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

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 access...

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Main Authors: Pearce, Amanda K., Travanut, Alessandra, Couturaud, Benoit, Taresco, Vincenzo, Howdle, Steven M., Alexander, Morgan R., Alexander, Cameron
Format: Article
Published: American Chemical Society 2017
Online Access:https://eprints.nottingham.ac.uk/46956/
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author Pearce, Amanda K.
Travanut, Alessandra
Couturaud, Benoit
Taresco, Vincenzo
Howdle, Steven M.
Alexander, Morgan R.
Alexander, Cameron
author_facet Pearce, Amanda K.
Travanut, Alessandra
Couturaud, Benoit
Taresco, Vincenzo
Howdle, Steven M.
Alexander, Morgan R.
Alexander, Cameron
author_sort Pearce, Amanda K.
building Nottingham Research Data Repository
collection Online Access
description 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.
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spelling nottingham-469562020-05-04T18:56:03Z https://eprints.nottingham.ac.uk/46956/ 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 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. American Chemical Society 2017-07-18 Article PeerReviewed Pearce, Amanda K., Travanut, Alessandra, Couturaud, Benoit, Taresco, Vincenzo, Howdle, Steven M., Alexander, Morgan R. and Alexander, Cameron (2017) Versatile routes to functional RAFT chain transfer agents through the Passerini multicomponent reaction. ACS Macro Letters, 6 (7). pp. 781-785. ISSN 2161-1653 http://pubs.acs.org/doi/abs/10.1021/acsmacrolett.7b00415 doi:10.1021/acsmacrolett.7b00415 doi:10.1021/acsmacrolett.7b00415
spellingShingle Pearce, Amanda K.
Travanut, Alessandra
Couturaud, Benoit
Taresco, Vincenzo
Howdle, Steven M.
Alexander, Morgan R.
Alexander, Cameron
Versatile routes to functional RAFT chain transfer agents through the Passerini multicomponent reaction
title Versatile routes to functional RAFT chain transfer agents through the Passerini multicomponent reaction
title_full Versatile routes to functional RAFT chain transfer agents through the Passerini multicomponent reaction
title_fullStr Versatile routes to functional RAFT chain transfer agents through the Passerini multicomponent reaction
title_full_unstemmed Versatile routes to functional RAFT chain transfer agents through the Passerini multicomponent reaction
title_short Versatile routes to functional RAFT chain transfer agents through the Passerini multicomponent reaction
title_sort versatile routes to functional raft chain transfer agents through the passerini multicomponent reaction
url https://eprints.nottingham.ac.uk/46956/
https://eprints.nottingham.ac.uk/46956/
https://eprints.nottingham.ac.uk/46956/