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Versatile routes to functional RAFT chain transfer agents through the Passerini multicomponent reaction

Pearce, Amanda K.; Travanut, Alessandra; Couturaud, Benoit; Taresco, Vincenzo; Howdle, Steven M.; Alexander, Morgan R.; Alexander, Cameron

Authors

Amanda K. Pearce

Alessandra Travanut

Benoit Couturaud



Abstract

The widespread adoption of RAFT polymerization stems partly from the ease and utility of installing a functional chain transfer agent onto the ends of the generated polymer chains. In parallel, the Passerini multicomponent reaction offers great versatility in converting a wide range of easily accessible building blocks to functional materials. In this work, we have combined the two approaches such that a single, commonly available, RAFT agent is used in Passerini reactions to generate a variety of multifunctional RAFT chain transfer agents containing ester linkages. Reactions to generate the multifunctional RAFT agents took place under mild conditions and in good yields. The resulting Passerini-RAFT agents were able to exert control over radical polymerization to generate materials of well-defined molecular weights and dispersity. Furthermore, the presence in these polymer cores of ester and amide functionality through the Passerini chemistries, provided regions in the materials which are inherently biodegradable, facilitating any subsequent biomedical applications. The work overall thus demonstrates a versatile and facile synthetic route to multi functional RAFT chain transfer agents and biodegradable polymers.

Citation

Pearce, A. K., Travanut, A., Couturaud, B., Taresco, V., Howdle, S. M., Alexander, M. R., & Alexander, C. (2017). Versatile routes to functional RAFT chain transfer agents through the Passerini multicomponent reaction. ACS Macro Letters, 6(7), 781-785. https://doi.org/10.1021/acsmacrolett.7b00415

Journal Article Type Article
Acceptance Date Jun 30, 2017
Online Publication Date Jul 5, 2017
Publication Date Jul 18, 2017
Deposit Date Oct 3, 2017
Publicly Available Date Oct 3, 2017
Journal ACS Macro Letters
Electronic ISSN 2161-1653
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 6
Issue 7
Pages 781-785
DOI https://doi.org/10.1021/acsmacrolett.7b00415
Public URL http://eprints.nottingham.ac.uk/id/eprint/46956
Publisher URL http://pubs.acs.org/doi/abs/10.1021/acsmacrolett.7b00415
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
Additional Information This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Macro Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi...21/acsmacrolett.7b00415

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ACS Macro Letters Paper.pdf (630 Kb)
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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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