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

Manuel Noé Chaur Valencia,Richard D´Vries,Mónica Soto Monsalve,Héctor Fabio Zuluaga,Elkin Libardo Romero,Gustavo Gutierrez

doi:10.15446/rev.colomb.quim.v47n2.67115

Manuel Noé Chaur Valencia, Richard D´Vries + Show 4 more

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https://doi.org/10.15446/rev.colomb.quim.v47n2.67115

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Abstract

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.

Highlights

The synthesis, characterization, and identification of molecular systems potentially useful in the design of molecular machines is still a huge challenge for supramolecular chemistry researchers [1, 2]
For 1-Z, the 1H-NMR spectra show the existence of an intramolecular H-bond after irradiation with UV light since all the signals changed their chemical shift
The solid-state structural investigation trough single-crystal X-ray diffraction reveals a crystal packaging governed by N1–H1···N3 hydrogen bond, forming inverted dimers along [010] direction

Summary

Introduction

The synthesis, characterization, and identification of molecular systems potentially useful in the design of molecular machines is still a huge challenge for supramolecular chemistry researchers [1, 2] In this regard, some organic compounds with double bonds (C=C, C=N, or N=N) are of special interest due to their reversible photochemical and thermal reactions. 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 [5,6,7,8,9], addition of metal ions [10,11,12,13,14], and pH changes [15]. The E-isomer can act as a ligand similar to terpydine for metal-ion coordination [16, 17]

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