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Photoswitch generation using mechanical force

Hu, Xiaoran and McFadden, Molly Elizabeth and Barber, Ross and Robb, Maxwell J. (2019) Photoswitch generation using mechanical force. In: 258th ACS National Meeting & Exposition, 25-29 August 2019, San Diego, CA.

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The field of polymer mechanochem. investigates the use of mech. force to promote selective chem. transformations. Polymer chains transduce external mech. forces to a particular covalent bond in mech. sensitive mols. called mechanophores, resulting in a specific chem. reaction. We report on a new mechanophore based on a cyclopentadienemaleimide Diels-Alder adduct that undergoes a retro-[4+2] cycloaddn. reaction promoted by mech. force to reveal a diarylethene (DAE) photoswitch. Initially, the mechanophore is photochem. inert because it does not possess the necessary 6p electronic framework required for electocyclization; however, ultrasound-induced mech. activation of the mechanophore covalently linked to polymer chains generates a DAE photoswitch, which isomerizes between colorless and colored forms upon exposure to UV and visible light. Control expts. confirm the mech. origin of the revealed photochromic activity and illustrate the thermal stability and reversible switching properties of the cyclopentadiene-based DAE photoswitch.

Item Type:Conference or Workshop Item (Paper)
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URLURL TypeDescription Website
Hu, Xiaoran0000-0001-7598-4516
McFadden, Molly Elizabeth0000-0003-3174-6385
Barber, Ross0000-0003-0434-847X
Robb, Maxwell J.0000-0002-0528-9857
Additional Information:© 2019 American Chemical Society.
Record Number:CaltechAUTHORS:20190812-090137189
Persistent URL:
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:97750
Deposited By: Tony Diaz
Deposited On:12 Aug 2019 17:35
Last Modified:09 Mar 2020 13:19

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