Synergy of Dynamic Covalent and Click Methodologies in Dendrimer Synthesis: A Study of Thiol-Ene Reactions in Material Science

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<p>This thesis proves the feasibility of protecting maleimide functionalities with furan via dynamic thermally controlled Diels-Alder cycloaddition reactions, for use in one-pot dendrimer syntheses. Dendrimers up to [G-2] were prepared using the designer monomer compound.</p> <p>This thesis will also prove, synthetically and computationally, the selective properties of thiol-ene click reactions. N-substituted allyl and propargyl maleimides were prepared and orthogonally reacted with thiols to prove the selectivity of the reactions. Base catalyzed thiol-ene click is selective for electron poor alkenes while the radical-mediated reaction while robust is non-selective. Thus, by utilizing the differences in reactivity, selective thiol-ene can take place by reacting base-catalyzed functionalities prior to radical-mediated addition.</p>

    Item Description
    Name(s)
    Thesis advisor: Northrop, Brian H.
    Thesis advisor: Fry, Albert J.
    Thesis advisor: Pringle, Wallace C.
    Date
    May 02, 2013
    Extent
    105 pages
    Language
    eng
    Genre
    Physical Form
    electronic
    Discipline
    Rights and Use
    In Copyright - Non-Commercial Use Permitted
    Digital Collection
    PID
    ir:2544