Since their characterization as enclosed membrane sacs, vesicles have garnered great attention in applications ranging from drug and cosmetic delivery to cell membrane dynamics studies as well as microreactors and artificial cells. In order to pursue these goals, simple and highly controllable formation techniques become necessary. With this in mind, photo-induced micelle to vesicle transitions have been achieved through the use of a variety of “click” reactions. First, a visible light, radical generating photoinitiator was used to reduce copper (II) to copper (I), thereby catalyzing the Copper-catalyzed Azide-Alkyne Cycloaddition (CuAAC) reaction which has been used previously in the formation of vesicles through the addition of an azide functionalized, aliphatic tail to an alkyne functionalized lysolipid. Building upon this idea, new lysolipids were synthesized with either a thiol or a vinyl sulfone functionality. These new lipids could then undergo thiol-ene or thiol-Michael reactions to add appropriately functionalized aliphatic tails to the lysolipids upon exposure to visible light in conjunction with a photosensitizer and photo-base, UV light, or free base. This range in formation conditions greatly widens the ability to form vesicles in a simple, highly controllable manner while the range in chemistries opens up possibilities for specialized vesicles, responsive to multiple stimuli.

Photo-induced vesicle formation using "click" chemistries

251st National Meeting (2016)

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