FULL PAPER
* E-mail: samyeldaly@yahoo.com
Received June 19, 2011; revised August 10, 2011; accepted August 25, 2011.
Chin. J. Chem. 2011, 29, 2557—2561 © 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim 2557
Effect of Medium Acidity and Photostability of 3-(4-Dimethyl-
amino-phenyl)-1-(2,5-dimethyl-thiophen-3-yl)-propenone
(DDTP): A New Green Emitting Laser Dye
El-Daly, Samy A.*
,a,b
Asiri, Abdullah M.
a,c
Khan, Salman A.
a
Alamry, Khalid A.
a
Hussein, Mahmoud A.
a,d
a
Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589,
Saudi Arabia
b
Department of Chemistry, Faculty of Science, Tanta University, 31527 Tanta, Egypt
c
The Center of Excellence for Advanced Materials, King Abdul Aziz University, Jeddah 21589, P.O. Box 80203,
Saudi Arabia
d
Polymer Chemistry Lab, Chemistry Department, Faculty of Science, Assiut University, Assiut, 71516, Egypt
On the line of a previous work on the spectral properties of some of heteroaryl chalcone, the effect of medium
acidity and photoreactivity of 3-(4-dimethylamino-phenyl)-1-(2,5-dimethyl-thiophen-3-yl)-propenone (DDTP) has
been investigated in dimethylformamide and in chloromethane solvents such as methylenechloride, chloroform and
carbon tetrachloride. The dye solution (ca. 5×10
-4
mol•L
-1
in DMF) gives a good laser emission in the range 470
—560 nm with emission maximum at 515 nm upon pumping by nitrogen laser (λ
ex
=337.1 nm). The laser parame-
ters such as gain coefficient (α), emission cross section (σ
e
) and half life energy (E
1/2
) at maximum laser emission
are also determined.
Keywords 3-(4-dimethylamino-phenyl)-1-(2,5-dimethyl-thiophen-3-yl)-propenone, laser dyes, effect of acidity,
possibility
Introduction
Chalcone derivatives have been reported earlier as
important probes of medium viscosity.
1
This property is
particularly important in assessing the microenviron-
ments in micelles, microemulsions and vesicles.
2
Chal-
cones are known as physiological active substances
produced within tissues that appear to control the mito-
sis of the cell of specific tissues that produce them.
3
Hetro-aryl chalcone derivatives have several applica-
tions in many areas such as in food industry,
4
fluores-
cent probes for sensing DNA
5
and photoreactive poly-
mers.
6
Also, chalcones have been used for numerous
optical applications including photo-alignment layer of
liquid crystal display.
7
Therefore, the photophysical
properties of chalcones containing alkyl amino group as
electron donor have been studied.
8-11
In earlier studies
12-14
we reported the photophysical
and laser emission from some aryl chalcones derivatives.
This paper represents a continuation of our systematic
studies of donor-acceptor aromatic derivatives separated
by ethenyl bridge.
We reported, the laser activity of another chalcone
derivative namely 3-(4-dimethylamino-phenyl)-1-(2,5-
demethyl-thiophen-3-yl)-propenone (DDTP).
Experimental
DDTP was synthesized and purified as described
previously
15,16
and its purity was confirmed by elemen-
tal analysis and
1
H NMR and
13
C NMR. All solvents
used were of spectroscopic grade and were preliminarily
checked for the absence of absorbing or fluorescent
impurities within the scanned spectral ranges. UV-visi-
ble electronic absorption spectra were recorded on Shi-
madzu UV-160A spectrophotometer with band-pass of
N
CH
3
H
3
C
S
H
3
C
CH
3
O
N
+
CH
3
H
3
C
S
H
3
C
CH
3
O
-
DDTP
Ground state Excited state