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Published October 31, 2018 | Supplemental Material
Journal Article Open

Mechanochemical Regulation of a Photochemical Reaction


We introduce the concept of mechanochemically gated photoswitching. Mechanical regulation of a photochemical reaction is exemplified using a newly designed mechanophore based on a cyclopentadiene–maleimide Diels–Alder adduct. Ultrasound-induced mechanical activation of the photochemically inert mechanophore in polymers generates a diarylethene photoswitch via a retro-[4 + 2] cycloaddition reaction that photoisomerizes between colorless and colored states upon exposure to UV and visible light. Control experiments demonstrate the thermal stability of the cyclopentadiene–maleimide adduct and confirm the mechanical origin of the "unlocked" photochromic reactivity. This technology holds promise for applications such as lithography and stress-sensing, enabling the mechanical history of polymeric materials to be recorded and read on-demand.

Additional Information

© 2018 American Chemical Society. Received: September 5, 2018; Published: October 17, 2018. We thank Dr. Scott Virgil for assistance with chromatography and helpful discussions and the Caltech Center for Catalysis and Chemical Synthesis for access to equipment. We also thank Larry Henling for assistance with X-ray crystallography. Financial support from Caltech and the Dow Next Generation Educator Fund is gratefully acknowledged financial interests. The authors declare no competing financial interest.

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Supplemental Material - ja8b09628_si_001.pdf

Supplemental Material - ja8b09628_si_002.cif


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