Dyes That Bear Thiazolylazo Groups as Chromogenic Chemosensors for Metal Cations

A family of dyes (L 1-L 6) that contain a thiazolylazo group as signalling subunit and several macrocyclic cavities with different ring sizes and type and number of heteroatoms as binding sites has been synthesized and characterized. Solutions of L 1-L 6 in acetonitrile show broad and structureless...

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Autores: Ábalos Aguado, Tatiana, Moragues Pons, María Esperanza, Royo Calvo, Santiago, Jiménez, Diego, Soto Camino, Juan, Gil Grau, Salvador, Cano, Joan, Martínez-Máñez, Ramón|||0000-0001-5873-9674, Sancenón Galarza, Félix|||0000-0002-5205-7135
Tipo de recurso: artículo
Fecha de publicación:2012
País:España
Institución:Universitat Politècnica de València (UPV)
Repositorio:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
Idioma:inglés
OAI Identifier:oai:riunet.upv.es:10251/50542
Acceso en línea:https://riunet.upv.es/handle/10251/50542
Access Level:acceso abierto
Palabra clave:Azodyes
Cation sensors
Chemosensors
Density functional calculations
Dyes
Lead
Mercury
QUIMICA ANALITICA
QUIMICA INORGANICA
QUIMICA ORGANICA
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spelling Dyes That Bear Thiazolylazo Groups as Chromogenic Chemosensors for Metal CationsÁbalos Aguado, TatianaMoragues Pons, María EsperanzaRoyo Calvo, SantiagoJiménez, DiegoSoto Camino, JuanGil Grau, SalvadorCano, JoanMartínez-Máñez, Ramón|||0000-0001-5873-9674Sancenón Galarza, Félix|||0000-0002-5205-7135AzodyesCation sensorsChemosensorsDensity functional calculationsDyesLeadMercuryQUIMICA ANALITICAQUIMICA INORGANICAQUIMICA ORGANICAA family of dyes (L 1-L 6) that contain a thiazolylazo group as signalling subunit and several macrocyclic cavities with different ring sizes and type and number of heteroatoms as binding sites has been synthesized and characterized. Solutions of L 1-L 6 in acetonitrile show broad and structureless absorption bands in the 554-577 nm range with typicalmolar absorption coefficients that range from 20000 to 32000 M -1 cm -1. A detailed protonation study was carried out with solutions of L 1, L 2 and L 5 in acetonitrile. Addition of one equivalent of protons to L 1 and L 2 resulted in the development of a new band at 425 and 370 nm, respectively, which was ascribed to protonation in the aniline nitrogen. In contrast, protonation of L 5 resulted in a bathochromic shift of 25 nm of the absorption band that was conceivable with protonation of one of the nitrogen atoms of the azo moiety. These results were in agreement with 1H NMR spectroscopic data. Theoretical studies on the model ligand L 1 and on different possible protonation species were also performed by using density functional theory (DFT) quantum mechanical calculations. Colour modulations in solutions of L 1-L 6 in acetonitrile in the presence of the metal cations Fe 3+, Ni 2+, Zn 2+, Cd 2+, Pb 2+ and Hg 2+ have been studied. A selective chromogenic response of L 4 in the presence of Pb 2+ and L 5 in the presence of Hg 2+ was observed. To get a better insight into the chromophoric nature in the presence of metal cations, the interaction of Hg 2+ with the model compound L 1 in two different coordination modes was studied theoretically by using density functional theory (DFT) quantum mechanical calculations.Financial support by the Spanish Ministerio de Ciencia e Innovacion (MICINN) through projects MAT2009-14564-C04-01, CTQ2010-15364, Molecular Nanoscience (Consolider Ingenio CSD2007-00010) and Generalitat Valenciana (PROMETEO/2009/016 and PROMETEO/2009/108) is gratefully acknowledged.Wiley-VCH VerlagDepartamento de QuímicaEscuela Técnica Superior de Ingeniería IndustrialInstituto Interuniversitario de Investigación de Reconocimiento Molecular y Desarrollo TecnológicoRepositorio Institucional de la Universitat Politècnica de València Riunet20122012-01-01journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfapplication/pdfhttps://riunet.upv.es/handle/10251/50542reponame:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valénciainstname:Universitat Politècnica de València (UPV)InglésengMinisterio de Educación y Ciencia https://doi.org/10.13039/501100008743 CSD2007-00010 NANOCIENCIA MOLECULARMinisterio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 MAT2009-14564-C04-01 Nanomateriales Hibridos Para El Desarrollo De "Puertas Moleculares" De Aplicacion En Procesos De Reconocimiento Y Terapeutica Y Para La Deteccion De Explosivos.Generalitat Valenciana https://doi.org/10.13039/501100003359 PROMETEO09%2F2009%2F016 Ayuda prometeo 2009 para el grupo de diseño y desarrollo de sensoresMinisterio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 CTQ2010-15364 MAGNETISMO MOLECULAR: COMPUESTOS DE COORDINACION MAGNETICOS MULTIFUNCIONALESopen accesshttp://purl.org/coar/access_right/c_abf2Reserva de todos los derechoshttp://rightsstatements.org/vocab/InC/1.0/info:eu-repo/semantics/openAccessoai:riunet.upv.es:10251/505422026-06-13T07:49:27Z
dc.title.none.fl_str_mv Dyes That Bear Thiazolylazo Groups as Chromogenic Chemosensors for Metal Cations
title Dyes That Bear Thiazolylazo Groups as Chromogenic Chemosensors for Metal Cations
spellingShingle Dyes That Bear Thiazolylazo Groups as Chromogenic Chemosensors for Metal Cations
Ábalos Aguado, Tatiana
Azodyes
Cation sensors
Chemosensors
Density functional calculations
Dyes
Lead
Mercury
QUIMICA ANALITICA
QUIMICA INORGANICA
QUIMICA ORGANICA
title_short Dyes That Bear Thiazolylazo Groups as Chromogenic Chemosensors for Metal Cations
title_full Dyes That Bear Thiazolylazo Groups as Chromogenic Chemosensors for Metal Cations
title_fullStr Dyes That Bear Thiazolylazo Groups as Chromogenic Chemosensors for Metal Cations
title_full_unstemmed Dyes That Bear Thiazolylazo Groups as Chromogenic Chemosensors for Metal Cations
title_sort Dyes That Bear Thiazolylazo Groups as Chromogenic Chemosensors for Metal Cations
dc.creator.none.fl_str_mv Ábalos Aguado, Tatiana
Moragues Pons, María Esperanza
Royo Calvo, Santiago
Jiménez, Diego
Soto Camino, Juan
Gil Grau, Salvador
Cano, Joan
Martínez-Máñez, Ramón|||0000-0001-5873-9674
Sancenón Galarza, Félix|||0000-0002-5205-7135
author Ábalos Aguado, Tatiana
author_facet Ábalos Aguado, Tatiana
Moragues Pons, María Esperanza
Royo Calvo, Santiago
Jiménez, Diego
Soto Camino, Juan
Gil Grau, Salvador
Cano, Joan
Martínez-Máñez, Ramón|||0000-0001-5873-9674
Sancenón Galarza, Félix|||0000-0002-5205-7135
author_role author
author2 Moragues Pons, María Esperanza
Royo Calvo, Santiago
Jiménez, Diego
Soto Camino, Juan
Gil Grau, Salvador
Cano, Joan
Martínez-Máñez, Ramón|||0000-0001-5873-9674
Sancenón Galarza, Félix|||0000-0002-5205-7135
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Departamento de Química
Escuela Técnica Superior de Ingeniería Industrial
Instituto Interuniversitario de Investigación de Reconocimiento Molecular y Desarrollo Tecnológico
Repositorio Institucional de la Universitat Politècnica de València Riunet
dc.subject.none.fl_str_mv Azodyes
Cation sensors
Chemosensors
Density functional calculations
Dyes
Lead
Mercury
QUIMICA ANALITICA
QUIMICA INORGANICA
QUIMICA ORGANICA
topic Azodyes
Cation sensors
Chemosensors
Density functional calculations
Dyes
Lead
Mercury
QUIMICA ANALITICA
QUIMICA INORGANICA
QUIMICA ORGANICA
description A family of dyes (L 1-L 6) that contain a thiazolylazo group as signalling subunit and several macrocyclic cavities with different ring sizes and type and number of heteroatoms as binding sites has been synthesized and characterized. Solutions of L 1-L 6 in acetonitrile show broad and structureless absorption bands in the 554-577 nm range with typicalmolar absorption coefficients that range from 20000 to 32000 M -1 cm -1. A detailed protonation study was carried out with solutions of L 1, L 2 and L 5 in acetonitrile. Addition of one equivalent of protons to L 1 and L 2 resulted in the development of a new band at 425 and 370 nm, respectively, which was ascribed to protonation in the aniline nitrogen. In contrast, protonation of L 5 resulted in a bathochromic shift of 25 nm of the absorption band that was conceivable with protonation of one of the nitrogen atoms of the azo moiety. These results were in agreement with 1H NMR spectroscopic data. Theoretical studies on the model ligand L 1 and on different possible protonation species were also performed by using density functional theory (DFT) quantum mechanical calculations. Colour modulations in solutions of L 1-L 6 in acetonitrile in the presence of the metal cations Fe 3+, Ni 2+, Zn 2+, Cd 2+, Pb 2+ and Hg 2+ have been studied. A selective chromogenic response of L 4 in the presence of Pb 2+ and L 5 in the presence of Hg 2+ was observed. To get a better insight into the chromophoric nature in the presence of metal cations, the interaction of Hg 2+ with the model compound L 1 in two different coordination modes was studied theoretically by using density functional theory (DFT) quantum mechanical calculations.
publishDate 2012
dc.date.none.fl_str_mv 2012
2012-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://riunet.upv.es/handle/10251/50542
url https://riunet.upv.es/handle/10251/50542
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Ministerio de Educación y Ciencia https://doi.org/10.13039/501100008743 CSD2007-00010 NANOCIENCIA MOLECULAR
Ministerio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 MAT2009-14564-C04-01 Nanomateriales Hibridos Para El Desarrollo De "Puertas Moleculares" De Aplicacion En Procesos De Reconocimiento Y Terapeutica Y Para La Deteccion De Explosivos.
Generalitat Valenciana https://doi.org/10.13039/501100003359 PROMETEO09%2F2009%2F016 Ayuda prometeo 2009 para el grupo de diseño y desarrollo de sensores
Ministerio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 CTQ2010-15364 MAGNETISMO MOLECULAR: COMPUESTOS DE COORDINACION MAGNETICOS MULTIFUNCIONALES
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Reserva de todos los derechos
http://rightsstatements.org/vocab/InC/1.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Reserva de todos los derechos
http://rightsstatements.org/vocab/InC/1.0/
eu_rights_str_mv openAccess
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:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
instname:Universitat Politècnica de València (UPV)
instname_str Universitat Politècnica de València (UPV)
reponame_str RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
collection RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300719

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