Recent synthetic developments have produced a new class of recyclable thermosets based on the formation of Hexahydrotriazine networks – polyhexahydrotriazines (PHTs). From their very recent synthesis, this material platform has garnered significant attention for a spectrum of applications that relies on an overlap between synthetic chemistry, supramolecular interactions with metal ions and their reactivity towards heteroatoms such as sulfur, for instance. Through fundamental studies, which include experimental analytical tools (UV-Vis & NMR titrations) and computational modeling, a variety of metal ions metal ions from different groups of elements such as Na+, Ca2+, Zn2+ and Ag2+ were shown to associate with hexahydrotriazines (HTs) in solution. However, their interaction with HTs is not solely a supramolecular association in all cases. Harder Lewis-acid metals lead to irreversible changes in the HTs spectrum, suggesting that some metals lead to chemical changes in the HT. The interaction between HTs and metal ions were exploited in the development of a low cost fluorimeter-based detection system, where changes in the HT’s absorption at short wave UV-light (255 nm) are converted into visible light with a fluorescent indicator that enables detection with a silicon photodetector. This device was found sensitive enough to detect trace amounts of heavy metals (&lt;10ppb) in aqueous solutions. Furthermore, understanding the interactions between HTs and metal ions facilitated the development of anti-microbial PHT coatings where Ag2+ ions are bound to the HT moieties of PHT films and give rise to these properties. In addition to their interactions with metal ions HTs are highly reactive towards inorganic compounds such as thiols. A reactivity that can be exploited for a wide range of applications that includes novel polymer forming reactions and polymer compositions as well as smart coatings for sulfur sequestration and even as a method for the detection of thiols.

From synthetic developments to applications: Hexahydrotriazines as a materials platform for industrial solutions

251st National Meeting (2016)

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