Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer

Autores
Santamarina, Sofia Carla; Heredia, Daniel Alejandro; Durantini, Andres Matías; Durantini, Edgardo Néstor
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
5,10,15,20-tetrakis-[4-(ethynyl)phenyl]porphyrin (TEP) was synthesized from the condensation of 4-(ethynyl)benzaldehyde and pyrrole catalyzed by boron trifluoride diethyl etherate in dichloromethane (DCM). After oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and purification, TEP was obtained in 34% yield. This porphyrin was metaled with Zn(II) acetate in DCM/methanol to produce the complex ZnTEP in 98% yield. A homocoupling reaction of terminal alkynes of ZnTEP to diynes was used to synthesize conjugated polymer organogel (ZnTEPP). The reaction was co-catalyzed by PdCl2(PPh3)2 and CuI in tetrahydrofuran. The solvent was evaporated to obtain xerogel and the SEM images showed microporous structure. In addition, spectroscopic and photodynamic studies of ZnTEPP indicated that the porphyrin unit retains its properties as a photosensitizer. Thus, this polymer is an interesting material with potential applications in forming photoactive aseptic surfaces.
Fil: Santamarina, Sofia Carla. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Fil: Heredia, Daniel Alejandro. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Fil: Durantini, Andres Matías. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Fil: Durantini, Edgardo Néstor. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Materia
PORPHYRIN
POLYMER
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:11336/146216
Acceder
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network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as PhotosensitizerSantamarina, Sofia CarlaHeredia, Daniel AlejandroDurantini, Andres MatíasDurantini, Edgardo NéstorPORPHYRINPOLYMERhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/15,10,15,20-tetrakis-[4-(ethynyl)phenyl]porphyrin (TEP) was synthesized from the condensation of 4-(ethynyl)benzaldehyde and pyrrole catalyzed by boron trifluoride diethyl etherate in dichloromethane (DCM). After oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and purification, TEP was obtained in 34% yield. This porphyrin was metaled with Zn(II) acetate in DCM/methanol to produce the complex ZnTEP in 98% yield. A homocoupling reaction of terminal alkynes of ZnTEP to diynes was used to synthesize conjugated polymer organogel (ZnTEPP). The reaction was co-catalyzed by PdCl2(PPh3)2 and CuI in tetrahydrofuran. The solvent was evaporated to obtain xerogel and the SEM images showed microporous structure. In addition, spectroscopic and photodynamic studies of ZnTEPP indicated that the porphyrin unit retains its properties as a photosensitizer. Thus, this polymer is an interesting material with potential applications in forming photoactive aseptic surfaces.Fil: Santamarina, Sofia Carla. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; ArgentinaFil: Heredia, Daniel Alejandro. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; ArgentinaFil: Durantini, Andres Matías. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; ArgentinaFil: Durantini, Edgardo Néstor. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; ArgentinaMolecular Diversity Preservation International2020-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/146216Santamarina, Sofia Carla; Heredia, Daniel Alejandro; Durantini, Andres Matías; Durantini, Edgardo Néstor; Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer; Molecular Diversity Preservation International; Chemistry Proceedings; 3; 1; 11-2020; 1-72673-4583CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2673-4583/3/1/94info:eu-repo/semantics/altIdentifier/doi/10.3390/ecsoc-24-08317info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:17:00Zoai:ri.conicet.gov.ar:11336/146216instacron: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 15:17:01.213CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer
title Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer
spellingShingle Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer
Santamarina, Sofia Carla
PORPHYRIN
POLYMER
title_short Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer
title_full Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer
title_fullStr Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer
title_full_unstemmed Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer
title_sort Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer
dc.creator.none.fl_str_mv Santamarina, Sofia Carla
Heredia, Daniel Alejandro
Durantini, Andres Matías
Durantini, Edgardo Néstor
author Santamarina, Sofia Carla
author_facet Santamarina, Sofia Carla
Heredia, Daniel Alejandro
Durantini, Andres Matías
Durantini, Edgardo Néstor
author_role author
author2 Heredia, Daniel Alejandro
Durantini, Andres Matías
Durantini, Edgardo Néstor
author2_role author
author
author
dc.subject.none.fl_str_mv PORPHYRIN
POLYMER
topic PORPHYRIN
POLYMER
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 5,10,15,20-tetrakis-[4-(ethynyl)phenyl]porphyrin (TEP) was synthesized from the condensation of 4-(ethynyl)benzaldehyde and pyrrole catalyzed by boron trifluoride diethyl etherate in dichloromethane (DCM). After oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and purification, TEP was obtained in 34% yield. This porphyrin was metaled with Zn(II) acetate in DCM/methanol to produce the complex ZnTEP in 98% yield. A homocoupling reaction of terminal alkynes of ZnTEP to diynes was used to synthesize conjugated polymer organogel (ZnTEPP). The reaction was co-catalyzed by PdCl2(PPh3)2 and CuI in tetrahydrofuran. The solvent was evaporated to obtain xerogel and the SEM images showed microporous structure. In addition, spectroscopic and photodynamic studies of ZnTEPP indicated that the porphyrin unit retains its properties as a photosensitizer. Thus, this polymer is an interesting material with potential applications in forming photoactive aseptic surfaces.
Fil: Santamarina, Sofia Carla. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Fil: Heredia, Daniel Alejandro. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Fil: Durantini, Andres Matías. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Fil: Durantini, Edgardo Néstor. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
description 5,10,15,20-tetrakis-[4-(ethynyl)phenyl]porphyrin (TEP) was synthesized from the condensation of 4-(ethynyl)benzaldehyde and pyrrole catalyzed by boron trifluoride diethyl etherate in dichloromethane (DCM). After oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and purification, TEP was obtained in 34% yield. This porphyrin was metaled with Zn(II) acetate in DCM/methanol to produce the complex ZnTEP in 98% yield. A homocoupling reaction of terminal alkynes of ZnTEP to diynes was used to synthesize conjugated polymer organogel (ZnTEPP). The reaction was co-catalyzed by PdCl2(PPh3)2 and CuI in tetrahydrofuran. The solvent was evaporated to obtain xerogel and the SEM images showed microporous structure. In addition, spectroscopic and photodynamic studies of ZnTEPP indicated that the porphyrin unit retains its properties as a photosensitizer. Thus, this polymer is an interesting material with potential applications in forming photoactive aseptic surfaces.
publishDate 2020
dc.date.none.fl_str_mv 2020-11
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/11336/146216
Santamarina, Sofia Carla; Heredia, Daniel Alejandro; Durantini, Andres Matías; Durantini, Edgardo Néstor; Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer; Molecular Diversity Preservation International; Chemistry Proceedings; 3; 1; 11-2020; 1-7
2673-4583
CONICET Digital
CONICET
url http://hdl.handle.net/11336/146216
identifier_str_mv Santamarina, Sofia Carla; Heredia, Daniel Alejandro; Durantini, Andres Matías; Durantini, Edgardo Néstor; Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer; Molecular Diversity Preservation International; Chemistry Proceedings; 3; 1; 11-2020; 1-7
2673-4583
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://www.mdpi.com/2673-4583/3/1/94
info:eu-repo/semantics/altIdentifier/doi/10.3390/ecsoc-24-08317
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 Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
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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