A Polymer with "locked" Degradability: Superior Backbone Stability and Accessible Degradability Enabled by Mechanophore Installation

Tze Gang Hsu, Junfeng Zhou, Hsin Wei Su, Briana R. Schrage, Christopher J. Ziegler, Junpeng Wang

Research output: Contribution to journalArticlepeer-review

93 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)2100-2104
Number of pages5
JournalJournal of the American Chemical Society
Volume142
Issue number5
DOIs
StatePublished - Feb 5 2020
Externally publishedYes

Funding

This work is supported by The University of Akron startup support. The single-crystal structure was characterized with an X-ray diffractometer supported by the National Science Foundation (CHE-0840446). We thank S. Snyder and C. Wesdemiotis for mass spectrometry analysis and P. Shieh for helpful discussion on the restoration part.

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