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


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.


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.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:polymer mechanochemistry, mechanochemistry, organic chemistry, physical organic chemistry, small molecule release
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Restricted to Caltech community only
Research Advisor(s):
  • Robb, Maxwell J.
Thesis Committee:
  • Fu, Gregory C. (chair)
  • Reisman, Sarah E.
  • Wei, Lu
  • Robb, Maxwell J.
Defense Date:24 January 2024
Funding AgencyGrant Number
American Chemical Society Petroleum Research Fund61638-DNI7
National Institute of General Medical Sciences of the National Institutes of HealthR35GM150988
Beckman Young Investigator AwardUNSPECIFIED
Record Number:CaltechTHESIS:03012024-065205159
Persistent URL:
Related URLs:
URLURL TypeDescription of article adapted for chapter 1 of article adapted for chapter 2 of article adapted for chapter 2 adapted for chapter 3 adapted for chapter 4
Zeng, Tian0000-0001-5957-3442
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:16311
Deposited By: Tian Zeng
Deposited On:27 Mar 2024 21:28
Last Modified:27 Mar 2024 21:28

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