Multiple Dynamics of Hydrazone Based Compounds

Romero, Elkin L.; D’Vries, Richard F.; Zuluaga, Fabio; Chaur, Manuel N.

doi:10.5935/0103-5053.20150092

Cited by 20 publications

(30 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Compound 1-E was synthesized by the partial oxidation of 2 with selenium dioxide in dioxane, followed by condensation of 3 with the hydrazine derivative 4 in ethanol (7). The condensation reaction led to the formation of the corresponding E-hydrazone, which was identified by the singlet at 12.43 ppm corresponding to the NH proton (3).…”

Section: Resultsmentioning

confidence: 99%

“…The hydrazone derivative (E)-2-((2-(4-Chlorophenylhydrazono)methyl) quinoline 1-E was synthesized following the same synthetic protocol as reported in the literature (7). A mixture of 2-methylquinoline (200 mg, 1.40 mmol) and selenium dioxide (263.5 mg, 2.37 mmol) was dissolved in dry dioxane (20 mL).…”

Section: Synthesis Of Hydrazone Derivativesmentioning

confidence: 99%

“…Likewise, the study of electronic and electrochemical properties of configurational isomers has not been well documented, at least for hydrazone derivatives, where there are only a few recent reports (7,18). Electrochemistry of E/Z configurational isomers is important to demonstrate their potential use as molecular photoswitches and electronic devices.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

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.

View full text Add to dashboard Cite

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.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Hydrazone Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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.

View full text Add to dashboard Cite

show abstract

“…Over the past two decades, the designa nd construction of molecular machines [1][2][3] that can act like molecular switches, [4,5] brakes, [6][7][8] and motors [9] have been developed, inspiredb y their natural, macroscopic, and biological analogs, [10] attracting ag reat interest for advancement in the nanotechnology field. [11] In fact, the art of building smallm olecular machinery for whichm otions can be directed in ac ontrolled manner from the outsidew as awarded with the Nobel Prize to Sir Fraser Stoddart, Jean-Pierre Sauvage, and Ben Feringa in 2016.…”

Section: Introductionmentioning

confidence: 99%

Photochemical and Electrochemical Triggered Bis(hydrazone) Switch

Gordillo

Soto‐Monsalve

Carmona‐Vargas

et al. 2017

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

Herein, we report the synthesis of a double hydrazone capable of undergoing photochemical E/Z isomerization through the imine double bonds. The bis(hydrazone) 1-E,E can be considered as a "two-arm" system in which the controlled movement of each arm is obtained by photo-modulation, making possible the appearance of two isolable metastable isomeric states 1-E,Z and 1-Z,Z. Such states are characterized by very specific structural, optical, and electrochemical properties. The latter allows the reversible return from either 1-E,Z or 1-Z,Z to the 1-E,E state. Our results are of great importance in the further development of molecular machines and photochemically controlled reactions by introducing for the first time double hydrazones as tunable photochemical switches.

show abstract

“…Some organic molecular compounds can be used in the design of potential new solid state materials used, for example, in non-linear optics, 1, 2 molecular machines 3,4 or biological process. 5 The design and synthesis of molecular complexes have also been used to develop new solid forms of active pharmaceutical ingredients 6 and for the analysis of the structural changes associated with different physical or chemical stimuli in supramolecular complexes or polymeric compounds.…”

Section: Introductionmentioning

confidence: 99%

Order–disorder phase transition induced by proton transfer in a co-crystal of 2,4-dichlorobenzoic acid and trimethylamine N-oxide

et al. 2017

View full text Add to dashboard Cite

This version is available at https://strathprints.strath.ac.uk/61034/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.ukThe Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output. Journal Name ARTICLEThis journal is © The Royal Society of Chemistry 20xx J. Name., 2013, 00, 1-3 | 1 The crystalline binary adduct between the trimethylamine N-oxide (TMANO) and 2,4-dichlorobenzoic acid (2,4-DCBA) molecules was obtained by slow evaporation from acetonitrile. The obtained molecular complex is formed by a racemic mixture of molecular complexes crystallizing in the orthorhombic space group Pbca. An exhaustive analysis of the temperature dependence of the cell parameters and the behavior of the acidic hydrogen position and carboxilate group were studied by single crystal and powder X-ray diffraction, FT-IR spectroscopy and theoretical calculations. The molecular system was thermally characterized, subsequently demonstrating a order-disorder transition. Finally, the intermolecular interactions were analyzed via Hirshfeld surface analysis.

show abstract

Multiple Dynamics of Hydrazone Based Compounds

Cited by 20 publications

References 5 publications

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

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

Photochemical and Electrochemical Triggered Bis(hydrazone) Switch

Order–disorder phase transition induced by proton transfer in a co-crystal of 2,4-dichlorobenzoic acid and trimethylamine N-oxide

Contact Info

Product

Resources

About