Proof of concept analysis of using photo-click chemistry on ionic liquid monomers with propargyl functionality

Abstract

Click chemistry refers to a specific set of organic chemistry reactions that proceed under mild conditions, are high yielding, and are extremely selective. Due to their orthogonality, these types of reactions have opened doors for the fabrication of materials of many kinds. This work explores the applicability of click chemistry used in conjunction with ionic liquids. ☐ The kinetics of light initiated click chemistry reactions of CuAAC and thiol-yne on ionic liquids functionalized with alkyne are examined, setting up the foundation for many applications including but not limited to ion-containing membranes, adhesives, and organic catalysts. Photo-click chemistry is a recent discovery and all its facets have not been explored yet. While it is evident that photo-click reactions have made the already friendly click reactions even more amicable, there is a vast gap in the literature on the fundamentals of this reaction. ☐ It was observed that the cationic structure of the ionic liquid monomer and the presence of the anion significantly affect the kinetics of the click reactions. For the CuAAC reaction, the fastest kinetics were produced by a weakly coordinating anion and aromatic structure cation combination and it was deduced that anions which strongly interact with Cu(I) inhibit the reaction. Additionally, it was discovered that the polarity of the thiol monomer has an effect on the thiol-yne click reaction. A more polar thiol in thiol-yne reactions with ionic liquids appears to facilitate the reaction to proceed to full conversion.