5-Aryloxy substitution enables efficient mechanically triggered release from a synthetically accessible masked 2-furylcarbinol mechanophore
Polymers that release small molecules in response to mechanical force are attractive materials for a wide variety of applications. Here, we report a new mechanophore platform based on a masked 2-furylcarbinol derivative that incorporates a 5-aryloxy group, which serves as both an electron-rich substituent to accelerate molecular release and the position of polymer attachment proximal to the furan–maleimide junction. The mechanophore is readily synthesized and efficiently releases both phenol and arylamine payloads following mechanical activation.
Additional Information© The Royal Society of Chemistry 2021. Submitted 31 Aug 2021. Accepted 29 Sep 2021. First published 29 Sep 2021. We acknowledge the Center for Catalysis and Chemical Synthesis of the Beckman Institute at Caltech for access to equipment. Financial support for this work was provided by the Arnold and Mabel Beckman Foundation through a Beckman Young Investigator Award and the Donors of the American Chemical Society Petroleum Research Fund through a Doctoral New Investigator Award (Grant No. 61638-DNI7). There are no conflicts to declare.
Supplemental Material - d1cc04886d1.pdf