Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides

Autores
Bergkamp, Jesse J.; Sherman, Benjamin D.; Mariño Ochoa, Ernesto; Palacios, Rodrigo Emiliano; Cosa, Gonzlao; Moore, Thomas A.; Gust, Devens; Moore, Ana L.
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A series of axial phenoxy substituted octabutoxy silicon phthalocyanines bearing ethyl carboxylic ester and diethyl phosphonate groups have been prepared from the corresponding phenols in pyridine. Axial bis-hydroxy silicon phthalocyanine was prepared using an adaptation of a reported protocol [1, 2] from the octabutoxy free-base phthalocyanine. The phenols bear either carboxylic ester or phosphonate groups, which upon deprotection can serve as anchoring groups for attaching the phthalocyanines to semiconducting metal oxides used in dye sensitized solar cells (DSSCs). All the phthalocyanines of the series absorb in the near infra-red region: 758-776 nm. The first oxidation potential for each phenoxy derivative occurs near 0.55 V vs. SCE as measured by cyclic voltammetry, with all falling within a 10 mV range. This indicates that these dyes will have sufficient energy in the photo-excited state to drive the reduction of protons to hydrogen. Taking into account the absorption and electrochemical potentials, these dyes are promising candidates for use in dual-threshold photo-electrochemical cells.
Fil: Bergkamp, Jesse J.. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados Unidos
Fil: Sherman, Benjamin D.. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados Unidos
Fil: Mariño Ochoa, Ernesto. Instituto Tecnológico de Monterrey; México
Fil: Palacios, Rodrigo Emiliano. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; Argentina
Fil: Cosa, Gonzlao. McGill University. Department of Chemistry; Canadá
Fil: Moore, Thomas A.. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados Unidos
Fil: Gust, Devens. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados Unidos
Fil: Moore, Ana L.. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados Unidos
Materia
AXIAL PHENOXY LINKAGE
ELECTROCHEMISTRY
SILICON PHTHALOCYANINES
SYNTHESIS
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:11336/193467
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/193467
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxidesBergkamp, Jesse J.Sherman, Benjamin D.Mariño Ochoa, ErnestoPalacios, Rodrigo EmilianoCosa, GonzlaoMoore, Thomas A.Gust, DevensMoore, Ana L.AXIAL PHENOXY LINKAGEELECTROCHEMISTRYSILICON PHTHALOCYANINESSYNTHESIShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of axial phenoxy substituted octabutoxy silicon phthalocyanines bearing ethyl carboxylic ester and diethyl phosphonate groups have been prepared from the corresponding phenols in pyridine. Axial bis-hydroxy silicon phthalocyanine was prepared using an adaptation of a reported protocol [1, 2] from the octabutoxy free-base phthalocyanine. The phenols bear either carboxylic ester or phosphonate groups, which upon deprotection can serve as anchoring groups for attaching the phthalocyanines to semiconducting metal oxides used in dye sensitized solar cells (DSSCs). All the phthalocyanines of the series absorb in the near infra-red region: 758-776 nm. The first oxidation potential for each phenoxy derivative occurs near 0.55 V vs. SCE as measured by cyclic voltammetry, with all falling within a 10 mV range. This indicates that these dyes will have sufficient energy in the photo-excited state to drive the reduction of protons to hydrogen. Taking into account the absorption and electrochemical potentials, these dyes are promising candidates for use in dual-threshold photo-electrochemical cells.Fil: Bergkamp, Jesse J.. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados UnidosFil: Sherman, Benjamin D.. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados UnidosFil: Mariño Ochoa, Ernesto. Instituto Tecnológico de Monterrey; MéxicoFil: Palacios, Rodrigo Emiliano. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; ArgentinaFil: Cosa, Gonzlao. McGill University. Department of Chemistry; CanadáFil: Moore, Thomas A.. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados UnidosFil: Gust, Devens. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados UnidosFil: Moore, Ana L.. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados UnidosWorld Sci Publ Co Inc2011-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/193467Bergkamp, Jesse J.; Sherman, Benjamin D.; Mariño Ochoa, Ernesto; Palacios, Rodrigo Emiliano; Cosa, Gonzlao; et al.; Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides; World Sci Publ Co Inc; Journal Of Porphyrins And Phthalocyanines; 15; 9-10; 10-2011; 943-9501088-42461099-1409CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1142/S1088424611003847info:eu-repo/semantics/altIdentifier/url/https://www.worldscientific.com/doi/abs/10.1142/S1088424611003847info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:11:31Zoai:ri.conicet.gov.ar:11336/193467instacron: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 15:11:31.55CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides
title Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides
spellingShingle Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides
Bergkamp, Jesse J.
AXIAL PHENOXY LINKAGE
ELECTROCHEMISTRY
SILICON PHTHALOCYANINES
SYNTHESIS
title_short Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides
title_full Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides
title_fullStr Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides
title_full_unstemmed Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides
title_sort Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides
dc.creator.none.fl_str_mv Bergkamp, Jesse J.
Sherman, Benjamin D.
Mariño Ochoa, Ernesto
Palacios, Rodrigo Emiliano
Cosa, Gonzlao
Moore, Thomas A.
Gust, Devens
Moore, Ana L.
author Bergkamp, Jesse J.
author_facet Bergkamp, Jesse J.
Sherman, Benjamin D.
Mariño Ochoa, Ernesto
Palacios, Rodrigo Emiliano
Cosa, Gonzlao
Moore, Thomas A.
Gust, Devens
Moore, Ana L.
author_role author
author2 Sherman, Benjamin D.
Mariño Ochoa, Ernesto
Palacios, Rodrigo Emiliano
Cosa, Gonzlao
Moore, Thomas A.
Gust, Devens
Moore, Ana L.
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv AXIAL PHENOXY LINKAGE
ELECTROCHEMISTRY
SILICON PHTHALOCYANINES
SYNTHESIS
topic AXIAL PHENOXY LINKAGE
ELECTROCHEMISTRY
SILICON PHTHALOCYANINES
SYNTHESIS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A series of axial phenoxy substituted octabutoxy silicon phthalocyanines bearing ethyl carboxylic ester and diethyl phosphonate groups have been prepared from the corresponding phenols in pyridine. Axial bis-hydroxy silicon phthalocyanine was prepared using an adaptation of a reported protocol [1, 2] from the octabutoxy free-base phthalocyanine. The phenols bear either carboxylic ester or phosphonate groups, which upon deprotection can serve as anchoring groups for attaching the phthalocyanines to semiconducting metal oxides used in dye sensitized solar cells (DSSCs). All the phthalocyanines of the series absorb in the near infra-red region: 758-776 nm. The first oxidation potential for each phenoxy derivative occurs near 0.55 V vs. SCE as measured by cyclic voltammetry, with all falling within a 10 mV range. This indicates that these dyes will have sufficient energy in the photo-excited state to drive the reduction of protons to hydrogen. Taking into account the absorption and electrochemical potentials, these dyes are promising candidates for use in dual-threshold photo-electrochemical cells.
Fil: Bergkamp, Jesse J.. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados Unidos
Fil: Sherman, Benjamin D.. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados Unidos
Fil: Mariño Ochoa, Ernesto. Instituto Tecnológico de Monterrey; México
Fil: Palacios, Rodrigo Emiliano. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; Argentina
Fil: Cosa, Gonzlao. McGill University. Department of Chemistry; Canadá
Fil: Moore, Thomas A.. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados Unidos
Fil: Gust, Devens. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados Unidos
Fil: Moore, Ana L.. Center For Bio-inspired Solar Fuel Production; Estados Unidos. Arizona State University; Estados Unidos
description A series of axial phenoxy substituted octabutoxy silicon phthalocyanines bearing ethyl carboxylic ester and diethyl phosphonate groups have been prepared from the corresponding phenols in pyridine. Axial bis-hydroxy silicon phthalocyanine was prepared using an adaptation of a reported protocol [1, 2] from the octabutoxy free-base phthalocyanine. The phenols bear either carboxylic ester or phosphonate groups, which upon deprotection can serve as anchoring groups for attaching the phthalocyanines to semiconducting metal oxides used in dye sensitized solar cells (DSSCs). All the phthalocyanines of the series absorb in the near infra-red region: 758-776 nm. The first oxidation potential for each phenoxy derivative occurs near 0.55 V vs. SCE as measured by cyclic voltammetry, with all falling within a 10 mV range. This indicates that these dyes will have sufficient energy in the photo-excited state to drive the reduction of protons to hydrogen. Taking into account the absorption and electrochemical potentials, these dyes are promising candidates for use in dual-threshold photo-electrochemical cells.
publishDate 2011
dc.date.none.fl_str_mv 2011-10
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/11336/193467
Bergkamp, Jesse J.; Sherman, Benjamin D.; Mariño Ochoa, Ernesto; Palacios, Rodrigo Emiliano; Cosa, Gonzlao; et al.; Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides; World Sci Publ Co Inc; Journal Of Porphyrins And Phthalocyanines; 15; 9-10; 10-2011; 943-950
1088-4246
1099-1409
CONICET Digital
CONICET
url http://hdl.handle.net/11336/193467
identifier_str_mv Bergkamp, Jesse J.; Sherman, Benjamin D.; Mariño Ochoa, Ernesto; Palacios, Rodrigo Emiliano; Cosa, Gonzlao; et al.; Synthesis and characterization of silicon phthalocyanines bearing axial phenoxyl groups for attachment to semiconducting metal oxides; World Sci Publ Co Inc; Journal Of Porphyrins And Phthalocyanines; 15; 9-10; 10-2011; 943-950
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/doi/10.1142/S1088424611003847
info:eu-repo/semantics/altIdentifier/url/https://www.worldscientific.com/doi/abs/10.1142/S1088424611003847
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
_version_ 1846083263537348608
score 13.22299

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