Nitroanilines as Quenchers of Pyrene Fluorescence

Autores
Agudelo Morales, Carlos E.; Silva, Oscar Fernando; Galian, Raquel Eugenia; Pérez Prieto, Julia
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The quenching of pyrene and 1‐methylpyrene fluorescence by nitroanilines (NAs), such as 2‐, 3‐, and 4‐nitroaniline (2‐NA, 3‐NA, and 4‐NA, respectively), 4‐methyl‐3‐nitroaniline (4‐M‐3‐NA), 2‐methyl‐4‐nitroaniline (2‐M‐4‐NA), and 4‐methyl‐3,5‐dinitroaniline (4‐M‐3,5‐DNA), are studied in toluene and 1,4‐dioxane. Steady‐state fluorescence data show the higher efficiency of the 4‐NAs as quenchers and fit with a sphere‐of‐action model. This suggests a 4‐NA tendency of being in close proximity to the fluorophore, which could be connected with their high polarity/hyperpolarizability. In addition, emission and excitation spectra evidence the formation of emissive pyrene—NA ground‐state complexes in the case of the 4‐NAs and, in a minor degree, in the 2‐NA. Moreover, time‐resolved fluorescence experiments show that increasing amounts of NA decrease the pyrene fluorescence lifetime to a degree that depends on the NA nature and is larger in the less viscous solvent (toluene). Although the NA absorption and the pyrene (Py) emission overlap, we found no evidence of dipole–dipole energy transfer from the pyrene singlet excited state (1Py) to the NAs; this could be due to the low NA concentration used in these experiments. Transient absorption spectra show that the formation of the pyrene triplet excited state (3Py) is barely affected by the presence of the NAs in spite of their efficiency in 1Py quenching, suggesting the involvement of 1Py—NA exciplexes which—after intersystem crossing—decay efficiently into 3Py.
Fil: Agudelo Morales, Carlos E.. Universidad de Valencia; España
Fil: Silva, Oscar Fernando. Universidad de Valencia; España
Fil: Galian, Raquel Eugenia. Universidad de Valencia; España
Fil: Pérez Prieto, Julia. Universidad de Valencia; España
Materia
Pireno
Fotoquimica
Anilinas
Desactivacion
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:11336/62074

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network_name_str CONICET Digital (CONICET)
spelling Nitroanilines as Quenchers of Pyrene FluorescenceAgudelo Morales, Carlos E.Silva, Oscar FernandoGalian, Raquel EugeniaPérez Prieto, JuliaPirenoFotoquimicaAnilinasDesactivacionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The quenching of pyrene and 1‐methylpyrene fluorescence by nitroanilines (NAs), such as 2‐, 3‐, and 4‐nitroaniline (2‐NA, 3‐NA, and 4‐NA, respectively), 4‐methyl‐3‐nitroaniline (4‐M‐3‐NA), 2‐methyl‐4‐nitroaniline (2‐M‐4‐NA), and 4‐methyl‐3,5‐dinitroaniline (4‐M‐3,5‐DNA), are studied in toluene and 1,4‐dioxane. Steady‐state fluorescence data show the higher efficiency of the 4‐NAs as quenchers and fit with a sphere‐of‐action model. This suggests a 4‐NA tendency of being in close proximity to the fluorophore, which could be connected with their high polarity/hyperpolarizability. In addition, emission and excitation spectra evidence the formation of emissive pyrene—NA ground‐state complexes in the case of the 4‐NAs and, in a minor degree, in the 2‐NA. Moreover, time‐resolved fluorescence experiments show that increasing amounts of NA decrease the pyrene fluorescence lifetime to a degree that depends on the NA nature and is larger in the less viscous solvent (toluene). Although the NA absorption and the pyrene (Py) emission overlap, we found no evidence of dipole–dipole energy transfer from the pyrene singlet excited state (1Py) to the NAs; this could be due to the low NA concentration used in these experiments. Transient absorption spectra show that the formation of the pyrene triplet excited state (3Py) is barely affected by the presence of the NAs in spite of their efficiency in 1Py quenching, suggesting the involvement of 1Py—NA exciplexes which—after intersystem crossing—decay efficiently into 3Py.Fil: Agudelo Morales, Carlos E.. Universidad de Valencia; EspañaFil: Silva, Oscar Fernando. Universidad de Valencia; EspañaFil: Galian, Raquel Eugenia. Universidad de Valencia; EspañaFil: Pérez Prieto, Julia. Universidad de Valencia; EspañaWiley VCH Verlag2012-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/62074Agudelo Morales, Carlos E.; Silva, Oscar Fernando; Galian, Raquel Eugenia; Pérez Prieto, Julia; Nitroanilines as Quenchers of Pyrene Fluorescence; Wiley VCH Verlag; Chemphyschem; 13; 18; 12-2012; 4195-42011439-4235CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/cphc.201200637info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/cphc.201200637info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:56:05Zoai:ri.conicet.gov.ar:11336/62074instacron: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:34982025-09-29 09:56:05.642CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Nitroanilines as Quenchers of Pyrene Fluorescence
title Nitroanilines as Quenchers of Pyrene Fluorescence
spellingShingle Nitroanilines as Quenchers of Pyrene Fluorescence
Agudelo Morales, Carlos E.
Pireno
Fotoquimica
Anilinas
Desactivacion
title_short Nitroanilines as Quenchers of Pyrene Fluorescence
title_full Nitroanilines as Quenchers of Pyrene Fluorescence
title_fullStr Nitroanilines as Quenchers of Pyrene Fluorescence
title_full_unstemmed Nitroanilines as Quenchers of Pyrene Fluorescence
title_sort Nitroanilines as Quenchers of Pyrene Fluorescence
dc.creator.none.fl_str_mv Agudelo Morales, Carlos E.
Silva, Oscar Fernando
Galian, Raquel Eugenia
Pérez Prieto, Julia
author Agudelo Morales, Carlos E.
author_facet Agudelo Morales, Carlos E.
Silva, Oscar Fernando
Galian, Raquel Eugenia
Pérez Prieto, Julia
author_role author
author2 Silva, Oscar Fernando
Galian, Raquel Eugenia
Pérez Prieto, Julia
author2_role author
author
author
dc.subject.none.fl_str_mv Pireno
Fotoquimica
Anilinas
Desactivacion
topic Pireno
Fotoquimica
Anilinas
Desactivacion
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The quenching of pyrene and 1‐methylpyrene fluorescence by nitroanilines (NAs), such as 2‐, 3‐, and 4‐nitroaniline (2‐NA, 3‐NA, and 4‐NA, respectively), 4‐methyl‐3‐nitroaniline (4‐M‐3‐NA), 2‐methyl‐4‐nitroaniline (2‐M‐4‐NA), and 4‐methyl‐3,5‐dinitroaniline (4‐M‐3,5‐DNA), are studied in toluene and 1,4‐dioxane. Steady‐state fluorescence data show the higher efficiency of the 4‐NAs as quenchers and fit with a sphere‐of‐action model. This suggests a 4‐NA tendency of being in close proximity to the fluorophore, which could be connected with their high polarity/hyperpolarizability. In addition, emission and excitation spectra evidence the formation of emissive pyrene—NA ground‐state complexes in the case of the 4‐NAs and, in a minor degree, in the 2‐NA. Moreover, time‐resolved fluorescence experiments show that increasing amounts of NA decrease the pyrene fluorescence lifetime to a degree that depends on the NA nature and is larger in the less viscous solvent (toluene). Although the NA absorption and the pyrene (Py) emission overlap, we found no evidence of dipole–dipole energy transfer from the pyrene singlet excited state (1Py) to the NAs; this could be due to the low NA concentration used in these experiments. Transient absorption spectra show that the formation of the pyrene triplet excited state (3Py) is barely affected by the presence of the NAs in spite of their efficiency in 1Py quenching, suggesting the involvement of 1Py—NA exciplexes which—after intersystem crossing—decay efficiently into 3Py.
Fil: Agudelo Morales, Carlos E.. Universidad de Valencia; España
Fil: Silva, Oscar Fernando. Universidad de Valencia; España
Fil: Galian, Raquel Eugenia. Universidad de Valencia; España
Fil: Pérez Prieto, Julia. Universidad de Valencia; España
description The quenching of pyrene and 1‐methylpyrene fluorescence by nitroanilines (NAs), such as 2‐, 3‐, and 4‐nitroaniline (2‐NA, 3‐NA, and 4‐NA, respectively), 4‐methyl‐3‐nitroaniline (4‐M‐3‐NA), 2‐methyl‐4‐nitroaniline (2‐M‐4‐NA), and 4‐methyl‐3,5‐dinitroaniline (4‐M‐3,5‐DNA), are studied in toluene and 1,4‐dioxane. Steady‐state fluorescence data show the higher efficiency of the 4‐NAs as quenchers and fit with a sphere‐of‐action model. This suggests a 4‐NA tendency of being in close proximity to the fluorophore, which could be connected with their high polarity/hyperpolarizability. In addition, emission and excitation spectra evidence the formation of emissive pyrene—NA ground‐state complexes in the case of the 4‐NAs and, in a minor degree, in the 2‐NA. Moreover, time‐resolved fluorescence experiments show that increasing amounts of NA decrease the pyrene fluorescence lifetime to a degree that depends on the NA nature and is larger in the less viscous solvent (toluene). Although the NA absorption and the pyrene (Py) emission overlap, we found no evidence of dipole–dipole energy transfer from the pyrene singlet excited state (1Py) to the NAs; this could be due to the low NA concentration used in these experiments. Transient absorption spectra show that the formation of the pyrene triplet excited state (3Py) is barely affected by the presence of the NAs in spite of their efficiency in 1Py quenching, suggesting the involvement of 1Py—NA exciplexes which—after intersystem crossing—decay efficiently into 3Py.
publishDate 2012
dc.date.none.fl_str_mv 2012-12
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/11336/62074
Agudelo Morales, Carlos E.; Silva, Oscar Fernando; Galian, Raquel Eugenia; Pérez Prieto, Julia; Nitroanilines as Quenchers of Pyrene Fluorescence; Wiley VCH Verlag; Chemphyschem; 13; 18; 12-2012; 4195-4201
1439-4235
CONICET Digital
CONICET
url http://hdl.handle.net/11336/62074
identifier_str_mv Agudelo Morales, Carlos E.; Silva, Oscar Fernando; Galian, Raquel Eugenia; Pérez Prieto, Julia; Nitroanilines as Quenchers of Pyrene Fluorescence; Wiley VCH Verlag; Chemphyschem; 13; 18; 12-2012; 4195-4201
1439-4235
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/cphc.201200637
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/cphc.201200637
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 Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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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