Grafting of adipic anhydride to carbon nanotubes through a Diels-Alder cycloaddition/oxidation cascade reaction

Detalhes bibliográficos
Autor(a) principal: Araújo, Rui Filipe
Data de Publicação: 2016
Outros Autores: Proença, M. Fernanda R. P., Silva, Carlos J. R., Castro, Tarsila Gabriel, Melle-Franco, M., Paiva, M. C., Vilar-Rodil, Silvia, Tascón, Juan Manuel D.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/39188
Resumo: Accepted Manuscript
id RCAP_159e17936cebc6ee62e291b17a0eb06a
oai_identifier_str oai:repositorium.sdum.uminho.pt:1822/39188
network_acronym_str RCAP
network_name_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository_id_str 7160
spelling Grafting of adipic anhydride to carbon nanotubes through a Diels-Alder cycloaddition/oxidation cascade reactionCarbon nanotubesDiels-Alder cycloaddition reactionFunctionalizationCiências Naturais::Ciências QuímicasScience & TechnologyAccepted ManuscriptDifferent reactions have been reported for the successful functionalization of carbon nanotubes (CNT). The Diels-Alder cycloaddition is recognized as a plausible chemical approach, but few reports are known where this strategy has been used. In this study, the functionalization was performed by 1,3-butadiene generated from 3-sulfolene under heating conditions in diglyme. This simple and easily scalable method resulted in functionalized CNT with mass losses of 10 - 23 % by thermogravimetric analysis (nitrogen atmosphere). The functionalization was also supported by acid-base titration, elemental analysis, temperature programmed desorption and X-ray photoelectron spectroscopy. The high content in oxygen detected on the CNT surface was assigned to anhydride formation due to a cascade oxidation of the alkene groups generated in the cycloaddition reaction. The complete evolution of the alkene leads to a grafting density of 4.2 mmol g-1 for the anhydride moiety. Ab-initio calculations in CNT model systems indicate that the Diels-Alder addition of butadiene is a feasible process and that subsequent oxidation reactions may result in the formation of the anhydride moiety. The presence of the anhydride group is a valuable asset for grafting a multitude of complex molecules, namely through the nucleophilic addition of amines.Centro de Química and Instituto de Polímeros e Compósitos of the University of Minho and Fundação para a Ciência e Tecnologia (FCT) through the Portuguese NMR network (RNRMN), the Project F-COMP-01-0124-FEDER-022716 (ref. FCT PEst-C/QUI/UI0686/2011) FEDER-COMPETE, Project PEst-C/CTM/LA0025/2013 (Strategic Project - LA 25-2013-2014) and also Project Scope UID/CEC/00319/2013. TG Castro acknowledges FCT for a doctoral grant (SFRH/BD/79195/2011) RF Araújo for a Post-doc grant (SFRH/BPD/88920/2012) and MMF also acknowledges FCT through the program Ciência 2008. Access to computing resources funded by the Project "Search-ON2: Revitalization of HPC infrastructure of UMinho" (NORTE-07-0162-FEDER-000086) is also gratefully acknowledged.ElsevierUniversidade do MinhoAraújo, Rui FilipeProença, M. Fernanda R. P.Silva, Carlos J. R.Castro, Tarsila GabrielMelle-Franco, M.Paiva, M. C.Vilar-Rodil, SilviaTascón, Juan Manuel D.2016-032016-03-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/39188engR.F. Araújo, M.F. Proença, C.J. Silva, T.G. Castro, M. Melle-Franco, M.C. Paiva, S. Vilar-Rodil, J.M.D. Tascón, Grafting of adipic anhydride to carbon nanotubes through a Diels- Alder cycloaddition/oxidation cascade reaction, Carbon (2015), doi: 10.1016/j.carbon.2015.11.0040008-622310.1016/j.carbon.2015.11.004http://www.sciencedirect.com/science/article/pii/S0008622315304152info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:54:12Zoai:repositorium.sdum.uminho.pt:1822/39188Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:53:44.953491Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Grafting of adipic anhydride to carbon nanotubes through a Diels-Alder cycloaddition/oxidation cascade reaction
title Grafting of adipic anhydride to carbon nanotubes through a Diels-Alder cycloaddition/oxidation cascade reaction
spellingShingle Grafting of adipic anhydride to carbon nanotubes through a Diels-Alder cycloaddition/oxidation cascade reaction
Araújo, Rui Filipe
Carbon nanotubes
Diels-Alder cycloaddition reaction
Functionalization
Ciências Naturais::Ciências Químicas
Science & Technology
title_short Grafting of adipic anhydride to carbon nanotubes through a Diels-Alder cycloaddition/oxidation cascade reaction
title_full Grafting of adipic anhydride to carbon nanotubes through a Diels-Alder cycloaddition/oxidation cascade reaction
title_fullStr Grafting of adipic anhydride to carbon nanotubes through a Diels-Alder cycloaddition/oxidation cascade reaction
title_full_unstemmed Grafting of adipic anhydride to carbon nanotubes through a Diels-Alder cycloaddition/oxidation cascade reaction
title_sort Grafting of adipic anhydride to carbon nanotubes through a Diels-Alder cycloaddition/oxidation cascade reaction
author Araújo, Rui Filipe
author_facet Araújo, Rui Filipe
Proença, M. Fernanda R. P.
Silva, Carlos J. R.
Castro, Tarsila Gabriel
Melle-Franco, M.
Paiva, M. C.
Vilar-Rodil, Silvia
Tascón, Juan Manuel D.
author_role author
author2 Proença, M. Fernanda R. P.
Silva, Carlos J. R.
Castro, Tarsila Gabriel
Melle-Franco, M.
Paiva, M. C.
Vilar-Rodil, Silvia
Tascón, Juan Manuel D.
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Araújo, Rui Filipe
Proença, M. Fernanda R. P.
Silva, Carlos J. R.
Castro, Tarsila Gabriel
Melle-Franco, M.
Paiva, M. C.
Vilar-Rodil, Silvia
Tascón, Juan Manuel D.
dc.subject.por.fl_str_mv Carbon nanotubes
Diels-Alder cycloaddition reaction
Functionalization
Ciências Naturais::Ciências Químicas
Science & Technology
topic Carbon nanotubes
Diels-Alder cycloaddition reaction
Functionalization
Ciências Naturais::Ciências Químicas
Science & Technology
description Accepted Manuscript
publishDate 2016
dc.date.none.fl_str_mv 2016-03
2016-03-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/1822/39188
url http://hdl.handle.net/1822/39188
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv R.F. Araújo, M.F. Proença, C.J. Silva, T.G. Castro, M. Melle-Franco, M.C. Paiva, S. Vilar-Rodil, J.M.D. Tascón, Grafting of adipic anhydride to carbon nanotubes through a Diels- Alder cycloaddition/oxidation cascade reaction, Carbon (2015), doi: 10.1016/j.carbon.2015.11.004
0008-6223
10.1016/j.carbon.2015.11.004
http://www.sciencedirect.com/science/article/pii/S0008622315304152
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv
_version_ 1799133134860582912

Registros relacionados