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Abstract :
[en] Among the click member family, triazoline dione (TAD) compounds can be used as a dienophile in a
Diels-Alder type reaction respecting the features of the click chemistry concept1,2. Herein, simple and ultrafast macromolecular functionalization under mild conditions using TAD click chemistry is introduced. Aliphatic polycarbonates (APCs) are chosen as macromolecular platform since this family of polymers present all the prerequisites to be used as biomaterials (biocompatibility and biodegradability)3,4. Those 'clickable' copolymers are synthetized by ring-opening polymerization (ROP) of cyclocarbonate carrying diene dangling functions. Post-modification with various TAD based compounds were carried out in optimised conditions and the effectiveness of the reaction was assessed with the traditional characterisation tools. Impacts on final thermal
properties were evidenced by DSC where shift of the glass transition temperature was observed. A degradability study in different storage conditions also demonstrates the impact of the nature of the lateral function on the shelf-stability of the resulting polymer. This study provides the proof of concept of the APCs functionalization using TAD click-chemistry and
constitutes a key step in the macromolecular design of well-tailored biomaterials.
References
1) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions.
Angew. Chemie Int. Ed. 2001, 40 (11), 2004-2021
2) Billiet, S.; Bruycker, K. De; Driessen, F. Triazolinediones Enable Ultrafast and Reversible Click Chemistry for the Design
of Dynamic Polymer Systems. Nat. Chem. 2014, No. August, 1-7
3) Tempelaar, S.; Mespouille, L.; Coulembier, O.; Dubois, P.; Dove, A. P. Synthesis and Post-Polymerisation Modifications
of Aliphatic Poly(carbonate)s Prepared by Ring-Opening Polymerisation. Chem. Soc. Rev. 2013, 42 (3), 1312-1336
4) Mespouille, L.; Coulembier, O.; Kawalec, M.; Dove, A. P.; Dubois, P. Implementation of Metal-Free Ring-Opening
Polymerization in the Preparation of Aliphatic Polycarbonate Materials. Prog. Polym. Sci. 2014, 39 (6), 1144-1164
