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Post-Synthetic ‘Click’ Synthesis of RAFT Polymers with Pendant Self-Immolative Triazoles

preprint
submitted on 31.12.2020, 12:53 and posted on 04.01.2021, 04:54 by Timothy Forder, Peter Maschmeyer, Haoxiang Zeng, Derrick Roberts

Self-immolative linkers offer efficient mechanisms for deprotecting ‘caged’ functional groups in response to specific stimuli. Herein we describe a convenient ‘click’ chemistry method for introducing pendant self-immolative linkers to a polymer backbone through post-polymerization modification. The intro duced triazole rings serve both to anchor the stimuli-cleavable trigger groups to the polymer backbone, while also forming a functional part of the self-immolation cascade. We investigate the polymerization kinetics, post-synthetic modification, and self-immolation mechanism of a model polymer system, and discuss avenues for future studies on poly-pendant self-immolative triazoles as a modular, stimuli-responsive macromolecule platform.

Funding

DE190100797

History

Email Address of Submitting Author

derrick.roberts@sydney.edu.au

Institution

The University of Sydney

Country

Australia

ORCID For Submitting Author

0000-0002-4663-7475

Declaration of Conflict of Interest

No conflict of interest to declare