Alcaide, M.; Santos, F.; Pais, V.; Carvalho, J.; Collado, D.; Pérez-Inestrosa, E.; Arteaga, JF.... (2017). Electronic and Functional Scope of Boronic Acid Derived Salicylidenehydrazone (BASHY) Complexes as Fluorescent Dyes. The Journal of Organic Chemistry. 82(14):7151-7158. https://doi.org/10.1021/acs.joc.7b00601
Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/148007
Título:
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Electronic and Functional Scope of Boronic Acid Derived Salicylidenehydrazone (BASHY) Complexes as Fluorescent Dyes
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Autor:
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Alcaide, M.M.
Santos, F.M.F.
Pais, V.F.
Carvalho, J.I.
Collado, Daniel
Pérez-Inestrosa, E.
Arteaga, Jesus F.
Bosca Mayans, Francisco
Gois, P.M P.
Pischel, Uwe
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Entidad UPV:
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Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química
Universitat Politècnica de València. Departamento de Proyectos de Ingeniería - Departament de Projectes d'Enginyeria
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Fecha difusión:
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Resumen:
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[EN] A series of boronic acid derived salicylidenehydrazone (BASHY) complexes was prepared and photophysically characterized. The dye platform can be modified by (a) electronic tuning along the cyanine-type axis via ...[+]
[EN] A series of boronic acid derived salicylidenehydrazone (BASHY) complexes was prepared and photophysically characterized. The dye platform can be modified by (a) electronic tuning along the cyanine-type axis via modification of the donor-acceptor pair and (b) functional tuning via the boronic acid residue. On the one hand, approach (a) allows the control of photophysical parameters such as Stokes shift, emission color, and two-photon absorption (2PA) cross section. The resulting dyes show emission light-up behavior in nonpolar media and are characterized by high fluorescence quantum yields (ca. 0.5-0.7) and brightness (ca. 35000-40000 M-1 cm(-1)). Moreover, the 2PA cross sections reach values in the order of 200-300 GM. On the other hand, the variation of the dye structure through the boronic acid derived moiety (approach (b)) enables the functionalization of the BASHY platform for a broad spectrum of potential applications, ranging from biorelevant contexts to optoelectronic materials. Importantly, this functionalization is generally electronically orthogonal with respect to the dye's photophysical properties, which are only determined by the electronic structure of the cyanine-type backbone (approach (a)). Rare exceptions to this generalization are the presence of redox-active residues (such a triphenylamine or pyrene). Finally, the advantageous photophysics is complemented by a significant photostability.
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Palabras clave:
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2-Photon absorption
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Bodipy dyes
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Highly fluorescent
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Molecular logic
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Probes
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Fluorophores
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Chromophore
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Design
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Enhancement
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Derivatives
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Derechos de uso:
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Cerrado |
Fuente:
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The Journal of Organic Chemistry. (issn:
0022-3263
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DOI:
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10.1021/acs.joc.7b00601
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Editorial:
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American Chemical Society
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Versión del editor:
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https://doi.org/10.1021/acs.joc.7b00601
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Código del Proyecto:
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info:eu-repo/grantAgreement/FCT/5876/147348/PT/Research Institute for Medicines/
...[+]
info:eu-repo/grantAgreement/FCT/5876/147348/PT/Research Institute for Medicines/
info:eu-repo/grantAgreement/MINECO//CTQ2014-54729-C2-2-P/ES/DISEÑO DE NUEVAS PRODROGAS ANTICANCERIGENAS FOTOACTIVABLES/
info:eu-repo/grantAgreement/MINECO//CTQ2014-54729-C2-1-P/ES/DISEÑO Y CARACTERIZACION DE NUEVOS FLUOROFOROS CONTENIENDO BORO Y SUS APLICACIONES/
info:eu-repo/grantAgreement/SFRH/BD/94779/2013/
info:eu-repo/grantAgreement/MINECO//CTQ2013-41339-P/ES/SINTESIS Y FUNCIONALIZACION DE ESTRUCTURAS DENDRIMERICAS BAPAD SOLUBLES Y FIJADAS EN SUPERFICES SOLIDAS. APLICACIONES EN DIAGNOSTICO Y BIOTECNOLOGIA/
info:eu-repo/grantAgreement/PTDC/QEQ-QOR/1434/2014/
info:eu-repo/grantAgreement/MINECO//CTQ2015-71896-REDT/ES/RED DE FOTOQUIMICA BIOLOGICA/
info:eu-repo/grantAgreement/Junta de Andalucía//P12-FQM-2140/
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Agradecimientos:
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The financial support by Spanish MINECO (grants CTQ2014-54729-C2-1-P, CTQ2014-54729-C2-2-P, CTQ2013-41339-P, and CTQ2015-71896-REDT), the Junta de Andalucia (grant P12-FQM-2140), and Portuguese FCT (grants SFRH/BD/94779/2013, ...[+]
The financial support by Spanish MINECO (grants CTQ2014-54729-C2-1-P, CTQ2014-54729-C2-2-P, CTQ2013-41339-P, and CTQ2015-71896-REDT), the Junta de Andalucia (grant P12-FQM-2140), and Portuguese FCT (grants SFRH/BD/94779/2013, PTDC/QEQ-QOR/1434/2014, iMed.ULisboa grant UID/DTP/04138/2013) is gratefully acknowledged.
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Tipo:
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Artículo
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