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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/62074
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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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1844613687272275968 |
score |
13.070432 |