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Experimental and Theoretical Study of O-Substituent Effect on the Fluorescence of 8-Hydroxyquinoline
The synthesis and characterization of different ether and ester derivatives of 8-hydroxyquinoline have been made. UV-visible and fluorescence spectra of these compounds have revealed spectral dependence on both solvent and O-substituent. The fluorescence intensity of ether derivatives revealed highe...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4346927/ https://www.ncbi.nlm.nih.gov/pubmed/25674853 http://dx.doi.org/10.3390/ijms16023804 |
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author | Zayed, Mohie E. M. El-Shishtawy, Reda M. Elroby, Shaaban A. Obaid, Abdullah Y. Al-amshany, Zahra M. |
author_facet | Zayed, Mohie E. M. El-Shishtawy, Reda M. Elroby, Shaaban A. Obaid, Abdullah Y. Al-amshany, Zahra M. |
author_sort | Zayed, Mohie E. M. |
collection | PubMed |
description | The synthesis and characterization of different ether and ester derivatives of 8-hydroxyquinoline have been made. UV-visible and fluorescence spectra of these compounds have revealed spectral dependence on both solvent and O-substituent. The fluorescence intensity of ether derivatives revealed higher intensity for 8-octyloxyquinoline compared with 8-methoxyquinoline, whereas those of ester derivatives had less fluorescence than 8-hydroxyquinoline. Theoretical calculations based on Time-dependent density functional theory (TD-DFT) were carried out for the quinolin-8-yl benzoate(8-OateQ) compound to understand the effect of O-substituent on the electronic absorption of 8-hydroxyquinaline (8-HQ). The calculations revealed comparable results with those obtained from the experimental data. Optimized geometrical structure was calculated with DFT at B3LYP/6-311++G** level of theory. The results indicated that 8-OateQ is not a coplanar structure. The absorption spectra of the compound were computed in gas-phase and solvent using B3LYP and CAM-B3LYP methods with 6-311++G ** basis set. The agreement between calculated and experimental wavelengths was very good at CAM-B3LYP/6-311++G** level of theory. |
format | Online Article Text |
id | pubmed-4346927 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-43469272015-04-03 Experimental and Theoretical Study of O-Substituent Effect on the Fluorescence of 8-Hydroxyquinoline Zayed, Mohie E. M. El-Shishtawy, Reda M. Elroby, Shaaban A. Obaid, Abdullah Y. Al-amshany, Zahra M. Int J Mol Sci Article The synthesis and characterization of different ether and ester derivatives of 8-hydroxyquinoline have been made. UV-visible and fluorescence spectra of these compounds have revealed spectral dependence on both solvent and O-substituent. The fluorescence intensity of ether derivatives revealed higher intensity for 8-octyloxyquinoline compared with 8-methoxyquinoline, whereas those of ester derivatives had less fluorescence than 8-hydroxyquinoline. Theoretical calculations based on Time-dependent density functional theory (TD-DFT) were carried out for the quinolin-8-yl benzoate(8-OateQ) compound to understand the effect of O-substituent on the electronic absorption of 8-hydroxyquinaline (8-HQ). The calculations revealed comparable results with those obtained from the experimental data. Optimized geometrical structure was calculated with DFT at B3LYP/6-311++G** level of theory. The results indicated that 8-OateQ is not a coplanar structure. The absorption spectra of the compound were computed in gas-phase and solvent using B3LYP and CAM-B3LYP methods with 6-311++G ** basis set. The agreement between calculated and experimental wavelengths was very good at CAM-B3LYP/6-311++G** level of theory. MDPI 2015-02-10 /pmc/articles/PMC4346927/ /pubmed/25674853 http://dx.doi.org/10.3390/ijms16023804 Text en © 2015 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Zayed, Mohie E. M. El-Shishtawy, Reda M. Elroby, Shaaban A. Obaid, Abdullah Y. Al-amshany, Zahra M. Experimental and Theoretical Study of O-Substituent Effect on the Fluorescence of 8-Hydroxyquinoline |
title | Experimental and Theoretical Study of O-Substituent Effect on the Fluorescence of 8-Hydroxyquinoline |
title_full | Experimental and Theoretical Study of O-Substituent Effect on the Fluorescence of 8-Hydroxyquinoline |
title_fullStr | Experimental and Theoretical Study of O-Substituent Effect on the Fluorescence of 8-Hydroxyquinoline |
title_full_unstemmed | Experimental and Theoretical Study of O-Substituent Effect on the Fluorescence of 8-Hydroxyquinoline |
title_short | Experimental and Theoretical Study of O-Substituent Effect on the Fluorescence of 8-Hydroxyquinoline |
title_sort | experimental and theoretical study of o-substituent effect on the fluorescence of 8-hydroxyquinoline |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4346927/ https://www.ncbi.nlm.nih.gov/pubmed/25674853 http://dx.doi.org/10.3390/ijms16023804 |
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