Synthetic vesicles have a wide range of applications, including their use as microreactors, drug delivery mechanisms, and artificial cell membranes. For these applications, the systems require enhanced control, which can be attained through the use of photo-initiated chemistries to modify vesicle behavior. As a primary goal, we aimed to incorporate a photo-initiation system into the generation of vesicles using the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, which has been shown previously to allow for the production of vesicles <i>in situ</i>, however this previous system lacked spatial and temporal control. To do this, various water-soluble, visible-light photoinitiators were substituted in place of reducing agents, to allow for the reduction of copper upon the exposure to light. Successful generation of vesicles upon exposure to light in a spatially defined manner, as imaged on a fluorescent microscope, gave proof of the enhanced control afforded by the incorporation of a photo-initiation system. Beyond the use of the CuAAC reaction to photo-initiate vesicle formation, phospholipid precursors containing a thiol functional group have been synthesized to expand the possible click reactions available for vesicle generation. Finally, to enhance the functionality of fully formed vesicles, spiropyran moieties have been incorporated into the azide containing reactants to allow for a two wavelength system of visible light initiated vesicle generation followed by UV induced disruption.

Manipulation of vesicle formation and characteristics using photo-initiated chemistry

249th National Meeting (2015)

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