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Int. J. Mol. Sci. 2015, 16(2), 3804-3819; doi:10.3390/ijms16023804

Experimental and Theoretical Study of O-Substituent Effect on the Fluorescence of 8-Hydroxyquinoline

1
Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah B.O.208203, Saudi Arabia
2
Dyeing, Printing and Textile Auxiliaries Department, Textile Research Division, National Research Center, Dokki, Cairo 12622, Egypt
3
Chemistry Department, Faculty of Science, Beni Suef University, Beni Suef 6251, Egypt
*
Author to whom correspondence should be addressed.
Academic Editor: Habil. Mihai V. Putz
Received: 12 December 2014 / Accepted: 29 January 2015 / Published: 10 February 2015
(This article belongs to the Special Issue Chemical Bond and Bonding 2015)
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Abstract

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. View Full-Text
Keywords: ether and ester derivatives; 8-hydroxyquinoline (8-HQ); UV-visible and fluorescence spectra; TD-DFT calculations; electronic absorption; natural transition orbital (NTO) ether and ester derivatives; 8-hydroxyquinoline (8-HQ); UV-visible and fluorescence spectra; TD-DFT calculations; electronic absorption; natural transition orbital (NTO)
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Zayed, M.E.M.; El-Shishtawy, R.M.; Elroby, S.A.; Obaid, A.Y.; Al-amshany, Z.M. Experimental and Theoretical Study of O-Substituent Effect on the Fluorescence of 8-Hydroxyquinoline. Int. J. Mol. Sci. 2015, 16, 3804-3819.

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