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Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognition

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Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognition

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dc.contributor.author Santos Figueroa, Luis Enrique es_ES
dc.contributor.author Moragues Pons, María Esperanza es_ES
dc.contributor.author Raposo, M. Manuela M. es_ES
dc.contributor.author Batista, Rosa M.F. es_ES
dc.contributor.author Costa, Susana P. G. es_ES
dc.contributor.author Ferreira, R. Cristina M. es_ES
dc.contributor.author Sancenón Galarza, Félix es_ES
dc.contributor.author Martínez Mañez, Ramón es_ES
dc.contributor.author Ros-Lis, José Vicente es_ES
dc.contributor.author Soto Camino, Juan es_ES
dc.date.accessioned 2014-05-09T14:16:45Z
dc.date.issued 2012-07-24
dc.identifier.issn 1477-0520
dc.identifier.uri http://hdl.handle.net/10251/37361
dc.description.abstract 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. es_ES
dc.description.sponsorship 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. en_EN
dc.language Inglés es_ES
dc.publisher Royal Society of Chemistry es_ES
dc.relation.ispartof Organic and Biomolecular Chemistry es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Acetate anions es_ES
dc.subject Acetonitrile solutions es_ES
dc.subject Anion recognition es_ES
dc.subject Chemo-sensors es_ES
dc.subject Dihydrogen phosphate es_ES
dc.subject Electron donors es_ES
dc.subject Emission bands es_ES
dc.subject Fluorescence studies es_ES
dc.subject Heterocyclic systems es_ES
dc.subject Hydrogen bonding interactions es_ES
dc.subject Hydrogen sulphate es_ES
dc.subject Red-shifted emission es_ES
dc.subject Spectrophotometric titrations es_ES
dc.subject Thiosemicarbazones es_ES
dc.subject Bromine compounds es_ES
dc.subject Chlorine compounds es_ES
dc.subject Cyanides es_ES
dc.subject Deprotonation es_ES
dc.subject Hydrogen bonds es_ES
dc.subject Phenols es_ES
dc.subject Thioureas es_ES
dc.subject Volatile fatty acids es_ES
dc.subject Negative ions es_ES
dc.subject.classification QUIMICA ANALITICA es_ES
dc.subject.classification QUIMICA INORGANICA es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognition es_ES
dc.type Artículo es_ES
dc.embargo.lift 10000-01-01
dc.embargo.terms forever es_ES
dc.identifier.doi 10.1039/c2ob26200b
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//MAT2009-14564-C04-01/ES/Nanomateriales Hibridos Para El Desarrollo De "Puertas Moleculares" De Aplicacion En Procesos De Reconocimiento Y Terapeutica Y Para La Deteccion De Explosivos./ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/FCT/SFRH/SFRH/BPD/79333/2011/PT/ en_EN
dc.relation.projectID info:eu-repo/grantAgreement/Generalitat Valenciana//PROMETEO09%2F2009%2F016/ES/Ayuda prometeo 2009 para el grupo de diseño y desarrollo de sensores/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/FCT//PEst-C/QUI/UI0686/2011/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/FCT//F-COMP-01-0124-FEDER-022716/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Santos Figueroa, LE.; Moragues Pons, ME.; Raposo, MMM.; Batista, RM.; Costa, SPG.; Ferreira, RCM.; Sancenón Galarza, F.... (2012). Synthesis and evaluation of thiosemicarbazones functionalized with furylmoieties as new chemosensors for anion recognition. Organic and Biomolecular Chemistry. 10(36):7418-7428. https://doi.org/10.1039/c2ob26200b es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/doi:10.1039/c2ob26200b es_ES
dc.description.upvformatpinicio 7418 es_ES
dc.description.upvformatpfin 7428 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 10 es_ES
dc.description.issue 36 es_ES
dc.relation.senia 223941
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Ministerio de Ciencia e Innovación es_ES
dc.contributor.funder Fundação para a Ciência e a Tecnologia, Portugal
dc.contributor.funder Fundación Carolina
dc.contributor.funder Universidad Pedagógica Nacional Francisco Morazán, Honduras
dc.contributor.funder Universidade do Minho
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