- -

Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence

RiuNet: Repositorio Institucional de la Universidad Politécnica de Valencia

Compartir/Enviar a

Citas

Estadísticas

  • Estadisticas de Uso

Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence

Mostrar el registro sencillo del ítem

Ficheros en el ítem

Thumbnail
Nombre: Pais;Neumann;Vayá ...
Tamaño: 1.219Mb
Formato: PDF
Descripción: Versión editorial
Abrir
dc.contributor.author Pais, Vania F. es_ES
dc.contributor.author Neumann, T. es_ES
dc.contributor.author Vayá Pérez, Ignacio es_ES
dc.contributor.author Jiménez Molero, María Consuelo es_ES
dc.contributor.author Ros, Abel es_ES
dc.contributor.author Pischel, Uwe es_ES
dc.date.accessioned 2020-11-07T04:32:41Z
dc.date.available 2020-11-07T04:32:41Z
dc.date.issued 2019-11-04 es_ES
dc.identifier.issn 1860-5397 es_ES
dc.identifier.uri http://hdl.handle.net/10251/154390
dc.description.abstract [EN] Four new dyes that derive from borylated arylisoquinolines were prepared, containing a third aryl residue (naphthyl, 4-methoxynaphthyl, pyrenyl or anthryl) that is linked via an additional stereogenic axis. The triaryl cores were synthesized by Suzuki couplings and then transformed into boronic acid esters by employing an Ir(I)-catalyzed reaction. The chromophores show dual emission behavior, where the long-wavelength emission band can reach maxima close to 600 nm in polar solvents. The fluorescence quantum yields of the dyes are generally in the range of 0.2¿0.4, reaching in some cases values as high as 0.5¿0.6. Laserflash photolysis provided evidence for the existence of excited triplet states. The dyes form fluoroboronate complexes with fluoride anions, leading to the observation of the quenching of the long-wavelength emission band and ratiometric response by the build-up of a hypsochromically shifted emission signal. es_ES
dc.description.sponsorship Funding by the Spanish Ministry of Economy, Industry, and Competitiveness (CTQ2014-54729-C2-1-P for U.P., CTQ2013-48164-C2-1-P and CTQ2013-48164-C2-2-P for A.R., Ramon y Cajal contracts RYC-2013-12585 for A.R. and RYC-2015-17737 for I.V.), the Spanish Ministry of Science, Innovation, and Universities (CTQ2017-89832-P for U.P., CTQ2016-78875-P for M.C.J., and CTQ2017-89416-R for I.V.), the European Research and Development Fund, and the Andalusian Government (2012/FQM-2140 for U.P., 2009/FQM-4537 and 2012/FQM-1078 for A.R) is gratefully acknowledged. es_ES
dc.language Inglés es_ES
dc.publisher Beilstein-Institut es_ES
dc.relation.ispartof Beilstein Journal of Organic Chemistry es_ES
dc.rights Reconocimiento (by) es_ES
dc.subject Arylisoquinolines es_ES
dc.subject Transient absorption spectroscoppy es_ES
dc.subject Anions es_ES
dc.subject Dyes es_ES
dc.subject Fluorescence es_ES
dc.subject Laser-flash photolysis es_ES
dc.subject Organoboron es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.3762/BJOC.15.254 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//CTQ2013-48164-C2-1-P/ES/SISTEMAS CATALITICOS Y REACTIVOS DE NUEVA GENERACION PARA APLICACIONES EN SINTESIS ASIMETRICA/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//CTQ2013-48164-C2-2-P/ES/SISTEMAS CATALITICOS Y REACTIVOS DE NUEVA GENERACION PARA APLICACIONES EN SINTESIS ASIMETRICA/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//RYC-2013-12585/ES/RYC-2013-12585/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-89832-P/ES/APLICACIONES DE LIBERACION DE HUESPEDES INDUCIDA POR LUZ EN SISTEMAS SUPRAMOLECULARES/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/Junta de Andalucía//P09-FQM-4537/ES/Estrategias Innovadoras En Catálisis Asimétrica. Aplicaciones A La Síntesis De Compuestos De Alto Valor Añadido/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/Junta de Andalucía//P12-FQM-1078/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//CTQ2014-54729-C2-1-P/ES/DISEÑO Y CARACTERIZACION DE NUEVOS FLUOROFOROS CONTENIENDO BORO Y SUS APLICACIONES/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/Junta de Andalucía//P12-FQM-2140/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//RYC-2015-17737/ES/RYC-2015-17737/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//CTQ2016-78875-P/ES/CONTROL SUPRAMOLECULAR DE LA FOTORREACTIVIDAD EN MEDIOS MICROHETEROGENOS BASADOS EN AMINOACIDOS: GELES MOLECULARES Y PROTEINAS TRANSPORTADORAS COMO NANORREACTORES/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-89416-R/ES/FUNCIONALIZACION DE NANOPARTICULAS DE ORO CON MARCADORES BIOLOGICOS Y SENSIBILIZADORES DE OXIGENO SINGLETE PARA SU USO EN BIOMEDICINA/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Pais, VF.; Neumann, T.; Vayá Pérez, I.; Jiménez Molero, MC.; Ros, A.; Pischel, U. (2019). Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence. Beilstein Journal of Organic Chemistry. 15:2612-2622. https://doi.org/10.3762/BJOC.15.254 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.3762/BJOC.15.254 es_ES
dc.description.upvformatpinicio 2612 es_ES
dc.description.upvformatpfin 2622 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 15 es_ES
dc.identifier.pmid 31807196 es_ES
dc.identifier.pmcid PMC6880824 es_ES
dc.relation.pasarela S\396620 es_ES
dc.contributor.funder Junta de Andalucía es_ES
dc.contributor.funder Agencia Estatal de Investigación es_ES
dc.contributor.funder European Regional Development Fund es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES
dc.description.references Frath, D., Massue, J., Ulrich, G., & Ziessel, R. (2014). Lumineszierende Materialien: Fixierung von π-konjugierten und heterocyclischen Liganden mit Bor(III). Angewandte Chemie, 126(9), 2322-2342. doi:10.1002/ange.201305554 es_ES
dc.description.references Ji, L., Griesbeck, S., & Marder, T. B. (2017). Recent developments in and perspectives on three-coordinate boron materials: a bright future. Chemical Science, 8(2), 846-863. doi:10.1039/c6sc04245g es_ES
dc.description.references Vanga, M., Lalancette, R. A., & Jäkle, F. (2019). Controlling the Optoelectronic Properties of Pyrene by Regioselective Lewis Base‐Directed Electrophilic Aromatic Borylation. Chemistry – A European Journal, 25(43), 10133-10140. doi:10.1002/chem.201901231 es_ES
dc.description.references Alcaide, M. M., Santos, F. M. F., Pais, V. F., Carvalho, J. I., Collado, D., Pérez-Inestrosa, E., … Pischel, U. (2017). Electronic and Functional Scope of Boronic Acid Derived Salicylidenehydrazone (BASHY) Complexes as Fluorescent Dyes. The Journal of Organic Chemistry, 82(14), 7151-7158. doi:10.1021/acs.joc.7b00601 es_ES
dc.description.references Bozdemir, O. A., Guliyev, R., Buyukcakir, O., Selcuk, S., Kolemen, S., Gulseren, G., … Akkaya, E. U. (2010). Selective Manipulation of ICT and PET Processes in Styryl-Bodipy Derivatives: Applications in Molecular Logic and Fluorescence Sensing of Metal Ions. Journal of the American Chemical Society, 132(23), 8029-8036. doi:10.1021/ja1008163 es_ES
dc.description.references Niu, L.-Y., Guan, Y.-S., Chen, Y.-Z., Wu, L.-Z., Tung, C.-H., & Yang, Q.-Z. (2012). BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine. Journal of the American Chemical Society, 134(46), 18928-18931. doi:10.1021/ja309079f es_ES
dc.description.references Zheng, Q., Xu, G., & Prasad, P. N. (2008). Conformationally Restricted Dipyrromethene Boron Difluoride (BODIPY) Dyes: Highly Fluorescent, Multicolored Probes for Cellular Imaging. Chemistry - A European Journal, 14(19), 5812-5819. doi:10.1002/chem.200800309 es_ES
dc.description.references Han, J., Loudet, A., Barhoumi, R., Burghardt, R. C., & Burgess, K. (2009). A Ratiometric pH Reporter For Imaging Protein-dye Conjugates In Living Cells. Journal of the American Chemical Society, 131(5), 1642-1643. doi:10.1021/ja8073374 es_ES
dc.description.references Kolemen, S., Işık, M., Kim, G. M., Kim, D., Geng, H., Buyuktemiz, M., … Akkaya, E. U. (2015). Intracellular Modulation of Excited-State Dynamics in a Chromophore Dyad: Differential Enhancement of Photocytotoxicity Targeting Cancer Cells. Angewandte Chemie, 127(18), 5430-5434. doi:10.1002/ange.201411962 es_ES
dc.description.references Bachollet, S. P. J. T., Volz, D., Fiser, B., Münch, S., Rönicke, F., Carrillo, J., … Harrity, J. P. A. (2016). A Modular Class of Fluorescent Difluoroboranes: Synthesis, Structure, Optical Properties, Theoretical Calculations and Applications for Biological Imaging. Chemistry - A European Journal, 22(35), 12430-12438. doi:10.1002/chem.201601915 es_ES
dc.description.references Frath, D., Didier, P., Mély, Y., Massue, J., & Ulrich, G. (2017). Vectorization and Intracellular Distribution of a Two-Photon-Absorbing, Near-Infrared-Emitting π-Extended Boranil Dye. ChemPhotoChem, 1(4), 109-112. doi:10.1002/cptc.201700012 es_ES
dc.description.references Melaimi, M., & Gabbaï, F. P. (2005). A Heteronuclear Bidentate Lewis Acid as a Phosphorescent Fluoride Sensor. Journal of the American Chemical Society, 127(27), 9680-9681. doi:10.1021/ja053058s es_ES
dc.description.references Hudnall, T. W., Kim, Y.-M., Bebbington, M. W. P., Bourissou, D., & Gabbaï, F. P. (2008). Fluoride Ion Chelation By a Bidentate Phosphonium/Borane Lewis Acid. Journal of the American Chemical Society, 130(33), 10890-10891. doi:10.1021/ja804492y es_ES
dc.description.references Wade, C. R., Broomsgrove, A. E. J., Aldridge, S., & Gabbaï, F. P. (2010). Fluoride Ion Complexation and Sensing Using Organoboron Compounds. Chemical Reviews, 110(7), 3958-3984. doi:10.1021/cr900401a es_ES
dc.description.references Bai, D.-R., Liu, X.-Y., & Wang, S. (2007). Charge-Transfer Emission Involving Three-Coordinate Organoboron: V-Shape versus U-Shape and Impact of the Spacer on Dual Emission and Fluorescent Sensing. Chemistry - A European Journal, 13(20), 5713-5723. doi:10.1002/chem.200700364 es_ES
dc.description.references Proń, A., Zhou, G., Norouzi-Arasi, H., Baumgarten, M., & Müllen, K. (2009). Controlling the Charge Transfer in Phenylene-Bridged Borylene−Amine π-Conjugated Systems. Organic Letters, 11(16), 3550-3553. doi:10.1021/ol9012487 es_ES
dc.description.references Pan, H., Fu, G.-L., Zhao, Y.-H., & Zhao, C.-H. (2011). Through-Space Charge-Transfer Emitting Biphenyls Containing a Boryl and an Amino Group at theo,o′-Positions. Organic Letters, 13(18), 4830-4833. doi:10.1021/ol201909r es_ES
dc.description.references Bonn, A. G., & Wenger, O. S. (2015). Charge Transfer Emission in Oligotriarylamine–Triarylborane Compounds. The Journal of Organic Chemistry, 80(8), 4097-4107. doi:10.1021/acs.joc.5b00416 es_ES
dc.description.references Pais, V. F., Lineros, M., López-Rodríguez, R., El-Sheshtawy, H. S., Fernández, R., Lassaletta, J. M., … Pischel, U. (2013). Preparation and pH-Switching of Fluorescent Borylated Arylisoquinolines for Multilevel Molecular Logic. The Journal of Organic Chemistry, 78(16), 7949-7961. doi:10.1021/jo401147t es_ES
dc.description.references Pais, V. F., Lassaletta, J. M., Fernández, R., El-Sheshtawy, H. S., Ros, A., & Pischel, U. (2014). Organic Fluorescent Thermometers Based on Borylated Arylisoquinoline Dyes. Chemistry - A European Journal, 20(25), 7638-7645. doi:10.1002/chem.201402027 es_ES
dc.description.references Domínguez, Z., López-Rodríguez, R., Álvarez, E., Abbate, S., Longhi, G., Pischel, U., & Ros, A. (2018). Azabora[5]helicene Charge-Transfer Dyes Show Efficient and Spectrally Variable Circularly Polarized Luminescence. Chemistry - A European Journal, 24(48), 12660-12668. doi:10.1002/chem.201801908 es_ES
dc.description.references Zhu, L., Shabbir, S. H., Gray, M., Lynch, V. M., Sorey, S., & Anslyn, E. V. (2006). A Structural Investigation of the N−B Interaction in ano-(N,N-Dialkylaminomethyl)arylboronate System. Journal of the American Chemical Society, 128(4), 1222-1232. doi:10.1021/ja055817c es_ES
dc.description.references Boscá, F., Cuquerella, M. C., Pais, V. F., Ros, A., & Pischel, U. (2017). Excited-State Pathways of Four-Coordinate N,C-Chelate Organoboron Dyes. ChemPhotoChem, 2(1), 34-41. doi:10.1002/cptc.201700176 es_ES
dc.description.references Hara, M., Tojo, S., Kawai, K., & Majima, T. (2004). Formation and decay of pyrene radical cation and pyrene dimer radical cation in the absence and presence of cyclodextrins during resonant two-photon ionization of pyrene and sodium 1-pyrene sulfonate. Phys. Chem. Chem. Phys., 6(13), 3215-3220. doi:10.1039/b403409k es_ES
dc.description.references Melhuish, W. H. (1960). A STANDARD FLUORESCENCE SPECTRUM FOR CALIBRATING SPECTRO-FLUOROPHOTOMETERS. The Journal of Physical Chemistry, 64(6), 762-764. doi:10.1021/j100835a014 es_ES
dc.description.references Melhuish, W. H. (1961). QUANTUM EFFICIENCIES OF FLUORESCENCE OF ORGANIC SUBSTANCES: EFFECT OF SOLVENT AND CONCENTRATION OF THE FLUORESCENT SOLUTE1. The Journal of Physical Chemistry, 65(2), 229-235. doi:10.1021/j100820a009 es_ES
dc.subject.ods 03.- Garantizar una vida saludable y promover el bienestar para todos y todas en todas las edades es_ES


Este ítem aparece en la(s) siguiente(s) colección(ones)

Mostrar el registro sencillo del ítem