American Journal of Chemistry 2015, 5(3A): 48-51
DOI: 10.5923/c.chemistry.201501.07
4-Hydroxycoumarins as New Fluorescent Compounds:
Synthesis and Characterization
Yasameen K. Al-Majedy
1,2,*
, Ahmed A. Al-Amiery
1,2
, Abdul Amir H. Kadhum
1
, Abu Bakar Mohamad
1
1
Department of Chemical and Process Engineering, Universiti Kebangsaan Malaysia (UKM)
2
Chemical Division, Department of Applied Science, University of Technology Baghdad, Iraq
Abstract New 4-hydroxycoumarins compounds were designed, synthesized and characterized as fluorescent
compounds. Absorption and fluorescence spectra of these derivatives have been investigated in alcoholic media. The
substituting groups with varying electron donating ability exhibits fluorescence at a longer wavelength i.e. 420-460 nm in
ethanol in compound (1-5). Compounds 1-5 exhibited high quantum yield in ethanol. The fluorescence intensities of
compounds 2 and 5 were extremely strong. Compounds 2 and 5 exhibited high fluorescent quantum yields in solution
compared to compounds 1,3,4.
Keywords Fluorescence, 4-hydroxy-coumarin, Emission, Synthesis
1. Introduction
Fluorescent compounds play an important role in solid
state lighting, solar energy conversion and as biomarkers in
the life sciences [1-6]. As an important group of organic
heterocycles, coumarin derivatives have been found to
possess versatile pharmacological/biological activities,
which can display anticancer [7, 8], anti-HIV [9], antiviral
[10], antimicrobial [11], anti-inflammatory [12, 13], and
antioxidant [14] activities, 4-Hydroxycoumarin and its
derivatives have been effectively used as anticoagulants for
the treatment of disorders in which there is excessive or
undesirable clotting, such as thrombophlebitis [15],
pulmonary embolism [16], and certain cardiac conditions
[17]. Moreover, their unique photochemical and
photophysical properties make them useful in a variety of
optical application such as in optical brighteners, laser dyes,
nonlinear optical chromophores, solar collector systems and
organic lightemitting diodes (LED). Coumarin fluorescent
probes or labels have extensive and diverse applications, as
they exhibit extended spectral range and high emission
quantum yields [18]. Coumarin-based fluorescent
chemodosimeter with salicylaldehyde functionality were
used as a binding site for selective detection of cyanide
anions over other anions in water at biological pH [19],
Shihai Zhou et al., [20] have studied 3-(2-benzothiiazolyl)
coumarins for their fluorescent properties in which the
coumarin acts as a donor while the benzothiazole moiety
* Corresponding author:
drab@eng.ukm.my (Yasameen K. Al-Majedy)
Published online at http://journal.sapub.org/chemistry
Copyright © 2015 Scientific & Academic Publishing. All Rights Reserved
Scheme 1. Reaction sequences of the synthesized compounds
acts an acceptor. P Moeckli et al., [21] introduced some
new red fluorescent coumarin molecules by keeping
electron donating group on 7th position of the coumarin
ring and withdrawing group on 3-position. The oxygen