4.8 Article

Mechanochemical Regulation of a Photochemical Reaction

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 43, Pages 14073-14077

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b09628

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Funding

  1. Caltech
  2. Dow Next Generation Educator Fund

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We introduce the concept of mechano-chemically 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.

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