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.
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http://dx.doi.org/10.1039/d1cc04886d | DOI Listing |
J Am Chem Soc
August 2024
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
J Am Chem Soc
January 2024
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
Polymers that release small molecules in response to mechanical force are promising for a variety of applications including drug delivery, catalysis, and sensing. While a number of mechanophores have been developed for the release of covalently bound payloads, existing strategies are either limited in cargo scope or, in the case of more general mechanophore designs, are restricted to the release of one or two cargo molecules per polymer chain. Herein, we introduce a nonscissile mechanophore based on a masked 2-furylcarbinol derivative that enables the preparation of multimechanophore polymers with ultrahigh payload capacity.
View Article and Find Full Text PDFProc Natl Acad Sci U S A
September 2023
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125.
External control of chemical reactions in biological settings with spatial and temporal precision is a grand challenge for noninvasive diagnostic and therapeutic applications. While light is a conventional stimulus for remote chemical activation, its penetration is severely attenuated in tissues, which limits biological applicability. On the other hand, ultrasound is a biocompatible remote energy source that is highly penetrant and offers a wide range of functional tunability.
View Article and Find Full Text PDFACS Macro Lett
August 2022
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
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.
View Article and Find Full Text PDFChem Commun (Camb)
October 2021
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
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.
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