- -

On the Ion-Pair Recognition and Indication Features of a Fluorescent Heteroditopic Host Based on a BODIPY Core

RiuNet: Repositorio Institucional de la Universidad Politécnica de Valencia

Compartir/Enviar a

Citas

Estadísticas

  • Estadisticas de Uso

On the Ion-Pair Recognition and Indication Features of a Fluorescent Heteroditopic Host Based on a BODIPY Core

Mostrar el registro completo del ítem

Gotor, R.; Costero Nieto, AM.; Gil Grau, S.; Gaviña, P.; Rurack, K. (2014). On the Ion-Pair Recognition and Indication Features of a Fluorescent Heteroditopic Host Based on a BODIPY Core. European Journal of Organic Chemistry. 2014(19):4005-4013. https://doi.org/10.1002/ejoc.201402214

Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/67400

Ficheros en el ítem

[Cerrado]
Nombre: Gotor;Ana M. ...
Tamaño: 914.2Kb
Formato: PDF
Descripción: Versión editorial
Solicitar una copia al autor

Metadatos del ítem

Título: On the Ion-Pair Recognition and Indication Features of a Fluorescent Heteroditopic Host Based on a BODIPY Core
Autor: Gotor, R. Costero Nieto, Ana María Gil Grau, Salvador Gaviña, P. Rurack, K.
Entidad UPV: Universitat Politècnica de València. Instituto de Reconocimiento Molecular y Desarrollo Tecnológico - Institut de Reconeixement Molecular i Desenvolupament Tecnològic
Fecha difusión:
Resumen:
A fluorescent heteroditopic host for ion pairs and zwitterionic species has been synthesized. Its affinity towards a series of anions, cations and ion pairs in acetonitrile has been assessed, and the spectroscopic response ...[+]
Palabras clave: Sensors , Receptors , Ion-pair recognition , Zwitterion recognition , Fluorescence
Derechos de uso: Cerrado
Fuente:
European Journal of Organic Chemistry. (issn: 1434-193X )
DOI: 10.1002/ejoc.201402214
Editorial:
Wiley-VCH Verlag
Versión del editor: http://dx.doi.org/10.1002/ejoc.201402214
Código del Proyecto:
info:eu-repo/grantAgreement/MINECO//MAT2012-38429-C04-02/ES/QUIMIOSENSORES CROMOGENICOS Y FLUOROGENICOS PARA LA DETECCION DE EXPLOSIVOS Y GASES PELIGROSOS/
Agradecimientos:
Financial support from the Spanish Government (project MAT2012-38429-C04-02) is gratefully acknowledged. R. G. is grateful to the Spanish Ministry of Education for an FPU grant. The Universidad de Valencia (SCSIE) is also ...[+]
Tipo: Artículo

References

P. A. Gale Supramolecular Chemistry: From Molecules to Nanomaterials vol. 1-8 Chichester UK 2012

Izatt, R. M., Pawlak, K., Bradshaw, J. S., & Bruening, R. L. (1995). Thermodynamic and Kinetic Data for Macrocycle Interaction with Cations, Anions, and Neutral Molecules. Chemical Reviews, 95(7), 2529-2586. doi:10.1021/cr00039a010

Martínez-Máñez, R., & Sancenón, F. (2003). Fluorogenic and Chromogenic Chemosensors and Reagents for Anions. Chemical Reviews, 103(11), 4419-4476. doi:10.1021/cr010421e [+]
P. A. Gale Supramolecular Chemistry: From Molecules to Nanomaterials vol. 1-8 Chichester UK 2012

Izatt, R. M., Pawlak, K., Bradshaw, J. S., & Bruening, R. L. (1995). Thermodynamic and Kinetic Data for Macrocycle Interaction with Cations, Anions, and Neutral Molecules. Chemical Reviews, 95(7), 2529-2586. doi:10.1021/cr00039a010

Martínez-Máñez, R., & Sancenón, F. (2003). Fluorogenic and Chromogenic Chemosensors and Reagents for Anions. Chemical Reviews, 103(11), 4419-4476. doi:10.1021/cr010421e

Kim, S. K., & Sessler, J. L. (2010). Ion pair receptors. Chemical Society Reviews, 39(10), 3784. doi:10.1039/c002694h

Scheerder, J., van Duynhoven, J. P. M., Engbersen, J. F. J., & Reinhoudt, D. N. (1996). Solubilization of NaX Salts in Chloroform by Bifunctional Receptors. Angewandte Chemie International Edition in English, 35(10), 1090-1093. doi:10.1002/anie.199610901

Rudkevich, D. M., Mercer-Chalmers, J. D., Verboom, W., Ungaro, R., de Jong, F., & Reinhoudt, D. N. (1995). Bifunctional Recognition: Simultaneous Transport of Cations and Anions through a Supported Liquid Membrane. Journal of the American Chemical Society, 117(22), 6124-6125. doi:10.1021/ja00127a027

Mahoney, J. M., Marshall, R. A., Beatty, A. M., Smith, B. D., Camiolo, S., & Gale, P. A. (2001). Complexation of Alkali Chloride Contact Ion-Pairs Using A 2,5-Diamidopyrrole Crown Macrobicycle. Journal of Supramolecular Chemistry, 1(4-6), 289-292. doi:10.1016/s1472-7862(02)00068-0

Galan, A., Andreu, D., Echavarren, A. M., Prados, P., & De Mendoza, J. (1992). A receptor for the enantioselective recognition of phenylalanine and tryptophan under neutral conditions. Journal of the American Chemical Society, 114(4), 1511-1512. doi:10.1021/ja00030a074

Rudkevich, D. M., Shivanyuk, A. N., Brzozka, Z., Verboom, W., & Reinhoudt, D. N. (1995). A Self-Assembled Bifunctional Receptor. Angewandte Chemie International Edition in English, 34(19), 2124-2126. doi:10.1002/anie.199521241

Liu, H., Shao, X.-B., Jia, M.-X., Jiang, X.-K., Li, Z.-T., & Chen, G.-J. (2005). Selective recognition of sodium cyanide and potassium cyanide by diaza-crown ether-capped Zn-porphyrin receptors in polar solvents. Tetrahedron, 61(34), 8095-8100. doi:10.1016/j.tet.2005.06.058

Gunning, P., Benniston, A. C., & Peacock, R. D. (2004). A modular ditopic crown-shielded phosphate ion-pair receptor. Chemical Communications, (19), 2226. doi:10.1039/b409132a

Lankshear, M. D., Cowley, A. R., & Beer, P. D. (2006). Cooperative AND receptor for ion-pairs. Chemical Communications, (6), 612. doi:10.1039/b515634c

Lankshear, M. D., Dudley, I. M., Chan, K.-M., Cowley, A. R., Santos, S. M., Felix, V., & Beer, P. D. (2008). Cooperative AND Ion-Pair Recognition by Heteroditopic Calix[4]diquinone Receptors. Chemistry - A European Journal, 14(7), 2248-2263. doi:10.1002/chem.200701347

De Silva, A. P., McClean, G. D., & Pagliari, S. (2003). Direct detection of ion pairs by fluorescence enhancement. Chemical Communications, (16), 2010. doi:10.1039/b305262a

Sessler, J. L., & Brucker, E. A. (1995). The first «crowned» expanded porphyrin. Tetrahedron Letters, 36(8), 1175-1176. doi:10.1016/0040-4039(94)02490-3

Descalzo, A. B., Xu, H.-J., Shen, Z., & Rurack, K. (2008). Red/Near-infrared Boron-Dipyrromethene Dyes as Strongly Emitting Fluorophores. Annals of the New York Academy of Sciences, 1130(1), 164-171. doi:10.1196/annals.1430.016

Wang, Y.-W., Descalzo, A. B., Shen, Z., You, X.-Z., & Rurack, K. (2010). Dihydronaphthalene-Fused Boron-Dipyrromethene (BODIPY) Dyes: Insight into the Electronic and Conformational Tuning Modes of BODIPY Fluorophores. Chemistry - A European Journal, 16(9), 2887-2903. doi:10.1002/chem.200902527

Loudet, A., & Burgess, K. (2007). BODIPY Dyes and Their Derivatives:  Syntheses and Spectroscopic Properties. Chemical Reviews, 107(11), 4891-4932. doi:10.1021/cr078381n

Boens, N., Leen, V., & Dehaen, W. (2012). Fluorescent indicators based on BODIPY. Chem. Soc. Rev., 41(3), 1130-1172. doi:10.1039/c1cs15132k

Atilgan, S., Kutuk, I., & Ozdemir, T. (2010). A near IR di-styryl BODIPY-based ratiometric fluorescent chemosensor for Hg(II). Tetrahedron Letters, 51(6), 892-894. doi:10.1016/j.tetlet.2009.12.025

Bura, T., & Ziessel, R. (2010). Design, synthesis and redox properties of a fluorene platform linking two different Bodipy dyes. Tetrahedron Letters, 51(21), 2875-2879. doi:10.1016/j.tetlet.2010.03.095

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

Yin, Z., Tam, A. Y.-Y., Wong, K. M.-C., Tao, C.-H., Li, B., Poon, C.-T., … Yam, V. W.-W. (2012). Functionalized BODIPY with various sensory units – a versatile colorimetric and luminescent probe for pH and ions. Dalton Transactions, 41(37), 11340. doi:10.1039/c2dt30446e

Gotor, R., Costero, A. M., Gil, S., Parra, M., Gaviña, P., & Rurack, K. (2013). Boolean operations mediated by an ion-pair receptor of a multi-readout molecular logic gate. Chemical Communications, 49(94), 11056. doi:10.1039/c3cc45377d

Rurack, K., Kollmannsberger, M., & Daub, J. (2001). Molecular Switching in the Near Infrared (NIR) with a Functionalized Boron-Dipyrromethene Dye. Angewandte Chemie International Edition, 40(2), 385-387. doi:10.1002/1521-3773(20010119)40:2<385::aid-anie385>3.0.co;2-f

Kollmannsberger, M., Rurack, K., Resch-Genger, U., & Daub, J. (1998). Ultrafast Charge Transfer in Amino-Substituted Boron Dipyrromethene Dyes and Its Inhibition by Cation Complexation:  A New Design Concept for Highly Sensitive Fluorescent Probes. The Journal of Physical Chemistry A, 102(50), 10211-10220. doi:10.1021/jp982701c

Qin, W., Baruah, M., Sliwa, M., Van der Auweraer, M., De Borggraeve, W. M., Beljonne, D., … Boens, N. (2008). Ratiometric, Fluorescent BODIPY Dye with Aza Crown Ether Functionality: Synthesis, Solvatochromism, and Metal Ion Complex Formation. The Journal of Physical Chemistry A, 112(27), 6104-6114. doi:10.1021/jp800261v

Qin, W., Baruah, M., Stefan, A., Van der Auweraer, M., & Boens, N. (2005). Photophysical Properties of BODIPY-Derived Hydroxyaryl Fluorescent pH Probes in Solution. ChemPhysChem, 6(11), 2343-2351. doi:10.1002/cphc.200500341

Baruah, M., Qin, W., Basarić, N., De Borggraeve, W. M., & Boens, N. (2005). BODIPY-Based Hydroxyaryl Derivatives as Fluorescent pH Probes. The Journal of Organic Chemistry, 70(10), 4152-4157. doi:10.1021/jo0503714

Yu, Y.-H., Descalzo, A. B., Shen, Z., Röhr, H., Liu, Q., Wang, Y.-W., … You, X.-Z. (2006). Mono- and Di(dimethylamino)styryl-Substituted Borondipyrromethene and Borondiindomethene Dyes with Intense Near-Infrared Fluorescence. Chemistry – An Asian Journal, 1(1-2), 176-187. doi:10.1002/asia.200600042

Rurack, K., Trieflinger, C., Koval’chuck, A., & Daub, J. (2007). An Ionically Driven Molecular IMPLICATION Gate Operating in Fluorescence Mode. Chemistry - A European Journal, 13(32), 8998-9003. doi:10.1002/chem.200700858

unpublished results

Gokel, G. W., Leevy, W. M., & Weber, M. E. (2004). Crown Ethers:  Sensors for Ions and Molecular Scaffolds for Materials and Biological Models. Chemical Reviews, 104(5), 2723-2750. doi:10.1021/cr020080k

Gale, P. A., Anzenbacher Jr., P., & Sessler, J. L. (2001). Calixpyrroles II. Coordination Chemistry Reviews, 222(1), 57-102. doi:10.1016/s0010-8545(01)00346-0

SPECFIT 32™ GLOBAL ANALYSIS SYSTEM

Miyaji, H., Sato, W., Sessler, J. L., & Lynch, V. M. (2000). A ‘building block’ approach to functionalized calix[4]pyrroles. Tetrahedron Letters, 41(9), 1369-1373. doi:10.1016/s0040-4039(99)02295-9

Miyaji, H., Sato, W., & Sessler, J. L. (2000). Naked-Eye Detection of Anions in Dichloromethane: Colorimetric Anion Sensors Based on Calix[4]pyrrole. Angewandte Chemie International Edition, 39(10), 1777-1780. doi:10.1002/(sici)1521-3773(20000515)39:10<1777::aid-anie1777>3.0.co;2-e

Nishiyabu, R., Palacios, M. A., Dehaen, W., & Anzenbacher, P. (2006). Synthesis, Structure, Anion Binding, and Sensing by Calix[4]pyrrole Isomers. Journal of the American Chemical Society, 128(35), 11496-11504. doi:10.1021/ja0622150

Chauhan, S. M. S., Garg, B., & Bisht, T. (2009). Synthesis and anion binding of 2-arylazo-meso-octamethylcalix[4]pyrroles. Supramolecular Chemistry, 21(5), 394-400. doi:10.1080/10610270802061192

Rettig, W. (1994). Photoinduced charge separation via twisted intramolecular charge transfer states. Topics in Current Chemistry, 253-299. doi:10.1007/3-540-57565-0_78

Röhr, H., Trieflinger, C., Rurack, K., & Daub, J. (2006). Proton- and Redox-Controlled Switching of Photo- and Electrochemiluminescence in Thiophenyl-Substituted Boron-Dipyrromethene Dyes. Chemistry - A European Journal, 12(3), 689-700. doi:10.1002/chem.200500729

Baruah, M., Qin, W., Vallée, R. A. L., Beljonne, D., Rohand, T., Dehaen, W., & Boens, N. (2005). A Highly Potassium-Selective Ratiometric Fluorescent Indicator Based on BODIPY Azacrown Ether Excitable with Visible Light. Organic Letters, 7(20), 4377-4380. doi:10.1021/ol051603o

Gromov, S. P., Dmitrieva, S. N., Vedernikov, A. I., Kurchavov, N. A., Kuz’mina, L. G., Sazonov, S. K., … Ushakov, E. N. (2013). Synthesis, Structure, and Characterization of Chromo(fluoro)ionophores with Cation-Triggered Emission Based on N-Methylaza-Crown-Ether Styryl Dyes. The Journal of Organic Chemistry, 78(19), 9834-9847. doi:10.1021/jo401555a

Rurack, K., Bricks, J. L., Reck, G., Radeglia, R., & Resch-Genger, U. (2000). Chalcone-Analogue Dyes Emitting in the Near-Infrared (NIR):  Influence of Donor−Acceptor Substitution and Cation Complexation on Their Spectroscopic Properties and X-ray Structure. The Journal of Physical Chemistry A, 104(14), 3087-3109. doi:10.1021/jp994269k

Carman, P. C. (1978). Ionic association in acetonitrile and in formamide. Journal of Solution Chemistry, 7(11), 845-858. doi:10.1007/bf00650812

Gotor, R., Costero, A. M., Gaviña, P., Gil, S., & Parra, M. (2013). Binding and Fluorescent Sensing of Dicarboxylates by a Bis(calix[4]pyrrole)-Substituted BODIPY Dye. European Journal of Organic Chemistry, 2013(8), 1515-1520. doi:10.1002/ejoc.201201504

Nishiyabu, R., & Anzenbacher, P. (2006). 1,3-Indane-Based Chromogenic Calixpyrroles with Push−Pull Chromophores:  Synthesis and Anion Sensing. Organic Letters, 8(3), 359-362. doi:10.1021/ol0521782

[-]

recommendations

 

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

Mostrar el registro completo del ítem