Synthesis and functionalization of new polyhalogenated BODIPY dyes. Study of their photophysical properties and singlet oxygen generation

Autores
Ortiz, Maria J.; Agarrabeitia, Antonia R.; Duran Sampedro, Gonzalo; Bañuelos Prieto, Jorge; Lopez, Teresa Arbeloa; Massad, Walter Alfredo; Montejano, Hernan Alfredo; Garcia, Norman Andino; Lopez Arbeloa, Iñigo
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A theoretical and experimental study on the iodination of BODIPY dyes with different degrees of substitution has been developed. Polyhalogenated BODIPYs synthesized in this work are the first examples of this type of dyes with more than two halogen atoms in the BODIPY core and they can be selectively functionalized. Surprisingly, the position in which halogen is attached has a marked effect in the photophysical properties and modulates the fluorescence capacity of the resulting BODIPY. These iodinated BODIPYs are efficient singlet oxygen generators.
Fil: Ortiz, Maria J.. Universidad Complutense de Madrid. Facultad de Ciencias Químicas; España
Fil: Agarrabeitia, Antonia R.. Universidad Complutense de Madrid. Facultad de Ciencias Químicas; España
Fil: Duran Sampedro, Gonzalo. Universidad Complutense de Madrid. Facultad de Ciencias Químicas; España
Fil: Bañuelos Prieto, Jorge. Universidad del País Vasco; España
Fil: Lopez, Teresa Arbeloa. Universidad del País Vasco; España
Fil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Montejano, Hernan Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Garcia, Norman Andino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Lopez Arbeloa, Iñigo. Universidad del País Vasco; España
Materia
Polyiodinated BODIPYs
Electrophilic substitution reactions
Nucleophilic substitution reactions
Singlet oxygen generation
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:11336/268695
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/268695
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and functionalization of new polyhalogenated BODIPY dyes. Study of their photophysical properties and singlet oxygen generationOrtiz, Maria J.Agarrabeitia, Antonia R.Duran Sampedro, GonzaloBañuelos Prieto, JorgeLopez, Teresa ArbeloaMassad, Walter AlfredoMontejano, Hernan AlfredoGarcia, Norman AndinoLopez Arbeloa, IñigoPolyiodinated BODIPYsElectrophilic substitution reactionsNucleophilic substitution reactionsSinglet oxygen generationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A theoretical and experimental study on the iodination of BODIPY dyes with different degrees of substitution has been developed. Polyhalogenated BODIPYs synthesized in this work are the first examples of this type of dyes with more than two halogen atoms in the BODIPY core and they can be selectively functionalized. Surprisingly, the position in which halogen is attached has a marked effect in the photophysical properties and modulates the fluorescence capacity of the resulting BODIPY. These iodinated BODIPYs are efficient singlet oxygen generators.Fil: Ortiz, Maria J.. Universidad Complutense de Madrid. Facultad de Ciencias Químicas; EspañaFil: Agarrabeitia, Antonia R.. Universidad Complutense de Madrid. Facultad de Ciencias Químicas; EspañaFil: Duran Sampedro, Gonzalo. Universidad Complutense de Madrid. Facultad de Ciencias Químicas; EspañaFil: Bañuelos Prieto, Jorge. Universidad del País Vasco; EspañaFil: Lopez, Teresa Arbeloa. Universidad del País Vasco; EspañaFil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Montejano, Hernan Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Garcia, Norman Andino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Lopez Arbeloa, Iñigo. Universidad del País Vasco; EspañaPergamon-Elsevier Science Ltd2012-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/268695Ortiz, Maria J.; Agarrabeitia, Antonia R.; Duran Sampedro, Gonzalo; Bañuelos Prieto, Jorge; Lopez, Teresa Arbeloa; et al.; Synthesis and functionalization of new polyhalogenated BODIPY dyes. Study of their photophysical properties and singlet oxygen generation; Pergamon-Elsevier Science Ltd; Tetrahedron; 68; 4; 1-2012; 1153-11620040-4020CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0040402011018254info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2011.11.070info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:00:22Zoai:ri.conicet.gov.ar:11336/268695instacron: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:34982025-10-22 11:00:22.63CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and functionalization of new polyhalogenated BODIPY dyes. Study of their photophysical properties and singlet oxygen generation
title Synthesis and functionalization of new polyhalogenated BODIPY dyes. Study of their photophysical properties and singlet oxygen generation
spellingShingle Synthesis and functionalization of new polyhalogenated BODIPY dyes. Study of their photophysical properties and singlet oxygen generation
Ortiz, Maria J.
Polyiodinated BODIPYs
Electrophilic substitution reactions
Nucleophilic substitution reactions
Singlet oxygen generation
title_short Synthesis and functionalization of new polyhalogenated BODIPY dyes. Study of their photophysical properties and singlet oxygen generation
title_full Synthesis and functionalization of new polyhalogenated BODIPY dyes. Study of their photophysical properties and singlet oxygen generation
title_fullStr Synthesis and functionalization of new polyhalogenated BODIPY dyes. Study of their photophysical properties and singlet oxygen generation
title_full_unstemmed Synthesis and functionalization of new polyhalogenated BODIPY dyes. Study of their photophysical properties and singlet oxygen generation
title_sort Synthesis and functionalization of new polyhalogenated BODIPY dyes. Study of their photophysical properties and singlet oxygen generation
dc.creator.none.fl_str_mv Ortiz, Maria J.
Agarrabeitia, Antonia R.
Duran Sampedro, Gonzalo
Bañuelos Prieto, Jorge
Lopez, Teresa Arbeloa
Massad, Walter Alfredo
Montejano, Hernan Alfredo
Garcia, Norman Andino
Lopez Arbeloa, Iñigo
author Ortiz, Maria J.
author_facet Ortiz, Maria J.
Agarrabeitia, Antonia R.
Duran Sampedro, Gonzalo
Bañuelos Prieto, Jorge
Lopez, Teresa Arbeloa
Massad, Walter Alfredo
Montejano, Hernan Alfredo
Garcia, Norman Andino
Lopez Arbeloa, Iñigo
author_role author
author2 Agarrabeitia, Antonia R.
Duran Sampedro, Gonzalo
Bañuelos Prieto, Jorge
Lopez, Teresa Arbeloa
Massad, Walter Alfredo
Montejano, Hernan Alfredo
Garcia, Norman Andino
Lopez Arbeloa, Iñigo
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Polyiodinated BODIPYs
Electrophilic substitution reactions
Nucleophilic substitution reactions
Singlet oxygen generation
topic Polyiodinated BODIPYs
Electrophilic substitution reactions
Nucleophilic substitution reactions
Singlet oxygen generation
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 theoretical and experimental study on the iodination of BODIPY dyes with different degrees of substitution has been developed. Polyhalogenated BODIPYs synthesized in this work are the first examples of this type of dyes with more than two halogen atoms in the BODIPY core and they can be selectively functionalized. Surprisingly, the position in which halogen is attached has a marked effect in the photophysical properties and modulates the fluorescence capacity of the resulting BODIPY. These iodinated BODIPYs are efficient singlet oxygen generators.
Fil: Ortiz, Maria J.. Universidad Complutense de Madrid. Facultad de Ciencias Químicas; España
Fil: Agarrabeitia, Antonia R.. Universidad Complutense de Madrid. Facultad de Ciencias Químicas; España
Fil: Duran Sampedro, Gonzalo. Universidad Complutense de Madrid. Facultad de Ciencias Químicas; España
Fil: Bañuelos Prieto, Jorge. Universidad del País Vasco; España
Fil: Lopez, Teresa Arbeloa. Universidad del País Vasco; España
Fil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Montejano, Hernan Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Garcia, Norman Andino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Lopez Arbeloa, Iñigo. Universidad del País Vasco; España
description A theoretical and experimental study on the iodination of BODIPY dyes with different degrees of substitution has been developed. Polyhalogenated BODIPYs synthesized in this work are the first examples of this type of dyes with more than two halogen atoms in the BODIPY core and they can be selectively functionalized. Surprisingly, the position in which halogen is attached has a marked effect in the photophysical properties and modulates the fluorescence capacity of the resulting BODIPY. These iodinated BODIPYs are efficient singlet oxygen generators.
publishDate 2012
dc.date.none.fl_str_mv 2012-01
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/11336/268695
Ortiz, Maria J.; Agarrabeitia, Antonia R.; Duran Sampedro, Gonzalo; Bañuelos Prieto, Jorge; Lopez, Teresa Arbeloa; et al.; Synthesis and functionalization of new polyhalogenated BODIPY dyes. Study of their photophysical properties and singlet oxygen generation; Pergamon-Elsevier Science Ltd; Tetrahedron; 68; 4; 1-2012; 1153-1162
0040-4020
CONICET Digital
CONICET
url http://hdl.handle.net/11336/268695
identifier_str_mv Ortiz, Maria J.; Agarrabeitia, Antonia R.; Duran Sampedro, Gonzalo; Bañuelos Prieto, Jorge; Lopez, Teresa Arbeloa; et al.; Synthesis and functionalization of new polyhalogenated BODIPY dyes. Study of their photophysical properties and singlet oxygen generation; Pergamon-Elsevier Science Ltd; Tetrahedron; 68; 4; 1-2012; 1153-1162
0040-4020
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.sciencedirect.com/science/article/abs/pii/S0040402011018254
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2011.11.070
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
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
_version_ 1846781162980114432
score 12.982451

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