Masked 2-Furylcarbinol Derivatives: A Modular and General Platform for Mechanically Triggered Molecular Release

Citation

Zeng, Tian (2024) Masked 2-Furylcarbinol Derivatives: A Modular and General Platform for Mechanically Triggered Molecular Release. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/2vm9-5415. https://resolver.caltech.edu/CaltechTHESIS:03012024-065205159

Abstract

Stimuli-responsive polymers that undergo chemical transformations when exposed to external stimuli are attractive materials for a wide range of applications, such as targeted drug delivery, sensing, and catalysis. Within the emerging field of polymer mechanochemistry, mechanical force is harnessed to promote productive chemical transformations in stress-responsive molecules known as mechanophores. My research over the past several years has focused on the development of a modular and general mechanophore platform capable of releasing covalently-bound payloads in response to mechanical force. I envision that the further advancement of this design will not only aid in a deeper understanding of the design principles of mechanophores, but also enable new technologies, including non-invasive spatiotemporal delivery of bioactivate small molecules and self-healing materials.

Chapter 1 reviews the recent process of the development of small molecule-releasing mechanophores and provide an overview of the masked 2-furylcarbinol derivatives we developed that enables a mechanically gated release cascade. Chapter 2 describes our initial demonstration of mechanically gated small molecule release from our mechanophore and the subsequent structural-property investigation to optimize for faster release rates. In Chapter 3, an alternative mechanophore design is introduced that has a shortened synthetic sequence while maintaining a fast release kinetics. In Chapter 4, we address the challenge of low release capacity from previous designs with a novel mechanophore that can be incorporated into multimechanophore polymers. Finally, Chapter 5 demonstrates the use of our modular and general release platform to trigger the depolymerization of a self-immolative polymer.

Thesis Files