Unclicking the Click: A Depolymerizable Clicked Polymer via Two Consecutive Single-Crystal-to-Single-Crystal Reactions

We report here a clicked polymer that can be depolymerized by a declicking reaction. A designed dipeptide monomer, upon heating its crystals, underwent a single-crystal-to-single-crystal topochemical ene-azide cycloaddition polymerization to form a triazoline-linked polymer, which upon further heati...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2024-11, p.e202417905
Main Authors: Sebastian, Bichu, Sureshan, Kana M
Format: Article
Language:English
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Summary:We report here a clicked polymer that can be depolymerized by a declicking reaction. A designed dipeptide monomer, upon heating its crystals, underwent a single-crystal-to-single-crystal topochemical ene-azide cycloaddition polymerization to form a triazoline-linked polymer, which upon further heating, underwent a remarkable SCSC denitrogenation, resulting in an imine-linked polymer quantitatively. As both the TEAC polymerization and the denitrogenation occurred in SCSC fashion, the structures of the triazoline-linked polymer and the imine-linked polymer could be determined at atomic resolution by SCXRD. Acid hydrolysis of the imine-linked polymer leads to quantitative depolymerization, yielding a dipeptide, showcasing the degradability and depolymerizability of such polymers. This solid-state click polymerization and denitrogenation yielding depolymerizable polymer is attractive over the usual click polymers that cannot be unclicked.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202417905