Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activity

Autores
Agazzi, Maximiliano Luis; Almodovar, Vitor A. S.; Gsponer, Natalia Soledad; Bertolotti, Sonia Graciela; Tomé, Augusto C.; Durantini, Edgardo Néstor
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Chromophore-fullerene C60 hybrids possess interesting properties that enable them to act as heavy atom-free photosensitizers and reactive oxygen species (ROS) producers. Here, two new diketopyrrolopyrrole-C60 conjugates were efficiently synthesized and characterized. The conjugates show broadband absorption in the visible spectral region, in which diketopyrrolopyrrole dyes act as light-harvesting antenna with very high capacity to populate excited triplet states. Furthermore, the ability of diketopyrrolopyrrole-C60 systems to generate singlet molecular oxygen was explored for the first time in solvents of different polarities. The experimental results show that these architectures exhibit very high production rates of this ROS. In addition, a preliminary study on Staphylococcus aureus cell suspensions indicates that both conjugates exhibit phototoxicity after irradiation with green LED light. Thus, the data obtained provide evidence that these diketopyrrolopyrrole-C60 architectures act as potential heavy atom-free photosensitizers in photodynamic inactivation of microorganisms and other singlet oxygen-mediated applications.
Fil: Agazzi, Maximiliano Luis. 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: Almodovar, Vitor A. S.. Universidade de Aveiro; Portugal
Fil: Gsponer, Natalia Soledad. 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: Bertolotti, Sonia Graciela. 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: Tomé, Augusto C.. Universidade de Aveiro; Portugal
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
DIKETOPYRROLOPYRROLE
FULLERENE
SYNTHESIS
PHOTODYNAMIC ACTIVITY
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:11336/136053
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/136053
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activityAgazzi, Maximiliano LuisAlmodovar, Vitor A. S.Gsponer, Natalia SoledadBertolotti, Sonia GracielaTomé, Augusto C.Durantini, Edgardo NéstorDIKETOPYRROLOPYRROLEFULLERENESYNTHESISPHOTODYNAMIC ACTIVITYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Chromophore-fullerene C60 hybrids possess interesting properties that enable them to act as heavy atom-free photosensitizers and reactive oxygen species (ROS) producers. Here, two new diketopyrrolopyrrole-C60 conjugates were efficiently synthesized and characterized. The conjugates show broadband absorption in the visible spectral region, in which diketopyrrolopyrrole dyes act as light-harvesting antenna with very high capacity to populate excited triplet states. Furthermore, the ability of diketopyrrolopyrrole-C60 systems to generate singlet molecular oxygen was explored for the first time in solvents of different polarities. The experimental results show that these architectures exhibit very high production rates of this ROS. In addition, a preliminary study on Staphylococcus aureus cell suspensions indicates that both conjugates exhibit phototoxicity after irradiation with green LED light. Thus, the data obtained provide evidence that these diketopyrrolopyrrole-C60 architectures act as potential heavy atom-free photosensitizers in photodynamic inactivation of microorganisms and other singlet oxygen-mediated applications.Fil: Agazzi, Maximiliano Luis. 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: Almodovar, Vitor A. S.. Universidade de Aveiro; PortugalFil: Gsponer, Natalia Soledad. 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: Bertolotti, Sonia Graciela. 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: Tomé, Augusto C.. Universidade de Aveiro; PortugalFil: 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; ArgentinaRoyal Society of Chemistry2020-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/136053Agazzi, Maximiliano Luis; Almodovar, Vitor A. S.; Gsponer, Natalia Soledad; Bertolotti, Sonia Graciela; Tomé, Augusto C.; et al.; Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activity; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 18; 7; 2-2020; 1449-14611477-05201477-0539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://xlink.rsc.org/?DOI=C9OB02487Einfo:eu-repo/semantics/altIdentifier/doi/10.1039/C9OB02487Einfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:18:48Zoai:ri.conicet.gov.ar:11336/136053instacron: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 15:18:48.687CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activity
title Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activity
spellingShingle Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activity
Agazzi, Maximiliano Luis
DIKETOPYRROLOPYRROLE
FULLERENE
SYNTHESIS
PHOTODYNAMIC ACTIVITY
title_short Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activity
title_full Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activity
title_fullStr Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activity
title_full_unstemmed Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activity
title_sort Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activity
dc.creator.none.fl_str_mv Agazzi, Maximiliano Luis
Almodovar, Vitor A. S.
Gsponer, Natalia Soledad
Bertolotti, Sonia Graciela
Tomé, Augusto C.
Durantini, Edgardo Néstor
author Agazzi, Maximiliano Luis
author_facet Agazzi, Maximiliano Luis
Almodovar, Vitor A. S.
Gsponer, Natalia Soledad
Bertolotti, Sonia Graciela
Tomé, Augusto C.
Durantini, Edgardo Néstor
author_role author
author2 Almodovar, Vitor A. S.
Gsponer, Natalia Soledad
Bertolotti, Sonia Graciela
Tomé, Augusto C.
Durantini, Edgardo Néstor
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv DIKETOPYRROLOPYRROLE
FULLERENE
SYNTHESIS
PHOTODYNAMIC ACTIVITY
topic DIKETOPYRROLOPYRROLE
FULLERENE
SYNTHESIS
PHOTODYNAMIC ACTIVITY
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Chromophore-fullerene C60 hybrids possess interesting properties that enable them to act as heavy atom-free photosensitizers and reactive oxygen species (ROS) producers. Here, two new diketopyrrolopyrrole-C60 conjugates were efficiently synthesized and characterized. The conjugates show broadband absorption in the visible spectral region, in which diketopyrrolopyrrole dyes act as light-harvesting antenna with very high capacity to populate excited triplet states. Furthermore, the ability of diketopyrrolopyrrole-C60 systems to generate singlet molecular oxygen was explored for the first time in solvents of different polarities. The experimental results show that these architectures exhibit very high production rates of this ROS. In addition, a preliminary study on Staphylococcus aureus cell suspensions indicates that both conjugates exhibit phototoxicity after irradiation with green LED light. Thus, the data obtained provide evidence that these diketopyrrolopyrrole-C60 architectures act as potential heavy atom-free photosensitizers in photodynamic inactivation of microorganisms and other singlet oxygen-mediated applications.
Fil: Agazzi, Maximiliano Luis. 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: Almodovar, Vitor A. S.. Universidade de Aveiro; Portugal
Fil: Gsponer, Natalia Soledad. 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: Bertolotti, Sonia Graciela. 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: Tomé, Augusto C.. Universidade de Aveiro; Portugal
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 Chromophore-fullerene C60 hybrids possess interesting properties that enable them to act as heavy atom-free photosensitizers and reactive oxygen species (ROS) producers. Here, two new diketopyrrolopyrrole-C60 conjugates were efficiently synthesized and characterized. The conjugates show broadband absorption in the visible spectral region, in which diketopyrrolopyrrole dyes act as light-harvesting antenna with very high capacity to populate excited triplet states. Furthermore, the ability of diketopyrrolopyrrole-C60 systems to generate singlet molecular oxygen was explored for the first time in solvents of different polarities. The experimental results show that these architectures exhibit very high production rates of this ROS. In addition, a preliminary study on Staphylococcus aureus cell suspensions indicates that both conjugates exhibit phototoxicity after irradiation with green LED light. Thus, the data obtained provide evidence that these diketopyrrolopyrrole-C60 architectures act as potential heavy atom-free photosensitizers in photodynamic inactivation of microorganisms and other singlet oxygen-mediated applications.
publishDate 2020
dc.date.none.fl_str_mv 2020-02
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/11336/136053
Agazzi, Maximiliano Luis; Almodovar, Vitor A. S.; Gsponer, Natalia Soledad; Bertolotti, Sonia Graciela; Tomé, Augusto C.; et al.; Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activity; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 18; 7; 2-2020; 1449-1461
1477-0520
1477-0539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/136053
identifier_str_mv Agazzi, Maximiliano Luis; Almodovar, Vitor A. S.; Gsponer, Natalia Soledad; Bertolotti, Sonia Graciela; Tomé, Augusto C.; et al.; Diketopyrrolopyrrole-fullerene C60 architectures as highly efficient heavy atom-free photosensitizers: Synthesis, photophysical properties and photodynamic activity; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 18; 7; 2-2020; 1449-1461
1477-0520
1477-0539
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://xlink.rsc.org/?DOI=C9OB02487E
info:eu-repo/semantics/altIdentifier/doi/10.1039/C9OB02487E
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
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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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