Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognition
A family of heterocyclic thiosemicarbazone dyes (3a-f and 4) containing furyl groups was synthesized in good yields, characterized and their response in acetonitrile in the presence of selected anions was studied. Acetonitrile solutions of 3a-f and 4 showed absorption bands in the 335-396 nm range w...
| Autores: | , , , , , , , , , |
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| Formato: | artículo |
| Fecha de publicación: | 2012 |
| País: | España |
| Recursos: | Universitat Politècnica de València (UPV) |
| Repositorio: | RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia |
| Idioma: | inglés |
| OAI Identifier: | oai:riunet.upv.es:10251/37361 |
| Acesso em linha: | https://riunet.upv.es/handle/10251/37361 |
| Access Level: | acceso abierto |
| Palavra-chave: | Acetate anions Acetonitrile solutions Anion recognition Chemo-sensors Dihydrogen phosphate Electron donors Emission bands Fluorescence studies Heterocyclic systems Hydrogen bonding interactions Hydrogen sulphate Red-shifted emission Spectrophotometric titrations Thiosemicarbazones Bromine compounds Chlorine compounds Cyanides Deprotonation Hydrogen bonds Phenols Thioureas Volatile fatty acids Negative ions QUIMICA ANALITICA QUIMICA INORGANICA QUIMICA ORGANICA |
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| dc.title.none.fl_str_mv |
Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognition |
| title |
Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognition |
| spellingShingle |
Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognition Santos Figueroa, Luis Enrique Acetate anions Acetonitrile solutions Anion recognition Chemo-sensors Dihydrogen phosphate Electron donors Emission bands Fluorescence studies Heterocyclic systems Hydrogen bonding interactions Hydrogen sulphate Red-shifted emission Spectrophotometric titrations Thiosemicarbazones Bromine compounds Chlorine compounds Cyanides Deprotonation Hydrogen bonds Phenols Thioureas Volatile fatty acids Negative ions QUIMICA ANALITICA QUIMICA INORGANICA QUIMICA ORGANICA |
| title_short |
Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognition |
| title_full |
Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognition |
| title_fullStr |
Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognition |
| title_full_unstemmed |
Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognition |
| title_sort |
Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognition |
| dc.creator.none.fl_str_mv |
Santos Figueroa, Luis Enrique Moragues Pons, María Esperanza Raposo, M. Manuela M. Batista, Rosa M.F. Costa, Susana P. G. Ferreira, R. Cristina M. Ros-Lis, José Vicente Soto Camino, Juan Sancenón Galarza, Félix|||0000-0002-5205-7135 Martínez-Máñez, Ramón|||0000-0001-5873-9674 |
| author |
Santos Figueroa, Luis Enrique |
| author_facet |
Santos Figueroa, Luis Enrique Moragues Pons, María Esperanza Raposo, M. Manuela M. Batista, Rosa M.F. Costa, Susana P. G. Ferreira, R. Cristina M. Ros-Lis, José Vicente Soto Camino, Juan Sancenón Galarza, Félix|||0000-0002-5205-7135 Martínez-Máñez, Ramón|||0000-0001-5873-9674 |
| author_role |
author |
| author2 |
Moragues Pons, María Esperanza Raposo, M. Manuela M. Batista, Rosa M.F. Costa, Susana P. G. Ferreira, R. Cristina M. Ros-Lis, José Vicente Soto Camino, Juan Sancenón Galarza, Félix|||0000-0002-5205-7135 Martínez-Máñez, Ramón|||0000-0001-5873-9674 |
| author2_role |
author 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 Generalitat Valenciana Ministerio de Ciencia e Innovación Fundação para a Ciência e a Tecnologia, Portugal Fundación Carolina Universidad Pedagógica Nacional Francisco Morazán, Honduras Universidade do Minho Repositorio Institucional de la Universitat Politècnica de València Riunet |
| dc.subject.none.fl_str_mv |
Acetate anions Acetonitrile solutions Anion recognition Chemo-sensors Dihydrogen phosphate Electron donors Emission bands Fluorescence studies Heterocyclic systems Hydrogen bonding interactions Hydrogen sulphate Red-shifted emission Spectrophotometric titrations Thiosemicarbazones Bromine compounds Chlorine compounds Cyanides Deprotonation Hydrogen bonds Phenols Thioureas Volatile fatty acids Negative ions QUIMICA ANALITICA QUIMICA INORGANICA QUIMICA ORGANICA |
| topic |
Acetate anions Acetonitrile solutions Anion recognition Chemo-sensors Dihydrogen phosphate Electron donors Emission bands Fluorescence studies Heterocyclic systems Hydrogen bonding interactions Hydrogen sulphate Red-shifted emission Spectrophotometric titrations Thiosemicarbazones Bromine compounds Chlorine compounds Cyanides Deprotonation Hydrogen bonds Phenols Thioureas Volatile fatty acids Negative ions QUIMICA ANALITICA QUIMICA INORGANICA QUIMICA ORGANICA |
| description |
A family of heterocyclic thiosemicarbazone dyes (3a-f and 4) containing furyl groups was synthesized in good yields, characterized and their response in acetonitrile in the presence of selected anions was studied. Acetonitrile solutions of 3a-f and 4 showed absorption bands in the 335-396 nm range which are modulated by the electron donor or acceptor strength of the heterocyclic systems appended to the thiosemicarbazone moiety. Fluoride, chloride, bromide, iodide, dihydrogen phosphate, hydrogen sulphate, nitrate, acetate and cyanide anions were used in recognition studies. From these anions, only sensing features were seen for fluoride, cyanide, acetate and dihydrogen phosphate. Two clearly different chromo-fluorogenic behaviours were observed: (i) a small shift of the absorption band due to the coordination of the anions with the thiourea protons and (ii) the appearance of a new red shifted band due to deprotonation. For the latter effect, a change in the colour of solution from pale yellow to purple was observed. Fluorescence studies were also in agreement with the different effects observed in the UV/Vis titrations. In this case, hydrogen bonding interactions were visible through the enhancement of the emission band, whereas deprotonation induced the appearance of a new red-shifted emission. Logarithms of stability constants for the two processes (complex formation + deprotonation) for receptors 3a-f in the presence of fluoride and acetate anions were determined from spectrophotometric titrations using the HypSpec V1.1.18 program. Semi-empirical calculations to evaluate the hydrogen-donating ability of the receptors and a prospective electrochemical characterization of compound 3b in the presence of fluoride were also performed. © 2012 The Royal Society of Chemistry. |
| publishDate |
2012 |
| dc.date.none.fl_str_mv |
2012 2012-07-24 |
| 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/10251/37361 |
| url |
https://riunet.upv.es/handle/10251/37361 |
| dc.language.none.fl_str_mv |
Inglés eng |
| language_invalid_str_mv |
Inglés |
| language |
eng |
| dc.relation.none.fl_str_mv |
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 Fundação para a Ciência e a Tecnologia, Portugal https://doi.org/10.13039/501100001871 PEst-C%2FQUI%2FUI0686%2F2011 Fundação para a Ciência e a Tecnologia, Portugal https://doi.org/10.13039/501100001871 F-COMP-01-0124-FEDER-022716 Fundação para a Ciência e a Tecnologia, Portugal https://doi.org/10.13039/501100001871 SFRH SFRH%2FBPD%2F79333%2F2011 |
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open access http://purl.org/coar/access_right/c_abf2 Reserva de todos los derechos http://rightsstatements.org/vocab/InC/1.0/ |
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info:eu-repo/semantics/openAccess |
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open access http://purl.org/coar/access_right/c_abf2 Reserva de todos los derechos http://rightsstatements.org/vocab/InC/1.0/ |
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openAccess |
| dc.format.none.fl_str_mv |
application/pdf application/pdf |
| dc.publisher.none.fl_str_mv |
Royal Society of Chemistry |
| publisher.none.fl_str_mv |
Royal Society of Chemistry |
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reponame:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia instname:Universitat Politècnica de València (UPV) |
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Universitat Politècnica de València (UPV) |
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RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia |
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RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia |
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1869417413780439040 |
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Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognitionSantos Figueroa, Luis EnriqueMoragues Pons, María EsperanzaRaposo, M. Manuela M.Batista, Rosa M.F.Costa, Susana P. G.Ferreira, R. Cristina M.Ros-Lis, José VicenteSoto Camino, JuanSancenón Galarza, Félix|||0000-0002-5205-7135Martínez-Máñez, Ramón|||0000-0001-5873-9674Acetate anionsAcetonitrile solutionsAnion recognitionChemo-sensorsDihydrogen phosphateElectron donorsEmission bandsFluorescence studiesHeterocyclic systemsHydrogen bonding interactionsHydrogen sulphateRed-shifted emissionSpectrophotometric titrationsThiosemicarbazonesBromine compoundsChlorine compoundsCyanidesDeprotonationHydrogen bondsPhenolsThioureasVolatile fatty acidsNegative ionsQUIMICA ANALITICAQUIMICA INORGANICAQUIMICA ORGANICAA family of heterocyclic thiosemicarbazone dyes (3a-f and 4) containing furyl groups was synthesized in good yields, characterized and their response in acetonitrile in the presence of selected anions was studied. Acetonitrile solutions of 3a-f and 4 showed absorption bands in the 335-396 nm range which are modulated by the electron donor or acceptor strength of the heterocyclic systems appended to the thiosemicarbazone moiety. Fluoride, chloride, bromide, iodide, dihydrogen phosphate, hydrogen sulphate, nitrate, acetate and cyanide anions were used in recognition studies. From these anions, only sensing features were seen for fluoride, cyanide, acetate and dihydrogen phosphate. Two clearly different chromo-fluorogenic behaviours were observed: (i) a small shift of the absorption band due to the coordination of the anions with the thiourea protons and (ii) the appearance of a new red shifted band due to deprotonation. For the latter effect, a change in the colour of solution from pale yellow to purple was observed. Fluorescence studies were also in agreement with the different effects observed in the UV/Vis titrations. In this case, hydrogen bonding interactions were visible through the enhancement of the emission band, whereas deprotonation induced the appearance of a new red-shifted emission. Logarithms of stability constants for the two processes (complex formation + deprotonation) for receptors 3a-f in the presence of fluoride and acetate anions were determined from spectrophotometric titrations using the HypSpec V1.1.18 program. Semi-empirical calculations to evaluate the hydrogen-donating ability of the receptors and a prospective electrochemical characterization of compound 3b in the presence of fluoride were also performed. © 2012 The Royal Society of Chemistry.We thank the Spanish Government (project MAT2009-14564-C04-01) and the Generalitat Valenciana (project PROMETEO/2009/016) for support. We are also grateful to the Fundacao para a Ciencia e Tecnologia (Portugal) and FEDER-COMPETE for financial support through the Centro de Quimica - Universidade do Minho, Project PEst-C/QUI/UI0686/2011 (F-COMP-01-0124-FEDER-022716) and a Post-doctoral grant to R. M. F. Batista (SFRH/BPD/79333/2011). The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re-equipment, with funds from FCT. The authors are also indebted to the programme "Accoes Integradas Luso-Espanholas/CRUP", for bilateral agreement number E-144/10. Thanks also go to the Fundacion Carolina and UPNFM-Honduras for a doctoral grant to L. E. Santos-Figueroa and the Spanish Ministry of Science and Innovation for an FPU grant to M. E. Moragues.Royal Society of ChemistryDepartamento de QuímicaEscuela Técnica Superior de Ingeniería IndustrialInstituto Interuniversitario de Investigación de Reconocimiento Molecular y Desarrollo TecnológicoGeneralitat ValencianaMinisterio de Ciencia e InnovaciónFundação para a Ciência e a Tecnologia, PortugalFundación CarolinaUniversidad Pedagógica Nacional Francisco Morazán, HondurasUniversidade do MinhoRepositorio Institucional de la Universitat Politècnica de València Riunet20122012-07-24journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfapplication/pdfhttps://riunet.upv.es/handle/10251/37361reponame:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valénciainstname:Universitat Politècnica de València (UPV)InglésengMinisterio 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 sensoresFundação para a Ciência e a Tecnologia, Portugal https://doi.org/10.13039/501100001871 PEst-C%2FQUI%2FUI0686%2F2011Fundação para a Ciência e a Tecnologia, Portugal https://doi.org/10.13039/501100001871 F-COMP-01-0124-FEDER-022716Fundação para a Ciência e a Tecnologia, Portugal https://doi.org/10.13039/501100001871 SFRH SFRH%2FBPD%2F79333%2F2011open 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:10251/373612026-06-13T07:49:27Z |
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15,300719 |