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Incorporation of a Tethered Alcohol Enables Efficient Mechanically Triggered Release in Aprotic Environments

Husic, Corey C. and Hu, Xiaoran and Robb, Maxwell J. (2022) Incorporation of a Tethered Alcohol Enables Efficient Mechanically Triggered Release in Aprotic Environments. ACS Macro Letters, 11 (8). pp. 948-953. ISSN 2161-1653. doi:10.1021/acsmacrolett.2c00344. https://resolver.caltech.edu/CaltechAUTHORS:20220711-652680000

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Abstract

Polymers that release small molecules in response to mechanical force are promising for a wide variety of applications. While offering a general platform for mechanically triggered release, previous mechanophore designs based on masked 2-furylcarbinol derivatives are limited to polar protic solvent environments for efficient release of the chemical payload. Here, we report a masked furfuryl carbonate mechanophore incorporating a tethered primary alcohol that enables efficient release of a hydroxycoumarin cargo in the absence of a protic solvent. Density functional calculations also implicate an intramolecular hydrogen bonding interaction between the tethered alcohol and the carbonyl oxygen of the carbonate that reduces the activation barrier for carbonate fragmentation leading to molecular release. This new mechanophore design expands the generality of the masked 2-furylcarbinol platform for mechanically triggered release, enabling the implementation of this strategy in a wider range of chemical environments.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acsmacrolett.2c00344DOIArticle
ORCID:
AuthorORCID
Husic, Corey C.0000-0003-0248-7484
Hu, Xiaoran0000-0001-7598-4516
Robb, Maxwell J.0000-0002-0528-9857
Additional Information:© 2022 American Chemical Society. Received 3 June 2022. Accepted 7 July 2022. Published online 11 July 2022. This research was supported by the Arnold and Mabel Beckman Foundation through a Beckman Young Investigator Award. We thank the Center for Catalysis and Chemical Synthesis of the Beckman Institute at Caltech for access to equipment. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
Arnold and Mabel Beckman FoundationUNSPECIFIED
Subject Keywords:Adducts, Alcohols, Inorganic carbon compounds, Organic reactions, Polymers
Issue or Number:8
DOI:10.1021/acsmacrolett.2c00344
Record Number:CaltechAUTHORS:20220711-652680000
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20220711-652680000
Official Citation:Incorporation of a Tethered Alcohol Enables Efficient Mechanically Triggered Release in Aprotic Environments. Corey C. Husic, Xiaoran Hu, and Maxwell J. Robb. ACS Macro Letters 2022 11 (8), 948-953; DOI: 10.1021/acsmacrolett.2c00344
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:115464
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:12 Jul 2022 15:29
Last Modified:24 Aug 2022 21:29

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