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

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 deriva...

Full description

Autores:
Chaur Valencia, Manuel Noé
Romero, Elkin Libardo
Gutierrez, Gustavo
Soto Monsalve, Mónica
D´Vries, Richard
Zuluaga, Héctor Fabio
Tipo de recurso:
Article of journal
Fecha de publicación:
2018
Institución:
Universidad Nacional de Colombia
Repositorio:
Universidad Nacional de Colombia
Idioma:
spa
OAI Identifier:
oai:repositorio.unal.edu.co:unal/66242
Acceso en línea:
https://repositorio.unal.edu.co/handle/unal/66242
http://bdigital.unal.edu.co/67266/
Palabra clave:
54 Química y ciencias afines / Chemistry
Hydrazone derivatives
configurational dynamic
single XRD
DFT calculations
electrochemistry
derivados hidrazónicos
dinámica configuracional
cristalografía de rayos X
cálculos DFT
electroquímica
derivados de hidrazonas
Dinâmica configuracional
Cristalografia de Raios-X
Cálculos DFT
Eletroquímica
Rights
openAccess
License
Atribución-NoComercial 4.0 Internacional
Description
Summary: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 the UV-light induced configurational change. Therefore, 1-E can be regarded as potential photo-electrochemical switch.