1. PRF #: 56464 2. Title: Unlocking the Rich Mechanochemistry of Aziridines Using Triazoline Synthons

Introduction. The aim of this research program is to uncover the mechanochemical potential of aziridines and train the next generation of scientists. Aziridines are reactive three-member ring structures that, when embedded in a polymer main chain or side chain, function as cross-linking points. Accessing polyaziridines, however, is challenging and few examples exist. Our approach does not involve the direct synthesis of polyaziridines but rather an indirect route via the thermal or photochemical decomposition of polytriazolines. We intend to use triazolines as aziridine synthons. This approach circumvents the majority of synthetic challenges associated with synthesizing aziridines from other organic precursors and allows for a more comprehensive investigation of high density aziridine-containing polymers. Once the polyaziridines are in hand, we intend to probe how the application of mechanical force impacts the conversion of these strained three member rings into reactive intermediates (Scheme 1). We intend to mechanochemically generate azomethine ylides (structure 3, Scheme 1) from aziridine precursors (structure 2, Scheme 1) and explore productive chemistries associated with these reactive intermediates including cross-linking (strengthening) as well as heterocycle formation (increase in structural complexity).