Effect of chemical functionalization on the electrochemical properties of conducting polymers. Modification of polyaniline by diazonium ion coupling and subsequent reductive degrad...

Autores
Acevedo, Diego Fernando; Rivarola, Claudia Rosana; Miras, María C.; Barbero, César Alfredo
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The electrochemical properties of polyaniline (PANI) can be altered by coupling the polymer with aryldiazonium ions. The ions are synthesized by diazotization of aromatic primary amines (1-aminoanthraquinone, sulphadiazine and 4-cyanoaniline) bearing functional groups which are then linked to the polyaniline backbone. All materials produced are electroactive, suggesting that the reaction involves coupling of the diazonium ion with the aromatic rings and not nucleophilic substitution by the aminic nitrogen of PANI on the aryl cations. The electrochemical properties of the modified polymers are different to those of PANI, likely due to electronic and steric effects of the attached groups. Reductive degradation of the azo linkages, using dithionite ion, removes the attached moieties leaving primary amino groups attached to the polyaniline backbone. In that way, the effect of the attached groups on the electrochemical properties of PANI is eliminated. FTIR spectroscopy measurement of the different polymers supports the proposed mechanism. Using the method a polymer containing redox (anthraquinone) groups, which could be used for charge storage, is obtained. Additionally a material containing sulphadiazine moieties, which can be released in vivo by bacterial activity, is also produced. The molecule is a well-known sulfa drug with bacteriostatic activity. The reaction sequence seems to be of general application to modify polyanilines, by attaching functional groups, and then to produce a PANI backbone bearing primary amino groups. Evidence is presented on the kinetic control of attached group removal.
Fil: Acevedo, Diego Fernando. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; Argentina
Fil: Rivarola, Claudia Rosana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Miras, María C.. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Barbero, César Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; Argentina
Materia
AMINO GROUPS
DIAZO
FUNCTIONALIZATION
POLYANILINE
REDUCTION
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:11336/189550
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/189550
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Effect of chemical functionalization on the electrochemical properties of conducting polymers. Modification of polyaniline by diazonium ion coupling and subsequent reductive degradationAcevedo, Diego FernandoRivarola, Claudia RosanaMiras, María C.Barbero, César AlfredoAMINO GROUPSDIAZOFUNCTIONALIZATIONPOLYANILINEREDUCTIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The electrochemical properties of polyaniline (PANI) can be altered by coupling the polymer with aryldiazonium ions. The ions are synthesized by diazotization of aromatic primary amines (1-aminoanthraquinone, sulphadiazine and 4-cyanoaniline) bearing functional groups which are then linked to the polyaniline backbone. All materials produced are electroactive, suggesting that the reaction involves coupling of the diazonium ion with the aromatic rings and not nucleophilic substitution by the aminic nitrogen of PANI on the aryl cations. The electrochemical properties of the modified polymers are different to those of PANI, likely due to electronic and steric effects of the attached groups. Reductive degradation of the azo linkages, using dithionite ion, removes the attached moieties leaving primary amino groups attached to the polyaniline backbone. In that way, the effect of the attached groups on the electrochemical properties of PANI is eliminated. FTIR spectroscopy measurement of the different polymers supports the proposed mechanism. Using the method a polymer containing redox (anthraquinone) groups, which could be used for charge storage, is obtained. Additionally a material containing sulphadiazine moieties, which can be released in vivo by bacterial activity, is also produced. The molecule is a well-known sulfa drug with bacteriostatic activity. The reaction sequence seems to be of general application to modify polyanilines, by attaching functional groups, and then to produce a PANI backbone bearing primary amino groups. Evidence is presented on the kinetic control of attached group removal.Fil: Acevedo, Diego Fernando. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; ArgentinaFil: Rivarola, Claudia Rosana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Miras, María C.. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Barbero, César Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; ArgentinaPergamon-Elsevier Science Ltd2011-04-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/189550Acevedo, Diego Fernando; Rivarola, Claudia Rosana; Miras, María C.; Barbero, César Alfredo; Effect of chemical functionalization on the electrochemical properties of conducting polymers. Modification of polyaniline by diazonium ion coupling and subsequent reductive degradation; Pergamon-Elsevier Science Ltd; Electrochimica Acta; 56; 10; 1-4-2011; 3468-34730013-4686CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.electacta.2011.01.041info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0013468611001022info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:40:37Zoai:ri.conicet.gov.ar:11336/189550instacron: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 10:40:37.35CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Effect of chemical functionalization on the electrochemical properties of conducting polymers. Modification of polyaniline by diazonium ion coupling and subsequent reductive degradation
title Effect of chemical functionalization on the electrochemical properties of conducting polymers. Modification of polyaniline by diazonium ion coupling and subsequent reductive degradation
spellingShingle Effect of chemical functionalization on the electrochemical properties of conducting polymers. Modification of polyaniline by diazonium ion coupling and subsequent reductive degradation
Acevedo, Diego Fernando
AMINO GROUPS
DIAZO
FUNCTIONALIZATION
POLYANILINE
REDUCTION
title_short Effect of chemical functionalization on the electrochemical properties of conducting polymers. Modification of polyaniline by diazonium ion coupling and subsequent reductive degradation
title_full Effect of chemical functionalization on the electrochemical properties of conducting polymers. Modification of polyaniline by diazonium ion coupling and subsequent reductive degradation
title_fullStr Effect of chemical functionalization on the electrochemical properties of conducting polymers. Modification of polyaniline by diazonium ion coupling and subsequent reductive degradation
title_full_unstemmed Effect of chemical functionalization on the electrochemical properties of conducting polymers. Modification of polyaniline by diazonium ion coupling and subsequent reductive degradation
title_sort Effect of chemical functionalization on the electrochemical properties of conducting polymers. Modification of polyaniline by diazonium ion coupling and subsequent reductive degradation
dc.creator.none.fl_str_mv Acevedo, Diego Fernando
Rivarola, Claudia Rosana
Miras, María C.
Barbero, César Alfredo
author Acevedo, Diego Fernando
author_facet Acevedo, Diego Fernando
Rivarola, Claudia Rosana
Miras, María C.
Barbero, César Alfredo
author_role author
author2 Rivarola, Claudia Rosana
Miras, María C.
Barbero, César Alfredo
author2_role author
author
author
dc.subject.none.fl_str_mv AMINO GROUPS
DIAZO
FUNCTIONALIZATION
POLYANILINE
REDUCTION
topic AMINO GROUPS
DIAZO
FUNCTIONALIZATION
POLYANILINE
REDUCTION
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 electrochemical properties of polyaniline (PANI) can be altered by coupling the polymer with aryldiazonium ions. The ions are synthesized by diazotization of aromatic primary amines (1-aminoanthraquinone, sulphadiazine and 4-cyanoaniline) bearing functional groups which are then linked to the polyaniline backbone. All materials produced are electroactive, suggesting that the reaction involves coupling of the diazonium ion with the aromatic rings and not nucleophilic substitution by the aminic nitrogen of PANI on the aryl cations. The electrochemical properties of the modified polymers are different to those of PANI, likely due to electronic and steric effects of the attached groups. Reductive degradation of the azo linkages, using dithionite ion, removes the attached moieties leaving primary amino groups attached to the polyaniline backbone. In that way, the effect of the attached groups on the electrochemical properties of PANI is eliminated. FTIR spectroscopy measurement of the different polymers supports the proposed mechanism. Using the method a polymer containing redox (anthraquinone) groups, which could be used for charge storage, is obtained. Additionally a material containing sulphadiazine moieties, which can be released in vivo by bacterial activity, is also produced. The molecule is a well-known sulfa drug with bacteriostatic activity. The reaction sequence seems to be of general application to modify polyanilines, by attaching functional groups, and then to produce a PANI backbone bearing primary amino groups. Evidence is presented on the kinetic control of attached group removal.
Fil: Acevedo, Diego Fernando. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; Argentina
Fil: Rivarola, Claudia Rosana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Miras, María C.. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Barbero, César Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; Argentina
description The electrochemical properties of polyaniline (PANI) can be altered by coupling the polymer with aryldiazonium ions. The ions are synthesized by diazotization of aromatic primary amines (1-aminoanthraquinone, sulphadiazine and 4-cyanoaniline) bearing functional groups which are then linked to the polyaniline backbone. All materials produced are electroactive, suggesting that the reaction involves coupling of the diazonium ion with the aromatic rings and not nucleophilic substitution by the aminic nitrogen of PANI on the aryl cations. The electrochemical properties of the modified polymers are different to those of PANI, likely due to electronic and steric effects of the attached groups. Reductive degradation of the azo linkages, using dithionite ion, removes the attached moieties leaving primary amino groups attached to the polyaniline backbone. In that way, the effect of the attached groups on the electrochemical properties of PANI is eliminated. FTIR spectroscopy measurement of the different polymers supports the proposed mechanism. Using the method a polymer containing redox (anthraquinone) groups, which could be used for charge storage, is obtained. Additionally a material containing sulphadiazine moieties, which can be released in vivo by bacterial activity, is also produced. The molecule is a well-known sulfa drug with bacteriostatic activity. The reaction sequence seems to be of general application to modify polyanilines, by attaching functional groups, and then to produce a PANI backbone bearing primary amino groups. Evidence is presented on the kinetic control of attached group removal.
publishDate 2011
dc.date.none.fl_str_mv 2011-04-01
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/11336/189550
Acevedo, Diego Fernando; Rivarola, Claudia Rosana; Miras, María C.; Barbero, César Alfredo; Effect of chemical functionalization on the electrochemical properties of conducting polymers. Modification of polyaniline by diazonium ion coupling and subsequent reductive degradation; Pergamon-Elsevier Science Ltd; Electrochimica Acta; 56; 10; 1-4-2011; 3468-3473
0013-4686
CONICET Digital
CONICET
url http://hdl.handle.net/11336/189550
identifier_str_mv Acevedo, Diego Fernando; Rivarola, Claudia Rosana; Miras, María C.; Barbero, César Alfredo; Effect of chemical functionalization on the electrochemical properties of conducting polymers. Modification of polyaniline by diazonium ion coupling and subsequent reductive degradation; Pergamon-Elsevier Science Ltd; Electrochimica Acta; 56; 10; 1-4-2011; 3468-3473
0013-4686
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.electacta.2011.01.041
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0013468611001022
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
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
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score 13.070432

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