CPOS Seminar:Controlled Synthesis of Degradable Diels–Alder Polymers Using Single-Component Cyclopentadiene Derivatives

Speaker: Thi M. Tran , PhD Student, Department of Chemistry and Biochemistry, UCSB

Abstract:   Cyclopentadiene (Cp) is known for its high reactivity and propensity to dimerize, making monomer synthesis and polymerization notoriously challenging. In fact, despite its long history and compelling chemistry, only two reports have appeared in the literature since the first attempt to homopolymerize Cp by Staudinger in 1926. Despite the potential applications as de-polymerizable and functional materials, Cp polymers remained underexplored due to the lack of controlled structures over the past century. Herein, we present a strategy to synthesize and isolate well-defined Cp monomer derivatives under mild conditions, which allows access to better-defined homopolymers, including network and linear structures. The first part of the talk will focus on monitoring the polymerization of a tetra-telechelic Cp monomer upon isolation and characterization of the resulting polymer network. Mechanical properties are also investigated, including creep–recovery, shape memory, and tensile behaviors. Interestingly, the tensile test reflects a tough and elastic material, in contrast to prior Cp-based homopolymer networks. In the later part, I will discuss about the future work to synthesize linear Cp homopolymers and the potential applications in closed-loop recycling. Overall, this work provides a versatile platform to access and study new cyclopentadiene-based and better-defined homopolymers with potential applications ranging from shape-memory polymers to closed-loop recycling.