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5-Aryloxy substitution enables efficient mechanically triggered release from a synthetically accessible masked 2-furylcarbinol mechanophore

Zeng, Tian and Hu, Xiaoran and Robb, Maxwell J. (2021) 5-Aryloxy substitution enables efficient mechanically triggered release from a synthetically accessible masked 2-furylcarbinol mechanophore. Chemical Communications, 57 (85). pp. 11173-11176. ISSN 1359-7345. doi:10.1039/d1cc04886d. https://resolver.caltech.edu/CaltechAUTHORS:20211008-224614821

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Abstract

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1039/d1cc04886dDOIArticle
ORCID:
AuthorORCID
Zeng, Tian0000-0001-5957-3442
Hu, Xiaoran0000-0001-7598-4516
Robb, Maxwell J.0000-0002-0528-9857
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.
Funders:
Funding AgencyGrant Number
Arnold and Mabel Beckman FoundationUNSPECIFIED
American Chemical Society Petroleum Research Fund61638-DNI7
Issue or Number:85
DOI:10.1039/d1cc04886d
Record Number:CaltechAUTHORS:20211008-224614821
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20211008-224614821
Official Citation:5-Aryloxy substitution enables efficient mechanically triggered release from a synthetically accessible masked 2-furylcarbinol mechanophore. Chem. Commun., 2021, 57, 11173-11176; DOI: 10.1039/d1cc04886d
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:111314
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:12 Oct 2021 20:36
Last Modified:28 Oct 2021 22:02

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