Role of the medium on the C343 inter/intramolecular hydrogen bond interactions. An absorption, emission, and 1HNMR investigation of C343 in benzene/n-heptane mixtures

Autores
Gutierrez Cifuentes, Jorge Andres; Falcone, Ruben Dario; Chessa, Juana Josefa; Correa, Nestor Mariano
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
C343, a common molecular probe utilized in solvation dynamics experiments, was studied in homogeneous media. Absorption, emission, and 1HNMR spectroscopies were used to investigate the behavior of C343 in benzene and in benzene/n-heptane mixtures. We demonstrate the implications of the medium polarity, measured as the Kamlet-Taft polarity-polarizability (π) parameter, in the C343 inter/intramolecular hydrogen bond (H-bond) interactions and the role that this interaction plays in the dimerization process of the dye. In pure benzene, the dimer prevails because the intermolecular H-bond interaction is favored. On the other hand, as the n-heptane content increases the intramolecular H-bond is the strongest and the C343 monomer is favored. As the polarity of the medium decreases, the solvophobic interaction makes that C343 monomer species experiences a more complicated aggregation process beyond the simple monomer dimer equilibrium present in pure benzene. Thus, the addition of n-heptane to the mixture yields a C343 higher-order aggregates species. Thus, our work reveals the importance that the medium has on the behavior of a widespread dye used as chromophore for very different systems such as homogeneous and microheterogenous media. This is very important since the use of chromophores without understanding its chemistry can induce artifacts into the interpretation of solvation dynamics in heterogeneous environments, in particular, those provided by biological systems such as proteins. Considerable care in choosing and characterizing the system is required to analyze the results fully.
Fil: Gutierrez Cifuentes, Jorge Andres. 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: Falcone, Ruben Dario. 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: Chessa, Juana Josefa. 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: Correa, Nestor Mariano. 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
Materia
COUMARIN C343
HOMOGENEOUS MEDIA
INTRAMOLECULAR H-BOND
INTERMOLECULAR H-BOND
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:11336/132460
Acceder
id CONICETDig_da4b70d7f283388bed585fe8b790288a
oai_identifier_str oai:ri.conicet.gov.ar:11336/132460
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Role of the medium on the C343 inter/intramolecular hydrogen bond interactions. An absorption, emission, and 1HNMR investigation of C343 in benzene/n-heptane mixturesGutierrez Cifuentes, Jorge AndresFalcone, Ruben DarioChessa, Juana JosefaCorrea, Nestor MarianoCOUMARIN C343HOMOGENEOUS MEDIAINTRAMOLECULAR H-BONDINTERMOLECULAR H-BONDhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1C343, a common molecular probe utilized in solvation dynamics experiments, was studied in homogeneous media. Absorption, emission, and 1HNMR spectroscopies were used to investigate the behavior of C343 in benzene and in benzene/n-heptane mixtures. We demonstrate the implications of the medium polarity, measured as the Kamlet-Taft polarity-polarizability (π) parameter, in the C343 inter/intramolecular hydrogen bond (H-bond) interactions and the role that this interaction plays in the dimerization process of the dye. In pure benzene, the dimer prevails because the intermolecular H-bond interaction is favored. On the other hand, as the n-heptane content increases the intramolecular H-bond is the strongest and the C343 monomer is favored. As the polarity of the medium decreases, the solvophobic interaction makes that C343 monomer species experiences a more complicated aggregation process beyond the simple monomer dimer equilibrium present in pure benzene. Thus, the addition of n-heptane to the mixture yields a C343 higher-order aggregates species. Thus, our work reveals the importance that the medium has on the behavior of a widespread dye used as chromophore for very different systems such as homogeneous and microheterogenous media. This is very important since the use of chromophores without understanding its chemistry can induce artifacts into the interpretation of solvation dynamics in heterogeneous environments, in particular, those provided by biological systems such as proteins. Considerable care in choosing and characterizing the system is required to analyze the results fully.Fil: Gutierrez Cifuentes, Jorge Andres. 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: Falcone, Ruben Dario. 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: Chessa, Juana Josefa. 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: Correa, Nestor Mariano. 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; ArgentinaAmerican Chemical Society2010-07-21info: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/11336/132460Gutierrez Cifuentes, Jorge Andres; Falcone, Ruben Dario; Chessa, Juana Josefa; Correa, Nestor Mariano; Role of the medium on the C343 inter/intramolecular hydrogen bond interactions. An absorption, emission, and 1HNMR investigation of C343 in benzene/n-heptane mixtures; American Chemical Society; Journal of Physical Chemistry A; 114; 27; 21-7-2010; 7326-73301089-5639CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jp102136einfo:eu-repo/semantics/altIdentifier/doi/10.1021/jp102136einfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:52:41Zoai:ri.conicet.gov.ar:11336/132460instacron: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 09:52:41.718CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Role of the medium on the C343 inter/intramolecular hydrogen bond interactions. An absorption, emission, and 1HNMR investigation of C343 in benzene/n-heptane mixtures
title Role of the medium on the C343 inter/intramolecular hydrogen bond interactions. An absorption, emission, and 1HNMR investigation of C343 in benzene/n-heptane mixtures
spellingShingle Role of the medium on the C343 inter/intramolecular hydrogen bond interactions. An absorption, emission, and 1HNMR investigation of C343 in benzene/n-heptane mixtures
Gutierrez Cifuentes, Jorge Andres
COUMARIN C343
HOMOGENEOUS MEDIA
INTRAMOLECULAR H-BOND
INTERMOLECULAR H-BOND
title_short Role of the medium on the C343 inter/intramolecular hydrogen bond interactions. An absorption, emission, and 1HNMR investigation of C343 in benzene/n-heptane mixtures
title_full Role of the medium on the C343 inter/intramolecular hydrogen bond interactions. An absorption, emission, and 1HNMR investigation of C343 in benzene/n-heptane mixtures
title_fullStr Role of the medium on the C343 inter/intramolecular hydrogen bond interactions. An absorption, emission, and 1HNMR investigation of C343 in benzene/n-heptane mixtures
title_full_unstemmed Role of the medium on the C343 inter/intramolecular hydrogen bond interactions. An absorption, emission, and 1HNMR investigation of C343 in benzene/n-heptane mixtures
title_sort Role of the medium on the C343 inter/intramolecular hydrogen bond interactions. An absorption, emission, and 1HNMR investigation of C343 in benzene/n-heptane mixtures
dc.creator.none.fl_str_mv Gutierrez Cifuentes, Jorge Andres
Falcone, Ruben Dario
Chessa, Juana Josefa
Correa, Nestor Mariano
author Gutierrez Cifuentes, Jorge Andres
author_facet Gutierrez Cifuentes, Jorge Andres
Falcone, Ruben Dario
Chessa, Juana Josefa
Correa, Nestor Mariano
author_role author
author2 Falcone, Ruben Dario
Chessa, Juana Josefa
Correa, Nestor Mariano
author2_role author
author
author
dc.subject.none.fl_str_mv COUMARIN C343
HOMOGENEOUS MEDIA
INTRAMOLECULAR H-BOND
INTERMOLECULAR H-BOND
topic COUMARIN C343
HOMOGENEOUS MEDIA
INTRAMOLECULAR H-BOND
INTERMOLECULAR H-BOND
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv C343, a common molecular probe utilized in solvation dynamics experiments, was studied in homogeneous media. Absorption, emission, and 1HNMR spectroscopies were used to investigate the behavior of C343 in benzene and in benzene/n-heptane mixtures. We demonstrate the implications of the medium polarity, measured as the Kamlet-Taft polarity-polarizability (π) parameter, in the C343 inter/intramolecular hydrogen bond (H-bond) interactions and the role that this interaction plays in the dimerization process of the dye. In pure benzene, the dimer prevails because the intermolecular H-bond interaction is favored. On the other hand, as the n-heptane content increases the intramolecular H-bond is the strongest and the C343 monomer is favored. As the polarity of the medium decreases, the solvophobic interaction makes that C343 monomer species experiences a more complicated aggregation process beyond the simple monomer dimer equilibrium present in pure benzene. Thus, the addition of n-heptane to the mixture yields a C343 higher-order aggregates species. Thus, our work reveals the importance that the medium has on the behavior of a widespread dye used as chromophore for very different systems such as homogeneous and microheterogenous media. This is very important since the use of chromophores without understanding its chemistry can induce artifacts into the interpretation of solvation dynamics in heterogeneous environments, in particular, those provided by biological systems such as proteins. Considerable care in choosing and characterizing the system is required to analyze the results fully.
Fil: Gutierrez Cifuentes, Jorge Andres. 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: Falcone, Ruben Dario. 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: Chessa, Juana Josefa. 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: Correa, Nestor Mariano. 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
description C343, a common molecular probe utilized in solvation dynamics experiments, was studied in homogeneous media. Absorption, emission, and 1HNMR spectroscopies were used to investigate the behavior of C343 in benzene and in benzene/n-heptane mixtures. We demonstrate the implications of the medium polarity, measured as the Kamlet-Taft polarity-polarizability (π) parameter, in the C343 inter/intramolecular hydrogen bond (H-bond) interactions and the role that this interaction plays in the dimerization process of the dye. In pure benzene, the dimer prevails because the intermolecular H-bond interaction is favored. On the other hand, as the n-heptane content increases the intramolecular H-bond is the strongest and the C343 monomer is favored. As the polarity of the medium decreases, the solvophobic interaction makes that C343 monomer species experiences a more complicated aggregation process beyond the simple monomer dimer equilibrium present in pure benzene. Thus, the addition of n-heptane to the mixture yields a C343 higher-order aggregates species. Thus, our work reveals the importance that the medium has on the behavior of a widespread dye used as chromophore for very different systems such as homogeneous and microheterogenous media. This is very important since the use of chromophores without understanding its chemistry can induce artifacts into the interpretation of solvation dynamics in heterogeneous environments, in particular, those provided by biological systems such as proteins. Considerable care in choosing and characterizing the system is required to analyze the results fully.
publishDate 2010
dc.date.none.fl_str_mv 2010-07-21
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/11336/132460
Gutierrez Cifuentes, Jorge Andres; Falcone, Ruben Dario; Chessa, Juana Josefa; Correa, Nestor Mariano; Role of the medium on the C343 inter/intramolecular hydrogen bond interactions. An absorption, emission, and 1HNMR investigation of C343 in benzene/n-heptane mixtures; American Chemical Society; Journal of Physical Chemistry A; 114; 27; 21-7-2010; 7326-7330
1089-5639
CONICET Digital
CONICET
url http://hdl.handle.net/11336/132460
identifier_str_mv Gutierrez Cifuentes, Jorge Andres; Falcone, Ruben Dario; Chessa, Juana Josefa; Correa, Nestor Mariano; Role of the medium on the C343 inter/intramolecular hydrogen bond interactions. An absorption, emission, and 1HNMR investigation of C343 in benzene/n-heptane mixtures; American Chemical Society; Journal of Physical Chemistry A; 114; 27; 21-7-2010; 7326-7330
1089-5639
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://pubs.acs.org/doi/10.1021/jp102136e
info:eu-repo/semantics/altIdentifier/doi/10.1021/jp102136e
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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 13.070432

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