Synthesis and Electrochemical Properties of a Novel Mono-meso-ferrocenyl Porphyrin

Autores
Niemevz, Fernando; Lazaro Martinez, Juan Manuel; Carballo, Romina Raquel; Rezzano, Irene Noemí; Buldain, Graciela Yolanda
Año de publicación
2006
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A synthetic route to mono-meso-ferrocenyl porphyrins using a MacDonald-type 2+2 condensation is described. In this method, the substituted diformyldipyrrylmethane 4 is treated with the dicarboxydipyrrylmethane 6. The 5-ferrocenyldipyrrylmethane was obtained by condensation of benzyl 3-methyl-4-ethylpyrrol-2-carboxylate with ferrocenecarboxaldehyde in the presence of p-toluenesulfonic acid. The unequivocal assignment of all proton resonances in the new porphyrin was achieved by means of a detailed analysis of its H-H NOESY correlations. Interestingly, we noticed that the ferrocenyl group introduces an element of asymmetry in the molecule. The corresponding Co(II) and Ni(II) complexes were also prepared. In cyclic voltammograms of the free base and the Co or Ni complexes all voltammetric peaks disappear after four consecutive scans. This result suggests no film formation in any of them.
Fil: Niemevz, Fernando. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica II; Argentina
Fil: Lazaro Martinez, Juan Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica II; Argentina
Fil: Carballo, Romina Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Analítica y Fisicoquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Rezzano, Irene Noemí. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Analítica y Fisicoquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Buldain, Graciela Yolanda. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica II; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Materia
ELECTROCHEMISTRY
MESO-FERROCENYL PORPHYRIN
PORPHYRIN 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:11336/139722
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and Electrochemical Properties of a Novel Mono-meso-ferrocenyl PorphyrinNiemevz, FernandoLazaro Martinez, Juan ManuelCarballo, Romina RaquelRezzano, Irene NoemíBuldain, Graciela YolandaELECTROCHEMISTRYMESO-FERROCENYL PORPHYRINPORPHYRIN SYNTHESIShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A synthetic route to mono-meso-ferrocenyl porphyrins using a MacDonald-type 2+2 condensation is described. In this method, the substituted diformyldipyrrylmethane 4 is treated with the dicarboxydipyrrylmethane 6. The 5-ferrocenyldipyrrylmethane was obtained by condensation of benzyl 3-methyl-4-ethylpyrrol-2-carboxylate with ferrocenecarboxaldehyde in the presence of p-toluenesulfonic acid. The unequivocal assignment of all proton resonances in the new porphyrin was achieved by means of a detailed analysis of its H-H NOESY correlations. Interestingly, we noticed that the ferrocenyl group introduces an element of asymmetry in the molecule. The corresponding Co(II) and Ni(II) complexes were also prepared. In cyclic voltammograms of the free base and the Co or Ni complexes all voltammetric peaks disappear after four consecutive scans. This result suggests no film formation in any of them.Fil: Niemevz, Fernando. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica II; ArgentinaFil: Lazaro Martinez, Juan Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica II; ArgentinaFil: Carballo, Romina Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Analítica y Fisicoquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Rezzano, Irene Noemí. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Analítica y Fisicoquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Buldain, Graciela Yolanda. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica II; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaGeorg Thieme Verlag Kg2006-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/139722Niemevz, Fernando; Lazaro Martinez, Juan Manuel; Carballo, Romina Raquel; Rezzano, Irene Noemí; Buldain, Graciela Yolanda; Synthesis and Electrochemical Properties of a Novel Mono-meso-ferrocenyl Porphyrin; Georg Thieme Verlag Kg; Synthesis-stuttgart; 5; 3-2006; 870-8740039-7881CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-2006-926330info:eu-repo/semantics/altIdentifier/doi/10.1055/s-2006-926330info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:15:13Zoai:ri.conicet.gov.ar:11336/139722instacron: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 15:15:13.372CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and Electrochemical Properties of a Novel Mono-meso-ferrocenyl Porphyrin
title Synthesis and Electrochemical Properties of a Novel Mono-meso-ferrocenyl Porphyrin
spellingShingle Synthesis and Electrochemical Properties of a Novel Mono-meso-ferrocenyl Porphyrin
Niemevz, Fernando
ELECTROCHEMISTRY
MESO-FERROCENYL PORPHYRIN
PORPHYRIN SYNTHESIS
title_short Synthesis and Electrochemical Properties of a Novel Mono-meso-ferrocenyl Porphyrin
title_full Synthesis and Electrochemical Properties of a Novel Mono-meso-ferrocenyl Porphyrin
title_fullStr Synthesis and Electrochemical Properties of a Novel Mono-meso-ferrocenyl Porphyrin
title_full_unstemmed Synthesis and Electrochemical Properties of a Novel Mono-meso-ferrocenyl Porphyrin
title_sort Synthesis and Electrochemical Properties of a Novel Mono-meso-ferrocenyl Porphyrin
dc.creator.none.fl_str_mv Niemevz, Fernando
Lazaro Martinez, Juan Manuel
Carballo, Romina Raquel
Rezzano, Irene Noemí
Buldain, Graciela Yolanda
author Niemevz, Fernando
author_facet Niemevz, Fernando
Lazaro Martinez, Juan Manuel
Carballo, Romina Raquel
Rezzano, Irene Noemí
Buldain, Graciela Yolanda
author_role author
author2 Lazaro Martinez, Juan Manuel
Carballo, Romina Raquel
Rezzano, Irene Noemí
Buldain, Graciela Yolanda
author2_role author
author
author
author
dc.subject.none.fl_str_mv ELECTROCHEMISTRY
MESO-FERROCENYL PORPHYRIN
PORPHYRIN SYNTHESIS
topic ELECTROCHEMISTRY
MESO-FERROCENYL PORPHYRIN
PORPHYRIN 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 synthetic route to mono-meso-ferrocenyl porphyrins using a MacDonald-type 2+2 condensation is described. In this method, the substituted diformyldipyrrylmethane 4 is treated with the dicarboxydipyrrylmethane 6. The 5-ferrocenyldipyrrylmethane was obtained by condensation of benzyl 3-methyl-4-ethylpyrrol-2-carboxylate with ferrocenecarboxaldehyde in the presence of p-toluenesulfonic acid. The unequivocal assignment of all proton resonances in the new porphyrin was achieved by means of a detailed analysis of its H-H NOESY correlations. Interestingly, we noticed that the ferrocenyl group introduces an element of asymmetry in the molecule. The corresponding Co(II) and Ni(II) complexes were also prepared. In cyclic voltammograms of the free base and the Co or Ni complexes all voltammetric peaks disappear after four consecutive scans. This result suggests no film formation in any of them.
Fil: Niemevz, Fernando. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica II; Argentina
Fil: Lazaro Martinez, Juan Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica II; Argentina
Fil: Carballo, Romina Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Analítica y Fisicoquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Rezzano, Irene Noemí. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Analítica y Fisicoquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Buldain, Graciela Yolanda. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica II; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
description A synthetic route to mono-meso-ferrocenyl porphyrins using a MacDonald-type 2+2 condensation is described. In this method, the substituted diformyldipyrrylmethane 4 is treated with the dicarboxydipyrrylmethane 6. The 5-ferrocenyldipyrrylmethane was obtained by condensation of benzyl 3-methyl-4-ethylpyrrol-2-carboxylate with ferrocenecarboxaldehyde in the presence of p-toluenesulfonic acid. The unequivocal assignment of all proton resonances in the new porphyrin was achieved by means of a detailed analysis of its H-H NOESY correlations. Interestingly, we noticed that the ferrocenyl group introduces an element of asymmetry in the molecule. The corresponding Co(II) and Ni(II) complexes were also prepared. In cyclic voltammograms of the free base and the Co or Ni complexes all voltammetric peaks disappear after four consecutive scans. This result suggests no film formation in any of them.
publishDate 2006
dc.date.none.fl_str_mv 2006-03
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/11336/139722
Niemevz, Fernando; Lazaro Martinez, Juan Manuel; Carballo, Romina Raquel; Rezzano, Irene Noemí; Buldain, Graciela Yolanda; Synthesis and Electrochemical Properties of a Novel Mono-meso-ferrocenyl Porphyrin; Georg Thieme Verlag Kg; Synthesis-stuttgart; 5; 3-2006; 870-874
0039-7881
CONICET Digital
CONICET
url http://hdl.handle.net/11336/139722
identifier_str_mv Niemevz, Fernando; Lazaro Martinez, Juan Manuel; Carballo, Romina Raquel; Rezzano, Irene Noemí; Buldain, Graciela Yolanda; Synthesis and Electrochemical Properties of a Novel Mono-meso-ferrocenyl Porphyrin; Georg Thieme Verlag Kg; Synthesis-stuttgart; 5; 3-2006; 870-874
0039-7881
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.thieme-connect.com/products/ejournals/abstract/10.1055/s-2006-926330
info:eu-repo/semantics/altIdentifier/doi/10.1055/s-2006-926330
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
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Georg Thieme Verlag Kg
publisher.none.fl_str_mv Georg Thieme Verlag Kg
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_ 1846083299756212224
score 13.22299

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