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

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

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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

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Title: Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence
Author: Pais, Vania F. Neumann, T. Vayá Pérez, Ignacio Jiménez Molero, María Consuelo Ros, Abel Pischel, Uwe
UPV Unit: Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química
Universitat Politècnica de València. Departamento de Química - Departament de Química
Issued date:
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 ...[+]
Subjects: Arylisoquinolines , Transient absorption spectroscoppy , Anions , Dyes , Fluorescence , Laser-flash photolysis , Organoboron
Copyrigths: Reconocimiento (by)
Source:
Beilstein Journal of Organic Chemistry. (issn: 1860-5397 )
DOI: 10.3762/BJOC.15.254
Publisher:
Beilstein-Institut
Publisher version: https://doi.org/10.3762/BJOC.15.254
Project ID:
info:eu-repo/grantAgreement/MINECO//CTQ2013-48164-C2-1-P/ES/SISTEMAS CATALITICOS Y REACTIVOS DE NUEVA GENERACION PARA APLICACIONES EN SINTESIS ASIMETRICA/
...[+]
info:eu-repo/grantAgreement/MINECO//CTQ2013-48164-C2-1-P/ES/SISTEMAS CATALITICOS Y REACTIVOS DE NUEVA GENERACION PARA APLICACIONES EN SINTESIS ASIMETRICA/
info:eu-repo/grantAgreement/MINECO//CTQ2013-48164-C2-2-P/ES/SISTEMAS CATALITICOS Y REACTIVOS DE NUEVA GENERACION PARA APLICACIONES EN SINTESIS ASIMETRICA/
info:eu-repo/grantAgreement/MINECO//RYC-2013-12585/ES/RYC-2013-12585/
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/
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/
info:eu-repo/grantAgreement/Junta de Andalucía//P12-FQM-1078/
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/Junta de Andalucía//P12-FQM-2140/
info:eu-repo/grantAgreement/MINECO//RYC-2015-17737/ES/RYC-2015-17737/
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/
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/
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Thanks:
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 ...[+]
Type: Artículo

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

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

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 [+]
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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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