Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle

Autores
Gauna, Gabriela Alejandra; Cobice, Diego; Awruch, Josefina
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
N-(3,4-dicyanophenyl)piperidine-2,6-dione (2) and 4- phthalimidophthalonitrile (3) were synthesized in 24% and 74% yield respectively, using 4-aminophthalonitrile as the starting material. Treatment of 2 and 3 with zinc acetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene gave respectively phthalocyanines 4 and 5, whose reduction with diborane afforded dyes 6 and 7. Quaternization of 6 and 7 with iodomethane gave cationic zinc(II) phthalocyanines 8 and 9 respectively. A bathochromic shift was observed in the absorption spectra when amino and ammonium groups were present near the macrocycle in comparison with those dyes carrying alkylamino and quaternary alkyl ammonium salts as peripheral substituents.
Fil: Gauna, Gabriela Alejandra. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Cobice, Diego. University of Edinburgh; Reino Unido
Fil: Awruch, Josefina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
4-AMINOPHTHALONITRILE
DIBORANE
PHOTOPHYSICAL PROPERTIES
REDUCTION
ZINC(II) PHTHALOCYANINES
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:11336/197846
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycleGauna, Gabriela AlejandraCobice, DiegoAwruch, Josefina4-AMINOPHTHALONITRILEDIBORANEPHOTOPHYSICAL PROPERTIESREDUCTIONZINC(II) PHTHALOCYANINEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1N-(3,4-dicyanophenyl)piperidine-2,6-dione (2) and 4- phthalimidophthalonitrile (3) were synthesized in 24% and 74% yield respectively, using 4-aminophthalonitrile as the starting material. Treatment of 2 and 3 with zinc acetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene gave respectively phthalocyanines 4 and 5, whose reduction with diborane afforded dyes 6 and 7. Quaternization of 6 and 7 with iodomethane gave cationic zinc(II) phthalocyanines 8 and 9 respectively. A bathochromic shift was observed in the absorption spectra when amino and ammonium groups were present near the macrocycle in comparison with those dyes carrying alkylamino and quaternary alkyl ammonium salts as peripheral substituents.Fil: Gauna, Gabriela Alejandra. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Cobice, Diego. University of Edinburgh; Reino UnidoFil: Awruch, Josefina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaPergamon-Elsevier Science Ltd2012-10info: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/11336/197846Gauna, Gabriela Alejandra; Cobice, Diego; Awruch, Josefina; Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle; Pergamon-Elsevier Science Ltd; Polyhedron; 46; 1; 10-2012; 90-940277-5387CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.poly.2012.07.089info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0277538712005426info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:04:53Zoai:ri.conicet.gov.ar:11336/197846instacron: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 13:04:53.885CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle
title Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle
spellingShingle Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle
Gauna, Gabriela Alejandra
4-AMINOPHTHALONITRILE
DIBORANE
PHOTOPHYSICAL PROPERTIES
REDUCTION
ZINC(II) PHTHALOCYANINES
title_short Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle
title_full Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle
title_fullStr Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle
title_full_unstemmed Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle
title_sort Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle
dc.creator.none.fl_str_mv Gauna, Gabriela Alejandra
Cobice, Diego
Awruch, Josefina
author Gauna, Gabriela Alejandra
author_facet Gauna, Gabriela Alejandra
Cobice, Diego
Awruch, Josefina
author_role author
author2 Cobice, Diego
Awruch, Josefina
author2_role author
author
dc.subject.none.fl_str_mv 4-AMINOPHTHALONITRILE
DIBORANE
PHOTOPHYSICAL PROPERTIES
REDUCTION
ZINC(II) PHTHALOCYANINES
topic 4-AMINOPHTHALONITRILE
DIBORANE
PHOTOPHYSICAL PROPERTIES
REDUCTION
ZINC(II) PHTHALOCYANINES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv N-(3,4-dicyanophenyl)piperidine-2,6-dione (2) and 4- phthalimidophthalonitrile (3) were synthesized in 24% and 74% yield respectively, using 4-aminophthalonitrile as the starting material. Treatment of 2 and 3 with zinc acetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene gave respectively phthalocyanines 4 and 5, whose reduction with diborane afforded dyes 6 and 7. Quaternization of 6 and 7 with iodomethane gave cationic zinc(II) phthalocyanines 8 and 9 respectively. A bathochromic shift was observed in the absorption spectra when amino and ammonium groups were present near the macrocycle in comparison with those dyes carrying alkylamino and quaternary alkyl ammonium salts as peripheral substituents.
Fil: Gauna, Gabriela Alejandra. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Cobice, Diego. University of Edinburgh; Reino Unido
Fil: Awruch, Josefina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description N-(3,4-dicyanophenyl)piperidine-2,6-dione (2) and 4- phthalimidophthalonitrile (3) were synthesized in 24% and 74% yield respectively, using 4-aminophthalonitrile as the starting material. Treatment of 2 and 3 with zinc acetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene gave respectively phthalocyanines 4 and 5, whose reduction with diborane afforded dyes 6 and 7. Quaternization of 6 and 7 with iodomethane gave cationic zinc(II) phthalocyanines 8 and 9 respectively. A bathochromic shift was observed in the absorption spectra when amino and ammonium groups were present near the macrocycle in comparison with those dyes carrying alkylamino and quaternary alkyl ammonium salts as peripheral substituents.
publishDate 2012
dc.date.none.fl_str_mv 2012-10
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/11336/197846
Gauna, Gabriela Alejandra; Cobice, Diego; Awruch, Josefina; Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle; Pergamon-Elsevier Science Ltd; Polyhedron; 46; 1; 10-2012; 90-94
0277-5387
CONICET Digital
CONICET
url http://hdl.handle.net/11336/197846
identifier_str_mv Gauna, Gabriela Alejandra; Cobice, Diego; Awruch, Josefina; Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle; Pergamon-Elsevier Science Ltd; Polyhedron; 46; 1; 10-2012; 90-94
0277-5387
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.poly.2012.07.089
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0277538712005426
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 Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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 12.993085

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