From NMP to RAFT and thiol-ene chemistry by in situ functionalization of nitroxide chain ends

Autores
Petton, Lionel; Ciolino, Andrés Eduardo; Stamenović, Milan M.; Espeel, Pieter; Du Prez, Filip E.
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A straightforward, novel strategy based on the in situ functionalization of polymers prepared by nitroxide-mediated polymerization (NMP), for the use as an extension toward block copolymers and post-polymerization modifications, has been investigated. The nitroxide end group is exchanged for a thiocarbonylthio end group by a rapid transfer reaction with bis(thiobenzoyl) disulfide to generate in situ reversible addition-fragmentation chain transfer (RAFT) macroinitiators. Moreover, not only have these macroinitiators been used in chain extension and block copolymerization experiments by the RAFT process but also a thiol-terminated polymer is synthesized by aminolysis of the RAFT end group and subsequently reacted with dodecyl vinyl ether by thiol-ene chemistry. A strategy based on the controlled addition of a disulfide during NMP is investigated for the synthesis of macro-CTA's. These compounds are subsequently used to obtain block copolymers by RAFT polymerization and also reduced to thiols for further functionalization of the polymer chain-ends by thiol-ene chemistry.
Fil: Petton, Lionel. University of Ghent; Bélgica
Fil: Ciolino, Andrés Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina. University of Ghent; Bélgica
Fil: Stamenović, Milan M.. University of Ghent; Bélgica
Fil: Espeel, Pieter. University of Ghent; Bélgica
Fil: Du Prez, Filip E.. University of Ghent; Bélgica
Materia
Block Copolymers
Functionalization of Polymers
Nitroxide-Mediated Polymerization
Reversible Addition-Fragmentation Chain Transfer
Thiol-Ene Chemistry
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/77138
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/77138
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling From NMP to RAFT and thiol-ene chemistry by in situ functionalization of nitroxide chain endsPetton, LionelCiolino, Andrés EduardoStamenović, Milan M.Espeel, PieterDu Prez, Filip E.Block CopolymersFunctionalization of PolymersNitroxide-Mediated PolymerizationReversible Addition-Fragmentation Chain TransferThiol-Ene Chemistryhttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2A straightforward, novel strategy based on the in situ functionalization of polymers prepared by nitroxide-mediated polymerization (NMP), for the use as an extension toward block copolymers and post-polymerization modifications, has been investigated. The nitroxide end group is exchanged for a thiocarbonylthio end group by a rapid transfer reaction with bis(thiobenzoyl) disulfide to generate in situ reversible addition-fragmentation chain transfer (RAFT) macroinitiators. Moreover, not only have these macroinitiators been used in chain extension and block copolymerization experiments by the RAFT process but also a thiol-terminated polymer is synthesized by aminolysis of the RAFT end group and subsequently reacted with dodecyl vinyl ether by thiol-ene chemistry. A strategy based on the controlled addition of a disulfide during NMP is investigated for the synthesis of macro-CTA's. These compounds are subsequently used to obtain block copolymers by RAFT polymerization and also reduced to thiols for further functionalization of the polymer chain-ends by thiol-ene chemistry.Fil: Petton, Lionel. University of Ghent; BélgicaFil: Ciolino, Andrés Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina. University of Ghent; BélgicaFil: Stamenović, Milan M.. University of Ghent; BélgicaFil: Espeel, Pieter. University of Ghent; BélgicaFil: Du Prez, Filip E.. University of Ghent; BélgicaWiley VCH Verlag2012-08-25info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/77138Petton, Lionel; Ciolino, Andrés Eduardo; Stamenović, Milan M.; Espeel, Pieter; Du Prez, Filip E.; From NMP to RAFT and thiol-ene chemistry by in situ functionalization of nitroxide chain ends; Wiley VCH Verlag; Macromolecular Rapid Communications; 33; 15; 25-8-2012; 1310-13151022-1336CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/marc.201200207info:eu-repo/semantics/altIdentifier/doi/10.1002/marc.201200207info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:48:13Zoai:ri.conicet.gov.ar:11336/77138instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 14:48:13.779CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv From NMP to RAFT and thiol-ene chemistry by in situ functionalization of nitroxide chain ends
title From NMP to RAFT and thiol-ene chemistry by in situ functionalization of nitroxide chain ends
spellingShingle From NMP to RAFT and thiol-ene chemistry by in situ functionalization of nitroxide chain ends
Petton, Lionel
Block Copolymers
Functionalization of Polymers
Nitroxide-Mediated Polymerization
Reversible Addition-Fragmentation Chain Transfer
Thiol-Ene Chemistry
title_short From NMP to RAFT and thiol-ene chemistry by in situ functionalization of nitroxide chain ends
title_full From NMP to RAFT and thiol-ene chemistry by in situ functionalization of nitroxide chain ends
title_fullStr From NMP to RAFT and thiol-ene chemistry by in situ functionalization of nitroxide chain ends
title_full_unstemmed From NMP to RAFT and thiol-ene chemistry by in situ functionalization of nitroxide chain ends
title_sort From NMP to RAFT and thiol-ene chemistry by in situ functionalization of nitroxide chain ends
dc.creator.none.fl_str_mv Petton, Lionel
Ciolino, Andrés Eduardo
Stamenović, Milan M.
Espeel, Pieter
Du Prez, Filip E.
author Petton, Lionel
author_facet Petton, Lionel
Ciolino, Andrés Eduardo
Stamenović, Milan M.
Espeel, Pieter
Du Prez, Filip E.
author_role author
author2 Ciolino, Andrés Eduardo
Stamenović, Milan M.
Espeel, Pieter
Du Prez, Filip E.
author2_role author
author
author
author
dc.subject.none.fl_str_mv Block Copolymers
Functionalization of Polymers
Nitroxide-Mediated Polymerization
Reversible Addition-Fragmentation Chain Transfer
Thiol-Ene Chemistry
topic Block Copolymers
Functionalization of Polymers
Nitroxide-Mediated Polymerization
Reversible Addition-Fragmentation Chain Transfer
Thiol-Ene Chemistry
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv A straightforward, novel strategy based on the in situ functionalization of polymers prepared by nitroxide-mediated polymerization (NMP), for the use as an extension toward block copolymers and post-polymerization modifications, has been investigated. The nitroxide end group is exchanged for a thiocarbonylthio end group by a rapid transfer reaction with bis(thiobenzoyl) disulfide to generate in situ reversible addition-fragmentation chain transfer (RAFT) macroinitiators. Moreover, not only have these macroinitiators been used in chain extension and block copolymerization experiments by the RAFT process but also a thiol-terminated polymer is synthesized by aminolysis of the RAFT end group and subsequently reacted with dodecyl vinyl ether by thiol-ene chemistry. A strategy based on the controlled addition of a disulfide during NMP is investigated for the synthesis of macro-CTA's. These compounds are subsequently used to obtain block copolymers by RAFT polymerization and also reduced to thiols for further functionalization of the polymer chain-ends by thiol-ene chemistry.
Fil: Petton, Lionel. University of Ghent; Bélgica
Fil: Ciolino, Andrés Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina. University of Ghent; Bélgica
Fil: Stamenović, Milan M.. University of Ghent; Bélgica
Fil: Espeel, Pieter. University of Ghent; Bélgica
Fil: Du Prez, Filip E.. University of Ghent; Bélgica
description A straightforward, novel strategy based on the in situ functionalization of polymers prepared by nitroxide-mediated polymerization (NMP), for the use as an extension toward block copolymers and post-polymerization modifications, has been investigated. The nitroxide end group is exchanged for a thiocarbonylthio end group by a rapid transfer reaction with bis(thiobenzoyl) disulfide to generate in situ reversible addition-fragmentation chain transfer (RAFT) macroinitiators. Moreover, not only have these macroinitiators been used in chain extension and block copolymerization experiments by the RAFT process but also a thiol-terminated polymer is synthesized by aminolysis of the RAFT end group and subsequently reacted with dodecyl vinyl ether by thiol-ene chemistry. A strategy based on the controlled addition of a disulfide during NMP is investigated for the synthesis of macro-CTA's. These compounds are subsequently used to obtain block copolymers by RAFT polymerization and also reduced to thiols for further functionalization of the polymer chain-ends by thiol-ene chemistry.
publishDate 2012
dc.date.none.fl_str_mv 2012-08-25
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/77138
Petton, Lionel; Ciolino, Andrés Eduardo; Stamenović, Milan M.; Espeel, Pieter; Du Prez, Filip E.; From NMP to RAFT and thiol-ene chemistry by in situ functionalization of nitroxide chain ends; Wiley VCH Verlag; Macromolecular Rapid Communications; 33; 15; 25-8-2012; 1310-1315
1022-1336
CONICET Digital
CONICET
url http://hdl.handle.net/11336/77138
identifier_str_mv Petton, Lionel; Ciolino, Andrés Eduardo; Stamenović, Milan M.; Espeel, Pieter; Du Prez, Filip E.; From NMP to RAFT and thiol-ene chemistry by in situ functionalization of nitroxide chain ends; Wiley VCH Verlag; Macromolecular Rapid Communications; 33; 15; 25-8-2012; 1310-1315
1022-1336
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/marc.201200207
info:eu-repo/semantics/altIdentifier/doi/10.1002/marc.201200207
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.22299

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