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A Polymer with “Locked” Degradability: Superior Backbone Stability and Accessible Degradability Enabled by Mechanophore Installation

Cite this: J. Am. Chem. Soc. 2020, 142, 5, 2100–2104
Publication Date (Web):January 15, 2020
https://doi.org/10.1021/jacs.9b12482
Copyright © 2020 American Chemical Society

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    Abstract

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    Though numerous applications require degradable polymers, there are surprisingly few polymer systems that combine superior stability and controllable degradability. Particularly, the degradability of a conventional degradable polymer is typically enabled by cleavable groups on the backbone, which can be attacked by stimuli in ambient conditions, causing undesirable material deterioration. Here we report a general strategy to overcome this issue: “locking” the degradability during handling and use of the polymers and “unlocking” it when degradation is needed. This strategy is demonstrated with a cyclobutane-fused lactone (CBL) polymer. The cyclobutane keeps polymer backbone intact under conditions that hydrolyze the lactone and allows the ester group to be recovered when undesirable hydrolysis occurs. When backbone degradation is needed, the degradability can be unlocked by mechanochemical activation that converts the polyCBL into a linear polyester. The rare combination of two intrinsically conflicting properties, i.e., backbone stability and accessible degradability, can make this polymer a potential option for new sustainable materials.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.9b12482.

    • Synthetic procedures, thermal characterization data, NMR spectra, and GPC traces, including Figures S1–S31, and Tables S1–S9 (PDF)

    • X-ray crystallographic data for M1 (CIF)

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