Grid-type complexes of M2+ (M = Co, Ni, and Zn) with highly soluble bis(hydrazone)thiopyrimidine-based ligands: Spectroscopy and electrochemical properties

Carmona‐Vargas, Christian C.; Váquiro, Ingri Y.; Jaramillo‐Gómez, Luz M.; Lehn, Jean‐Maríe; Chaur, Manuel N.

doi:10.1016/j.ica.2017.05.002

Cited by 20 publications

(13 citation statements)

References 35 publications

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“…In solution, they are capable of forming supramolecular rack and grid structures through metal complexation. Supramolecular grid structures are investigated for their electronic, magnetic, and self‐assembly properties, as well as for use in sensors and functional materials . Due to the high stability and selectivity in structure formation BTPs are promising candidates for the construction of hierarchic self‐assembled systems …”

Section: Introductionmentioning

confidence: 99%

Optically Functionalized Grid‐Type Complexes by a Post‐Assembly Strategy

Eggers

Ziener

2018

Chemistry A European J

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Bisterpyridine-based grid complexes can serve as supramolecular three-dimensional scaffolds for the construction of larger molecular assemblies. Through functionalization of the ligand with azide groups, followed by self-assembly and metal-free Huisgen reactions, eight pyrene molecules can be attached to the grid structure in a single reaction step. The orientation and proximity provided by the scaffold allows for tuning the fluorescence properties of the dye molecules.

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Section: Introductionmentioning

confidence: 99%

Optically Functionalized Grid‐Type Complexes by a Post‐Assembly Strategy

Eggers

Ziener

2018

Chemistry A European J

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“…It is well known that hydrazone derivatives are one of the most used compounds as building blocks for the formation of supramolecular systems because of the physical and chemical properties that they exhibit. These properties can be reversibly modulated in response to an external stimulus, either light (5-9), addition of metal ions (10)(11)(12)(13)(14), and pH changes (15). Hydrazone derivatives based on 2-quinoline are particularly interesting molecules for the development of photo-activated switches as, upon UV-light irradiation, the quinoline-nitrogen may form an intramolecular hydrogen bond with the N-H proton from a hydrazine moiety, thus stabilizing the Z isomer making even possible to isolate it and study its properties.…”

Section: Introductionmentioning

confidence: 99%

Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone

Chaur¹,

Romero²,

Gutiérrez

et al. 2018

Rev. colomb. quim.

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Análisisestructural, espectroscópico y teórico de un sistema molecular basado en la 2-((2-(4-clorofenilhidrazono) metil)quinolina AbstractResumen Resumo A novel molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl) quinoline (1-E) was synthesized. Interconversion of 1-E to its configurational isomer 1-Z was achieved using UV radiation (250 W Hg lamp). Such isomerization was monitored by ¹H-NMR. The results suggest that the hydrazone derivative can act as a chemical brake in solution. This molecular system was structurally (Single Crystal X-Ray diffraction and DFT calculations) and spectroscopically (NMR, UV, and IR) characterized. Electrochemical measurements showed that configurational changes induce differential redox behavior. In this regard, the reported quinoline system exhibits different dynamic absorption and electrochemical properties that are modulated by UV-light. Therefore, 1-E can be regarded as a potential photo-electrochemical switch.Se sintetizó un nuevo sistema molecular basado en 2-((2-(4-chlorofenilhidrazona) metil)quinolina. Del mismo modo, se evaluó la respuesta dinámica de este compuesto a radiación ultravioleta y formación de un enlace de hidrógeno intramolecular. Los resultados muestran que este derivado de hidrazona puede actuar como freno en solución. El sistema en mención es descrito estructural (Cristalografía de Rayos X y cálculos DFT) y espectroscópicamente (RMN, UV e IR). La interconversión de este sistema entre las configuraciones 1-E y 1-Z fue mediada por radiación UV y monitoreada a través de RMN-¹H. El estudio electroquímico mostró un comportamiento diferencial en función de su configuración, aspecto fundamental en el desarrollo de sistemas foto-y electroquímicamente modulados.Neste trabalho é apresentado um novo sistema molecular baseado na 2-((2-(4-clorofenilhidrazona)metil)quinolina, capaz de responder dinamicamente à radiação ultravioleta formando uma ligação de hidrogénio intramolecular que atua como um freio na solução. Este sistema é descrito estruturalmente (cristalografia de raios-X e DFT) e por diferentes técnicas espectroscópicas (RMN, de UV e de IV). Radiação UV foi usada para fazer a interconversão da hidrazona 1-E no seu isômero configuracional 1-Z. Este processo foi monitorado pelo RMN. As medidas eletroquímicas mostraram que as mudanças configuracionais entre os isômeros induzem a comportamentos redox diferentes, o que é uma caraterística chave no desenvolvimento de interruptores fotoelectroquímicos.

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“…Hydrazones have become in an important type of compounds for supramolecular chemistry due to the facile synthesis, ability to coordinate metal ions and the ability of interact with UV light to undergoing configurational changes (1)(2)(3)(4)(5)(6)(7)(8) . Special attention has been paid to double hydrazones containing the framework pyridine-pyrimidine-pyridine since these compounds are able of double coordinate metal ions in a terpyridine-like manner (6,8) .…”

Section: Introductionmentioning

confidence: 99%

Electrochemical studies of grid and linear type M^2+ (M=Zn, Cd and Pb) complexes of a bis-(hydrazone) bearing two symmetric carboxylic groups

Giraldo¹,

Romero²,

Chaur³

2018

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Herein we present the preparation of a bis-(hydrazone) containing a pyridine-pyrimidine-pyridine framework. This compound can be visualized as a double arm system able of coordinating two metal ions in a terpyridine-like manner. By NMR (1D and 2D) it was determined a transoid conformation and an E configuration around the two imine double bonds. Complexation with M2+ (M = Zn, Cd, and Pb) ions resulted in grid and linear type structures which were studied by cyclic and squared wave voltammetry at different temperatures. No linear correlations of the redox potentials as a function of temperature were observed. The latter is likely due to rearrangements in the structure or to spin crossover events. The present results deserve further studies on the electronic properties of these types of compounds for the development of smart materials.

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Grid-type complexes of M2+ (M = Co, Ni, and Zn) with highly soluble bis(hydrazone)thiopyrimidine-based ligands: Spectroscopy and electrochemical properties

Cited by 20 publications

References 35 publications

Optically Functionalized Grid‐Type Complexes by a Post‐Assembly Strategy

Optically Functionalized Grid‐Type Complexes by a Post‐Assembly Strategy

Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone

Electrochemical studies of grid and linear type M^2+ (M=Zn, Cd and Pb) complexes of a bis-(hydrazone) bearing two symmetric carboxylic groups

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