Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer

Autores
Mora, Sabrina Jimena; Heredia, Daniel Alejandro; Odella, Emmanuel; Vrudhula, Uma; Gust, Devens; Moore, Thomas A.; Moore, Ana L.
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Benzimidazole phenol-porphyrin dyads have been synthesized to study proton-coupled electron transfer (PCET) reactions induced by photoexcitation. High-potential porphyrins have been chosen to model P680, the photoactive chlorophyll cluster of photosynthetic photosystem II (PSII). They have either two or three pentafluorophenyl groups at the meso positions to impart the high redox potential. The benzimidazole phenol (BIP) moiety models the Tyrz-His190 pair of PSII, which is a redox mediator that shuttles electrons from the water oxidation catalyst to P680•+. The dyads consisting of a porphyrin and an unsubstituted BIP are designed to study one-electron one-proton transfer (E1PT) processes upon excitation of the porphyrin. When the BIP moiety is substituted with proton-accepting groups such as imines, one-electron two-proton transfer (E2PT) processes are expected to take place upon oxidation of the phenol by the excited state of the porphyrin. The bis-pentafluorophenyl porphyrins linked to BIPs provide platforms for introducing a variety of electron-accepting moieties and/or anchoring groups to attach semiconductor nanoparticles to the macrocycle. The triads thus formed will serve to study the PCET process involving the BIPs when the oxidation of the phenol is achieved by the photochemically produced radical cation of the porphyrin.
Fil: Mora, Sabrina Jimena. Arizona State University; Estados Unidos. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; 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: Odella, Emmanuel. Arizona State University; Estados Unidos. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Vrudhula, Uma. Arizona State University; Estados Unidos
Fil: Gust, Devens. Arizona State University; Estados Unidos
Fil: Moore, Thomas A.. Arizona State University; Estados Unidos
Fil: Moore, Ana L.. Arizona State University; Estados Unidos
Materia
BENZIMIDAZOLE DERIVATIVES
PENTAFLUOROPHENYL PORPHYRIN
PHOTOSYSTEM II
PROTON-COUPLED ELECTRON TRANSFER (PCET)
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:11336/128151
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/128151
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transferMora, Sabrina JimenaHeredia, Daniel AlejandroOdella, EmmanuelVrudhula, UmaGust, DevensMoore, Thomas A.Moore, Ana L.BENZIMIDAZOLE DERIVATIVESPENTAFLUOROPHENYL PORPHYRINPHOTOSYSTEM IIPROTON-COUPLED ELECTRON TRANSFER (PCET)https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Benzimidazole phenol-porphyrin dyads have been synthesized to study proton-coupled electron transfer (PCET) reactions induced by photoexcitation. High-potential porphyrins have been chosen to model P680, the photoactive chlorophyll cluster of photosynthetic photosystem II (PSII). They have either two or three pentafluorophenyl groups at the meso positions to impart the high redox potential. The benzimidazole phenol (BIP) moiety models the Tyrz-His190 pair of PSII, which is a redox mediator that shuttles electrons from the water oxidation catalyst to P680•+. The dyads consisting of a porphyrin and an unsubstituted BIP are designed to study one-electron one-proton transfer (E1PT) processes upon excitation of the porphyrin. When the BIP moiety is substituted with proton-accepting groups such as imines, one-electron two-proton transfer (E2PT) processes are expected to take place upon oxidation of the phenol by the excited state of the porphyrin. The bis-pentafluorophenyl porphyrins linked to BIPs provide platforms for introducing a variety of electron-accepting moieties and/or anchoring groups to attach semiconductor nanoparticles to the macrocycle. The triads thus formed will serve to study the PCET process involving the BIPs when the oxidation of the phenol is achieved by the photochemically produced radical cation of the porphyrin.Fil: Mora, Sabrina Jimena. Arizona State University; Estados Unidos. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; 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: Odella, Emmanuel. Arizona State University; Estados Unidos. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Vrudhula, Uma. Arizona State University; Estados UnidosFil: Gust, Devens. Arizona State University; Estados UnidosFil: Moore, Thomas A.. Arizona State University; Estados UnidosFil: Moore, Ana L.. Arizona State University; Estados UnidosWorld Sci Publ Co Inc2019-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/128151Mora, Sabrina Jimena; Heredia, Daniel Alejandro; Odella, Emmanuel; Vrudhula, Uma; Gust, Devens; et al.; Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer; World Sci Publ Co Inc; Journal Of Porphyrins And Phthalocyanines; 23; 11-12; 9-2019; 1336-13451088-42461099-1409CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.worldscientific.com/doi/abs/10.1142/S1088424619501189info:eu-repo/semantics/altIdentifier/doi/10.1142/S1088424619501189info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:24:06Zoai:ri.conicet.gov.ar:11336/128151instacron: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:34982025-09-10 13:24:06.996CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer
title Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer
spellingShingle Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer
Mora, Sabrina Jimena
BENZIMIDAZOLE DERIVATIVES
PENTAFLUOROPHENYL PORPHYRIN
PHOTOSYSTEM II
PROTON-COUPLED ELECTRON TRANSFER (PCET)
title_short Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer
title_full Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer
title_fullStr Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer
title_full_unstemmed Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer
title_sort Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer
dc.creator.none.fl_str_mv Mora, Sabrina Jimena
Heredia, Daniel Alejandro
Odella, Emmanuel
Vrudhula, Uma
Gust, Devens
Moore, Thomas A.
Moore, Ana L.
author Mora, Sabrina Jimena
author_facet Mora, Sabrina Jimena
Heredia, Daniel Alejandro
Odella, Emmanuel
Vrudhula, Uma
Gust, Devens
Moore, Thomas A.
Moore, Ana L.
author_role author
author2 Heredia, Daniel Alejandro
Odella, Emmanuel
Vrudhula, Uma
Gust, Devens
Moore, Thomas A.
Moore, Ana L.
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv BENZIMIDAZOLE DERIVATIVES
PENTAFLUOROPHENYL PORPHYRIN
PHOTOSYSTEM II
PROTON-COUPLED ELECTRON TRANSFER (PCET)
topic BENZIMIDAZOLE DERIVATIVES
PENTAFLUOROPHENYL PORPHYRIN
PHOTOSYSTEM II
PROTON-COUPLED ELECTRON TRANSFER (PCET)
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Benzimidazole phenol-porphyrin dyads have been synthesized to study proton-coupled electron transfer (PCET) reactions induced by photoexcitation. High-potential porphyrins have been chosen to model P680, the photoactive chlorophyll cluster of photosynthetic photosystem II (PSII). They have either two or three pentafluorophenyl groups at the meso positions to impart the high redox potential. The benzimidazole phenol (BIP) moiety models the Tyrz-His190 pair of PSII, which is a redox mediator that shuttles electrons from the water oxidation catalyst to P680•+. The dyads consisting of a porphyrin and an unsubstituted BIP are designed to study one-electron one-proton transfer (E1PT) processes upon excitation of the porphyrin. When the BIP moiety is substituted with proton-accepting groups such as imines, one-electron two-proton transfer (E2PT) processes are expected to take place upon oxidation of the phenol by the excited state of the porphyrin. The bis-pentafluorophenyl porphyrins linked to BIPs provide platforms for introducing a variety of electron-accepting moieties and/or anchoring groups to attach semiconductor nanoparticles to the macrocycle. The triads thus formed will serve to study the PCET process involving the BIPs when the oxidation of the phenol is achieved by the photochemically produced radical cation of the porphyrin.
Fil: Mora, Sabrina Jimena. Arizona State University; Estados Unidos. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; 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: Odella, Emmanuel. Arizona State University; Estados Unidos. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Vrudhula, Uma. Arizona State University; Estados Unidos
Fil: Gust, Devens. Arizona State University; Estados Unidos
Fil: Moore, Thomas A.. Arizona State University; Estados Unidos
Fil: Moore, Ana L.. Arizona State University; Estados Unidos
description Benzimidazole phenol-porphyrin dyads have been synthesized to study proton-coupled electron transfer (PCET) reactions induced by photoexcitation. High-potential porphyrins have been chosen to model P680, the photoactive chlorophyll cluster of photosynthetic photosystem II (PSII). They have either two or three pentafluorophenyl groups at the meso positions to impart the high redox potential. The benzimidazole phenol (BIP) moiety models the Tyrz-His190 pair of PSII, which is a redox mediator that shuttles electrons from the water oxidation catalyst to P680•+. The dyads consisting of a porphyrin and an unsubstituted BIP are designed to study one-electron one-proton transfer (E1PT) processes upon excitation of the porphyrin. When the BIP moiety is substituted with proton-accepting groups such as imines, one-electron two-proton transfer (E2PT) processes are expected to take place upon oxidation of the phenol by the excited state of the porphyrin. The bis-pentafluorophenyl porphyrins linked to BIPs provide platforms for introducing a variety of electron-accepting moieties and/or anchoring groups to attach semiconductor nanoparticles to the macrocycle. The triads thus formed will serve to study the PCET process involving the BIPs when the oxidation of the phenol is achieved by the photochemically produced radical cation of the porphyrin.
publishDate 2019
dc.date.none.fl_str_mv 2019-09
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/11336/128151
Mora, Sabrina Jimena; Heredia, Daniel Alejandro; Odella, Emmanuel; Vrudhula, Uma; Gust, Devens; et al.; Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer; World Sci Publ Co Inc; Journal Of Porphyrins And Phthalocyanines; 23; 11-12; 9-2019; 1336-1345
1088-4246
1099-1409
CONICET Digital
CONICET
url http://hdl.handle.net/11336/128151
identifier_str_mv Mora, Sabrina Jimena; Heredia, Daniel Alejandro; Odella, Emmanuel; Vrudhula, Uma; Gust, Devens; et al.; Design and synthesis of benzimidazole phenol-porphyrin dyads for the study of bioinspired photoinduced proton-coupled electron transfer; World Sci Publ Co Inc; Journal Of Porphyrins And Phthalocyanines; 23; 11-12; 9-2019; 1336-1345
1088-4246
1099-1409
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.worldscientific.com/doi/abs/10.1142/S1088424619501189
info:eu-repo/semantics/altIdentifier/doi/10.1142/S1088424619501189
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 World Sci Publ Co Inc
publisher.none.fl_str_mv World Sci Publ Co Inc
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 12.48226

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