Solid Phase Synthesis of <i>N</i>-Alkyl-bis-<i>o</i>-aminobenzamides for Metal Ion Sensing Based on a Fluorescent Dansyl Platform

Pina‐Luis, Georgina; Ochoa-Terán, Adrían; Rivero, Ignacio A.

doi:10.1021/cc8000772

Cited by 18 publications

(9 citation statements)

References 29 publications

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“…With Li + and Na + there is a decrease in fluorescence intensity, whereas with K + a notorious increase in fluorescence intensity was shown, see Figure 6. It has been described that the ionic radii produces a higher rigidity in the complex and activates the PET mechanism, which increases fluorescence intensity 16,17. On the other hand, data showed the influence of the bidentate amine on fluorescence intensity when coordination of the metal occurred, as seen in Figure 7.…”

Section: Resultsmentioning

confidence: 89%

Merrifield and Wang Resins Functionalized with Bidentate Amines: Useful Materials to Support Reducing Complexes and as Alkali Metal Sensors

Aguilar-Martínez

Vargas-Durazo

Lara

et al. 2013

Zeitschrift anorg allge chemie

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Eight chelating resins were synthesized in high yields by supporting 2‐aminomethylpyridine, 2,2′‐dipyridylamine, 1,2‐phenylenediamine and 1,2‐ethylenediamine on Merrifield and Wang resins, respectively. These resins were used both as support of reducing complexes and as alkali metal sensors. 16 stable and easy to prepare reducing complexes, derived from the chelating resins and LiBH4 and NaBH4, were prepared in good yields. These complexes showed chemoselectivity to reduce aldehydes in a low molar ratio and short time reactions. The fluorescence‐sensing behavior of the chelating resins for alkali metal was studied. The fluorescence response of the materials where 1, 2‐phenylenediamine is supported on Merrifield and Wang resins indicate that they behave as sensors for Li+and K+, respectively.

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Section: Resultsmentioning

confidence: 89%

Merrifield and Wang Resins Functionalized with Bidentate Amines: Useful Materials to Support Reducing Complexes and as Alkali Metal Sensors

Aguilar-Martínez

Vargas-Durazo

Lara

et al. 2013

Zeitschrift anorg allge chemie

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“…However, it should be mentioned here, for all these reported systems, almost all research have been performed in the solution state. Immobilizing fluorescent PET switches/sensors into solid state, which can fabricate them into device and may endow the resulting materials with interesting stimuli‐responsive properties, has remained a big challenge as their identical properties in solution usually cannot be retained.…”

Section: Methodsmentioning

confidence: 99%

Tuning the Photoinduced Electron Transfer in a Zr‐MOF: Toward Solid‐State Fluorescent Molecular Switch and Turn‐On Sensor

et al. 2018

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The immobilization of fluorescent photoinduced electron transfer (PET) switches/sensors into solid state, which usually cannot maintain their identical properties in solution, has remained a big challenge. Herein, a water-stable anthracene and maleimide appended zirconium-based-metal-organic framework (Zr-MOF; UiO-68-An/Ma) is reported. Unlike the regular intramolecular "fluorophore-spacer-receptor" format, the separated immobilization of fluorescent (anthracene) and acceptor (maleimide) groups into the framework of a multivariate MOF can also favor a pseudo-intramolecular fluorescent PET process, resulting in UiO-68-An/Ma with very weak fluorescence. Interestingly, after Diels-Alder reaction or thiol-ene reaction of maleimide groups, the pseudo-intramolecular fluorescent PET process in UiO-68-An/Ma fails and the solid-state fluorescence of the crystals is recovered. In addition, UiO-68-An/Ma shows an interesting application as solid-state fluorescent turn-on sensor for biothiols, with the naked eye response at a low concentration of 50 µmol L within 5 min. This study represents a general strategy to enable the efficient tuning of fluorescent PET switches/sensors in solid state, and considering the fluorescence of the PET-based MOFs can be restored after addition of analyte/target species, this research will definitely inspire to construct stimuli-responsive fluorescent MOFs for interesting applications (e.g., logic gate) in future.

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“…En la Figura 5 se muestra la disminución de intensidad de los compuestos con diferentes iones metálicos. [9] Por lo antes mencionado y al contar con la síntesis [10], [11] y los estudios anteriormente realizados con N-alquil-bis-o-aminobenzamidas (BOAB) es necesario realizar estudios de dichos compuestos en presencia de iones metálicos de interés ambiental. En el presente trabajo se estudiaron cinco compuestos BOAB (Figura 6) [12] con distinto espaciador intermedio en presencia de los iones metálicos Fe +2 , Cu +2 , Cd +2 , Hg +2 y Pb +2 .…”

Section: Revista De Ciencias Tecnológicas (Recit) Volumen 2 (3): 124-136unclassified

Estudio de propiedades fotofísicas de sensores del tipo bis-fluoroforicos y su aplicación en la detección de iones metálicos

2019

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Las ciudades industrializadas como Tijuana desechan gran cantidad de agua con contenido de elementos metálico, resultado de los subproductos, que representan un riesgo para la salud. Una alternativa propuesta es el uso de sensores químicos basados en diferentes mecanismos. El enfoque de este proyecto es el estudio de macromoléculas bis-o-aminobenzamida, como sensores selectores de iones metálicos con aplicación en el tratamiento de aguas residuales. Se estudió una serie de cinco compuestos bis-o-aminobenzamidas como sensores químicos capaces de seleccionar y coordinar con metales disueltos en el agua, además de poder remover estos metales en presencia del coagulante natural Pectina la cual fue extraída de la penca del nopal. Para ello se preparó distintas concentraciones de los cinco compuestos, se seleccionó la más adecuada para los análisis y se puso en contacto con soluciones de distintos iones. Los compuestos y su coordinación fueron evaluados por espectroscopias de fluorescencia, UV-Visible y potencial Zeta. Además, se obtuvo micrografías SEM a la remoción obtenida. Los cinco sensores evaluados presentan distintas intensidades de fluorescencia, al estar en contacto con algunos iones metálicos se formaba una coordinación que abate la emisión de fluorescencia. Se estudiaron las propiedades fluorescentes en solución variando la concentración de ligando y se realizó el estudio de su interacción con diferentes metales de interés ambiental. Se determinó la influencia de la naturaleza de la cadena central de interconexión en las propiedades fluorescentes de la biblioteca estudiada. Estos ligandos presentan características fluorescentes interesantes, lo que les confiere un valor potencial como sensores para metales, presentando una sensibilidad para el ion Cu+2 en todos los casos.

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Solid Phase Synthesis of N-Alkyl-bis-o-aminobenzamides for Metal Ion Sensing Based on a Fluorescent Dansyl Platform

Cited by 18 publications

References 29 publications

Merrifield and Wang Resins Functionalized with Bidentate Amines: Useful Materials to Support Reducing Complexes and as Alkali Metal Sensors

Merrifield and Wang Resins Functionalized with Bidentate Amines: Useful Materials to Support Reducing Complexes and as Alkali Metal Sensors

Tuning the Photoinduced Electron Transfer in a Zr‐MOF: Toward Solid‐State Fluorescent Molecular Switch and Turn‐On Sensor

Estudio de propiedades fotofísicas de sensores del tipo bis-fluoroforicos y su aplicación en la detección de iones metálicos

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