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Mechanically Triggered Small Molecule Release from a Masked Furfuryl Carbonate

Hu, Xiaoran and Zeng, Tian and Husic, Corey C. and Robb, Maxwell J. (2019) Mechanically Triggered Small Molecule Release from a Masked Furfuryl Carbonate. Journal of the American Chemical Society, 141 (38). pp. 15018-15023. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20190913-100336482

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Abstract

Stimuli-responsive polymers that release small molecules under mechanical stress are appealing targets for applications ranging from drug delivery to sensing. Here, we describe a modular mechanophore design platform for molecular release via a mechanically triggered cascade reaction. Mechanochemical activation of a furan–maleimide Diels–Alder adduct reveals a latent furfuryl carbonate that subsequently decomposes under mild conditions to release a covalently bound cargo molecule. The computationally guided design of a reactive secondary furfuryl carbonate enables the decomposition and release to proceed quickly at room temperature after unmasking via mechanical force. This general strategy is demonstrated using ultrasound-induced mechanical activation to release a fluorogenic coumarin payload from a polymer incorporating a chain-centered mechanophore.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jacs.9b08663DOIArticle
ORCID:
AuthorORCID
Hu, Xiaoran0000-0001-7598-4516
Zeng, Tian0000-0001-5957-3442
Husic, Corey C.0000-0003-0248-7484
Robb, Maxwell J.0000-0002-0528-9857
Additional Information:© 2019 American Chemical Society. Received: August 10, 2019; Published: September 13, 2019. Financial support from Caltech and the Dow Next Generation Educator Fund is gratefully acknowledged. We thank the Center for Catalysis and Chemical Synthesis of the Beckman Institute at Caltech for access to equipment and Larry Henling for assistance with X-ray crystallography. The authors declare no competing financial interests.
Funders:
Funding AgencyGrant Number
CaltechUNSPECIFIED
Dow Next Generation Educator FundUNSPECIFIED
Issue or Number:38
Record Number:CaltechAUTHORS:20190913-100336482
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20190913-100336482
Official Citation:Mechanically Triggered Small Molecule Release from a Masked Furfuryl Carbonate. Xiaoran Hu, Tian Zeng, Corey C. Husic, and Maxwell J. Robb. Journal of the American Chemical Society 2019 141 (38), 15018-15023. DOI: 10.1021/jacs.9b08663
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:98641
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:13 Sep 2019 17:15
Last Modified:03 Oct 2019 21:43

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