High-Throughput Discovery of Ferrocene Mechanophores with Enhanced Reactivity and Network Toughening
Name
kevlishvili-et-al-2025-high-throughput-discovery-of-ferrocene-mechanophores-with-enhanced-reactivity-and-network.pdf
Description
Published version
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6.47 MB
Format
Adobe PDF
Checksum (MD5)
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Author(s)
Kevlishvili, Ilia
Vakil, Jafer
Kastner, David W
Huang, Xiao
Craig, Stephen L
Kulik, Heather J
Date Issued
August 1, 2025
Journal
ACS Central Science
Publisher
American Chemical Society
Citation
Kevlishvili, Ilia, Vakil, Jafer, Kastner, David W, Huang, Xiao, Craig, Stephen L et al. 2025. "High-Throughput Discovery of Ferrocene Mechanophores with Enhanced Reactivity and Network Toughening." ACS Central Science.
Version
Final published version
Abstract
Mechanophores are molecules that undergo chemical changes in response to mechanical force, offering unique opportunities in chemistry, materials science, and drug delivery. However, many potential mechanophores remain unexplored. For example, ferrocenes are attractive targets as mechanophores due to their combination of high thermal stability and mechanochemical lability. However, the mechanochemical potential of ferrocene derivatives remains dramatically underexplored despite the synthesis of thousands of structurally diverse complexes. Herein, we report the computational, machine learning guided discovery of synthesizable ferrocene mechanophores. We identify over one hundred potential target ferrocene mechanophores with wide-ranging mechanochemical activity and use data-driven computational screening to identify a select number of promising complexes. We highlight design principles to alter their mechanochemical activation, including regio-controlled transition state stabilization through bulky groups and a change in mechanism through noncovalent ligand–ligand interactions. The computational screening is validated experimentally both at the polymer strand level through sonication experiments and at the network level, where a computationally discovered ferrocene mechanophore cross-linker leads to greater than 4-fold enhancement in material tearing energy. This work establishes a generalizable framework for the high-throughput discovery and rational design of mechanophores and offers insights into structure–activity relationships in mechanically responsive materials.
MIT Department
Massachusetts Institute of Technology. Department of Chemical Engineering
Massachusetts Institute of Technology. Department of Biological Engineering
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/acscentsci.5c00707
