Versatile Photofunctionalization of Carbon Nanotubes via [4+2] Cycloaddition: A Facile Route to Hybrid Nanomaterials

The [4 þ 2] photofunctionalization of carbon nanotubes of different characteristics, such as single-walled carbon nanotubes (0.9 and 1.4 nm diameter) or multiwalled carbon nanotubes (10 nm diameter), with aryl cyclobutyl amines 3 of diverse nature in the presence of common organic photocatalysts is...

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Detalles Bibliográficos
Autores: De Crescenzo, Giacomo, Sánchez Morena, Paula, Fraile Carrasco, Alberto, Blanco Fernández, Matías, Alemán Lara, José Julián
Tipo de recurso: artículo
Fecha de publicación:2025
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/730541
Acceso en línea:https://hdl.handle.net/10486/730541
https://dx.doi.org/10.1002/smsc.202500191
Access Level:acceso abierto
Palabra clave:carbon nanotubes
covalent functionalization
hybrid materials
photocatalysis
Química
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spelling Versatile Photofunctionalization of Carbon Nanotubes via [4+2] Cycloaddition: A Facile Route to Hybrid NanomaterialsDe Crescenzo, GiacomoSánchez Morena, PaulaFraile Carrasco, AlbertoBlanco Fernández, MatíasAlemán Lara, José Juliáncarbon nanotubescovalent functionalizationhybrid materialsphotocatalysisQuímicaThe [4 þ 2] photofunctionalization of carbon nanotubes of different characteristics, such as single-walled carbon nanotubes (0.9 and 1.4 nm diameter) or multiwalled carbon nanotubes (10 nm diameter), with aryl cyclobutyl amines 3 of diverse nature in the presence of common organic photocatalysts is presented. Through a facile synthetic protocol, a series of modified amines 3 is prepared, which undergo a photocatalyzed oxidative ring opening to subsequently react with the nanotube wall. Under the best reaction conditions (Rhodamine B, white light-emitting diode, 40 h), an 8–20% functionalization degree in the form of Ncyclohexylamine moieties is achieved. The reaction is general with respect to the type of nanotube employed, the electronic characteristics of the amine (decorated with electron-donating and electron-withdrawing groups), and it is homogeneous throughout the whole nanotube particle without affecting the morphology of the samples, as demonstrated by the characterization techniques performed. In addition, the method allows for postfunctionalization treatments by the onsurface hydrolysis of an ester-modified aryl cyclobutyl amine and subsequent amidation with amino-decorated organic polymer nanoparticles. Thus, a hybrid material with different properties compared to the simple composite is obtained using this photochemical carbon nanotubes functionalizationThis work was supported by MICINN (PID2021-122299NB-100, TED2021-129999B-C32, TED2021-130470B-100), VIRMAT Projects in response to COVID-19 financed by the ERDF-REACT-EU resources, “Comunidad de Madrid” for European Structural Funds (S2018/NMT-4367) and proyectos sinérgicos IþD (Y2020/NMT-6469WileyDepartamento de Química OrgánicaFacultad de CienciasGobierno de EspañaComunidad de Madrid20252025-11-30research articlehttp://purl.org/coar/resource_type/c_2df8fbb1VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10486/730541https://dx.doi.org/10.1002/smsc.202500191reponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengopen accesshttp://purl.org/coar/access_right/c_abf2Attribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:repositorio.uam.es:10486/7305412026-06-23T12:46:27Z
dc.title.none.fl_str_mv Versatile Photofunctionalization of Carbon Nanotubes via [4+2] Cycloaddition: A Facile Route to Hybrid Nanomaterials
title Versatile Photofunctionalization of Carbon Nanotubes via [4+2] Cycloaddition: A Facile Route to Hybrid Nanomaterials
spellingShingle Versatile Photofunctionalization of Carbon Nanotubes via [4+2] Cycloaddition: A Facile Route to Hybrid Nanomaterials
De Crescenzo, Giacomo
carbon nanotubes
covalent functionalization
hybrid materials
photocatalysis
Química
title_short Versatile Photofunctionalization of Carbon Nanotubes via [4+2] Cycloaddition: A Facile Route to Hybrid Nanomaterials
title_full Versatile Photofunctionalization of Carbon Nanotubes via [4+2] Cycloaddition: A Facile Route to Hybrid Nanomaterials
title_fullStr Versatile Photofunctionalization of Carbon Nanotubes via [4+2] Cycloaddition: A Facile Route to Hybrid Nanomaterials
title_full_unstemmed Versatile Photofunctionalization of Carbon Nanotubes via [4+2] Cycloaddition: A Facile Route to Hybrid Nanomaterials
title_sort Versatile Photofunctionalization of Carbon Nanotubes via [4+2] Cycloaddition: A Facile Route to Hybrid Nanomaterials
dc.creator.none.fl_str_mv De Crescenzo, Giacomo
Sánchez Morena, Paula
Fraile Carrasco, Alberto
Blanco Fernández, Matías
Alemán Lara, José Julián
author De Crescenzo, Giacomo
author_facet De Crescenzo, Giacomo
Sánchez Morena, Paula
Fraile Carrasco, Alberto
Blanco Fernández, Matías
Alemán Lara, José Julián
author_role author
author2 Sánchez Morena, Paula
Fraile Carrasco, Alberto
Blanco Fernández, Matías
Alemán Lara, José Julián
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Departamento de Química Orgánica
Facultad de Ciencias
Gobierno de España
Comunidad de Madrid
dc.subject.none.fl_str_mv carbon nanotubes
covalent functionalization
hybrid materials
photocatalysis
Química
topic carbon nanotubes
covalent functionalization
hybrid materials
photocatalysis
Química
description The [4 þ 2] photofunctionalization of carbon nanotubes of different characteristics, such as single-walled carbon nanotubes (0.9 and 1.4 nm diameter) or multiwalled carbon nanotubes (10 nm diameter), with aryl cyclobutyl amines 3 of diverse nature in the presence of common organic photocatalysts is presented. Through a facile synthetic protocol, a series of modified amines 3 is prepared, which undergo a photocatalyzed oxidative ring opening to subsequently react with the nanotube wall. Under the best reaction conditions (Rhodamine B, white light-emitting diode, 40 h), an 8–20% functionalization degree in the form of Ncyclohexylamine moieties is achieved. The reaction is general with respect to the type of nanotube employed, the electronic characteristics of the amine (decorated with electron-donating and electron-withdrawing groups), and it is homogeneous throughout the whole nanotube particle without affecting the morphology of the samples, as demonstrated by the characterization techniques performed. In addition, the method allows for postfunctionalization treatments by the onsurface hydrolysis of an ester-modified aryl cyclobutyl amine and subsequent amidation with amino-decorated organic polymer nanoparticles. Thus, a hybrid material with different properties compared to the simple composite is obtained using this photochemical carbon nanotubes functionalization
publishDate 2025
dc.date.none.fl_str_mv 2025
2025-11-30
dc.type.none.fl_str_mv research article
http://purl.org/coar/resource_type/c_2df8fbb1
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/10486/730541
https://dx.doi.org/10.1002/smsc.202500191
url https://hdl.handle.net/10486/730541
https://dx.doi.org/10.1002/smsc.202500191
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Biblos-e Archivo. Repositorio Institucional de la UAM
instname:Universidad Autónoma de Madrid
instname_str Universidad Autónoma de Madrid
reponame_str Biblos-e Archivo. Repositorio Institucional de la UAM
collection Biblos-e Archivo. Repositorio Institucional de la UAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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