Thiol-Maleimide Click Chemistry Approach to Efficient Synthesis of Dendrimers

Jiyoon Park, Wesleyan University

Abstract

Dendrimers are promising macromolecules to be applied in a wide range of biomedical applications, from carriers for drug delivery to diagnostic tools for imaging. Their globular structure, monodispersity, and surface multivalency afford them a superior position compared to liposomes and polymers that are the current options for such applications. The topic of dendrimer synthesis has been studied extensively, but were often hindered by tedious and inefficient protocols for their synthesis and purification. In this research, a click chemistry approach that relies on the unique reactivity of thiols and furan-maleimides in the divergent synthesis of dendrimers was investigated. Various synthetic routes to a thiol-maleimide branched monomer were explored and modified. N,N-bis(2-hydroxyethyl)-2-propenamide, a specific intermediate in the synthetic route, not only changed in its physical properties over time but also its signals disappeared from the 1H nuclear magnetic resonance spectrum of the product from subsequent reactions that utilized this diethanolacrylamide compound. Therefore, the energetic barrier for it to spontaneously polymerize was investigated computationally to understand the activation energy and the mechanism through which the polymerization occurs.

 

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