RUI: Terpenes as Versatile Building Blocks for Multivalent Polymeric and Nanoparticle Systems

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In this project funded by the Macromolecular, Supramolecular, and Nanochemistry Program in the Division of Chemistry, Professor Peter M. Iovine of the Department of Chemistry at the University of San Diego is transforming terpene building blocks into sustainable polymers and nanoparticles. Terpenes are a large and diverse class of natural compounds, produced by a variety of plants (particularly conifers such as pine trees) and by some insects. In this research, the team uses light to convert terpenes into defined nanostructures upon interaction with DNA. Structure-function relationships between these polymeric building blocks and the resultant nanoparticle stability, pH dependence and structure are determined. The project has broader impact by providing scientifically robust training opportunities for undergraduate students. Participating students acquire diverse training in small molecule and polymer synthesis, characterization, and nanomaterials development. Elements of this research are also incorporated into existing chemistry courses at the University of San Diego. This research is focused on the synthesis of new polymer and nanoparticle systems derived from terpenes. The innovation in the approach is two-fold. First, terpenes and terpene-containing polymers are synthetically modified such that the products display clusters of functional groups. These terpene-based building blocks are then assembled into defined nanostructures through ionic and/or non-covalent interactions leading to functional nanoparticles. The first thrust focuses on the creation of terpene-derived polycationic polymers and the complexation of these polymers by DNA to produce nanoparticles (polyplexes). The second thrust also starts with functional terpenes but focuses on polyborylation instead of polycationization. Once synthesized, polyborylated building blocks form complexes with Lewis basic polymers to produce a new class of boron-rich nanoparticles (boraplexes). The fundamental properties of terpene-derived. boron-rich nanoparticles are systematically investigated, and various factors that affect their assembly elucidated. This project has the potential to expand the utilization of terpenes as a sustainable chemical building block for polymer constructs and nanomaterials. The developed synthetic methodology could also impact development in application areas such as sustainable polyols, surfactants, coatings, and nanocomposites.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.