Design and application of a phenanthroline-based covalent triazine framework with Cu(I) for the heterogeneous synthesis of 2-aminobenzothiazoles

Design and application of a phenanthroline-based covalent triazine framework with Cu(I) for the heterogeneous synthesis of 2-aminobenzothiazoles Catalyst design is essential for advancing sustainable chemistry, particularly through heterogeneous systems that offer recyclability and environmental ben...

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Autores: Vega Fernández, Jorge, Capitán Aranda, María José, Álvarez Alonso, Jesús, Fraile Carrasco, Alberto, Alemán Lara, José Julián
Tipo de recurso: artículo
Fecha de publicación:2026
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:dnet:biblosearchi::733cab9408274cb77bb9b41879ab2234
Acceso en línea:https://hdl.handle.net/10486/777500
https://dx.doi.org/10.1021/acsami.6c05338
Access Level:acceso abierto
Palabra clave:heterogeneous catalysis
covalent triazine framework(CTF)
1,10-phenanthroline
copper(I)catalyst
2-aminobenzothiazole
C−Sbondformation
Química
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spelling Design and application of a phenanthroline-based covalent triazine framework with Cu(I) for the heterogeneous synthesis of 2-aminobenzothiazolesVega Fernández, JorgeCapitán Aranda, María JoséÁlvarez Alonso, JesúsFraile Carrasco, AlbertoAlemán Lara, José Juliánheterogeneous catalysiscovalent triazine framework(CTF)1,10-phenanthrolinecopper(I)catalyst2-aminobenzothiazoleC−SbondformationQuímicaDesign and application of a phenanthroline-based covalent triazine framework with Cu(I) for the heterogeneous synthesis of 2-aminobenzothiazoles Catalyst design is essential for advancing sustainable chemistry, particularly through heterogeneous systems that offer recyclability and environmental benefits. Herein, we report the synthesis and application of a novel covalent triazine framework (CTF) incorporating 1,10-phenanthroline units, which serve as coordination sites for Cu(I) ions. The resulting heterogeneous catalyst, Cu@Phen-CTF, was prepared through postsynthetic metalation and fully characterized by Fourier transform infrared, Raman, solid-state nuclear magnetic resonance, scanning electron microscopy/energy-dispersive X-ray, transmission electron microscopy, X-ray photoelectron spectroscopy, and Brunauer−Emmett−Teller surface area analysis, confirming successful Cu(I) incorporation and structural integrity. This catalyst was applied to the tandem cyclization of 2-iodoanilines with isothiocyanates to access pharmacologically relevant 2-aminobenzothiazole derivatives. The Cu@Phen-CTF system showed excellent catalytic activity under mild conditions (50 °C, toluene, 72 h), affording high yields and a broad substrate scope. Furthermore, the material demonstrated good thermal stability, negligible leaching, and high recyclability, maintaining performance across multiple catalytic cyclesFinancial support was provided by the Spanish Government (PID2024-155520NB-I00, ED2021-129999B-C32, and TED2021-130470B-100), "Comunidad de Madrid", and European Structural Funds (S2018/NMT-4367), "Proyectos Sinérgicos I+D (Y2020/NMT-6469)", and "Comunidad de Madrid" (SI1/PJI/2019-00237). VIRMAT Projects in response to COVID-19 were financed by the ERDF-REACTEU resourcesACSDepartamento de Química OrgánicaDepartamento de Física de la Materia CondensadaFacultad de CienciasComunidad de MadridGobierno de España20262026-05-04research articlehttp://purl.org/coar/resource_type/c_2df8fbb1VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10486/777500https://dx.doi.org/10.1021/acsami.6c05338reponame: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:dnet:biblosearchi::733cab9408274cb77bb9b41879ab22342026-06-23T12:46:27Z
dc.title.none.fl_str_mv Design and application of a phenanthroline-based covalent triazine framework with Cu(I) for the heterogeneous synthesis of 2-aminobenzothiazoles
title Design and application of a phenanthroline-based covalent triazine framework with Cu(I) for the heterogeneous synthesis of 2-aminobenzothiazoles
spellingShingle Design and application of a phenanthroline-based covalent triazine framework with Cu(I) for the heterogeneous synthesis of 2-aminobenzothiazoles
Vega Fernández, Jorge
heterogeneous catalysis
covalent triazine framework(CTF)
1,10-phenanthroline
copper(I)catalyst
2-aminobenzothiazole
C−Sbondformation
Química
title_short Design and application of a phenanthroline-based covalent triazine framework with Cu(I) for the heterogeneous synthesis of 2-aminobenzothiazoles
title_full Design and application of a phenanthroline-based covalent triazine framework with Cu(I) for the heterogeneous synthesis of 2-aminobenzothiazoles
title_fullStr Design and application of a phenanthroline-based covalent triazine framework with Cu(I) for the heterogeneous synthesis of 2-aminobenzothiazoles
title_full_unstemmed Design and application of a phenanthroline-based covalent triazine framework with Cu(I) for the heterogeneous synthesis of 2-aminobenzothiazoles
title_sort Design and application of a phenanthroline-based covalent triazine framework with Cu(I) for the heterogeneous synthesis of 2-aminobenzothiazoles
dc.creator.none.fl_str_mv Vega Fernández, Jorge
Capitán Aranda, María José
Álvarez Alonso, Jesús
Fraile Carrasco, Alberto
Alemán Lara, José Julián
author Vega Fernández, Jorge
author_facet Vega Fernández, Jorge
Capitán Aranda, María José
Álvarez Alonso, Jesús
Fraile Carrasco, Alberto
Alemán Lara, José Julián
author_role author
author2 Capitán Aranda, María José
Álvarez Alonso, Jesús
Fraile Carrasco, Alberto
Alemán Lara, José Julián
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Departamento de Química Orgánica
Departamento de Física de la Materia Condensada
Facultad de Ciencias
Comunidad de Madrid
Gobierno de España
dc.subject.none.fl_str_mv heterogeneous catalysis
covalent triazine framework(CTF)
1,10-phenanthroline
copper(I)catalyst
2-aminobenzothiazole
C−Sbondformation
Química
topic heterogeneous catalysis
covalent triazine framework(CTF)
1,10-phenanthroline
copper(I)catalyst
2-aminobenzothiazole
C−Sbondformation
Química
description Design and application of a phenanthroline-based covalent triazine framework with Cu(I) for the heterogeneous synthesis of 2-aminobenzothiazoles Catalyst design is essential for advancing sustainable chemistry, particularly through heterogeneous systems that offer recyclability and environmental benefits. Herein, we report the synthesis and application of a novel covalent triazine framework (CTF) incorporating 1,10-phenanthroline units, which serve as coordination sites for Cu(I) ions. The resulting heterogeneous catalyst, Cu@Phen-CTF, was prepared through postsynthetic metalation and fully characterized by Fourier transform infrared, Raman, solid-state nuclear magnetic resonance, scanning electron microscopy/energy-dispersive X-ray, transmission electron microscopy, X-ray photoelectron spectroscopy, and Brunauer−Emmett−Teller surface area analysis, confirming successful Cu(I) incorporation and structural integrity. This catalyst was applied to the tandem cyclization of 2-iodoanilines with isothiocyanates to access pharmacologically relevant 2-aminobenzothiazole derivatives. The Cu@Phen-CTF system showed excellent catalytic activity under mild conditions (50 °C, toluene, 72 h), affording high yields and a broad substrate scope. Furthermore, the material demonstrated good thermal stability, negligible leaching, and high recyclability, maintaining performance across multiple catalytic cycles
publishDate 2026
dc.date.none.fl_str_mv 2026
2026-05-04
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/10486/777500
https://dx.doi.org/10.1021/acsami.6c05338
url https://hdl.handle.net/10486/777500
https://dx.doi.org/10.1021/acsami.6c05338
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 ACS
publisher.none.fl_str_mv ACS
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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