A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species

Autores
Ramirez, Cristina Lujan; Mangione, Maria Ines; Bertolotti, Sonia Graciela; Arbeloa, Ernesto Maximiliano; Parise, Alejandro Ruben
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A series of N-phenyl-carbazole derivatives namely TCz (N-tolyl-carbazol), TCz-TCz (a 3,3´-linked dimer), and CzPh-CH2-PhCz (a methylene-bridged N-phenyl-carbazole), have been synthesized and studied by means of absorption and fluorescence spectra, DFT calculations, cyclic voltammetry and spectroelectrochemistry. It is concluded that the methylene bridge in CzPh-CH2-PhCz isolates the two TCz units, whereas TCz-TCz allows extending the electronic coupling along both carbazoles. Moreover, the phosphorescence spectrum of TCz-TCz showed a high energy triplet state (2.76 eV). It was observed that oxidation of CzPh-CH2-PhCz generates an electrochromic polymer containing TCz-TCz dimer units separated by methylene bridges. Oxidized TCz-TCz subunit was analyzed by EPR spectroscopy, and found to be a Class III mixed valence ion in Robin and Day classification. All results suggest that these molecules might be suitable as selective probes in fluorescence sensing or as host materials in electroluminescent devices.
Fil: Ramirez, Cristina Lujan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Biodiversidad y Biotecnología; Argentina. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina
Fil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Bertolotti, Sonia Graciela. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Arbeloa, Ernesto Maximiliano. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Parise, Alejandro Ruben. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Biodiversidad y Biotecnología; Argentina
Materia
CARBAZOLE
PHOTOPHYSICS
EXCITED STATES
MIXED VALENCE
ELECTROLUMINESCENT MATERIALS
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:11336/93143
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/93143
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized speciesRamirez, Cristina LujanMangione, Maria InesBertolotti, Sonia GracielaArbeloa, Ernesto MaximilianoParise, Alejandro RubenCARBAZOLEPHOTOPHYSICSEXCITED STATESMIXED VALENCEELECTROLUMINESCENT MATERIALShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of N-phenyl-carbazole derivatives namely TCz (N-tolyl-carbazol), TCz-TCz (a 3,3´-linked dimer), and CzPh-CH2-PhCz (a methylene-bridged N-phenyl-carbazole), have been synthesized and studied by means of absorption and fluorescence spectra, DFT calculations, cyclic voltammetry and spectroelectrochemistry. It is concluded that the methylene bridge in CzPh-CH2-PhCz isolates the two TCz units, whereas TCz-TCz allows extending the electronic coupling along both carbazoles. Moreover, the phosphorescence spectrum of TCz-TCz showed a high energy triplet state (2.76 eV). It was observed that oxidation of CzPh-CH2-PhCz generates an electrochromic polymer containing TCz-TCz dimer units separated by methylene bridges. Oxidized TCz-TCz subunit was analyzed by EPR spectroscopy, and found to be a Class III mixed valence ion in Robin and Day classification. All results suggest that these molecules might be suitable as selective probes in fluorescence sensing or as host materials in electroluminescent devices.Fil: Ramirez, Cristina Lujan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Biodiversidad y Biotecnología; Argentina. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; ArgentinaFil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Bertolotti, Sonia Graciela. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Arbeloa, Ernesto Maximiliano. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Parise, Alejandro Ruben. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Biodiversidad y Biotecnología; ArgentinaElsevier Science Sa2018-10-01info: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/11336/93143Ramirez, Cristina Lujan; Mangione, Maria Ines; Bertolotti, Sonia Graciela; Arbeloa, Ernesto Maximiliano; Parise, Alejandro Ruben; A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 365; 1-10-2018; 199-2071010-6030CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2018.07.039info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1010603018309900info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:00:27Zoai:ri.conicet.gov.ar:11336/93143instacron: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 10:00:27.65CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species
title A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species
spellingShingle A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species
Ramirez, Cristina Lujan
CARBAZOLE
PHOTOPHYSICS
EXCITED STATES
MIXED VALENCE
ELECTROLUMINESCENT MATERIALS
title_short A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species
title_full A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species
title_fullStr A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species
title_full_unstemmed A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species
title_sort A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species
dc.creator.none.fl_str_mv Ramirez, Cristina Lujan
Mangione, Maria Ines
Bertolotti, Sonia Graciela
Arbeloa, Ernesto Maximiliano
Parise, Alejandro Ruben
author Ramirez, Cristina Lujan
author_facet Ramirez, Cristina Lujan
Mangione, Maria Ines
Bertolotti, Sonia Graciela
Arbeloa, Ernesto Maximiliano
Parise, Alejandro Ruben
author_role author
author2 Mangione, Maria Ines
Bertolotti, Sonia Graciela
Arbeloa, Ernesto Maximiliano
Parise, Alejandro Ruben
author2_role author
author
author
author
dc.subject.none.fl_str_mv CARBAZOLE
PHOTOPHYSICS
EXCITED STATES
MIXED VALENCE
ELECTROLUMINESCENT MATERIALS
topic CARBAZOLE
PHOTOPHYSICS
EXCITED STATES
MIXED VALENCE
ELECTROLUMINESCENT MATERIALS
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 A series of N-phenyl-carbazole derivatives namely TCz (N-tolyl-carbazol), TCz-TCz (a 3,3´-linked dimer), and CzPh-CH2-PhCz (a methylene-bridged N-phenyl-carbazole), have been synthesized and studied by means of absorption and fluorescence spectra, DFT calculations, cyclic voltammetry and spectroelectrochemistry. It is concluded that the methylene bridge in CzPh-CH2-PhCz isolates the two TCz units, whereas TCz-TCz allows extending the electronic coupling along both carbazoles. Moreover, the phosphorescence spectrum of TCz-TCz showed a high energy triplet state (2.76 eV). It was observed that oxidation of CzPh-CH2-PhCz generates an electrochromic polymer containing TCz-TCz dimer units separated by methylene bridges. Oxidized TCz-TCz subunit was analyzed by EPR spectroscopy, and found to be a Class III mixed valence ion in Robin and Day classification. All results suggest that these molecules might be suitable as selective probes in fluorescence sensing or as host materials in electroluminescent devices.
Fil: Ramirez, Cristina Lujan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Biodiversidad y Biotecnología; Argentina. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina
Fil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Bertolotti, Sonia Graciela. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Arbeloa, Ernesto Maximiliano. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Parise, Alejandro Ruben. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Biodiversidad y Biotecnología; Argentina
description A series of N-phenyl-carbazole derivatives namely TCz (N-tolyl-carbazol), TCz-TCz (a 3,3´-linked dimer), and CzPh-CH2-PhCz (a methylene-bridged N-phenyl-carbazole), have been synthesized and studied by means of absorption and fluorescence spectra, DFT calculations, cyclic voltammetry and spectroelectrochemistry. It is concluded that the methylene bridge in CzPh-CH2-PhCz isolates the two TCz units, whereas TCz-TCz allows extending the electronic coupling along both carbazoles. Moreover, the phosphorescence spectrum of TCz-TCz showed a high energy triplet state (2.76 eV). It was observed that oxidation of CzPh-CH2-PhCz generates an electrochromic polymer containing TCz-TCz dimer units separated by methylene bridges. Oxidized TCz-TCz subunit was analyzed by EPR spectroscopy, and found to be a Class III mixed valence ion in Robin and Day classification. All results suggest that these molecules might be suitable as selective probes in fluorescence sensing or as host materials in electroluminescent devices.
publishDate 2018
dc.date.none.fl_str_mv 2018-10-01
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/11336/93143
Ramirez, Cristina Lujan; Mangione, Maria Ines; Bertolotti, Sonia Graciela; Arbeloa, Ernesto Maximiliano; Parise, Alejandro Ruben; A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 365; 1-10-2018; 199-207
1010-6030
CONICET Digital
CONICET
url http://hdl.handle.net/11336/93143
identifier_str_mv Ramirez, Cristina Lujan; Mangione, Maria Ines; Bertolotti, Sonia Graciela; Arbeloa, Ernesto Maximiliano; Parise, Alejandro Ruben; A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 365; 1-10-2018; 199-207
1010-6030
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.jphotochem.2018.07.039
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1010603018309900
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 Elsevier Science Sa
publisher.none.fl_str_mv Elsevier Science Sa
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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