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Article Dans Une Revue Journal of Polymer Science Part A: Polymer Chemistry Année : 2017

Heterofunctional RAFT-derived PNIPAM via cascade trithiocarbonate removal and thiol-yne coupling click reaction

Résumé

An efficient one-pot process to functionalize the α- and ω-positions of RAFT-derived poly(N-isopropylacrylamide) (PNIPAM) by two inherently different mechanistic pathways is reported. The method relies on the RAFT polymerization of NIPAM using a new alkyne-based RAFT agent, namely 2-cyano-5-oxo-5-(prop-2-yn-1-ylamino)pentan-2-yl dodecyltrithiocarbonate (COPYDC) and the combination of thiol-yne click chemistry and thiocarbonylthio chain-end removal reactions. COPYDC was prepared in good yield and used as an efficient chain transfer agent during the RAFT polymerization of NIPAM. Well-defined polymers with controlled molar masses and narrow dispersities (Đ = 1.18–1.26) are thus obtained. Cascade thiol-yne click reaction at the alkyne α-chain end and trithiocarbonate removal at the ω-chain end are successfully achieved using benzyl mercaptan and excess AIBN. The reported method provides a facile and mild route to heterofunctional telechelic RAFT polymers with predictable molar masses and low dispersities.
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Dates et versions

hal-02150749 , version 1 (07-06-2019)

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Maël Le Bohec, Sandie Piogé, Sagrario Pascual, Laurent Fontaine. Heterofunctional RAFT-derived PNIPAM via cascade trithiocarbonate removal and thiol-yne coupling click reaction. Journal of Polymer Science Part A: Polymer Chemistry, 2017, 55 (21), pp.3597-3606. ⟨10.1002/pola.28742⟩. ⟨hal-02150749⟩
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